If you’re looking to plan a cozy and romantic getaway from Boston, I’m so glad you’re here! With options ranging from incredible beach destinations by the ocean, to places in the mountains, and exciting city escapes, there are SO many amazing and fun places for you and partner to explore on a romantic weekend away.
Hi there, my name is Sam, and I’ve been exploring the northeast and New England regions for over 15 years now, and consider myself a bit of an expert on travel in this area. I live locally in the northeast, and my love affair with this region started when my husband and I planned our very first romantic getaway together to Vermont when we started dating. Since then, we’ve taken countless getaways together in New England and the northeast over the years (including going to Vermont for our honeymoon!).
So, I’m here to guide you on the best options from Boston, and because I’ve personally been to all of the destinations on this list, I can also give you great suggestions on where to stay, as well as some romantic things to do together. Some of these destinations are well-known places that I think are so worth the hype, and some are some lesser-visited places that I absolutely love, and think are wonderfully romantic.
With that, let’s get started, shall we?
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Charming & Romantic Getaways From Boston
1. Nantucket
Distance From Boston: 1 hour and 45 minutes of drive time, plus time on the ferry. Or, a 1-hour flight. Add extra time for driving in the summers (especially weekends).
If you live in Boston, then you’ve heard a lot about Nantucket, and there are plenty of reasons why it has captured the hearts of so many. Of all the places I’ve visited in New England in the last 15+ years, Nantucket always tops my list. Not only is it a wonderful island destination for all types of travelers, I also consider it to be one of the most romantic places in the region.
Between the charming, old-world scenery, stunning beaches, impressive resorts, picturesque downtown, cobblestoned streets, gorgeous lighthouses, rose-covered cottages, and amazing restaurants, Nantucket has all the ingredients for a romantic coastal getaway from Boston.
The biggest downside to Nantucket is cost, as it’s also one of the most expensive places to visit in New England. If visiting in the summer, you’ll need to have some extra room in your budget for your hotel stay. Summer is undoubtedly a magical time to visit the island, however, you can also save some money by visiting in the spring, fall, or holiday season.
Romantic Places To Stay On Nantucket:
❤️ White Elephant Resort: A luxury resort located in the heart of downtown, I highly recommend booking one of their cozy cottages, which are all individually decorated, and a short walk from Brant Point Lighthouse, shops, and restaurants. My husband and I adored our getaway in one of these cottages together!
❤️ The Wauwinet: One of the best luxury resorts on the island. Located on a secluded part of the island near the Coskata-Coatue Wildlife Refuge, the rooms here are splurge-worthy, and you’ll have access to a free shuttle into town, on-site dining, private beach access, and complimentary bikes to cruise around the island together.
❤️ Union Street Inn: For a more cozy boutique inn experience, this is the best options on the island. Rooms are filled with New England charm, and the included breakfast is absolutely amazing. Rated as the No. 1 small hotel in the U.S. on TripAdvisor, it’s also steps from downtown, so you can easily walk to shops and restaurants.
Romantic Things To Do On Nantucket:
→ Plan a beach day at one of the top beaches on the island. Some of my favorites include Madaket, Surfside, and Sconset.
→ Enjoy a gorgeous sunset from Madaket Beach, and then head to Millie’s after for great food and awesome cocktails.
→ For an extra romantic dinner, reserve a table at Galley Beach, which is, quite literally, on the beach, and has an epic sunset view. Be sure to order some champagne and cheers as the sun goes down!
→ Walk around the Sconset neighborhood to admire the rose-covered cottages (in-season), and enjoy the ocean views from the scenic Bluff Walk. Also be sure to stop by Sankaty Lighthouse!
→ Book a photo session together with Georgie Morley Photography. Not only is she a such a wonderfully kind person, but she’ll take incredible photos of you both to remember your trip by (see our own photos by her above!).
→ Explore the island on a bike or moped together.
Here are more of my Nantucket guides to help you plan:
- How Many Days You Need On Nantucket + Itinerary Options
- A Guide To Nantucket Lighthouses
- Ultimate Nantucket Day Trip Guide
- Cape Cod Vs. Nantucket
- Winter On Nantucket
- Nantucket Christmas Stroll Guide
2. Martha’s Vineyard
Distance From Boston: 1 hour and 45 minutes of drive time, plus time on the ferry. Or, a 45-minute flight. Add extra time for driving in the summers (especially weekends).
As much as I love Nantucket for it’s whimsy and romance, Martha’s Vineyard is also such a great destination for a couple’s getaway from Boston. The island is a bit bigger than Nantucket, but between the colorful gingerbread cottages, gorgeous beaches, amazing dining options, charming towns, and incredible hotel options, it makes for a very memorable getaway.
Also a well-known New England destination, I really do think Martha’s Vineyard deserves all the hype it receives – there are even very famous celebrities who own homes on the island (ahem, Ted Danson 😉). The island makes it so easy to feel like you’re miles away from reality, especially when you drive around to see the iconic red cliffs, quaint fishing villages, and beautiful lighthouses.
Romantic Places To Stay On Martha’s Vineyard:
❤️ Harbor View Hotel: The best luxury resort on the island! Located in picturesque Edgartown on the outskirts of the town center, this resort feels secluded, but is a short walk from everything the town has to offer, including waterfront access to Edgartown Lighthouse. Their amenities also include a pool with private cabanas, fantastic on-site dining, and bikes to use around the island.
❤️ The Winnetu: Another one of my favorite places to stay on the island. This incredible resort is a 5-minute walk to private beach access on South/Katama Beach, which is the best beach on the island. They also have on-site dining, amazing room options, and a pool.
❤️ Vineyard Square Hotel & Suites: Located in the heart of Edgartown, this boutique hotel is super cozy, and steps from shops and restaurants. For a romantic getaway, I recommend the harbor view rooms, or a room with a private balcony for your morning coffee.
Romantic Things To Do On Martha’s Vineyard:
→ Stroll around Oak Bluffs to see all the adorable gingerbread cottages.
→ Plan an amazing beach day, with South/Katama Beach being my favorite, but I also love Moshup Beach, and Philbin Beach (Philbin is resident permit-only in the summer, so this one is best-visited outside of summer).
