With over 2,500 miles of coastline in New England – plus more if you count tide coastline! – there are so many opportunities to explore beautiful islands just a short distance away. Whether you’re looking to take a longer vacation on a New England island, or enjoy a lovely day trip, you’ve come to the right place! This post is all about the best New England islands worth your time.
I’ve been exploring this region for 10+ years, and I’ve spent a lot of that time visiting the islands in New England. I’m excited to finally share my top islands worth visiting, tips for your trip, how to get there, and what to do once you arrive!
With that, let’s get started, shall we?
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Popular New England Islands Worth The Hype
Okay, so let’s begin with the popular New England islands that you’ve likely already heard of. And the truth is, these islands are well-known for a reason, and definitely worth visiting. So, of course, they make the top of my own list for islands to see when exploring the area.
1. Nantucket, Massachusetts
Without a doubt, one of the islands in this region I suggest you absolutely see is Nantucket, and it always tops of my list of best places to visit in New England. Just off the coast of Cape Cod in Massachusetts, Nantucket is one of those places that has a very distinct feel and atmosphere, while also being one of the most idyllic places in New England. It’s home to lighthouses, cobblestoned streets, historic houses, incredible restaurants, stunning beaches, and beautiful scenery at pretty much every turn.
While Nantucket tops my list of the best islands in the region, there’s one bit downside to visiting, and that’s cost. Nantucket is notoriously one of the most expensive destinations in New England, and can be cost-prohibitive for a lot of people. Hotels in the summer tend to start at around $500-$600/night, and can easily go up to $1,000/night for a higher-end hotel stay.
That said, it’s absolutely worth it, in my opinion, if you’re looking to splurge or celebrate a special occasion. Nantucket has some incredible hotels that are really worth the money, and feel extra luxurious and special. Plus, you can also find some cheaper rates if you visit in May, June, September, and October.
Nantucket also makes for a fantastic day trip from Cape Cod, and because so much of the island is centered around downtown, which is right where the ferry drops you off, it’s pretty easy to see a lot in a day. The island is also very bike-friendly, and moped rentals are also available near the ferry to cover more ground on a day trip.
Where To Stay On Nantucket:
→ The Wauwinet: Where to stay for secluded luxury with all the amenities.
→ The White Elephant: Where to stay for luxury in-town.
→ Union Street Inn: Where to stay in town with a cozy inn feel – voted the best small hotel in the U.S. by TripAdvisor!
How To Get To Nantucket:
Nantucket is only accessible by plane or ferry, and most people get to the island via ferry. Both Hyline Cruises and Steamship Authority offer ferry service from Cape Cod, and there’s also a seasonal ferry from Harwich Port on Cape Cod called the Freedom Ferry. Additionally, there’s a ferry from New Bedford, MA.
Best Things To Do:
- Explore the charming cobblestoned streets of downtown, visiting the amazing shops, too!
- Snap a photo of Brant Point Lighthouse.
- Enjoy the views from Step’s Beach.
- Meander through ‘Sconset, and see the beach, lighthouse, rose-covered cottages (when in bloom), and do the Bluff Walk.
- Get an ice cream from Juice Bar.
- Enjoy the sunset at Madaket Beach.
Some of my posts on Nantucket you may find helpful:
- Ultimate Nantucket Day Trip Guide
- How Many Days Do You Need On Nantucket?
- A Guide To Nantucket’s Lighthouses
- Winter On Nantucket
2. Martha’s Vineyard & Chappaquiddick, Massachusetts
The other island just off the coast of Cape Cod is Martha’s Vineyard, and it’s known for stunning bluffs, amazing beaches, and quaint towns – and I can confirm, all of this is truly fabulous! The Vineyard, as the locals call it, is larger than Nantucket and home to six cute little towns to explore, and so many incredible things to do.
Additionally, this island’s claim to fame has undoubtedly been its ties to the movie Jaws, as well as the vacation destination for former President Obama and his family. While there, you can also visit Chappaquiddick, which made headlines with the infamous Kennedy crash, but it’s home to stunning and unspoiled coastline and a beautiful lighthouse.
