2 Days in Boston: Best Weekend Itinerary 2021

Fun Fact: Boston is one of THE most historical cities in the United States. With America’s oldest restaurant, first public market, first public park, first public school, first subway system, and more – America’s City of Firsts tells the story of the beginning of our country. Aside from being steeped in history, this fast-talking, seafood-making, baseball-loving city is the perfect place to spend a fun filled weekend! Here’s the ultimate Weekend Itinerary for an awesome 2-day trip in Boston.

Where to Stay

Aloft Boston Seaport District

Tucked away in the Seaport District neighborhood is the Aloft Boston Seaport District hotel. Known for its modern design, bright flashes of color, and tech-forward amenities, the hotel gives off a buzzy and colorful vibe. Upon walking into the hotel, you’re greeted by high ceilings, mural art, a grand industrial staircase, and polished concrete set in an open-concept lobby. There are a few food options on-site, including the WXYZ bar, Re:fuel grab and go storefront and the Alma Gaúcha Prime Brazilian Steakhouse. We had such a great time staying with Aloft and loved how central the location was. Shout out to the staff too – they are all so kind!

Things to Do: Day 1

Stroll the Boston Freedom Trail (Free!)

No weekend itinerary would be complete without experiencing the core history of Boston on a walk through the past. The Freedom Trail is a 2.5 mile walk, snaking its way through to 16 major sites relating to the city’s founding and the Revolutionary War. You know that little part of your brain from middle school history class that goes off when you hear “Boston Tea Party” and “Paul Revere?” These stories, and more, come alive on the free walking tour with Free Tours By Foot. You’ll stop by America’s first public park, the site of the Boston Massacre, the Massachusetts State House, and more. Just be sure to tip your guide! Alternatively, you can walk the trail on your own with the online brochure as your guide. The free tour ends at the perfect place: Faneuil Hall.

Explore Faneuil Hall Marketplace and Quincy Market

Situated in the heart of downtown, Faneuil Hall Marketplace and Quincy Market is “America’s first open marketplace.” Built in 1741, the building was often at the center of protests, debates, and meetings for abolitionists, suffragists, labor unionists, and other activists. Today, the center of commerce hosts novelty pushcarts, independent stores, chain retailers, and restaurants. From magnets to clothing to bacon-wrapped scallops, it’s a one-stop-shop for lunch and shopping. During the day, you can find performers such as jugglers and escape artists performing in front of Quincy Market.

Gaze at Artwork at the Isabella Stewart Gardener Museum

Painting, sculptures, tapestries, knick-knacks, and more. Every room at the Isabella Stewart Gardener Museum is a work of art, meticulously curated to delight the senses. Over a dozen rooms, passageways, and galleries are nothing short of spectacular. Not to mention, the heart and soul of the museum: a spectacular courtyard featuring ancient Roman sculptures and lush greenery. Whether you’re an art aficionado or just like to look at pretty things, the Gardener Museum is a must-see stop on your Boston weekend itinerary. Plus, the museum is the site of the world’s largest art heist which still remains unsolved 30 years later.

Ride Through Beacon Hill & Catch a Pic on Acorn Street

With narrow cobblestone streets, brick rowhouses, and antique street lamps, Beacon Hill has an undeniable classic charm. Tucked behind the Massachusetts State House, the neighborhood is known for its picturesque setting reminiscent of the Revolutionary period. Visit Acorn Street, “America’s most photographed street,” to snag an iconic photo op on the steep hill. Stroll down Charles Street, the bustling boutique center. Even take a riverfront walk on the Esplanade. Beacon Hill is definitely worth making a quick stop to experience the European-style residential district.

Things to Do: Day 2

Waterfront Views at Fan Pier Park

Often referred to as the “crown jewel of the Boston Harbor,” Fan Pier Park boasts spectacular scenes and a great location in the heart of the harbor. Enjoy an unobstructed view of downtown while watching ferries, sailboats, and water taxis cruise across the Massachusetts Bay. The park itself offers green spaces, plenty of seating, and even a firepit in the cold months. Stroll toward the city on the Harborwalk, across Seaport Boulevard and down to Rowes Wharf – it’s a nice route to see the local architecture and people watch near the Ferry Terminal.