→ Plan a romantic sunset beach picnic in Menemsha – grab your fresh seafood dinner from either Larsen’s or Menemsha Fish Market, both of which are steps from the beach. Then, enjoy watching the sun go down over the water.
→ Plan a day to visit Aquinnah and see the red cliffs, the lighthouse, and Moshup Beach.
→ Explore the shops in beautiful Vineyard Haven and Edgartown (with Edgartown widely considered to be the prettiest on the island).
→ Book a sunset sail with Mad Max.
Here are more of my Martha’s Vineyard guides to help you plan:
- Best Things To Do On Martha’s Vineyard
- Martha’s Vineyard Day Trip Guide
- Nantucket vs. Martha’s Vineyard For A Day Trip
- Best Beaches On Martha’s Vineyard
- Martha’s Vineyard Without A Car
3. Cape Cod
Distance From Boston: Anywhere from just over an hour, to 2-3 hours, depending on traffic, and where on the Cape you go. Traffic is the most congested in the summers, especially on weekends.
I know, I know – if you live in Boston, it’s likely that everyone you know goes to Cape Cod. So this is a rather obvious choice for this list. However, I’ve been visiting the Cape since I was a kid, and continue to go a few times a year as an adult with my husband, and still find this to be one of the most romantic places in New England.
Cape Cod is home to some of the most stunning beaches in the country, and once you also experience the charming towns, incredible nature trails, beautiful lighthouses, and fantastic restaurants, it’s easy to see why so many people love it.
From Boston, you can also plan a getaway to the Cape without a car if you plan to take the seasonal ferry from the city to Provincetown. Once in Ptown, you can easily get around without a car, and rely on the seasonal shuttle to bring you to some of the nearby attractions and beaches. If you want to visit places outside of Ptown, I suggest you have a car with you.
I also think the Cape is wonderful year-round (yep, I’ve even been to Cape Cod in the winter!), so if you’re looking to plan a spring or fall getaway, this is another fantastic coastal destination to consider.
Romantic Places To Stay On Cape Cod:
❤️ Chatham Bars Inn: The only luxury resort on the Cape is worth every penny! You’ll get to enjoy their private beach with private cabanas, on-site dining and spa services, beautifully-appointed rooms (some of which have ocean views), and the resort is walkable to the heart of Chatham’s downtown.
❤️ Inn On The Beach: Located in Harwich Port, this beachfront hotel offers private beach access, and also has ocean-front rooms in their beach cottage that are especially romantic. You can also walk to Main Street for shops, dining, and some of the best ice cream at Sundae School.
Romantic Things To Do On Cape Cod:
→ Spend a perfect day at the beach, with Coast Guard, Nauset, and Cahoon Hollow being some of my favorites.
→ Explore the charming towns, with Chatham, Harwich Port, Provincetown, and Sandwich being my favorites.
→ Drive around to see the beautiful lighthouses, with Nauset Light being an especially famous one, as it’s featured on the Cape Cod chips bags.
→ Plan a beach sunset date night, and I have an entire guide on the best sunset spots on Cape Cod. to help you decide where to go.
→ Head out on a romantic sailing tour, with Captain Curley being a fantastic option (we loved our sail with him!).
→ Plan a romantic dinner date, with Buca’s Tuscan Road House, twenty-eight Atlantic, and Ocean House being perfect for a date night.
I have quite a few posts on Cape Cod to help you plan, but here are a few to get you started:
- Ultimate List Of Things To Do On Cape Cod
- Visiting Cape Cod For The First Time
- Best Towns To Stay In On Cape Cod
- What To Pack For Cape Cod
- A Guide To The 6 Cape Cod National Seashore Beaches
4. The Massachusetts North Shore
Distance From Boston: 30 minutes to 1 hour, depending on traffic, and where you stay.
Another obvious choice for a getaway from Boston is the North Shore region, and since so many of the beautiful destinations in this area are pretty close together, I’ve condensed it down into one suggestion for you. It’s easy to stay in one town, and drive around to the others in the same visit, even in just a weekend.
The North Shore is one of my favorite areas in Massachusetts, and includes Salem, Marblehead, Manchester-By-The-Sea, Gloucester, Rockport, Ipswich, Essex, and Newburyport. You’ll find such beautiful coastal scenery throughout these towns, romantic places to stay, charming shops and restaurants, and one amazing scenic drive that weaves through all the towns.
The Essex Coastal Scenic Byway is such a romantic drive to take in this area, and even if you live in Boston, and have already experienced these destinations, I can’t recommend the Byway enough to really take some time and appreciate the natural beauty of this area.
When you’re not driving the Byway, you can spend your day at beautiful beaches, exploring quaint fishing villages that feel like a postcard, seeing lighthouses, and eating fresh seafood.
Romantic Places To Stay On The North Shore:
❤️ Harbor Light Inn: Definitely my favorite place to stay in the region. This romantic and cozy, historic inn is in the heart of the historic district in Marblehead, and offers a quiet getaway in a very underrated destination in New England. I always love my stays here!
❤️ Beauport Gloucester: This luxury oceanfront resort is loaded with amenities like a rooftop pool and bar, complimentary bikes to explore the town, outdoor firepits, and direct beach access.
Romantic Things To Do On The North Shore:
→ Spend a day driving the Essex Coastal Scenic Byway.
→ Meander through Bearskin Neck in Rockport, and snap a photo with Motif 1, said to be the most painted building in the country.
→ Plan an afternoon in Newburyport, which is an incredibly charming town, home to Plum Island for beaches, and amazing shops and restaurants.
→ Tour Castle Hill at the Crane Estate in Ipswich, and visit Crane Beach, too!
→ Walk through the historic district in Marblehead, and take in the views from Castle Rock.
→ Enjoy Salem, which is so much more than it’s Halloween events!
Here are some posts that will help you plan a getaway to the North Shore:
- Things To Do In Newburyport, MA & Plum Island
- Things To Do In Rockport, MA
- Ultimate Salem, MA Day Trip Guide
- Things To Do In Marblehead, MA
5. Portsmouth & New Castle, NH
Distance From Boston: About 1 hour, plus more if traffic is congested.
