Shhh, don’t tell anyone, but I’m actually not a city person 😲 That said, I absolutely LOVE Boston.
Despite the fact that city atmospheres tend to overwhelm me, Boston is one that I always look forward to visiting. Between the historic charm, quaint neighborhoods, incredible museums, insane culinary scene, waterfront scenery, and its overall walkability, I always have an amazing time here.
This post is my absolutely perfect 3 day itinerary for Boston, which is geared toward first-timers. I’ve been visiting the city for over 10 years now, and have been in every season, taken week-long trips, day trips, and planned countless weekend getaways here. I’m so excited to point you in the right direction to have the most unforgettable time in this beautiful city.
Just be warned, though, you’ll probably fall in love with it and want to come back 😉
New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our Privacy Policy.
Boston 3 Day Itinerary: Overview
Day 1: Freedom Trail, Public Gardens, Beacon Hill & View Boston
Day 2: Isabella Stewart Gardner Museum, Fenway Park, Charles River Esplanade & Shopping
Day 3: Boston Tea Party & Ships Museum, Aquarium, Seaport, Lobster Rolls + Optional Whale Watch
Important Notes About This Itinerary:
I’ve mapped out three fully-planned days for you. I know some folks reading this will want the fully-planned days, and some folks may need to make adjustments that allow them to arrive in the city on Day 1, and leave on Day 3. I’ve made notes along the way for how I would make those adjustments so all types of travelers can follow this itinerary 😊
Day 1 Breakdown
MORNING
Begin your day by getting breakfast at Tatte (pronounced like latte 😉). There are now several locations all over Boston, and while it’s become of the most popular cafés, it’s one of those places that’s actually worth the hype. Each location is beautifully designed, and feels like a European café, and their menu is fantastic. You’ll find everything from grab-and-go items and baked goods, to great coffee/tea drinks and breakfast sandwiches. Dine in, or take it to go, depending on what time your Freedom Trail tour starts.
They also offer online ordering on their website, so you can place your order before heading over and have it ready for you.
Then, head out on your Freedom Trail tour.
So, why the Freedom Trail? What exactly is it? I’d love to tell you!
The Freedom Trail is Boston’s top thing to do, and it’s a 2.4 mile trail in the city that takes you to 16 historically-significant places, including the Paul Revere House, Faneuil Hall, and Boston Common. Even if you’re not a huge history person, it’s an incredible way to get to know the city, and the guides keep the tours really engaging and fun.
Tours typically begin at Boston Common, and end in Charlestown by the USS Constitution Museum. Most tours run about 2.5 hours long, and I have two amazing options for you …
Freedom Trail Tour Options:
✓ Paid guided small-group walking tour with a local expert
✓ Free audio tour by the NPS, so you can go at your own pace
Pro Tip: If you decide to take the guided tour and have some time before the tour begins, you can explore the Public Gardens, which is a short walk from the tour meeting place.
After your Freedom Trail tour, you’ll want to decide how to get back downtown for lunch. You can either take the T Green Line (Google Maps will show you how to do this 😉), grab an Uber/Lyft, or walk. Just be warned, the walk from Charlestown back to downtown Boston near my lunch recommendations is over 2 miles, or just under an hour.
LUNCH RECOMMENDATIONS
🍴 Parish Café: Amazing sandwiches created by local chefs around the city, plus their famous onion rings are so good. This is a more casual spot that does not take reservations, but I come here often.
🍴 Afternoon Tea at the Boston Public Library: This is a really cool experience and reservations are required. You’ll want to budget extra time to explore the inside of the library afterward, including the marble staircase at the Dartmouth entrance, Bates Hall reading room, the Courtyard (right by afternoon tea), and the stunning murals.
🍴 Beacon Hill Books & Café: This is now an iconic staple in the Beacon Hill neighborhood, which would be your next step after lunch anyway. The café offers lunch from 11a-3:30p, and then you can stroll through the various floors of this charming bookshop after. I would suggest reservations, even for lunch.
AFTERNOON
After lunch, I recommend exploring the Public Gardens and Beacon Hill, especially if you didn’t have time before your Freedom Trail tour. These two areas are right next to each other, making them easy to explore at the same time.