Eat at Union Oyster House

If there’s one restaurant I’d proclaim a “must-eat” in Boston, it’s Union Oyster House. Having opened in 1826, the eatery has been serving up traditional New England seafood for over 160 years. It’s officially the oldest continually-operating restaurant in America and a National Historic Landmark. Perched upon cobblestone streets, the authenticity of the building is preserved with its classic brick façade and antique interior. Slurp oysters at the famous semi-circle bar, sit at John F. Kennedy’s favorite booth, and stroll the two floors of artifacts and oddities that pepper the walls. Don’t forget to try the creamy clam chowder (with a dash of Tabasco, of course)!

Grab a Cannoli in the North End

Walking into the North End, also known as Little Italy, feels like stepping right onto a movie set. The neighborhood is filled to the brim with authentic Italian ristorantes, pizzerias, and bakeries. One of the most hailed spots in the neighborhood is Mike’s Pastry, dubbed the “Home of the Cannoli.” Turns out I don’t like cannolis very much, but people who do like them rave about how good they are. Keep in mind they’re cash only! For the best pizza in the North End, head over to Regina’s Pizzeria on Thatcher Street. They’re slinging up greasy, cheesy, tasty goodness that any pizza-lover would regret missing.

Find Your Zen in Boston Public Garden

Boston Public Garden is one of the dreamiest places in the city. Blooming flowers, weeping willow trees, ornamental statues, and a sense of stillness make it a peaceful escape from the hustle and bustle of downtown. Be sure to take a swan boat ride for a relaxing cruise across the Public Garden Lagoon! You’ll spot sunbathing ducks and teeny turtles along the way.

Tour Fenway Park

Fenway Park may be the oldest ballpark in Major League Baseball, but it carries some of the most electric energy ever. While we didn’t get to catch a game, the tour was well worth the trip. Rain, snow, or sun are clearly non-factors as millions of diehard baseball fans make the pilgrimage to America’s Most Beloved Ballpark every year. Take in the view atop the 27-foot-tall left field wall, dubbed the “Green Monster.” Relive the Red Sox World Series Wins. Stand in the exact spot where so much baseball history happens and feast your eyes on world series balls, jerseys, and more. Even as an “amateur fan,” I enjoyed the tour – it was very engaging, thanks to our guide.

How to Get Around

Walk – Boston is a walkable city, so it’s a great way to get your steps in, learn the layout, and save money!

MBTA – Boston’s subway system is a very convenient way to get around. Although learning a new rail system can be confusing, Google Maps can tell you which trains to take and even what time they arrive.

Uber/Lyft – Uber in Boston can be expensive – it can be $10 to travel a mile. I’d recommend only using it when you’re headed out to the Gardener Museum or Beacon Hill.

There you have it! A ready-to-go Boston weekend itinerary filled with local history, delicious food, art galore, and scenic stops.  I hope you have an amazing time on your trip! Be sure to tag me in your adventures!

This map was made with Wanderlog, a journey planner app

P.S. If you’re looking for more East Coast destinations in the U.S., be sure to check out these other destination guides:
Weekend Guide to the Poconos, Pennsylvania
Weekend Itinerary for Philadelphia, Pennsylvania
A Romantic Weekend Getaway in Asheville, North Carolina

Thank you so much to the team at Aloft Boston Seaport District for hosting me! Though our stay was hosted, all opinions are my own.


  • Marissa Strang

    Marissa Strang is a full-time lifestyle and travel blogger based out of the Washington, D.C. Metropolitan area. Travel is her number one passion, and she is on a mission to empower others to make travel a reality for their own lives as well. She’s a strong believer that everyone can experience the joy of exploring the world, no matter the way they look or their socioeconomic status. Marissa creates one-of-a-kind city guides, destination inspiration, and budget-friendly travel hacks for aspiring travelers, especially young travelers and minorities. By creating travel content through her blog, The Marissa Daily, she strives to help others make lifelong memories - one destination at a time. Her journey as a blogger for the past 3 years has led her to visit amazing places and build an engaged travel community that she cares for deeply. One of the principles Marissa lives by, and encourages others to abide by, is that when you look like your passport photo, it’s time to book a trip. Let's go places.

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