How to Spend a Weekend in Boston

A red brick building marked with the words " South Market" with a large clock tower in the background in a historic Boston neighbourhood

Boston might seem big, but this waterfront city is the perfect size to explore for a weekend getaway. It’s walkable historic core, bustling downtown and seaside vibe are all within easy reach to make for the quintessential New England experience. Here’s how to spend a weekend in Boston:


Evening:Check into the Seaport Hotel in the newly revamped Seaport District, right across from the Boston Harbour. Walk a few blocks to the pedestrian-friendly One Seaport shopping area and wander the shops under the twinkling string lights along your way. Stop for dinner at the Barking Crab for a fresh seafood dinner ( the crab cakes and chowder are great!). If you’d rather take in your dinner from the sea, check out the Spirit of Boston dinner cruise that leaves from the dock across from your hotel.

 (Note: I enjoyed the cheaper prices in this area and don't mind a nice morning stroll,but you may choose to stay in the busier historic district for easier access)
two men and a woman stand beneathe twinkle lights in the One Seaport shopping district in Boston


Morning: Take the 20-minute stroll along the waterfront to North Square and grab a heavenly cappuccino and pastry at Café Vittoria for breakfast. Explore the cobblestoned streets and historic buildings, stopping by the Paul Revere house for a quick tour on your way to Quincy Market. Stop for lunch here for lunch before moving on.

dim lighting and Italian Decor inside Cafe Vittoria in Boston
Inside the “back room” at Café Vittoria

Afternoon: Make your way to the Isabella Gardner Museum. This converted manor houses the eclectic treasures of the wealthy Isabella Stewart Gardner. Be sure to stop for some photos in the iconic indoor gardens. It can get very busy, so save time by buying tickets in advance.

a woman sits perched on a ledge looking at a garden inside the Isabella Gardner Museum

Evening: Grab some artisan cocktails or craft beer at one of the many lounges. Bonus points for a hidden bar!


Morning: After breakfast, start your morning with a 15 minute cab ride or subway trip to Back Bay. Start at Copley square, snapping a few pictures before taking the short walk to the nearby Boston Public Library. It’s domed ceilings, sky-high walls of old books and big wooden desks give all kinds of Harry Potter vibes.

Afternoon: Make your way from the Library towards Commonwealth Avenue and walk along this picturesque street towards the Boston Public Gardens. Cut through here towards Beacon Hill for a more insta-worthy walk. At the top of the gardens, duck out and find Acorn street for one of the most iconic views in the city. The cobblestoned streets and red brick buildings will make you feel as though you’ve stepped back into time.

Helpful hint: When I’m planning a walk in a new city with many sights along the way I create a google map with multiple pins in advanced so that I can follow it as I go. Save it your “maps” in the app and download it to be able to use offline. You’re good to go and explore!

Check out these travel apps I can’t live without

Evening: Say goodbye to Boston and head home!

a woman walks towards the setting sun along the Boston Harbour

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