While on the Vineyard, spend your days strolling through the adorable and colorful gingerbread cottages in Oak Bluffs, dining on fresh seafood, visiting the lighthouses, and of course, spending the day at the beach.
Where To Stay On Martha’s Vineyard:
→ Harbor View Hotel: Where to stay for luxury and a water view in one of the best towns on the island.
→ Vineyard Square Hotel & Suites: Where to stay within walking distance to shops and restaurants, and many rooms have a water view.
→ The Winnetu: Where to stay within walking distance to one of the best beaches, with a modern but homey resort feel.
How To Get To Martha’s Vineyard:
Martha’s Vineyard is accessible by ferry or plane, and most people choose to take the ferry. Both Steamship Authority and Hyline Cruises offer ferries from Cape Cod, and there are also ferry options from New Bedford, MA and Quonset, RI.
Best Things To Do:
- Take a drive (or this tour if you don’t have a car) out to Aquinnah to see the gorgeous cliffs, Moshup Beach, and grab an amazing lobster roll at Larsen’s or Menemsha Fish Market.
- Stay for sunset at Menemsha Beach, if you can!
- Walk around the famous gingerbread cottages in Oak Bluffs.
- Visit Edgartown Lighthouse.
- Shop in Edgartown and Vineyard Haven.
- Spend the day at South/Katama Beach, which is the best on the island (in my opinion 😉)
- Pick up local produce at Morning Glory Farm.
Some of my posts on Martha’s Vineyard you may find helpful:
- Best Things To Do On Martha’s Vineyard
- Nantucket vs. Martha’s Vineyard For A Day Trip
- Ultimate Martha’s Vineyard Day Trip Guide
- Martha’s Vineyard Without A Car
- Best Beaches On Martha’s Vineyard
3. Block Island, Rhode Island
One of my favorite islands to visit in this region is Block Island, which sits just off the coast of Point Judith, near Narragansett, RI. At only 9.7 square miles, Block Island is rather small, but what it lacks in size, it makes up for in gorgeous scenery, beautiful beaches, and lots of charm.
Once you arrive on the ferry, you’re already at the center of the island’s downtown area where most of the shops and restaurants are, and I definitely recommend planning some time to explore the cute shops. But I do recommend also having a plan in place to either bring your car over, or rent a car or bike to explore the island to see as much as possible – especially if you come over for just a day.
One thing I love about Block Island is that it can be a budget-friendly day trip, as so many things on the island are completely free – even the beaches in the summer (which is kind of unheard of in New England). While you’ll still have the cost of the ferry tickets and any food you purchase on the island, the beaches, lighthouse grounds, and many attractions are completely free.
Even though Block Island is small, it makes for a wonderful weekend getaway, or a longer vacation. But because of its manageable size, it’s also perfect for a day trip.
Where To Stay On Block Island:
→ The 1661 Inn: Where to stay close to shops and restaurants, with awesome views of the water.
→ The Atlantic Inn: Where to stay close to shops and restaurants with a cozy inn vibe.
→ Ballard’s Beach Resort: Where to stay in town that’s right on the beach, and best for those who want a party scene.
How To Get To Block Island:
Block Island is accessible by plane and ferry, with most people taking the ferry over. To fly to the island, you’ll depart from Westerly, RI and the flight only takes about 12 minutes.
The most common ferry to the island is the very appropriately named Block Island Ferry, which departs from Point Judith near Narragansett, RI. This ferry offers both high-speed and traditional ferry service, ranging from 30-60 minutes. There is also seasonal ferry service from Montauk, NY.
Best Things To Do:
- Enjoy the views from Monhegan Bluffs, which has a long staircase leading down to the beach.
- Spend a few hours at Ballard’s Beach for a lively bar scene, or head to Mansion or Crescent Beach for a more serene atmosphere.
- Walk out to North Lighthouse, located at the tip of the island.
- Also visit South East Lighthouse!
- Grab lunch or dinner at The Oar for a view of the harbor.
- Shop downtown at the boutiques.
- Grab ice cream at the Ice Cream Place.