At the Public Gardens, be sure to walk across the pedestrian Lagoon Bridge, and hop on a swan boat for a ride, if you’d like (open in season only).
To get to Beacon Hill from the gardens, you’ll want to exit the gardens on Beacon Street, and walk toward Charles or Chestnut. If using Google Maps, you may want to just put Acorn Street as your destination, which is widely-regarded as the prettiest street in Boston, and makes for an awesome photo spot.
Most of the shops in Beacon Hill are along Charles Street, including the famous Beacon Hill Books & Café (mentioned earlier as a possible lunch spot). You’ll also want to walk by Rouvalis Flowers, which has beautiful set-up outside, and feels a bit like Europe. But mostly, this area of the city is the most charming and picturesque, so just soak it all up while walking around.
Bonus: If you’re a fan of the show Cheers, and want to see the bar, it’s still standing in Boston. It can be found in Beacon Hill at 84 Beacon Street, and since it’s a working bar, you can go inside and order a drink and food if you want.
EVENING
View Boston is the observation deck at the top of the Prudential Tower, which is the second tallest building in the center. This is such a fun way to end your first day of sightseeing in the city, and it’s also one of the best places for sunset (if you can time your visit just right).
View Boston has both an indoor 360° observation room, and an outdoor deck, as well as a bar and restaurant if you wanted to get some pre-dinner drinks there, too. Lastly, on your way out, they have this really cool model of the entire city, which also features a lights and video show, and it’s honestly so much fun to watch. This took me by surprise on my first visit there! This part is on your way out – you can’t miss it 😉
Pro Tips For View Boston: Depending on the time of year and day of the week, View Boston can get pretty crowded around sunset (summer and fall are the busy season in Boston). The lines getting in the elevator to go up and get pretty long, so you’ll want to plan accordingly. If this doesn’t sound like it’s worth it for you, you could also go the next morning instead, which is usually a less busy time.
Also, I recommend getting tickets only a day or two before so you know if the weather will be nice for your visit. The views at the top won’t be as impressive if it’s super foggy!
→ Click here for View Boston tickets
For dinner this night, I recommend Select Oyster Bar, which is pretty much across the street from the Prudential Tower. This is an amazing alternative to Neptune Oyster, which is one of the most famous seafood restaurants in the city that doesn’t take reservations, and almost always has really long wait times. Select Oyster is run by the same Executive Chef, so the food and service is just as awesome, but they take reservations. Plan accordingly based on when you choose to experience View Boston (allow at least an hour for View Boston, but 90 minutes is probably best).
Did you arrive later in the day today?
No worries! If you don’t have a full day to explore today, I would simply skip the Freedom Trail tour, and do this in the morning tomorrow. This will allow you to fully customize your afternoon based on how much time you have, and you’ll likely still be able to do View Boston around sunset or before dinner.
Day 2 Breakdown
MORNING
Start your day with an awesome breakfast at Milkweed! I picked this for you today because it’s heading toward your first stop of the day, and serves a super fun breakfast menu. And, of course, the food is so delicious. Enjoy things like Lucky Charms pancakes, French toast, and omelettes.
Next, take a 15 minute walk to the Isabella Stewart Gardner Museum. This is what I call “a museum for people who don’t like museums,” because I can sometimes fall into that category, and totally understand. However, this is one of the best museums I’ve personally been to because it’s incredibly unique, and it’s also a more immersive art experience.
The museum is housed inside Isabella Stewart Gardner’s home, which is designed like a Venetian palace. The focal point of the palace is a stunning courtyard garden, and on each floor, you’ll find artwork displayed exactly as Isabella hung it when she lived there. It’s actually stipulated in her will that her artwork placement cannot be changed.
Fun Fact: This museum was the victim of the largest art heist in the entire world, which took place is 1990. Netflix did a fantastic documentary on it, if you want to watch it before your visit. But spoiler alert, the art was sadly never recovered.
Since this museum is located in the Fenway neighborhood, if you’re a baseball fan, it’s worth heading to Fenway Park while here for a tour.
Tours are typically on the hour throughout the day, so it’s pretty easy to work this into your itinerary. The park is only about a 15-minute walk from the museum, and since it’s the oldest baseball park in the U.S., it’s actually interesting, even if you’re not a sports person.