For a quaint city escape from Boston, Portsmouth is a fantastic destination to consider! It feels much more like a small town than a city (especially when compared to Boston), and combined with its fantastic downtown area, waterfront scenery, amazing dining options, and New England architecture, there are plenty of ways to have a romantic weekend together here.
Additionally, if you’re looking to explore this area, but want to stay in a quieter location, you can choose to stay in New Castle, NH, which is home to a fantastic hotel, and has lots of waterfront scenery so you feel a bit further away from every day life.
Romantic Places To Stay In Portsmouth & New Castle:
❤️ The Hotel Portsmouth: Located in the heart of the city, the boutique hotel is packed with character and lots of cozy New England vibes. They also have on-site parking, which is such a nice perk to make your getaway easier.
❤️ Wentworth By The Sea: Located in New Castle, this waterfront hotel has beautifully-decorated rooms, and offers a more peaceful atmosphere, but is only about 10 minutes from downtown Portsmouth.
Romantic Things To Do In Portsmouth:
→ Stroll along the waterfront area, which is also home to the beautiful Prescott Park.
→ Head out on a sunset or lighthouse cruise with Portsmouth Harbor Cruises.
→ Plan a lunch date at Elephantine, which has amazing coffee, drinks, baked goods, and light bites.
→ If you visit in the winter, be sure to visit the adorable outdoor ice rink to go skating together.
→ Step back in time together at the Strawbery Banke Museum.
→ Plan a dinner date at Botanica Restaurant and Gin Bar.
6. Mirbeau Inn & Spa In Plymouth
Distance From Boston: 1 hour
If you’re looking for the ultimate spa getaway from Boston, Mirbeau is one I love to suggest. Part romantic inn, and part full-service spa, it’s an all-in-one destination that makes it so easy to disconnect, spend quality time together, and also, get in some well-deserved pampering.
Located in Plymouth, just outside of the main downtown area, the resort feels very peaceful and secluded, and is designed to transport you to a French countryside setting. Once you’re there, you really don’t need to leave, as they have awesome on-site dining, a fitness center, and of course, all the spa amenities.
However, if you want to venture off the grounds, you’re a short drive to downtown Plymouth, which is loaded with all kinds of fun things to do.
❤️ Click Here Check Rates & Availability At Mirbeau Inn & Spa In Plymouth
Psst! I have some guides on this area you may like, including Visiting Plymouth, MA, and Is Mirbeau In Plymouth Worth It?
7. Cliff House On Cape Neddick, Maine
Distance From Boston: 1 hour and 30 minutes
Located in southern Maine, Cape Neddick is home to one of the most romantic coastal resorts my husband and I have ever stayed at – Cliff House. While I whole-heartedly recommend the popular nearby towns of Ogunquit and Kennebunkport for a romantic escape, there’s just something about Cliff House that makes it extra special and memorable.
Cliff House is only 10 minutes from downtown Ogunquit and York, and 35 minutes from Kennebunkport, making this a wonderfully centralized location to explore different areas of Maine’s coast.
While staying at the resort, you can enjoy the gorgeous infinity pool that overlooks the ocean, plan romantic date nights at the on-site restaurants, sip champagne on your private balcony, and stroll along the dramatic coastline on the resort’s own walking path.
❤️ Click here to check rates & availability at Cliff House in Maine
Psst! I have a detailed guide on Visiting Ogunquit, Maine if you’re looking for help planning your time there.
8. Migis Lodge On Lake Sebago, Maine
Distance From Boston: 2 hours and 15 minutes
I think Lake Sebago is a super under-rated destination in Maine, and there’s one reason in particular this can be an especially romantic getaway from Boston – Migis Lodge.
This all-inclusive resort right on the lake offers a quintessential Maine experience, and the best part is, all you need to do is just show up, and everything else is there waiting for you. All your meals are included (although, alcoholic drinks are extra), and the lake is steps from your room or cottage, depending on which you book.
What I think is so romantic about Migis Lodge is that dressy attire is a requirement for dining after 5:30pm, which forces you to go on a little date night together each night. Additionally, all water equipment is included with your stay (with the exception of personal motor equipment), so think romantic kayak or canoe rides around the lake 😉 If you know your way way around a sailboat, they also have those available.
Additionally, you’ll also enjoy lobster bakes by the lake, access to their fitness center, massage facilities (at an additional fee), pickleball and tennis courts, and of course, all the serene wooded grounds for a peaceful escape.
But, of course, you’re not contained to just the resort, and you won’t be far from everything else the Lake Sebago region has to offer. However, just fair warning, you may not want to leave the Migis Lodge grounds once you arrive!
❤️ Click here to check rates & availability at Migis Lodge on Lake Sebago
9. Camden, Maine
Distance From Boston: 3 hours and 15 minutes
It’s hard to pick one town in Maine as the most romantic, but Camden would definitely be on my short list. This small town on the Midcoast is full of charm, and Travel + Leisure even put it on their list of the top 16 most beautiful coastal towns in the entire world.
While on your drive up to Camden, you also have the option to stop in some wonderful places on the way to get a head start on your getaway, including Portsmouth, York/Cape Neddick, Ogunquit, Portland, and Wisacassett, which makes for a romantic mini road trip.
But while in Camden, you’ll get to experience small-town charm along the coast with a beautiful downtown area that’s very walkable, a picturesque harbor, wonderful shops and restaurants, hiking, and boating tours.
Romantic Places To Stay In Camden:
❤️ Camden Harbour Inn: My favorite place to stay when visiting. A traditional New England-style inn with modern updates, well as well an on-site spa, perfect location walkable to town, and home to one of the best restaurants in Camden, Natalie’s.
❤️ Grand Harbor Inn: A boutique hotel right on the water, most rooms have balconies overlooking the harbor, jacuzzi tubs, and fireplaces. It’s also situated right in town, so you can walk to shops and dining, and they bring you breakfast to your room each morning, which is so perfect for a romantic weekend together.
10. The White Mountains, NH
Distance From Boston: 2 hours and 10 minutes, to 2 hours and 30 minutes, depending on where in the area you stay.