- Hike the Clayhead Trail for awesome views (know there’s poison ivy on this trail, but if you come prepared and stick to the actual trail, you’ll be fine).
Psst! I have an entire post on a Block Island day trip, if you need more ideas and information!
4. Mount Desert Island, Maine
Home to Acadia National Park (referred to as the Crown Jewel of New England), Mount Desert Island is an absolute must to see for this reason! For a truly authentic Maine experience, it’s also hard to beat when it comes to boat tours, stunning coastline, and postcard-worthy moments all around.
While Mount Desert Island is located pretty far up the coast of Maine. It’s about 3 hours north of Portland, but it’s absolutely worth the effort, and there are plenty of amazing things to see on the drive from Portland to Acadia National Park to make it even more worthwhile.
Home to four great towns to explore, most people spend the bulk of their time in Bar Harbor, and of course, Acadia, and I whole heartedly agree with that recommendation. It would be easy to spend at least 3-4 days exploring everything the park has to offer, and Bar Harbor makes for a convenient home base that’s filled with coastal New England character.
Where To Stay On Mount Desert Island:
→ Bar Harbor Inn & Spa: Where to stay right in Bar Harbor that’s walkable to everything, with lots of amenities and water views.
→ The Claremont: Where to stay in Southwest Harbor for a more secluded, resort experience with awesome water views, and on-site dining.
→ Bar Harbor Villager Motel: Where to stay on a budget that’s walkable to everything in town, with spacious, updated rooms.
How To Get To Mount Desert Island:
The best way to get to Mount Desert Island is to drive. Even though it’s an island, it’s accessible by car, and since you’ll likely want a car to explore the sites once you arrive, it’s the most convenient way to get there, too.
Best Things To Do:
- Take this food tour to get a taste (literally!) of the local specialties.
- Cruise down Ocean Drive in the park for the most iconic coastal views.
- Take a hike! Some of my favorites are Great Head, Gorham, and the thrilling Beehive Trail.
- Have lunch at Jordan Pond House, and get their famous popovers.
- Enjoy sunrise at the top of Cadillac Mountain.
- Walk along Shore Path in downtown Bar Harbor for awesome coastal views.
- Take a lobster boat tour! Lulu’s and Acadia Lobster Cruise are both great options.
Psst! I have an entire post on the perfect Acadia National Park Itinerary if you need more ideas, as well as a guide on the Best Time To Visit Acadia National Park, and Best Places & Towns To Stay When Visiting Acadia National Park.
5. Aquidneck Island, Rhode Island (Basically, Newport 😉)
Aquidneck Island is home to Newport, Middletown, and Portsmouth, and this is a fantastic area of Rhode Island to explore when visiting New England.
Newport is where most people spend their time on the island, and for good reason. Famous for its Gilded Age mansions, the scenic Cliff Walk, historic neighborhoods, stunning hotels, incredible culinary scene, and harbor-front scenery, there’s plenty to do to spend at least a weekend here. But, Newport also makes for a great day trip!
If it’s beaches you’re looking for when you visit, then you’ll want to head to Middletown. While Newport proper does have some nice beaches, I think the best ones are in Middletown, which is just a short drive from Newport. I especially love Second Beach, if you’re looking for a recommendation 😉
Where To Stay On Aquidneck Island:
→ Castle Hill Inn: Where to stay for luxurious seclusion with all the amenities, and walkable to Castle Hill Lighthouse.
→ Chart House Inn: Where to stay right in Newport that’s walkable to everything, and loaded with charm (and a great breakfast is provided!).
→ The Brenton: Where to stay right in Newport that’s walkable to everything, and offers harbor views and a newly renovated, modern vibe.
How To Get To Aquidneck Island & Newport:
Aquidneck Island and its towns are accessible by car, and driving is the most convenient way to get there.
Best Things To Do:
- Enjoy the views from the gorgeous Cliff Walk.
- Explore Bowen’s Wharf.
- Enjoy shopping on Thames Street.
- Visit the mansions, and if you can pick just one, I highly recommend The Breakers.
- This very awesome food and history tour.
- Cruise along Ocean Drive for beautiful coastal views.
- Visit the beaches in Middletown.