However, this is completely optional!
→ Click here for Fenway Tickets
LUNCH RECOMMENDATION
🍴 Boston Burger Company (Boylston location): This place is such a fun burger joint, and it’s also only about a 10-minute walk from Fenway Park. They’re known for their crazy milkshakes and delicious burgers, but I also really love their fried pickles.
AFTERNOON
After lunch, I have two fun options for you: either head to Newbury Street and the South End for some shopping, or take a scenic walk along the Charles River Esplanade.
Shopping Option
Newbury Street is actually a pretty fun place for shopping, as many of the stores are housed inside historic brownstone buildings, making it a unique experience. While most of the shops are franchised brands, you’ll find some great places if you don’t have a lot of shopping near you back home (like me!).
After Newbury Street, you can also walk over to L.A. Burdick if you love chocolate, as this adorable little shop has amazing hot chocolate drinks, desserts, and of course, their famous chocolates. They’re mostly known for their mice and penguin chocolates, which are a fun treat to bring home with you.
After that, if you’re still up for some exploration, the South End is such an underrated part of the city that I love to recommend. You’ll find some cool shops in this neighborhood, and beautiful streets, too. I especially love SAULT for New England-branded clothing, as well as the newest candy shop in the area, Madeline’s. Additionally, check out Parkside Bookshop, and Concord Square, which is a pretty street to walk down.
Charles River Esplanade Option
The entrance you’ll take to the Esplanade from Boston Burger Company is located along Massachusetts Ave. You’ll want to stay on the right side, and take the little staircase down after crossing Storrow Drive. This paved pedestrian path follows the Charles River for really nice waterfront views.
You’ll walk for about a mile until you reach Fielder Dock, which is a great photo spot. Then you can cross the Arthur Fielder Footbridge back to Beacon Street near the Public Gardens. From there, you can enjoy some downtime before dinner.
DINNER RECOMMENDATION
🍴 Carmelina’s in the North End: This neighborhood is known for incredible Italian cuisine, and Carmelina’s is a fantastic spot for dinner. Reservations highly recommended.
After dinner, I recommend taking the short 1-minute walk over to Modern Pastry for some dessert. They’re usually open until about 10 or 12 at night, so you should have time to make it over there before they close. I recommend their lobster tails, triple chocolate cake, and tiramisu.
What about Mike’s?
While doing research for Boston, you may have heard that Mike’s is the best pastry shop in Boston, which is pretty close to Modern Pastry. It’s kind of known around the city that Mike’s is where the tourists go, and Modern Pastry is where the locals go. Having had both, I can say that both are great options, and the cannoli are actually really good at Mike’s. However, I prefer the selection at Modern Pastry more (since I’m not a big cannoli person), and think their desserts are a little better than Mike’s. But honestly, you can’t go wrong with either. So, maybe try both 😉
Did you need to do the Freedom Trail tour today?
If you arrived in the morning or afternoon the previous day, and were not able to do the Freedom Trail tour, I highly recommend it for today. I would suggest you do this in the morning, and then either take an Uber to Parish Café or the Boston Public Library for afternoon tea. Then, I’d explore the Public Gardens and Beacon Hill for the rest of your day. If you have time before dinner, add in the Esplanade, which is not far from Beacon Hill.
Day 3 Breakdown
MORNING
For breakfast this morning, you can either go back to Tatte and try something you didn’t get before, or head to Flour Bakery & Café, which has a Back Bay or Beacon Hill location. This is more of a quick breakfast option, so if you’re looking for something that’s a sit-down breakfast, Café Bonjour is also a fantastic option.
After breakfast, I’m offering three different options, depending on your interests:
After Breakfast Option 1:
Head to the Boston Tea Party & Ships Museum, which is honestly a really fun place to visit. This immersive experience brings the famous 1773 Boston Tea Party to life with interactive exhibits, live reenactments, and a chance to actually throw tea into the harbor. You can also climb aboard restored 18th-century ships, and see cool artifacts like a surviving tea chest.
A cool spot to check out at the museum is also Abigail’s Tea Room, which offers a very inexpensive bottomless tea tasting, where you can sample the five types of teas that were famously tossed overboard during the Tea Party. You can also upgrade to the option to have your tea in a souvenir mug to take home. You can visit Abigail’s without going into the museum.
