How to Spend a Weekend in Boston

How to Spend a Weekend in Boston

It’s crazy to think that it’s been almost five years since Chris and I moved to Boston. The time has felt like it’s flown by and inched along, all at the same time. We’ve visited almost every museum in the city, we’ve tried countless restaurants, we’ve walked hundreds of miles. Boston is a small but mighty city and is filled with so many amazing restaurants, activities, shops, beautiful architecture, and history. Whether you’ve visited before and are dying to get back, or have never been, here’s how to spend a weekend in Boston!

How to Spend a Weekend in Boston


Breakfast at Tatte

Tatte is a Boston staple and for good reason, it’s cute and delicious! I love their breakfast offerings and if you’re going to be spending the day exploring everything Boston has to offer, it’s the best for ensuring you’re full. My go-to is the breakfast sandwich and a cold brew, but all of their pastries are equally as delicious. Tatte has over 10 locations throughout the city, too, so it’s easy to stop into one no matter where you’re staying.

Isabella Stewart Gardner Museum & Museum of Fine Arts

These are two of my favorite museums in the city and they’re situated quite close to one another in the Fenway neighborhood, making it easy to visit both in one day! You can also get tickets to both as a package for a discount. If you were to only go to one, make it the Isabella Stewart Gardener Museum. The property is spectacular and a must-visit in the city. 

If you’re not familiar with the Isabella Stewart Gardener Museum heist, I highly recommend learning more about it through this Netflix special and this podcast prior to your visit. It’ll make it even more amazing!

Wine & Snacks at Nathálie

Located just a quick walk from the museums, Nathálie is known for its selection of organic wines and delicious snacks and is a perfect spot to stop before getting ready for the evening.

Blowout at Drybar

What better way to pamper yourself before dinner than with a blowout? I love popping into Drybar for a special occasion blow out and with locations in Back Bay and Downtown Crossing (close to Mariel), it’s easy to get your hair done and head straight to dinner! The head massage and now having to do your hair yourself is worth the price itself.

Dinner at Mariel

This Cuban-inspired lounge is situated in a former bank in Post Office Square. The atmosphere at Mariel is so fun, it has such an Instagrammable backdrop, and all of the food is absolutely delicious making it a fun spot to go with friends. The menu is tapas style, so come hungry!

After Dinner Drinks at Yvonne’s

Yvonne’s is Mariel’s chic but timeless older sister (and actually a sister restaurant!), perfect for after-dinner drinks. It’s moody, it’s cozy, and it has the best cocktail list in the city. 

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Coffee & Pastries at Greystone

Greystone is one of the South End’s most popular coffee shops, and for good reason! Located on the corner of Dartmouth and Appleton street, this quaint coffee shop is stunning on the inside and out. Seriously, their branding is SO good! I personally love the walk-up window for ordering coffee when the dog is with us but they just opened their indoor seating and I can’t wait to experience it.

Walk Through Back Bay & Down Commonwealth Avenue

Back Bay has so many nooks and crannies to explore and what better way to explore them than with a coffee in hand? Once you stop at Greystone, make your way over toward Comm Ave and take in the architecture along the way.

Read a Book in the Public Garden

After your walk down Comm Ave, take a break in the Public Garden and read a few pages of your current read before heading to Newbury Street to do some shopping. In the warmer months, the flowers throughout the garden are stunning, too!

Shop on Newbury Street

For years, Newbury had the same stores but as of late, they’ve really stepped up their game! There’s now a handful of stores we all know and love, including Mejuri, New Balance, Glossier, Anthropologie, Credo, Reformation, and so many more, that I know you’ll want to stop into. There are also several small local boutiques that you’ll fall in love with.

Lunch at Sonsie

Sonsie is such a great spot to go for lunch and its menu truly has something for everyone. The front of the restaurant has large windows with bistro tables facing toward them, which is so lovely. Make sure to get the gyoza!

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Dinner at Petit Robert Bistro

Petit Robert Bistro is one of my absolute favorite spots in the city, and I’ll bring friends and family any chance I get. The inside is chic and feels so cozy and romantic at night, and the patio is truly the best, especially during the warmer months. The menu is on the smaller side but they switch out some items seasonally, which I love! A few favorites are the cheese board, the steak frites, and the endive and squash salad. For cocktails, give the le verger and the rosé de la mer a try!

After Dinner Drinks and Live Music at Beehive

This jazz bar is a must-visit for after-dinner drinks and late-night live music! Live performances start at 9 PM on Thursdays, 10 PM on Fridays and Saturdays, and 7 PM on Sundays. They also have a phenomenal menu if you’re looking for a late-night snack or want to stop by for brunch or dinner during your visit.


Breakfast at Paramount

Paramount is a Boston staple. Located along Charles Street, it’s one of the very few dinner-style restaurants in the city with the best breakfast. I highly recommend going early, the line can get pretty long and they don’t take reservations. My favorite is the french toast!

Shop Along Charles Street

Charles Street has so many cute shops to pop into. Whether you’re shopping for a loved one, want to get a souvenir, or want a few new pieces in your wardrobe, Charles Street has something for everyone. A few of my favorites include Gus & Ruby, Credo (formerly Follain), Rouvalis Flowers, and Crush Boutique. Make sure to stop into Beacon Hill Books & Cafe, too!

Coffee at Blank Street

Blank Street is officially in Boston! With two locations (Beacon Hill and Back Bay), it’s a convenient stop to grab a cup of coffee. Once you’re done shopping, stop at their Charles Street location for some caffeine before making your way over to the Seaport.

Explore Seaport & Along Along the Water

This up-and-coming area of the city used to hold nothing but parking lots and old buildings. Now, it’s filled with contemporary buildings, delicious restaurants, and great shopping. Start by walking along the waterfront for stunning views of the city before grabbing some lunch and popping into some shops.

Lunch at Temezcal

Located at the further end of the Seaport, Temezcal is a must, especially if you love Mexican as much as me. Good luck figuring out what to get, everything is so delicious! Can’t recommend their margaritas enough, either.

Visit the Institute of Contemporary Art

On the smaller side, you can get through the ICA fairly quickly and if you’re into contemporary art, it’s a must-see. They occasionally have special exhibits and have first Fridays each month with live music and a bar in the evening.

Quick Dinner at Florentine Cafe

Florentine Cafe is one of my favorite North End spots. It’s cozy, the entire Florentine team is so friendly, and the food and cocktails are delicious. Before leaving the city, you have to stop in for a quick dinner. I would give my left arm for their gnocchi, it’s the best!

Psst… More Boston content this way!

Photography by Sam Brooks Photos

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