Psst! I have an entire post on planning the best day trip in Newport, RI if you’re looking for more ideas!
6. Plum Island, Massachusetts
Sitting off the coast of charming Newburyport, Plum Island is a wonderful destination to visit along the Massachusetts coast. While technically, Plum Island is home to four towns (Newburyport, Newbury, Rowly, and Ipswich), most people refer to the peninsula as the true Plum Island – which is where you’ll find the beaches.
Fun Fact: The island got its name because of the beach plum shrubs that sit along its dunes, so keep an eye out for them during your visit!
Plum Island is very small at only about 9 miles long. It’s mainly residential, but still offers some great restaurants to check out, a few shops, and lots of beautiful scenery. But what’s great about this area is that Plum Island is also a very short distance to the lovely city of Newburyport, which feels more like a small town than anything, and between these two destinations, you can have the best of both worlds. Enjoy the sun, sand, and beaches on Plum Island, and then hop over to Newburyport for some of the best shopping in New England, great dining, and history!
Where To Stay On Plum Island:
→ Blue Inn on the Beach: The only hotel on Plum Island, and you’re in luck because it’s an awesome boutique style hotel right on – you guessed it – the beach.
→ Compass Rose Inn: Where to stay in nearby Newburyport with a very cozy New England style inn vibe.
How To Get To Plum Island:
Plum Island is accessible by car, which is the most convenient way to get there.
Best Things To Do:
- Explore the trails, as well as coastal and marsh views, at the Parker River National Wildlife Refuge.
- Enjoy a day in the sand at Plum Island Beach.
- Shop local at Plum Island Soap Company!
- Grab fresh seafood at Bob Lobster (and see the famous abandoned Pink House is right across the street from here).
- Head into downtown Newburyport to visit the shops, walk the waterfront path, and have a lovely dinner.
Psst! I have an entire post on the best things to do in Newburyport and Plum Island if you’re looking for more info!
Islands To Get Away From It All
Okay, now that I’ve covered the most well-known islands that are worth visiting, let’s talk about some of the options in New England if you’re looking to get away from the crowds, or places that offer more off-the-beaten path activities that are very much worth your time. While pretty much all the islands on this list can offer feelings of escaping everyday life, these are the places I recommend that will having you feeling like you’re worlds away from reality 😊
7. Little River Lighthouse in Cutler, Maine
Did you know you can actually stay in a lighthouse in Maine? And at Little River Lighthouse, you have the entire island to yourself during this very fun and unique experience.
For anyone that’s a fan of lighthouses, and for those looking for a truly authentic New England experience, this is one of the best things to do during your trip. While it’s far up the coast of Maine (further north than Acadia!), it’s so worth it. And if you make the drive here, you can continue on to Lubec, Maine, which is home to West Quoddy Lighthouse and even more amazing hiking trails (I have a whole post about what to do in Lubec, Maine, if you’re curious 😉).
Organized by the Friends of Little River Lighthouse, you’ll get to stay on this 15-acre private island, that comes with your very own light station house (where you’ll sleep), and the lighthouse. During your overnight stay, you’ll have access to the lighthouse and all the peaceful walking trails around the island. And if you’re lucky to stay on a clear day, the sunset from the island is also amazing.
Click here for more information on staying overnight at Little River Lighthouse!
How To Get To Little River Lighthouse:
Once you make your reservation, you’ll receive directions to the dock at Cutler Harbor. From there, you’ll be taken via boat to the island and the lighthouse. This is also how you’ll get back to the mainland.
* It’s good to know that this experience is seasonal only, and only offered June through September.
8. Cabbage Island For A Traditional Maine Clambake
Located just off the coast of Boothbay Harbor, which just so happens to be one of my favorite towns to explore along Maine’s coast, you’ll find Cabbage Island. While this island is privately owned and completely residential, the owners host an incredible clam bake experience that’s such a treat to attend.
Since 1956, Cabbage Island Clambakes has been welcoming guests onto their property for an authentic and traditional Maine clam bake feast. The experience begins in Boothbay Harbor, where you’ll hop aboard a boat that brings you to the island. Once you arrive, your hosts will be ready for you, and serve up fresh lobster, fish chowder, steamers, and what they claim is the “best blueberry cake in Maine!”
