A Wicked Good Itinerary for a Boston Weekend Trip
Are you trying to plan the perfect Boston weekend trip? With cobblestone streets, centuries-old history, lobster rolls that’ll ruin you for life, and more must-see sights than time allows, narrowing it all down can feel like a full-time job.
That’s where I come in.
I’ve been to Boston more times than I can count. I visited before a girls’ road trip through New England, solo during a work conference, after cruising the Canadian coast, on the heels of a European vacation, and before catching the ferry to Martha’s Vineyard.
And no matter the reason for the visit, Boston always manages to surprise me. Each time I go, I find something new, whether it’s a tucked-away café, a hidden bit of history, or just a better way to do things.
This guide pulls together everything I’ve learned to help you plan an unforgettable long weekend in Boston.
Whether you’re tagging along with your partner or gathering with your best girlfriends, I’ve got the details covered, including where to stay, what to eat, how to get around, and how to see the very best of the city without burning out by Sunday.
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Pros and Cons of a Boston Weekend Trip
Boston is compact and made for walking. It’s bursting with history, filled with character, and surprisingly romantic. It also has solid public transportation, excellent food, and an unmatched blend of old and new.
On the flip side, hotels are pricey, and the city gets crowded, especially in summer and around major sports events or the New England fall foliage season.
And while it’s walkable, your feet will still stage a protest by day three. But with a solid plan (ahem, like this one), you’ll make the most of your time without wasting it googling where to go next.
How to Get Around Boston
Boston’s streets weren’t exactly designed with logic in mind. Some of the roads follow old cow paths, literally! But, it’s still easy to navigate once you know your options.
- Walking: You’ll do a lot of it. Bring good shoes. Nothing beats the New Balance 327 sneakers! I think these single handedly helped me alleviate my plantar fasciitis.
- The T: Boston’s subway system. It’s cheap and mostly reliable. Buy a CharlieCard or a one-day pass.
- Old Town Trolley Tours: The hop-on hop-off tour is one of my favorite ways to see a lot fast without the logistics headache.
- Boston Duck Tour: The Boston Duck Tour is a must if it’s your first visit. You’ll see the city on land and water, with a side of cheesy jokes.
- Uber/Lyft: Handy for late nights or tired legs.
- Water Taxi: I haven’t tried using a water taxi yet, but I just saw this was an option from Boston Logan to the Seaport and Central Wharf/Aquarium, so you may want to check it out.
Where to Stay on Your Weekend Trip to Boston
Boston has a wide range of hotel options, and your best choice depends on the vibe you’re going for. I’ve stayed in multiple neighborhoods, and each one offers something unique.
Here are the best hotels I can recommend for each area in Boston.
My Top Boston Hotel Picks
Renaissance Boston Seaport District
The Seaport District feels modern and polished, with water views and rooftop bars. The Renaissance Boston Seaport Hotel is ideal if you want to be close to the water, newer restaurants, and some of the best seafood around.
You’ll also be near the Institute of Contemporary Art and a beautiful section of the Boston Harborwalk.
The Dagny Boston – Downtown/Financial District
The Downtown/Central Business District is walkable to everything.
If you want to hit all the classic attractions without worrying about the T or Uber, stay downtown.
The Dagny Boston, formerly the Hilton, has been renovated and is a great pick. It’s close to the Freedom Trail, Faneuil Hall, the waterfront, and the North End.
InterContinental Boston – Downtown/Boston Harbor
Set right on the harbor and steps from the Boston Tea Party Ships & Museum, the InterContinental Boston luxury hotel is as convenient as it is beautiful. With its sleek, modern design and its ideal location, this hotel is perfect for those wanting a little pampering without sacrificing location.
Sheraton Boston Hotel – Back Bay
Back Bay is known for its charming brownstones, walkable streets, and easy access to shopping on Newbury Street, the Boston Public Garden, and Fenway.
I once stayed at the Sheraton Boston and loved how central it felt. It connects directly to the Prudential Center, so if the weather is bad, you can stay indoors and still shop and eat to your heart’s content.
The Whitney Hotel – Beacon Hill
Beacon Hill is the postcard-perfect part of Boston.
