Your Non Touristy Guide to a Girls Trip in Boston

Boston has become one of our favorite destinations to spend a girls trip. Since 2020, with one of our good friends moving there, we have visited this historic city at least once a year — each trip discovering a new characteristic of the rich Boston culture!

On our most recent trip, we spent the weekend adventuring, eating, and laughing our way through the city, and it was just what we needed.

If you’re craving a girls trip that feels sophisticated, easy, and not overdone, Boston might just be your next favorite spot. Here’s our non-touristy guide to a girls trip in Boston, packed with charming neighborhoods, local eats, and low-key gems you’ll actually want to revisit.

WHERE TO STAY

One thing about Boston is that you can experience a completely different trip depending on which neighborhoods you visit. The city is broken down into many neighborhoods, all with distinct vibes and something unique to offer. There is truly one for every personality on your girls trip!

Seaport: This is where you’ll find the best rooftop bars, cute restaurants, and great views of the city! We recently stayed at YOTEL Boston and found it to be in the perfect location! Walkable to lots of shops and food spots. They have a great rooftop bar and restaurant to check out if you want a “night in” with a beautiful sunset view.

Cambridge: Just across the river from downtown, Cambridge has a laid-back, historic charm that makes it feel like a totally different city. Home to Harvard and MIT, it’s full of pretty campuses, historic buildings, and cute coffee shops perfect for an afternoon stroll. We loved exploring the Harvard Square area, popping into Lovestruck Bookstore where they serve wine and cutesy vibes — it’s the perfect mix of culture and chill.

North End: If you’re craving Italian food, this is the place to be. The North End is Boston’s “Little Italy,” packed with pasta spots, cozy bakeries, and streets that feel like you’ve stepped into Europe. We loved wandering around, grabbing cannoli, and popping into family-owned restaurants — it’s the kind of neighborhood you come hungry and leave completely full.

South End: Think stylish brownstones, tree-lined streets, and some of the best brunch spots in Boston. This neighborhood has a creative, artsy vibe with tons of cute boutiques and galleries to explore. It’s a great spot if your trip is all about relaxing, eating well, and soaking up the cool local vibes.

WHERE TO EAT & DRINK

Let’s be honest: the bulk of our trip centered around food (and we regret nothing). From French pastries to lobster rolls that live rent-free in our minds, here are some of our favorite foodie finds:

• The Fed Rose Garden Terrace – Garden vibes in the city – This dreamy outdoor terrace at The Langham Hotel feels like a secret escape in the middle of downtown. Sip something floral, eat something farm fresh, and order the dessert — chef’s kiss.
• Canalside Food & Drinks – Chill waterfront hangs – A perfect spot to unwind after a day of exploring and shopping. Think fun bar, food court with a variety of local options, and a breezy patio seating right by the water. Lowkey, but in the best way.
• Sail Loft – Lobster rolls with a view – This casual spot in the North End has major “locals know” energy. Our favorite spot for Lobster rolls and a must stop every time we visit Boston.
• Pauli’s – okay, so hot lobster rolls are more your vibe – If you want a no-frills, lobster roll, Pauli’s is the move. They offer hot buttered ones that are uniquely delicious.
• Mariel – The cutest Cuban brunch spot – Think printed wallpaper, dreamy chandeliers, and a brunch menu that makes it hard to pick just one thing. You and the girls will want to get dressed up for this one!
• Colette – French restaurant ideal for kicking off a girls night out – A hidden gem with Parisian charm and the world’s best cosmos.
• Aquitaine – Classic French cuisine – Perfect for a slow dinner with great wine and even better service. Cozy, elegant, and delicious!
• Warren Tavern – a local favorite – One of the oldest bars in the country, and somehow still not a tourist trap. Our favorite thing to get there is their $1 oysters on their happy hour. Can’t beat it.

THINGS TO DO ON A GIRLS TRIP IN BOSTON

Believe it or not, there are other unique things to do in Boston aside from doing a walking tour of the Freedom Trail (no shade). If you’re looking for low-key but memorable experiences for a girls trip in Boston, here are our favorite spots.

Spend time at Tall Ship Boston

This is a great one to add to the list in the summer months. It’s literally a ship docked on the pier for guests to hang out at. You’ll find pop-up bars, local food vendors, and outdoor games. A very fun Boston activity to do with a group of friends and completely free to enter!

Play Pickleball at Harpoon Brewery

Grab a paddle, sip on a cold brew, and show off your skills on their outdoor pickleball courts. Perfect for some friendly competition with a side of craft beer. If you’re hungry, they have pizzas and pretzels with seasonal dipping sauces. The cinnamon pretzel was our favorite!

Do a Sightseeing Tour with Charles River Boat

Okay, this one is a little touristy, but it’s a must-do. Catch killer views of the Boston skyline, Harvard, MIT, and those iconic bridges. Perfect for snapping pics and chilling out on the water.

Visit the Boston Public Library

This library is a perfect spot if you are looking for something to do indoors. It features beautiful architecture like marble staircases and a beautiful courtyard, and it houses one of the countries oldest book collections. It also makes for a GREAT photo backdrop and is completely free!

Afternoon tea at courtyard Tea Room

Located inside the Boston Public Library, you can book an afternoon tea experience. Enjoy tea and pastries in the tea room after you’re done exploring the library. Although it’s not a very touristy attraction, there’s limited space in the team room, so you’ll want to book reservations in advance.

Fancy cocktails at Offsuit speakeasy

A girls trip is not complete without a fun spot to take in the vibes and enjoy fancy beverages (whether cocktails or mocktails!). Offsuit is a cozy speakeasy with moody lighting and a DJ that plays on the weekends. The space is not very big, so reservations are a must.

SOWA OPEN Market

This one’s a little trendy — and the vibe is unbeatable, especially on a sunny day! Grab a coffee or local pastry, wander the stalls, and pick up some one-of-a-kind finds like local art or handmade jewelry.

Sample Two-Day Girls’ Trip Itinerary

DAY 1: Exploring, snacking, and settling in

• Arrive in Boston (we flew direct from MSP and MKE)
• Lunch at Pauli’s in the North End — hot lobster rolls to kick things off right
• Wander through SOWA Market — grab a coffee and browse local stalls
• Afternoon tea at Courtyard Tea Room inside the Boston Public Library
• Evening drinks and dinner at The Fed Rose Garden Terrace — skillet-baked chocolate chip sundae
• Optional nightcap at Offsuit — speakeasy vibes you won’t be able to get enough of

DAY 2: Brunch, history, and harbor views

• Brunch at Mariel — start the day with a chic girls brunch at this tasty Cuban restaurant
• Head to Charles River for a sightseeing boat tour — see both sides of Boston & Cambridge
• Get off the tour at Canalside — grab a bite or drink and enjoy being next to the water (games + variety of food options = bonus)
• Try oysters at Warren Tavern
• Explore the Boston Public Library’s architecture or squeeze in shopping downtown
• Dinner at Aquitaine for elevated French fare
• Drinks at Ward 8 to end the night!

Final Thoughts

This trip reminded us that you don’t have to do all the things to have a great girls’ weekend. Sometimes it’s just about finding the right place, eating good food, and reconnecting with the people who get you. Boston, you were a dream.