Before and after your meal, you’re free to enjoy the idyllic waterfront property, so the whole experience really does feel like a mini escape from every day life.
The clam bake tends to sell out most nights, so reservations are highly recommended. Click here for more information!
Where To Stay Near Cabbage Island:
→ Spruce Point Inn: Where to stay in Boothbay Harbor that’s more secluded, and has an awesome resort feel.
→ Harborage Inn on the Waterfront: Where to stay in Boothbay Harbor that’s walkable to town, and provides nice views of the harbor.
How To Get To Cabbage Island:
You’ll want to park in Boothbay Harbor, and then find the Cabbage Island Clambake Pier on the harbor. A boat will take you to the island. It’s not possible to take your own private boat, or any other charter, to the island.
*It’s good to know that this experience is seasonal only, and only offered mid June through Labor Day.
9. Prudence Island, Rhode Island
Just off the coast of Aquidneck Island, you’ll find Prudence Island, which is more of a day trip destination for most folks. And while it doesn’t have hotels or facilities, it’s protected conservation lands (which makes up more than 80% of the island!), allows you feel like you’ve truly escaped reality.
Home to wonderful beaches, amazing nature trails, and a beautiful lighthouse, this is where to go to really escape it all for an authentic coastal New England vacation. While there are no hotels on the island, there are a few cottage rentals that you can check out and live like an islander during your stay!
Where To Stay On & Near Prudence Island:
→ Waterfront Cottage On Prudence Island: Where to stay if you want to be right on the island, have your own private beach, and gorgeous water views!
→ OceanCliff Hotel: Where to stay in Bristol with ocean views in a beautiful mansion estate.
→ William’s Grant Inn: Where to stay in Bristol for a cozy New England-style inn vibe with a great breakfast.
How To Get To Prudence Island:
Prudence Island is only accessible by private boat or ferry. The ferry departs from nearby Bristol.
Best Things To Do:
- Explore all the amazing conversation lands and nature trails.
- Visit Prudence Island lighthouse.
- See one of the last-remaining one-room schoolhouses in the region.
- Bring over a kayak to explore the shoreline (you can also kayak out to the lighthouse).
Note: If you stay on the island at a cottage rental, know that there is only one general store on the island, and they have a very limited selection. It’s best to bring everything you need over with you, including food, snacks, and supplies you’ll need for your stay.
One thing to be aware of is that there are a lot of ticks on Prudence Island, so if you’re not used to living in an area with ticks, you’ll want to come prepared. This shouldn’t be a big issue if you know how to do tick checks, but something to have on your radar.
10. Vinalhaven, Maine
Vinalhaven is a beautiful island to visit if you’re looking for more of a serene getaway mixed with a touch of adventure! Just off the coast of Rockland, Maine along the state’s Midcoast, the island is surrounded by the scenic waters of Penobscot Bay, offering amazing views of the Atlantic.
At 23 square miles, Vinalhaven is also the perfect size for a getaway – it’s a bit bigger than some of the smaller islands mentioned on this list, but it’s also manageable for an easy day trip. Additionally, it perfectly balances having a quaint Main Street for shopping and dining, with beautiful and unspoiled nature.
Vinalhaven’s claim to fame was its thriving granite quarrying history, as it was once the largest granite quarry in all of Maine. Now, its known for its beautiful coastline and granite cliffs, and well as its tight-knit community, which supports the local artisans that sell their work in the shops. You’ll also find fantastic restaurants on the island!
Where To Stay On Vinalhaven Island:
→ The Tidewater: The only hotel on the island!
→ Click here to check out vacation rentals on Vinalhaven for more options!
How To Get To Vinalhaven:
While the island does have a private airport, the best way to get there is by ferry. The ferry departs from Rockland, and takes about about 1 hour and 15 minutes.
Best Things To Do:
- Visit the island’s lighthouses.
- Shop local and handmade things along Main Street.
- Swim at the quarry ponds.
