This itinerary for Boston is the ultimate local’s guide to the perfect weekend in the city. It includes the most iconic historical landmarks, the best restaurants, scenic photo opportunities, & must-see museums. I grouped together attractions by location to minimize transportation time.
This itinerary has a pretty packed schedule, so bring your sneakers and buy an MBTA (subway) pass. Tweak the schedule to your preference if you want a slower pace.
Last Updated: July 17, 2024
[ez-toc]
Disclaimer: This website contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you.
3 Day Itinerary for Boston: Top Rated Tours
- Duck Tours (1,700+ Reviews)– This is one of Boston’s most popular (and cool) bus tours. It is the only bus tour that goes right into the Charles River. I recommend fitting it into your schedule on either Day 1 or Day 2. More details are on their site.
- Boston: Guided Walking Tour of the Freedom Trail (1K+ Reviews)
- Boston: Hop-Off-Hop-On Trolley Tour (1K+ Reviews) – You can hop on and off 14 stops in Boston while seeing around 100 points of interest! This is available in a one or two-day ticket.
- Boston Tea Party Museum & Interactive Tour (900+ Reviews) – Learn about the Boston tea party and take part of the action with live actors.
Day 1 of your Itinerary for Boston
The first day will be for exploring Back Bay & getting settled into the city.
Start your itinerary for Boston with a breakfast sandwich from Mike & Patty’s in the South End. They’re a casual takeout spot that is popular among locals. I recommend The Fancy (~$10), which includes two fried eggs, bacon, cheddar cheese, avocado, & house mayo on a multigrain. The Friendly Toast in the Back Bay is a great option for a sit-down breakfast
Stop 1: Boston Commons & the Boston Public Garden
After breakfast, head to the Boston Common & Boston Public Garden. They are the city’s most iconic parks! They have beautiful views of the Back Bay skyline, making it a perfect spot for pictures. In warmer weather, I recommend taking a swan boat ride at the Public Garden. In the winter, go ice skating at the Frog Pond in the Commons.
Stop 2: Newbury St, Copley Square, & Boston Public Library
After strolling through the parks, you’ll come across Newbury Street. The popular shopping street is 8 blocks (1 mile) long & is lined with various stores, cafes, restaurants, and galleries. You can find chains like Nike, Lululemon, H&M, Uniqlo, etc. here. The Prudential Center is an indoor mall one street over with plenty of high-end stores.
The Boston Public Library in Copley Square is an attraction just a block away. There are two sections of the library –the original section and the newly built section. The Renaissance-style architecture of the original side is beautiful, so check it out! There is also a courtyard and restaurant for afternoon tea.
Further Reading: 39 Completely Free Things to Do in Boston
Newbury Street has plenty of delicious lunch spots. If you want seafood, try Saltie Girl. An alternative, budget-friendly lunch option is Gre.Co. They sell my favorite Greek gyros in the city — the traditional pork gyro is my go-to. It’s a pita wrap filled with seasoned meat right off the spit, french fries, onions, tomatoes, and tzatziki sauce. It’s super flavorful and filling!
For dessert, try their “Yaya” loukoumades (Greek donuts) with Oreos and hazelnut. Learn more in this TikTok.
Another spot for dessert is Levain Bakery. The NYC-based chain is famous for its extra thick chocolate chip cookies! Each cookie is HUGE (6oz!) so I recommend splitting one between two people.
If you’re traveling on a budget, check out my 17+ Best Cheap Eats Boston to add to your itinerary for Boston!
Stop 3: Fenway Area
Once you finish browsing Newbury Street, drop off your shopping bags & take the Green Line to Kenmore/Fenway. It’s one of my favorite neighborhoods & is home to the college campuses Boston University, Northeastern University, & Simmons University.
I highly recommend seeing a Red Sox game at the famous Fenway Park. Before & after the game you can hang out at one of the lively bars on Lansdowne Street. Or, you can take a guided Fenway Park tour to learn more about the stadium and the team’s history and get special access to the park!