Cobblestone streets, gas lanterns, and charming corners everywhere you look. It’s a quieter and more romantic neighborhood, perfect for couples.
The Whitney Hotel is a boutique property that feels luxurious without being pretentious. It’s tucked near the Charles River and still walkable to Boston Common, the Public Garden, and downtown.
Best Things to Do in Boston by Neighborhood
To keep this guide organized and skimmable, I’ve broken Boston down by area and themed it around four main types of travelers: history lovers, sports fans, pop culture buffs, and classic tourists. Choose what suits you, or mix and match.
Back Bay & Fenway: History, Sports, and Skyline Views
🏟️ Fenway Park
Baseball fan or not, touring Fenway is iconic. If the Red Sox are in town, snag tickets early. The crowd energy is contagious.
📚 Boston Public Library
Yes, it’s a library, but it’s also jaw-droppingly beautiful. Don’t miss the courtyard.
🛍️ Newbury Street + Prudential Center
Boutiques, big brands, and coffee shops line Newbury. Then cut through the Prudential Center to find the View Boston Observation Deck for panoramic city views.
🌳 Boston Public Garden
Home to the swan boats, the “Make Way for Ducklings” statues, and some of the prettiest landscaping in the city. This is where locals relax and tourists snap photos.
Downtown & Waterfront: Pop Culture Meets Classic Boston
🍽️ Quincy Market at Faneuil Hall Marketplace
You can grab lunch here. It’s busy and touristy, yes, but for good reason. Try a bowl of New England clam chowder from Boston Chowda Co. and people-watch in the courtyard.
🏛️ Cheers Bar (Beacon Hill)
You’ll recognize the Cheers facade from the sitcom. The inside doesn’t look like the show set, but it’s still worth a stop for nostalgia’s sake and a quick drink.
Be sure to stop by the upstairs gift shop and take photos with the Cheers set.
🛍️ Boston Public Market
The Boston Public Market offers a wide selection of locally sourced items, including bagels, farm-fresh produce, and handmade New England gifts. It’s indoors, too, so a great rainy-day option.
🛳️ Boston Tea Party Ships & Museum
Throw (fake) tea into the harbor and learn just how fed up colonists were at The Boston Tea Party Ships & Museum.
This museum is Interactive with costumed guides and fun, even for non-history buffs.
North End: Italian Food and Colonial History
🍕 Regina Pizzeria
The original Regina location on Thacher Street is worth the wait—brick oven, crispy crust, and the best slice I’ve had in Boston.
🏠 Paul Revere House
One of the oldest buildings in the city and an easy stop on the Freedom Trail. Small but packed with Revolutionary War-era stories.
🍰 Mike’s Pastry or Modern Pastry
Cannoli wars are serious business in Boston. I’ve only tasted Mike’s, and it would be hard to beat. I won’t choose sides. Try them both and let me know what you think. Make sure to bring cash, since cards aren’t accepted.
⛪ Old North Church
Are you familiar with the phrase, “One if by land, two if by sea?” This is that church. Still standing, still beautiful, and a must for history lovers.
Seaport & South Boston: Waterfront Vibes and Contemporary Culture
🖼️ Institute of Contemporary Art (ICA)
Modern art in a sleek building right on the water. Whether you’re into the art or just want a scenic rooftop moment, this place is worth a visit.
🐳 Whale Watch or Harbor Cruise
Leave from Long Wharf or Seaport and spend a couple of hours on the water. Go for the sunset cruise or the educational whale watch. Either way, it’s a relaxing and scenic experience.
🍸 Waterfront Dinner
End your day with seafood and skyline views at Legal Sea Foods Harborside or Row 34. Order the lobster roll. Just do it.
A Complete 2-Day Boston Weekend Trip Itinerary
Day 1: Classic Boston Sights & Waterfront Fun
Start your weekend with breakfast at Tatte Bakery. There are several locations, but the one on Charles Street in Beacon Hill is cozy and close to Boston Common.
After breakfast, stroll through Boston Common and explore the Boston Public Garden. Snap a photo on the iconic Swan Boats or sit on a bench and people-watch.