- Take a scenic hike or walk – there are tons of nature preserves all over the island!
- Enjoy a night out at SKAL, a music bar with great food and drinks!
- Grab a lobster roll at Greet’s Eats Food Truck
Lesser-Known Islands For Exploring Nature
If you’re not familiar with the New England area, some of the these islands I talk about next may not be on your radar, but they should be! While many of these could also qualify for the “get away from it all” category I have above, I wanted to include them in this lesser-known section. Enjoy!
11. Peaks Island, Maine
Just off the coast of Portland, Maine, Peaks Island is a wonderful little day trip or island escape that not everyone knows about when visiting. The ferry ride only takes about 17 minutes (which is why it’s especially great for day trippers), and offers a unique atmosphere that balances seclusion with vibrant community life.
Peaks Island is very small, and just under 1 square mile, so even if you have a day, or half day, this is worthy excursion from Portland. Sprinkled with charming shops, wonderful restaurants, and tons of natural beauty, it’s a really great under-the-radar destination to check off your New England bucket list.
Where To Stay On Peaks Island:
→ Inn on Peaks Island: The only hotel on the island!
How To Get To Peaks Island:
Only accessible by ferry, which you can take from downtown Portland.
Best Things To Do:
- Visit the very unique umbrella cover museum (yep, you read that right 😉).
- Grab lunch on the water at Cockeyed Gull Restaurant.
- Rent a golf cart, or hop on a golf cart tour, to explore the island.
- Hit up Peaks Café and get one of their famous cinnamon rolls.
- Bike around the island to enjoy all the natural beauty and coastal views.
12. Grand Isle, Vermont
Vermont is the only New England state that doesn’t border the Atlantic ocean, but it is home to the region’s largest lake – Lake Champlain. There are a few islands along Lake Champlain in Vermont, with Grand Isle being the biggest, and that’s the one I recommend you visit.
The isles along Vermont’s shoreline aren’t as well-known unless you’re familiar with the area, but they make for a wonderful and less-crowded escape in the summer season. Perfectly encompassing both a relaxing waterfront atmosphere with Vermont’s natural beauty and rural charm, it’s a wonderful New England island to explore.
What sets Grand Isle apart is its rich agricultural heritage, featuring orchards, vineyards, and farm stands and farmer’s markets offering fresh local produce. You’ll also have the chance to discover the island’s scenic byways, enjoy biking, and try your hand at birdwatching.
Where To Stay On Grand Isle:
→ North Hero House: The only hotel on the island!
How To Get To Grand Isle:
The best way to get to the island is to drive, as it’s accessible by car. You can also take a ferry from New York.
Best Things To Do:
- Explore the beautiful state parks.
- Pop into the adorable Hero’s Welcome general store.
- Shop local and go apple picking at Hackett’s Orchard (seasonal).
- Enjoy the sunset from Grand Isle State Park.
- Visit Snow Farm Vineyard & Distillery.
13. Bailey Island, Maine
Along Maine’s Midcoast is the charming Bailey Island. And while it’s small at only about two miles long, it offers a wonderfully tranquil getaway along New England’s coastline.
Bailey Island is mostly residential, and is sprinkled with a few restaurants, shops, and things to do. But the biggest appeal here is the beautiful scenery and coastline. It truly feels like a Maine postcard! This is where to go if you want to get off the beaten path a bit, and experience an authentic Maine town.
Because of its size, it’s also perfect as a day trip, or as a stop while driving along Maine’s coast. In fact, it’s one of the places I recommend you stop when taking a road trip through the area! However, it also works as a relaxing getaway or longer vacation because there’s a lot to do nearby in places like Boothbay Harbor, Popham Beach State Park, and the lighthouses in Arrowsic.
Where To Stay On Bailey Island:
→ Bailey Island Motel: My personal favorite place to stay on the island!
How To Get To Bailey Island:
This island is only accessible by car, which is the best way to get here.
Best Things To Do:
- Enjoy the views from Giant’s Stairs.
- Visit Land’s End Gift Shop and Betty’s Seaside Creations.
- See the Bailey Island Cribstone Bridge, which is the only one of its kind in the entire country.