For an escape to the mountains, the White Mountains in New Hampshire are hard to beat. And while this is definitely more of an adventurous getaway with your partner, there are some wonderfully relaxing and easy-going things to do, too, as well as fantastic hotels to choose from.
This is a bigger region to visit that offers incredible hiking opportunities, train rides to New England’s highest peak and through the mountains, scenic drives, cute towns, breweries, distilleries, and so much more!
Romantic Places To Stay In The White Mountains:
❤️ Omni Mount Washington Resort: With sweeping views of the mountain vistas just steps outside the resort, you can also enjoy an on-site spa, dining, and a wide-range of activities at this historic property, depending on the season in which you visit.
❤️ Sugar Hill Inn: Located in the smaller, quieter town of Sugar Hill, this traditional New England-style inn is a renovated farmhouse set amongst the mountains, and includes an incredible breakfast with your stay. There are also rooms with whirlpool tubs and private outdoor spaces, and a super romantic and cozy restaurant on-site for dinner.
Romantic Things To Do In The White Mountains:
→ Take a scenic drive along the Kancamagus Highway, which is known for it’s fall foliage, but offers epic mountain views and gorgeous overlooks year round.
→ Visit Flume Gorge, which offers covered bridges and beautiful, wooded scenery with mountain views, and of course, the incredible gorge, which you get to walk through during your visit. It’s also a pretty easy and relaxing walk, which allows you time to talk while enjoying the scenery.
→ Take a ride together on The Cog, the mountain railway system that takes you to the top of Mount Washington, the highest peak in New England. In the winter season, they also still operate, but stop just short of the summit due to inclement weather. My husband and I have loved both types of excursions.
→ If you visit in the winter, definitely make reservations at Nestlenook Farms for a sleigh ride, or to skate on their picturesque pond (which might be the prettiest outdoor rink I’ve ever seen).
→ Take a scenic drive through Crawford Notch State Park to enjoy the incredible mountain views.
Here are some of my guides on the White Mountains to help you plan:
- Where To Stay In The White Mountains: Best Towns & Hotels
- Is Flume Gorge Worth Visiting?
- Things To Do In Lincoln, NH
- Things To Do In Littleton, NH
- Things To Do In Franconia, NH
11. Mystic, CT
Distance From Boston: 1.5 hours
Located right on the border of Rhode Island and Connecticut in the southeastern part of the state, Mystic is such an incredibly charming and fun trip to plan together. Every time my husband and I come here, we have such a relaxing time because there’s just enough to do that we’re never bored, but it’s also not overwhelming, and offers time to relax together.
Mystic sits right on Mystic River (yep, from the movie 😉), and is home to a lovely little Main Street with shops and restaurants, incredible bakery and donut spots, waterfront scenery, an awesome museum, the aquarium, wineries and vineyards, and lots more.
Most Romantic Place To Stay In Mystic:
❤️ Whalers Inn: Located in the heart of town center, this historic inn is equal parts cozy and modern, and walkable to everything in town.
❤️ Taber Inne & Suites: Located a short drive from town center, this is a more budget-friendly option, and is also super cozy. Many rooms come with fireplaces and jacuzzi tubs.
Romantic Things To Do In Mystic:
→ Visit Olde Mistik Village, which is an outdoor shopping area with unique shops, and designed to feel more like a little historic village. In fact, this area was used as the filming location for the Hallmark movie Christmas in Mystic, so that’s how cute it is 😉
→ Stroll down Main Street to visit the shops, and definitely swing by Sift Bakery or Young Buns Doughnuts for some treats!
→ Head to the Mystic Seaport Museum, where most of the museum is set outdoors along the river, and features old whaling boats and ships you can climb aboard into, and feel as though you’ve stepped back in time.
→ Spend an afternoon enjoying the animals at Mystic Aquarium.
Psst! I have a detailed guide on the Best Things To Do In Mystic, CT, if you need more ideas 😉
12. Litchfield Hills, CT
Distance From Boston: 2.5 – 3 hours, depending on which town you stay in
The northwest corner of Connecticut offers gorgeous countryside scenery, and a cluster of especially quaint and charming towns, making this such a fun getaway to take together if you’re looking for something a bit off-the-beaten-path. While this area is known for being a fantastic getaway destination, it’s not quite as busy as the more popular places on this list.
In fact, if you’re a fan of the show Gilmore Girls, one of the towns in this region is known for being the real Stars Hollow, as the show’s creator stayed at an inn in Washington, CT while creating the pilot for the series.
This area of the state is also small enough that you can easily take a few scenic drives and visit different towns with just a weekend, while still leaving you time to enjoy your hotel and relax together, too. This area is especially known for its fall foliage, which is a magical time to visit.
Most Romantic Places To Stay In The Litchfield Area:
❤️ The Mayflower Inn: Known as being one of the most luxurious and expensive places to stay in New England, it’s so worth it if it falls within your budget (it’s where Amy Sherman-Palladino stayed when she was looking for inspiration for the show 😉). The rooms here are stunning, and you’ll be able to enjoy amenities like a full-service spa and wellness center (known for their wellness retreats!), on-siting dining, a pool, and stunning scenery at every turn.
❤️ The Litchfield Inn: This is where I most-often stay when I visit this area, and absolutely love it. The grounds are peaceful and relaxing, and they have rooms ranging from classic inn-style rooms, to boutique, individually-decorated rooms. They also give you fresh-baked cookies when you arrive, and your stay includes an elevated continental breakfast.
Romantic Things To Do In The Litchfield Hills:
→ Take a scenic drive between the main towns, which are Litchfield, Kent, New Milford, and Washington. Each of these towns has their own charming atmosphere, and are worth exploring.
→ Visit Kent Falls State Park, where you’ll cross a covered bridge to Connecticut’s tallest waterfall.
→ Explore Mount Tom State Park and Topsmead State Park, both of which offer scenic nature and hiking trails.
→ Book a romantic dinner at Arethusa al tavolo.
13. New York City
Distance From Boston: 3.5 – 4 hours of drive time, maybe longer if traffic is congested. Other options are a 4-hour train ride, or a 1.5 hour (on average) flight.