Not interested in baseball? Visit the Museum of Fine Arts. The collection includes Renaissance-style paintings from Europe to mummies from ancient Egypt (my favorite exhibit).
The Museum feels endless! You’ll need 2+ hours to truly take in and enjoy all the exhibits. Admission is $27 for non-members, but check the site for discounts and special exhibits. NOTE: It closes at 5PM on Sunday-Wednesday. Plan accordingly!
Another museum nearby is the Isabella Stewart Gardner Museum. It has beautiful artwork from all over the world and a unique, Instagrammable courtyard. Admission here is $20, but check the site for discounts. (Fun Fact: you get free admission if your name is Isabella!)
For a casual dinner, head to Peterborough Street. There is a block lined with casual restaurants and plenty of outdoor bench seating. Ex: Rod Thai Family Taste for Thai, The Greek Gyro for Greek gyros, and El Pelon for Mexican food. There is something for everyone here.
Finish your night with dessert from Matcha Maiko. They’re famous for their premium matcha soft serves.
Further Reading: 25 Best Indoor Activities in Boston
Day 2 of your Itinerary for Boston
Get up early this day for all the historical Boston landmarks! I feature a LOT of food in this section of the itinerary for Boston, so pick and choose what sounds best to you.
Stop 1: Beacon Hill & Acorn Street
Start your day early and head over to Beacon Hill! This quaint neighborhood is super picturesque with brownstone homes and narrow cobblestone streets. As you walk through the neighborhood, stop by Acorn Street for pictures. The small cobblestone street is the most photographed in the city! I recommend going as early as possible to avoid other tourists being in your shots.
Next, head down to Charles Street (just blocks away from Acorn St!) for breakfast at Tatte Bakery and Cafe. It is a popular cafe among both locals and tourists. My favorite items here are the croque monsieur and the Shakshuka. If you’re in the mood for something lighter, their pistachio croissants are amazing! You really can’t go wrong with anything on their menu.
Further Reading: The Best Breakfast in Boston: 27 Must-Tries
Stop 2: Freedom Trail and Fanuiel Hall
After breakfast, walk the iconic Freedom Trail. It starts at the Boston Commons and extends 2.5 miles North to the neighborhood of Charlestown. The trail is marked by a red brick line on the ground, making it very easy to follow along. Give yourself around 2 hours if you’re looking to finish the entire trail, stopping at historical sites along the way.
In Downtown, come across Brattle Book Shop! This bookshop has a cool outdoor sale section in the warmer weather.
Another must-see spot along the trail is Faneuil Hall. It’s an outdoor shopping area and the perfect place to grab souvenirs. Right in the middle is the Quincy Market, a historic food hall with plenty of food stalls inside. I don’t recommend eating there, though. Most of the food is mediocre and overpriced since it caters to tourists.
The one Faneuil Hall stall I would recommend is Boston Chowda. They are known for their bread bowls with steaming hot clam chowder.
Stop 3: North End (Boston’s Little Italy)
As you walk along the Freedom Trail, don’t forget to check out the North End. I HIGHLY recommend getting a late lunch here on your itinerary for Boston. It is Boston’s Little Italy and there are so many good Italian restaurants and desserts to choose from. It’s a must-do for any itinerary for Boston, especially if you’re a foodie.
The #1 restaurant option for many people is Neptune Oyster. Must-tries include the Maine Lobster Rolls, Wellfleet Clam Chowder, and, of course, oysters. There is always a line, but it’s worth it!
Not in the mood for seafood? The best Italian restaurant is Carmelina’s on Hanover Street (if you’re able to get a reservation). I always get the Crazy Alfredo here– It’s a spicy alfredo with chicken, pancetta, and sausage.
You also must try one of the cannoli shops in the area. Bostonians have been debating which is the best for YEARS. The 3 top competing cannoli shops are Mike’s Pastry, (definitely the most famous one), Modern Pastry Shop, and Bova’s. They’re all amazing, but my personal favorite is Bova’s. Try the “florentine cannoli”! The shell is made with honey and almonds, making it crunchy and perfectly sweet.