- Take a seat at Sundrenched for an awesome meal right on the water.
- Set sail around the island on a schooner with Tevake.
14. Chebeague Island, Maine
Another wonderful island in Maine that strikes the perfect balance between serene vacation, New England charm, and stunning scenery is Chebeague Island. Off the coast of Portland, this little island is just about 5 miles long, and is a great place to disconnect, get in touch with nature, and enjoy everything that’s wonderful about Maine’s coastline.
Home to beautiful beaches, amazing sunsets, a unique golf course overlooking the ocean, and lots of unspoiled coastline to explore, this island is truly such a gem in New England!
Where To Stay On Chebeague Island:
→ Chebeague Island Inn: The only hotel on the island! This is a fantastic hotel for a relaxing getaway that includes access to their gardens (they let you pick flowers, too!), bikes, lawn games, and a gorgeous covered porch that overlooks the water.
How To Get To Chebeague Island:
The island is only accessible by ferry, which you can take from either Portland or Yarmouth.
Best Things To Do:
- Spend the day at the beach.
- Walk the sandbar out to Little Chebeague island.
- Enjoy the nature and walking trails on the island.
- If you’re staying at the Chebeague Inn, linger for a while on the gorgeous covered deck.
- Visit Second Wind Farm to pick up fresh produce from their stand, and buy a homemade wooden spoon to remember your trip by.
Psst! Curious how to pronounce Chebeague? No worries, because I was, too 😉 It’s pronounced shuh-big, and there’s not really an accent on either syllable.
15. Monhegan Island, Maine
Lastly on this list, I’d love to talk about the beautiful Monhegan Island in Maine. Sitting off the state’s Midcoast about 10 miles offshore, Monhegan Island is another one of those places that’s perfect for a true, remote New England escape.
Monhegan is unique in that you can’t bring your car over to the island, and pretty much everyone walks, drives a golf cart, or already has a car on the island. For this reason, Monhegan is a bit more challenging to visit as a tourist, but for a truly genuine Maine experience, it may be worth the effort! Most of the hotels and accommodations will help arrange for you to get to them, so it just requires a bit of communication and planning before arrival.
Once you get settled, though, you’ll be treated to lots of pristine nature to explore, as well as stunning coastline views. And despite how challenging it can be to arrive, there’s actually quite a bit to do, including nature trails, shops, dining, and boat tours. It’s also known for its artist colony, and its artistic legacy continues with studios and galleries showcasing the natural beauty of the island.
Where To Stay On Monhegan Island:
→ The Monhegan House: Breakfast and dinner are included with your stay!
→ The Island Inn: Breakfast is included with your stay!
How To Get To Monhegan Island:
Monhegan Island is only accessible by ferry, which you can take from Boothbay Harbor, Port Clyde or New Harbor. As mentioned, you can’t bring your car with you on the ferry, so plan accordingly.
Best Things To Do:
- Spend the afternoon at Monhegan Brewery.
- Explore the grounds of Monhegan Lighthouse.
- Enjoy over 9 miles of scenic nature and hiking trails, including a shipwreck site!
- Visit the Monhegan Museum of Art & History.
- Grab a table at Fish House Fish for an awesome view while you dine.
Editor’s Note on Island Ferries: Many New England islands are highly seasonal, and ferry schedules will offer the most options in the late spring through early fall. Outside of these time frames, you’ll want to check that they ferries are running at all, as it will be different for each island in the off and shoulder seasons.
Which New England Islands Make The Best Day Trips
Pretty much all the islands on this list, with the exception of Little River Lighthouse, make for great day trips. But for visiting in just one day, I think these are the best options:
- Nantucket
- Block Island
- Plum Island
- Prudence Island
- Peaks Island
- Vinalhaven Island
Best New England Islands For Longer Vacations
All of the islands on this list are perfect for longer vacations, with the exception of Cabbage Island (since it’s a dinner-only experience), and Prudence Island (since it’s residential only). However, I think these islands are best for longer vacations because of the amount of things to do, and options for accommodations:
- Nantucket
- Martha’s Vineyard
- Mount Desert Island
- Aquidneck Island
- Plum Island
- Block Island
- Monhegan Island
Best Time Of Year To Visit Islands In New England
All the islands mentioned on this list are seasonal, meaning they see most of their tourism in the spring, summer, and fall season, with July and August being the busiest time of the year. While some of the islands are accessible year-round, many businesses will close after October/November through April/May. So really, April-October are the best months to explore islands in this area.