New York City needs no introduction, but if you’re a city person through and through, and you’re just looking for a change of scenery, then this is the perfect romantic getaway to plan! And it’s also one of the few places on this list that doesn’t require a car, as you can take a train or fly between Boston and New York.
Of course, there are tons of things to enjoy in the Big Apple, and between the different neighborhoods, incredible museums, exciting culinary scene, the different parks, and the iconic hotels, there’s no way this isn’t a romantic trip to plan together.
Romantic Places To Stay In New York City:
❤️ The Plaza: I mean, it doesn’t get more iconic than this hotel, right? If it works with your budget, it’s worth it for the 5th Avenue location alone, as it’s steps from Central Park. With lavish rooms, as well as on-site dining and spa services, it’s such a treat to stay at The Plaza at least once in your lifetime, especially as a romantic getaway.
❤️ Made Hotel: This boutique hotel in the trendy NoMad neighborhood is centrally-located within Manhattan, and offers upscale, modern rooms in a moderate price range. Some of the rooms also have balconies overlooking the city for a relaxing cup of coffee in the morning, or a glass of wine at sunset.
Romantic Things To Do In New York City:
→ Take a stroll across the Brooklyn Bridge, and head over to the DUMBO neighborhood of Brooklyn. This bridge is pretty popular, and gets crowded, especially at sunset, but sunrise is especially quiet and romantic.
→ Get tickets to a broadway show, of course! Or, enjoy a performance by either the New York City Ballet, or American Ballet Theater.
→ Enjoy Afternoon Tea The Plaza hotel, which has been a tradition in the city for over 100 years.
→ Stroll through Central Park, especially view city skyline views from the Bow Bridge. The park is HUGE, and you could explore it for days and not see it all.
→ Meander through the West Village, which is one of the most charming areas of the city.
→ Spend the day admiring art at the MET.
Psst! If you’re looking to drive, I have an entire guide on the Best Stops To Make On A Boston To New York City Road Trip.
14. Mohonk Mountain House In New Paltz, NY
Distance From Boston: About 3.5 hours, depending on where in the region you stay
Mohonk Mountain House is a Victorian castle on top of a mountain, nestled along the Shawangunk Ridge, and it’s one of the most unique places I’ve ever experienced. The architecture of the resort alone is stunning, and since it’s home to over 1,300 acres of land, and has access to 8,000 acres in the Mohonk Preserve, it’s such an incredible place for a romantic getaway.
This all-inclusive resort is a nature-lover’s paradise, but is also one of the best places to plan a relaxing weekend. During your stay here, you’re steps from all the incredible trails on the resort grounds, as well as swimming and canoeing in the lake. On-site is also a spa, fantastic dining options, and cozy outdoor spaces to enjoy the views and scenery.
❤️ Click here to check rates & availability at Mohonk Mountain House
Psst! If an overnight stay isn’t within your budget, you can actually visit for just the day. I have an entire guide on on the Mohonk Mountain House Day Pass options, if you need more info.
15. Stowe, Vermont
Distance From Boston: 3 hours
One of the best mountain towns in Vermont is most definitely Stowe, and even after years of visiting this wonderful destination is all different seasons, it continues to impress me. While known as one of the top foliage places in the country, Stowe is also an incredible winter destination with world-class skiing, and incredible mountain scenery.
But because of it’s small-town charm, it’s also wonderfully romantic. Between the covered bridges, cozy dining options, memorable hotels and resorts, and stunning mountain vistas to enjoy, it really has everything you need in a Vermont getaway.
Romantic Places To Stay In Stowe:
❤️ The Lodge At Spruce Peak: Definitely one of the best resorts in Stowe, the lodge has direct access to the mountains and ski resort. But even if you’re not there to ski (or visiting in the winter), there’s also on-site dining, a spa, pool, and some rooms have incredible mountain views.
❤️ The Green Mountain Inn: This is actually my husband’s favorite places to stay when we come here for getaways. Located right on Main Street in the heart of the village, this historic property has lots of old-world charm, and has a wonderfully cozy vibe. They can also arrange massages for you both.
Romantic Things To Do In Stowe:
→ Take a scenic drive through Smugglers Notch, which is most known for being incredible during fall foliage season (this road is closed in the winter, so plan accordingly).
→ Visit the town’s covered bridges.
→ Plan an spa day at the Spruce Peak Resort (even if you’re not staying there).
→ Book a romantic dinner at Harrison’s.
I have a few posts on visiting Stowe that may help you plan your trip, including:
- Best Things To Do In Stowe, VT
- Guide To Visiting Stowe, VT In The Winter
- Best Stops To Make On A Boston To Stowe, VT Road Trip
16. Woodstock, Vermont
Distance From Boston: 2.5 hours
Known as the most idyllic town in Vermont, Woodstock is definitely one of the most romantic places to visit from Boston. The charming village is packed with quaint boutiques and restaurants, and after a stroll around, you’ll probably start wondering if you should move there.
Not only that, there are some fantastic places to stay during your visit, including a resort that’s referred to as Vermont’s most beautiful address. During your getaway here, enjoy small-town life while exploring picturesque streets, covered bridges, beautiful nature trails and farms, and dining at incredible restaurants.
Romantic Places To Stay In Woodstock:
❤️ The Woodstock Inn & Resort: Definitely the most romantic place to stay in town. It’s located in the heart of the village, so you can walk to shops and restaurants, and they have their own dining options and spa on-site. This resort is known as Vermont’s most beautiful address, and you also get free admission to Billings Farm by staying here.
❤️ 506 On The River Inn: Located a short drive from the village center, this cozy inn is located along the Ottauquechee River, and has a rustic farmhouse vibe that’s perfect for a getaway.
Romantic Things To Do In Woodstock:
→ Stroll along the picturesque streets in the village and visit all the boutiques and quaint shops.
→ Snap a photo together at Middle Covered Bridge, right in the village.
→ Book a spa day together at the Woodstock Inn (which you can do even if you’re not staying there).
→ Make reservations for dinner at the Lincoln Inn, which is one of the most memorable dining experiences we’ve ever had.
→ Walk the trails at the Marsh-Billings-Rockefeller historic park.