Other things to do in the North End include seeing the Paul Revere House and Old North Church.
Further Reading: Ultimate Guide to Boston’s Little Italy (best restaurants & things to do)
Stop 4: Seaport District
After you finish the Freedom Trail, you’ll likely be exhausted from all the walking. I recommend the Seaport District next. They have several waterfront rooftops to have a drink and unwind. Lookout Rooftop and Six West are the most popular rooftop bars boasting amazing skyline views. I recommend getting a reservation in advance since it fills up fast.
To end the day, walk along the harbor at Seaport. If it’s a Thursday, I recommend visiting the Institute of Contemporary Art. Admission is free every Thursday from 5-9PM!
Further Reading: 17 Fun Boston Restaurants & Unique Bars
Day 3 of your Itinerary for Boston
On Day 3 of the itinerary for Boston, I recommend venturing across the Charles River to Cambridge.
Stop 1: Harvard Square
Harvard is easily accessible from the Red Line Harvard Station. There you can check out Harvard Square, which is lined with shops and restaurants. For food, I recommend the famous sticky bun from Flour Bakery and Cafe. It’s warm, fluffy, and topped with toasted pecans.
Next, explore the Harvard University campus. If you can find the John Harvard Statue, rub his left shoe for good luck! The Harvard Museum of Natural History is also nearby. Admission is only $15 and the exhibits feature animals and plants from around the world. I recommend giving this place an hour to fully enjoy all the exhibitions.
Stop 2: Porter Square & Central Square
Once you’re done in Harvard Square, you’ll probably be hungry from all the walking.
My #1 lunch spot in the entire Boston area is located in Porter Square (Just 1 stop from Harvard Square on the Red Line). Lined with authentic Japanese food stalls, Lesley University’s unassuming food hall sells the BEST food.
If you’re in the mood for udon noodles, line up at Yume Ga Arukara. Their udon is freshly made and the restaurant has a small, intimate seating area. I highly recommend the Spicy Cold Niku (Beef) Udon here. It’s seriously the best udon I’ve ever had, and my favorite food spot on this itinerary for Boston.
Just a few food stalls over is Cafe Mami. They specialize in Japanese curry. It’s always perfectly seasoned, hearty, and comforting to eat. It’s best paired with chicken katsu (deep-fried chicken cutlet) and topped with an egg.
If you’re in the mood for shopping, Central Square is nearby. The area has plenty of thrift shops, bars, and trendy restaurants. New City Microcreamery is also located there. It’s a popular ice cream shop with cool flavors like baklava, creamsicle, and cannoli.
Stop 3: Charles River Esplanade
The Esplanade is Boston’s biggest greenway area. It is split between the Charles River and has an area in both Cambridge and Boston. Start in Cambridge and bike the trail to capture an incredible view of the Boston skyline. There is a bridge that crosses over the Boston side of the Esplanade as well. Conveniently, it brings you back to Back Bay.
Further Reading: 27 Unique Date Ideas in Boston
Stop 4: Chinatown
For dinner, head to Boston’s Chinatown. If you want high-quality food and a fun dining experience, grab hotpot at Happy Lamb Hot Pot or Shabu-Zen. Finish the meal with a Belgian waffle pop and boba from Sweet Waffles & Boba.
Further Reading: 25 Best Chinatown Restaurants in Boston
Stop 5: Speakeasy in Leather District
By now you’ll likely be exhausted from 3 full days of exploring. If you still have energy, I recommend finishing the day at Offsuit in Boston’s Leather District for drinks.
The speakeasy is hidden in an alleyway & you need to call a number to get inside. The interior is intimate and the cocktails are inventive. It is a great spot to relax and enjoy the atmosphere.