→ Click here for your Boston Tea Party & Ships Museum Tickets
After Breakfast Option 2: Whale Watch Tour
One of the best things to do in New England is a whale watch tour, primarily because of the proximity to the Stellwagen Bank National Marine Sanctuary, which is known for having very active marine wildlife.
While in Boston, you can easily hop on a tour right from the harbor, and set sail on a high-speed catamaran for a chance at seeing humpbacks, minkes, finbacks, seals, and more. The tour is about 3.5 hours long, so it’s definitely a time commitment, but one that I think is so worth it. I recommend booking the earliest tour possible to get back in time for lunch.
→ Click here to get tickets for the Whale Watch tour
After Breakfast Option 3:
The New England Aquarium is another great place to check out in the city. They have penguins, a Pacific giant octopus, jellyfish, seals, and sea lions. Plus, a lot more! This is a great option if you’re interested in wildlife, but don’t want to commit to the whale watch tour.
→ Click here to get your Aquarium tickets
AFTERNOON
Depending on which option you decided on, you’ll want to head to lunch next, and I recommend the Seaport area since it’s not far from all the optional activities mentioned. Today is a perfect day to grab some seafood, and Yankee Lobster or Row 34 are really great options in this area (I recommend the lobster roll to check this classic New England staple off your list).
If you’re looking for a sweet treat after lunch, Levain Cookies has a location in Seaport, and they’re worth the hype, in my opinion 😉
After lunch, take a walk to Fan Pier Park along the Harbor Walk, and take some photos with the city skyline in the background.
Then continue along the Harbor Walk to leave Seaport, and head to Christopher Columbus Waterfront Park. You’ll also walk past the back of the New England Aquarium, and you’ll actually be able to see the harbor seals from here without going inside, so keep an eye out.
If you have time and are still up for sightseeing, this park isn’t far from the Rose Kennedy Greenway, which is a small but very cool green space with gardens. It’s worth the short walk over, which should be less than 10 minutes from the waterfront park.
EVENING
For dinner, Yvonne’s is a popular restaurant that’s also very much worth the hype, and it’s definitely a fun, upscale experience – and a perfect way to end your getaway to Boston. Reservations are highly recommended, especially on weekends. The inside of the restaurant is such a cool space – it’s both Instagram-worthy and unique without being overly pretentious – and still remains very welcoming and cozy. And the food is fantastic.
Did you skip the Isabella Stewart Gardner Museum on Day 2?
If you had a later arrival on Day 1 and had to do the Freedom Trail tour on the morning of Day 2, that means you’ll have to skip the Isabella Stewart Gardner Museum. However, you also have the option of doing it today in the morning right when they open. I would add the museum into your options for the morning today, and decide which is a bigger priority for you.
If you decide to do the museum, you would be able to head to Seaport afterward for lunch, and still also explore of the other museums, enjoy the Harbor Walk and Christopher Columbus Park. You’ll likely need to Uber or take the T purple line from the museum to Seaport. Google Maps will tell you how to navigate this.
Where To Stay In Boston
Luxury: The Boston Harbor Hotel: If you’re looking to splurge and stay on the waterfront during your visit, this is one of the best options in the city. Located steps from the Harbor Walk and Aquarium, and a short walk to Seaport and Fan Pier Park, you’ll also enjoy amenities like on-site dining, massage services, a high-end fitness center, and beautifully-designed rooms.
→ Click here to check rates & availability at the Boston Harbor Hotel
Revere Hotel Boston Common: A great mid-range hotel that’s centrally-located. You’re just a couple of blocks from the Boston Common and Public Gardens, and a short walk to Beacon Hill and Newbury Street. They also have a nicer rooftop bar with awesome city views, which is perfect for cocktails before or after dinner.
→ Click here to check rates & availability at the Revere Hotel Boston Common
The Godfrey: Often on the more budget-friendly spectrum of moderate, this hotel is in a great location in the theater district, and also still feels high-end. You’re just a couple of blocks from Boston Common, and a short walk to the Public Gardens and Beacon Hill while staying here. They also have a great coffee shop attached to the hotel, as well as a bar for drinks. Rooms here tend to be on the smaller side, but are still really nice.