Psst! I have a detailed guide on Things To Do In Woodstock, VT, if you need more suggestions 😉
17. Westerly & Watch Hill, Rhode Island
Distance From Boston: 1 hour and 45 minutes
Westerly, and its small village Watch Hill, are home to some of the best and most beautiful beaches in Rhode Island, and while that’s reason enough to consider this for your romantic getaway from Boston, they’re also home to two incredible luxury resorts.
Both the Ocean House and the Weekapaug Inn are stand out resorts in New England, and offer an upscale coastal experience that’s nothing short of memorable and romantic. While these are definitely in the splurge category, for a special occasion, they’re hard to beat with all the incredible luxury amenities, and waterfront scenery.
But in addition to the beaches and resorts mentioned above, both Westerly and Watch Hill have charming downtown areas, and lots of fun things to do, without feeling too overwhelming to tackle in just a few days. Generally, you’ll typically find fewer crowds here in the summers compared to popular places like the Cape and the islands.
Another Romantic Place To Stay In Westerly:
❤️ The Hotel Maria: A more affordable option to the two resorts listed above, but still offers an amazing cozy and upscale oceanfront experience in a boutique hotel setting.
Romantic Things To Do In Westerly and Watch Hill:
→ Take a stroll out to Watch Hill Lighthouse.
→ Explore both downtown Westerly and the quaint village of Watch Hill.
→ Walk the shoreline of the beach at Napatree Point (featured in the photo above).
→ Book a sunset sail with Sail Trim Again Tours.
→ Make dinner reservations at the Ocean House’s COAST Restaurant, which was named one of CNN Traveler’s world’s best waterfront restaurants.
Psst! I have a detailed guide on Things To Do In Westerly & Watch Hill, RI, if you need more ideas 😉
18. Block Island, Rhode Island
Distance From Boston: 1.5 hours of driving, and a 30-60 minute ferry (depending on which ferry you take)
For a romantic island getaway with fewer crowds in the summer season, Block Island is such an amazing option, and this continues to be one of our favorite places to visit in New England. While it does still see crowds in the summertime, it feels less busy than Nantucket and Martha’s Vineyard, but that’s not the only reason to visit.
Block Island has miles of gorgeous beaches to explore, all of which are free to everyone to enjoy. Additionally, you’ll find a quaint downtown area along the waterfront with shops and restaurants, hiking and scenic nature trails, lighthouses, and so much beautiful scenery to take in.
Romantic Places To Stay On Block Island:
❤️ The 1661 Inn: This historic and stunning waterfront inn offers amazing views of the ocean, and the rooms here are beautifully-decorated, with options to book a room with ocean views and/or a balcony overlooking the water.
❤️ Avonlea, Jewel Of The Sea: This cozy waterfront inn has a stunning wrap-around porch with incredible ocean and harbor views, and a traditional New England vibe. Many of the rooms come with an ocean view, too.
Romantic Things To Do On Block Island:
→ Spend a day at one of the beautiful beaches, with Mansion Beach being one of my favorites on the island.
→ Head to Dorie’s Cove beach for a gorgeous sunset.
→ Enjoy the views from the Monhegan Bluffs staircase together, and walk down to the beach for a shoreline stroll.
→ Walk out to North Light lighthouse together, which requires you to walk across a beach. You’ll feel miles away from every day life out here!
Psst! I have a guide on taking a Block Island Day Trip, if you’d like more information on the island 😉
19. Newport Or Bristol, Rhode Island
Distance From Boston: 1 hour and 15 minutes
Newport is a well-known coastal city in New England, and it’s such a fantastic destination that never seems to disappoint. Between the historic streets and architecture, lighthouses, incredible dining opportunities, Gilded Age mansions, harbor-front scenery, boat tour options, and so much more, Newport just has that special quality to it that feels so romantic.
Newport is also home to some incredible hotels, and one of the best in the city is Castle Hill Inn. This oceanfront resort is a short drive outside of town, and has beautiful rooms and cottages to choose from, as well as on-site dining and a spa.
However, if you’ve already been to Newport, I also really love to suggest nearby Bristol, which is only about 30 minutes from downtown Newport. Bristol is a smaller coastal town loaded with charm and things to do, including the beautiful Blithewold Manor, a cute downtown, the East Bay Bike Path, great restaurants, and Independence Park.
More Romantic Places To Stay In Newport Or Bristol:
❤️ Chart House Inn: Located in the historic area of Newport, and just steps from downtown, this cozy and beautiful restored property includes an incredible gourmet breakfast with your stay.
❤️ William’s Grant Inn B&B: Located in Bristol, this small, historic inn has all the traditional New England vibes, and also includes a great breakfast each morning during your stay.
Psst! I have more guides on Newport, including an Ultimate Newport, RI Day Trip Guide, and Things To Do In Newport, RI In The Winter, if you need more ideas 😉
20. The Claremont In Southwest Harbor, Maine
Distance From Boston: 4.5 hours
There’s no doubt that Acadia National Park is one of the best things to do in New England, and if you’re looking to also make this a romantic trip together, I recommend staying at The Claremont in Southwest Harbor.
While I love Bar Harbor, the main town near the park, Southwest Harbor is smaller, less crowded, and has a more relaxed atmosphere. And, The Claremont resort is such a romantic hotel to use as your home base on Mount Desert Island. Of all the places I’ve stayed at over the years in this area, The Claremont continues to have the most romantic and secluded vibe.
Between the outdoor pool overlooking the ocean, private cabanas, gorgeous rooms, a stunning wrap-around porch, and on-site waterfront dining, it has everything you need for a more secluded getaway near Acadia.
❤️ Click here to check rates & availability at The Claremont
Some of my posts on the area to help you plan your trip:
- My Perfect Acadia National Park Itinerary
- Best & Worst Time To Visit Acadia National Park
- Best Towns & Places To Stay Near Acadia National Park
21. The Berkshires, Massachusetts
Distance From Boston: 2 hours and 15 minutes
Another fantastic option for a mountain getaway is The Berkshires in Massachusetts. Between all the quaint towns with idyllic Main Streets, incredible views and hiking trails, scenic drives, beautiful lakes, and rural scenery, it’s a wonderful way to escape city life together and enjoy everything at a slower pace.