Further Reading: One Day in Boston: The Ultimate Travel Guide & Itinerary
Other Top Attractions & Things to Do for your Itinerary for Boston
There are so many other great things to do in the city that this itinerary for Boston couldn’t fit! Check out the other best attractions:
- View Boston Observatory – ascend to the Prudential Tower’s 52nd floor for 360-degree panoramic views of the city! Only available by ticketed entrance.
- Museum of Science – This museum has over 30 exhibits, planetarium shows, and live presentations. Learn more on their site.
- New England Aquarium – There are thousands of marine animals and 4 stories in this aquarium. You can also see an IMAX movie at the Simons Theater or go whale watching. Check their site for more details.
- Boston’s Allston – Harvard Avenue and Beacon Street are lined with plenty of amazing restaurants and cafes. It is one of my favorite foodie spots in the city. A must-try here is Coreanos! They sell Korean-Mexican fusion dishes and everything is soo good. I recommend the chicken poppers + fries and Coreanos rice bowl. For dessert, try Pon De Joy for the city’s best mochi donuts.
- See a Celtics Game or Concert at TD Garden – Catch a Celtics game at TD Garden! It is located in the West End, next to the North End.
- Blue Hills Reservation – If you have a car, go on a Boston day trip to the Blue Hills in Milton for a hike. The Skyline Hike is a medium/difficult level hike with a view of the city at the top.
- Mapparium – A unique idea for your itinerary for Boston is the Mapparium. Located at the Mary Baker Eddy Library steps from Newbury Street, you can walk on a bridge in a dome-shaped room, surrounded by a colorful three-story tall globe on all sides of you. What else is cool about this place is how sound travels when you’re inside. Since it’s a perfect 360-degree sphere, you would be able to hear someone on the opposite end of the bridge — even if they’re whispering!
Further Reading: 25+ Fun Things to Do in Boston for Young Adults
General Tips for First-Timers in Boston
Neighborhoods to Stay in: I recommend staying in Back Bay or Downtown Boston if you want to be close to all the tourist attractions on your 3 day itinerary for Boston. Downtown is very central but can be sketchy at night. So, Back Bay would be my top pick.
Transportation: Boston’s city center is compact, so I recommend walking to see everything! The MBTA, or the subway system, is also easy to use. Buy a Charlie Card (Subway Pass) at a kiosk in a major station like Downtown Crossing or Back Bay. Each ride is around $2.40.
Weather/What to Pack: In the winter, definitely pack a thick jacket since Boston gets pretty cold (It can get less than 10 degrees in January).
Fall and spring are often mild (the 50s and 60s), and summer is hot and humid (75+ degrees). I recommend visiting during the spring for comfortable weather and fall for the foliage.
Further Reading: Best 25 Boston Summer Activities
Packing List for 3 Day Itinerary for Boston
Listed are some essentials to make your trip to Boston easier.
- Travel Backpack – I suggest investing in a durable travel backpack to minimize shoulder pain.
- Compact Travel Umbrella – Spring and summer in Boston can be quite rainy, so having a small umbrella for your bag is a game changer. I especially like the Leagera one because it comes with a case.
- Comfortable Sneakers – It’s likely that no matter what your itinerary for Boston is, you’ll be doing a lot of walking. A pair of comfortable shoes can make or break your trip.
- Sunglasses – The sun is strong in Boston’s summers, so having a pair of sunglasses (or Red Sox baseball cap!) comes in handy.
- Portable Charger
- Camera – A smartphone with a good camera usually works. However, a high-quality camera for photos or vlogs definitely elevates your travel shots.
Conclusion: 3-Day Itinerary for Boston
Thanks for reading this far and hopefully this 3 day itinerary for Boston has provided some help to you 🙂 This self-guided tour is how I would personally show someone around Boston for the first time. I included a mix of Boston’s best touristy things to do as well as local hidden gems.
Please leave a comment or send a message with any questions or feedback. Check out my other articles here.
Itineraries for other U.S cities:
Here are some other Boston food guides to add to your itinerary for Boston:
[…] my 3 day itinerary for Boston and best sandwich list […]