→ Click here to check rates & availability at The Godfrey
Visiting Boston – Answering Top Questions
Is 3 Days In Boston Enough Time?
Yes, you can definitely see and do a lot around Boston with just 3 days, even when parts of those days include travel. Because most of the city’s main tourist attractions are all within walking distance, it’s very easy to cover a lot of ground with a long weekend.
Of course, more time is always better, but 3 days is a great amount of time to spend exploring Boston.
Is Boston Expensive?
Yes, and that’s the biggest downside to visiting, unfortunately.
While you plan your getaway to Boston, you’ll want to consider this while pricing out hotels, and know that New England in general tends to be more expensive than many other areas around the U.S.
Best Time Of Year To Visit Boston
Boston’s high tourist season is June-October, which is when you can expect the highest prices at hotels, and the most crowds around the city. This is a great time to explore Boston, as many places will have outdoor seating this time of the year, the days are longer, and you have the best chance at rain-free weather.
That said, Boston does get pretty hot and humid in the summer season, so that’s something to consider.
Personally, I prefer to visit in the fall during foliage season, winter, and early spring. October is still a busy time to explore the city (and it’s also still very expensive around this time), but the fall vibes here are so amazing. It’s such a cozy and exciting fall destination, and it’s also not far from Salem.
I also love to visit in the winter. While the weather isn’t the best, the hotels are usually the cheapest around this time, and it’s a great season to explore all the top indoor attractions.
Lastly, I absolutely love April in Boston. Again, weather is tricky this time of the year, but seeing the cherry blossoms and magnolias in bloom all over the city is a pretty magical experience. This also tends to be one of the least-expensive times to visit (unless it’s Marathon weekend of course!).
Is Boston Walkable? Plus, Tips For Getting Around
Boston is very walkable! In fact, it often makes it into the top 3 of lists on walkable U.S. cities. As mentioned, most of the tourist attractions and top things to do are within a 1-2 miles radius of each other, at most. The vast majority of my visits to Boston, I walk everywhere.
In some cases, there may be some things you’ll want to see that require either an Uber or riding the T, which is Boston’s train/subway system. For shorter trips to the city, I usually recommend just taking an Uber to and from the airport to save time.
The T is also a great public transportation system that’s easy to use when following Google Maps. There are one day, and one week unlimited passes you can buy for the T, which is perfect if you plan to explore further outside of the main parts of the city, or don’t want to walk everywhere.
If you’re not into walking a lot, another fun option is the Hop On/Hop Off Trolley, which is a narrated tour that goes to many of the top places around the city, and is a great alternative to taking the T or Ubers everywhere.
Driving In? Here’s What To Do With Your Car
Because I only live about 3 hours from Boston, I always drive into the city. I use SpotHero to make a parking garage reservation near my hotel ahead of time for the duration of my stay, and never use my car while visiting the city.
Most hotels will offer on-site parking, which is the easiest option, of course, but it’s usually very expensive. If it works with your budget, though, this is super convenient.
What To Wear In Boston
Boston style is very casual – you don’t often see people super dressed up around the city. When I visit, most people are in sneakers, jeans, and casual tops. If planning a nice dinner out (say, Yvonne’s, as recommended), you’ll want to pack a nicer outfit.
Because there are a lot of uneven brick and cobblestone streets in the city, I always like to advise against wearing any kind of heel during your visit. At most, I’ll wear a chunky-heeled Chelsea boot if I need to dress up a little. If I’m attending a show, like the ballet, I will wear heels with a dress, but take an Uber to and from the theater (I’ve learned this the hard way 😉).
More Boston Guides You May Enjoy:
- Boston In The Spring Season
- Where To See Cherry Blossoms & Magnolias In Boston
- A Guide To Boston In The Fall Season
That’s A Wrap On The Perfect 3 Days In Boston Itinerary
And there you have it! My perfect 3 day itinerary for Boston. I hope you’ve found this helpful, and that you’re feeling ready and excited to plan your Boston long weekend getaway. And once you experience the charm of the city, it’ll be hard to not go back again and again. Happy planning!