The Berkshires also has an incredible culinary scene with some fantastic dining options available, making this a great choice for foodies.
Romantic Places To Stay In The Berkshires:
❤️ Red Lion Inn: One of the most iconic places to stay in the region. This inn is located right on the picturesque Main Street in Stockbridge, and offers very cozy rooms in a traditional New England style setting.
❤️ 33 Main: This quaint Annie Selkie boutique inn in Lenox offers beautifully-decorated rooms, each with their own style. And during your stay, enjoy a full gourmet breakfast each morning, fresh cookies upon arrival, and cocktail hours in the afternoons.
Romantic Things To Do In The Berkshires:
→ Heads out on a scenic drive along Route 7.
→ Rent a canoe or kayak to paddle around the gorgeous Cheshire Reservoir (pictured above!)
→ In season, drive to the top of Mount Greylock, the highest peak in The Berkshires, and enjoy the views together from the top.
→ Visit all the charming towns, with Lenox, Stockbridge, Williamstown, and Great Barrington being my favorities.
→ Book a memorable dining experience for dinner, and Once Upon A Table in Stockbridge is one of my favorites.
22. Manchester, VT
Distance From Boston: 3 hours and 15 minutes
One of the most romantic towns in southern Vermont is definitely Manchester, and my husband and I come here a lot when we need a little getaway together.
Manchester offers so many great things to do in a beautiful setting, including mountain views, a historic Main Street, awesome shopping, great restaurants, hiking, and lots more. It really has everything you need for an escape from the city!
Romantic Places To Stay In Manchester:
❤️ Kimpton Taconic: This beautiful property on Main Street offers a seasonal outdoor pool, tickets to Hildene included with your stay, and nightly happy hours. We really love Kimpton-brand hotels, and this property is especially lovely! They also have an amazing pet policy, where your pets can join you without any restrictions or additional fees.
❤️ Hill Farm Inn: Just 10 minutes outside of Manchester in Sunderland, this idyllic farm property is a dream come true. With mountain views, an outdoor pool, beautiful rooms, alpacas on the farm, a beautiful wrap-around porch to use, a swing hanging from a tree, and an awesome barn-turned-restaurant on the grounds, they really have everything for the perfect Vermont getaway.
Romantic Things To Do In Manchester:
→ Spend the day at Hildene, The Lincoln Family Home. Even if you’re not a history buff, the beautiful property, gardens, mountain views, and nature trails are all fantastic,
→ Book a memorable dinner at the Crooked Ram.
→ If visiting in the summer, take a drive to Dorset and go swimming at the marble quarry, and then swing by the Dorset farmer’s market and HN Williams General Store afterward (the last two are right next to each other).
→ Stroll through Manchester’s Main Street, which is divided into two parts: the historic area, and the town center area with shops and dining. Both are great!
→ Drive the Mount Equinox Skyline Drive for incredible mountain views (open seasonally).
23. Boothbay Harbor, Maine
Distance From Boston: 2 hours and 45 minutes
Boothbay Harbor is one of my favorite coastal towns in New England, and because it’s a small town loaded with character and beautiful scenery, it’s also wonderfully romantic.
Despite its size, Boothbay still offers a lot to do, especially if you’re looking to head out onto the water. There are so many great boat tours here that offer different experiences, as well as wonderful restaurants, botanical gardens, and unique charm around every turn. Boothbay is a largely seasonal destination, so to enjoy all the amenities, you’ll want to plan your trip in the spring, summer, and fall seasons.
Romantic Places To Stay In Boothbay Harbor:
❤️ Spruce Point Inn: A resort that’s a 10-minute drive to town center, but feels miles away. Enjoy amenities like complimentary kayaks, an outdoor pool, boat cruises that leave from the resort, as well as on-site dining and spa services.
❤️ Harborage Inn On The Waterfront: Located right in town and walkable to the shops and restaurants, this waterfront inn sits right on the harbor, and I can’t suggest Room 8’s panoramic water view enough!
Romantic Things To Do In Boothbay Harbor:
→ Book a sunset sailing cruise on a schooner.
→ Make a dinner reservation with Cabbage Island Clambakes, which is one of the most fun and unique experiences in New England.
→ Spend the afternoon at the Coastal Maine Botanical Gardens, which are so beautiful, and also have giant troll sculptures to look for, as well as scenic nature trails. This is a large garden that can easily take up an entire day.
→ Explore the downtown area’s shops.
→ Walk across the footbridge in town for lovely harbor views.
Psst! I have a full guide on Things To Do In Boothbay Harbor, Maine, if you need more tips for your itinerary.
24. Bethel, Maine
Distance From Boston: 3 hours
A lesser-talked about getaway destination in Maine is Bethel, and if you’re looking for a gorgeous mountain escape to a small town, this is an excellent choice.
Nestled into the Mahoosuc Range mountain range, Bethel has a quaint downtown area, fantastic hiking in nearby Grafton Notch State Park, a walking trail through town, a covered bridge, breweries, and the Sunday River Resort, which offers year-round activities outside of ski season.
While Bethel is great to visit year-round, it’s especially beautiful in the fall season because of its amazing foliage displays, which is my favorite time to visit. But winter is peak tourist season because of the highly-rated ski resort at Sunday River.
Most Romantic Place To Stay In Bethel:
❤️ GraceNote Inn & Spa: This cozy, and recently renovated historic inn is located just a few minutes from Sunday River, and offers beautifully-decorated rooms, a wonderful breakfast each morning, as well as on-site dining and spa services.
Romantic Things To Do In Bethel:
→ Take a scenic lift ride to a mountain top at Sunday River to enjoy the views together (summer and fall season).
→ Snap a photo together at the Sunday River Covered Bridge.
→ Take a scenic drive through Grafton Notch State Park, and go on an amazing hike together (Table Rock is especially worth it, and is especially awesome at sunset).
→ Book a table at the quaint and cozy Watershed Wood-Fired Kitchen, which serves fantastic pizzas and Italian cuisine.
Psst! I have an entire guide on Things To Do In Bethel, Maine to help you further plan your trip.
25. Lake Placid, New York
Distance From Boston: A 5-hour drive, or a 1.5 hour flight to Adirondack Regional Airport, and then a 30-minute drive or taxi to Lake Placid.