Next, walk the Freedom Trail, which begins at Boston Common and weaves through 16 historical landmarks.
You can do a self-guided tour or join a Freedom Trail tour with a guide in colonial garb. Both are informative, but the live commentary adds a little flair.
Be sure to stop at Faneuil Hall Marketplace for lunch and shopping. It’s touristy but still fun, especially if it’s your first time. Grab a lobster roll or clam chowder from one of the market stalls.
In the afternoon, visit the Paul Revere House in the North End. It’s one of the oldest buildings in downtown Boston and gives a real sense of what life was like in the 1700s.
Dinner should absolutely be at Regina Pizzeria in the North End. Order the classic margherita and thank me later. After dinner, grab cannoli from Mike’s or Modern Pastry and walk it off with an evening stroll along the waterfront.
Wrap up your day by catching the sunset along the Charles River Esplanade. It’s peaceful, scenic, and the perfect way to wind down after a full day of exploring.
Day 2: Gardens, Baseball, and Boston Icons
Start with coffee and a pastry from Flour Bakery (Back Bay or Fort Point).
Head to the Museum of Fine Arts or the Isabella Stewart Gardner Museum. The MFA is vast and traditional, while the Gardner Museum feels more personal and atmospheric.
After the museum, make a quick stop at the Boston Public Library in Copley Square. The courtyard and reading room are stunning, and yes, you can absolutely take photos.
From there, grab lunch at Boston Public Market. It’s a year-round indoor market with tons of local vendors. Try a Maine-style lobster roll or seasonal salad from one of the food stalls.
In the afternoon, head over to Fenway Park. Even if there’s no game, you can take a stadium tour. It’s a must-do for baseball fans.
Before dinner, pop into Cheers at the foot of Beacon Hill. Yes, the bar that inspired the sitcom. It’s touristy but fun, and the photo op is worth it.
Finish the day in the Seaport District. The views of the harbor are spectacular at sunset, and there are endless dining options. Look for rooftop bars if the weather is nice, or book a table at Legal Harborside or Row 34 for fresh seafood.
End the night with a harbor walk or, if you still have energy, a cocktail at Rooftop at The Envoy Hotel.
Possible Day Trips from Boston
If you’ve got an extra day or just want to plan for next time, Boston is surrounded by charming destinations worth the detour.
Cape Cod & Provincetown
Cape Cod makes for an ideal day trip, especially during the summer.
You can rent a car and drive about 2 hours to take a ferry to Martha’s Vineyard or a day trip to Nantucket. Or skip the traffic and take a direct ferry from Boston to Provincetown.
The Provincetown ferry leaves from the Seaport area and takes about 90 minutes. Tickets cost around $200 round-trip.
Once there, explore the art galleries, enjoy lobster rolls by the water, bask in the sun at the beach, or bike along the dunes. It’s a fun, beachy change of pace with great shopping and seafood.
Stowe, Vermont
A drive to Stowe, Vermont may make for a long day, but the drive from Boston to Stowe is one of my favorite drives, especially in the fall.
Concord & Lexington
History buffs should make the short drive to these two towns west of Boston.
You can visit the battlefields of the American Revolution, walk the same trails as Paul Revere, and visit Louisa May Alcott’s Orchard House.
Newport, Rhode Island
It’s about 90 minutes away, but Newport is worth the trip.
Tour the famous Gilded Age mansions, walk along the Cliff Walk, and enjoy oceanfront dining. It’s a glam escape that feels far from the city but is still easy to reach in a day.
Each of these trips adds a new flavor to your Boston weekend itinerary, whether you’re into spooky stories, seaside villages, or Revolutionary landmarks.
Boston in a Weekend
A Boston weekend trip doesn’t have to feel rushed or complicated.
With the right Boston itinerary, you can cover a lot of ground without overdoing it and still leave room for cannoli. Whether you’re in town for a girls’ getaway or sneaking off for a romantic weekend, Boston has just enough polish and grit to keep things interesting.
Want history? It’s on every corner. Want great food? Hope you packed your stretchy pants. Want a break from your everyday routine? This city’s got you.
And when in doubt, just follow the red bricks.