Each island is different, though, so it’s good to check each destination individually to see the best month to visit. For example, islands like Little River Lighthouse and Cabbage Island are only open in the summer for tourism, but places like Nantucket, Mount Desert Island, Martha’s Vineyard, and Aquidneck Island have year-round residents and can be visited in the fall and winter. In fact, Acadia is spectacular in the fall during peak foliage, and visiting Bar Harbor in the winter can be a nice off-season getaway!
It really just depends on what you’re looking to get out of your visit, and each island’s seasonality. But generally speaking, most people visit in the summer.
Best Islands Off The Massachusetts Coast
There are two main islands off the coast of Massachusetts: Nantucket and Martha’s Vineyard, and both of these are some of the best islands in New England to explore!
Cheaper Alternatives To Nantucket and Martha’s Vineyard
Hey, I get it – Nantucket and Martha’s Vineyard are not cheap to visit, especially in July and August! If you’re looking to take a longer vacation, but these islands don’t quite fit into your budget, I have a great recommendation for you – Cape Cod, of course!
Cape Cod is the closest “mainland” to these islands, and it has a similar feel (I use mainland in quotes because technically, you have to cross a bridge to get there, but it’s also not really an island).
While no place along the Massachusetts coastline is really all the cheap during high season, Cape Cod will offer tons more options in different price ranges than Nantucket and Martha’s Vineyard. Both these islands are some of the most pricey places to stay in New England, and while incredibly special, there’s also something very magical about Cape Cod and its stunning coastline. In fact, while I’ve stayed overnight on both these islands, I most often stay overnight on Cape Cod to save money. Also, I adore the Cape as whole, and it’s probably my most visited destination in New England 😊
Cape Cod has a lot of the same offerings as Nantucket and Martha’s Vineyard. You’ll find charming towns, tons of stunning beaches (especially along the Cape Cod National Seashore), lighthouses, shopping and dining, and lots more to do. While you won’t quite get the full effect of Nantucket’s idyllic charm, or the cute gingerbread cottages of Martha’s Vineyard, these will both be an easy ferry ride away as a day trip from Cape Cod!
Need some help planning your Cape Cod trip?
I have tons of posts about it! Here are a few to get you started:
- Best Towns To Stay In On Cape Cod
- First Timer’s Guide To Cape Cod
- Best Time To Visit Cape Cod
- Cape Cod vs. Nantucket: Which Is Best For You?
What Is The Largest New England Island?
By and far, the largest island in New England is Mount Desert Island, which is 108 square miles. In fact, Mount Desert Island is also the second largest island on the Eastern seaboard (Long Island in New York is the largest, in case you were curious 😉). But this comes as no surprise since it’s home to Acadia National Park.
To compare, the next largest islands in New England after Mount Desert Island are:
- Martha’s Vineyard – 87 square miles
- Nantucket – 47 square miles
- Aquidneck Island – 37 square miles
- Grand Isle – 35 square miles
More posts you may enjoy:
- The Perfect 7-Day New England Road Trip Itinerary
- The Best Time To Visit New England
- My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary
- The Most Incredible New England Resorts & Spas
- Best Day Trips In New England
- Must-See Towns On The New England Coast
- Is Acadia National Park Still Worth Visiting?
That’s A Wrap On The Best New England Island To Visit
And there you have it – the inside scoop on all the best New England islands worth visiting on your next trip! Whether you’re going straight for the popular islands of Nantucket, Martha’s Vineyard, or Mount Desert Island, or you’re hoping to explore something a bit lesser-known like Grand Isle, Vinalhaven, or the very cool Little River Lighthouse experience, one thing’s for sure: New England’s islands all offer incredible experiences that’ll be hard to forget.