Last on my list, while Lake Placid is quite a drive from Boston at 5 hours each way, I wanted to include it because it’s truly such a romantic destination to explore if you’re looking for a mountain escape, and has some really wonderful resorts to stay at. Plus, you also have the option to take an easy flight from Boston to a nearby airport, and only drive 30 minutes to town.
Nestled in the Adirondacks of New York, Lake Placid is one of the most charming places to explore in the Upstate region. While known for its Olympic ties and fantastic skiing, it’s truly a year-round destination with stunning mountain views, a lovely little downtown area, gorgeous Mirror Lake, awesome hiking trails, and tons more.
My husband and I have been here a few times in both fall and winter, and it’s always a memorable trip that’s equally adventurous and relaxing.
Romantic Places To Stay In Lake Placid:
❤️ Whiteface Lodge: Located a few minutes from town center, this stunning resort property offers luxury accommodations and amenities, including year-round indoor and outdoor hot tubs, a movie theater on-site, and old-fashioned bowling alley, on-site dining, and a spa. This place is quite literally a dream come true in the mountains!
❤️ Mirror Lake Inn & Spa: While not as flashy at Whiteface Lodge, the Mirror Lake Inn is also exceptional. Located within walking distance of town and just across from the lake, you’ll find very cozy rooms here, as well as on-site dining, and spa services.
Romantic Things To Do In Lake Placid:
→ Book a couples massage at the Mirror Lake Inn & Spa (the spa is open to the public).
→ Drive to the summit of Whiteface Mountain for amazing mountain views (open seasonally).
→ Explore Lake Placid’s adorable downtown, which has shops and restaurants, as well as views of Mirror Lake.
→ Go on one of the many hikes in the area, with Mount Jo being one of our favorites for an easy to moderate option that has incredible pay off. A few other great ones are Cobble Hill, Indian Head, or one of the high peaks.
→ Canoe around the lake with Mirror Lake Boat Rental.
Romantic Getaways From Boston – FAQ
Tips For Affordable Getaways From Boston
The New England area is notoriously expensive, which is one of the biggest downsides to this region. However, there are definitely some more affordable places to stay that’ll save you some money, and ways to stay on a budget.
Of course, camping is always a great way to save money, and also, camping is super romantic! Now that I’m older, my body can’t tolerate camping quite as much anymore, but my husband and I would camp a lot when we were younger to save money, and it was so incredibly romantic each time. Many places on this list offer some camping options, especially once you’re in the mountain areas (this will be more difficult once you get to the coast, though).
I also love to stay in motels to save a few bucks on my travels. While not romantic in a lavish way, clean and cozy motels still allow you to escape to most of the romantic places listed on this post, and it’ll be really hard to not have a memorable getaway, regardless of where you choose to stay.
Lastly, time of year makes a huge difference in the northeast, and traveling outside of peak season will save you a lot of money. I know when planning a romantic getaway, it’s often to celebrate a specific day, like an anniversary, so if you’re on a budget, consider going somewhere that’s not experiencing peak tourism.
For example, if you need to travel in July or August, avoid the top beach towns in this area, and instead, consider going to Vermont or the White Mountains. Or, if you’re celebrating a special occasion in the winter, avoid the top ski and winter destinations, and maybe head to the coast (which is so lovely and peaceful in the winter!).
Do You Need A Car To Take A Romantic Getaway From Boston?
Nope! However, depending on where you’re heading, it might be the best option. For some of the places on my list, you can take a ferry, a train, or a short flight. However, many of the places are best explored by car, and are easier to visit when you can drive the whole way.
This will depend on your specific plans, and what works best for your itinerary.
For example, I really recommend having a car in Vermont, the White Mountains, the Litchfield Hills, the Hudson Valley, and anywhere along the coast, especially in Maine. I’ve personally never found public transit options in the northeast, and New England specifically, to be all that convenient.
While there are some exceptions, like New York City and Provincetown on Cape Cod, generally, I’ve always found that having a car is the best choice, especially if you’re short on time.
Packing Tips For Your Getaway
In addition to packing your usual clothes and toiletries for the climate and season, here are a few additional things you may want to consider for your romantic trip together:
→ A tripod for your camera or phone (whichever you rely on to take pictures). This is so nice to have when you want to capture a fun moment between the two of you! I like this tripod for phones, and this tripod has been my go-to for my camera for years, and it’s still in great shape after a lot of use. I love that it’s lightweight and folds into a compact size that fits in backpacks.
→ If you love taking photos, I think having an instant polaroid camera with you is such a fun and romantic idea. It’s not necessary, of course, but for a romantic trip, there’s something special and whimsical about capturing some photos together in a polaroid that you can keep at your office desk or on your bedside table as a memento.
→ Reusable water bottle to stay hydrated throughout the day.
→ Date night outfits, especially if you’re planning on a more upscale romantic dinner date. This is especially important if you’re staying at Migis Lodge, which has a dress code after 5:30p.
→ Dramamine if you’re taking any boat tours, and you tend to get seasick.
→ A small medical pouch with medications, band-aids, etc. in case of any illnesses. It’s never fun to not feel great or get a bad blister while on a romantic trip together! Having these to help you feel better is always so nice to have on a romantic getaway (although, you can buy pretty much anything while at your destination, too).
More posts you may enjoy:
- The Perfect 7 Day New England Road Trip Itinerary
- Unforgettable Boston To Bar Harbor Road Trip Itinerary
- Best Stops To Make When Driving Between Boston & Portland, Maine
- Best Places To Visit In New England
- Fun Day Trips To Take In New England
That’s A Wrap On Romantic Getaways From Boston!
And there you have it! My top suggestions on the most romantic getaways from Boston you can take (in my humble opinion). While there are even more amazing options out there, of course, this list was lovingly put together based on my own experiences traveling the area, and discovering how romantic these places all are.
So, whether you’re looking for a mountain getaway for that incredible mountain air, a beach getaway that’s not too far away, or are looking for a different city vibe and New Year City is calling your name, one thing’s for sure – you have some absolutely fantastic options for the most memorable and romantic getaway with your special someone. Happy planning!
