Hop on the Freedom Trail to take an iconic tour of Boston. The 2.5 mile trail begins at the Boston Common and winds through 16 iconic landmarks, such as the Old North Church, and ends at the Bunker Hill Memorial in Charlestown. This is a great way to explore various areas of Boston and learn about the history along the way.
Visit one of the oldest neighbor hoods in Boston. Known as Boston's Little Italy, the neighborhood has tons of amazing restaurants, such as Nico Ristorante (Sam and Allie's favorite Boston restaurant), as well cafes, espresso bars, pastry shops, and Italian markets.
Take a stroll through the Boston Common and Boston Public Garden to enjoy the beautiful scenery and our dog Ty's favorite place to roam.
Grab a drink and some snacks at one of the oldest bars in the United States. Enjoy some music and a Sam Adams just a short walk from the North End, Haymarket, and Downtown Boston.
Explore the historic hall, shop at nearby boutiques, or enjoy a variety of local food vendors in the marketplace. With its charming cobblestone streets, street performers, and vibrant atmosphere, Faneuil Hall offers a unique and memorable experience right in the heart of Boston.
Haymarket is a vibrant indoor/outdoor market in Boston, offering fresh produce, local goods, and unique finds at unbeatable prices. Just a short walk from the North End, it’s a perfect spot for visitors to explore local flavors, enjoy the bustling atmosphere, and experience a piece of Boston’s rich history.
Walk down Boston's famous Newbury Street in Back Bay for some of the best shopping in the city.
One of Boston’s most picturesque neighborhoods. Wander the cobblestone streets, admire the gas lamps and brownstones, and snap a photo on Acorn Street, one of the most photographed streets in America. Don’t miss charming local shops along Charles Street, or grab a bite at Tatte Bakery or The Paramount.
Boston has no shortage of amazing places to eat and drink. Flour Bakery is a local favorite for pastries, sandwiches, and the city’s most famous sticky buns. For fresh seafood, head to Saltie Girl in Back Bay—don’t miss the lobster roll or chowder topped with fried clams. Lolita is perfect for late-night cocktails with a fun, moody vibe, while Krasi and Kava both serve delicious Mediterranean small plates in the Back Bay and South End. For bold Asian fusion flavors and a funky atmosphere, we love Myers + Chang. 75 Chestnut is a cozy Beacon Hill gem, and Regina Pizzeria (original North End location only!) is a must for classic Boston-style pizza. If you’re looking for a stylish rooftop dinner, Contessa offers incredible views and upscale Italian inside The Newbury Hotel (reservations in advance required!). Grill 23 is a favorite for steak in a timeless Back Bay setting, and Buttermilk & Bourbon is our go to favorite brunch spot.
One of our favorite things to do in Boston is walking the Esplanade, often with our dog Ty . We love stopping at the Owl’s Nest Beer Garden for a chilled beer, then sitting on the dock to take in the views of Cambridge and the iconic MIT skyline. You will always find lots of people enjoying the river docks.
We met at MIT back in 2016, so the campus will always be special to us. If you’re exploring Cambridge, take a walk through Killian Court, the grassy space that opens up to the iconic Great Dome, a classic photo spot and one of the most recognizable landmarks on campus. From there, you’ll get beautiful views of the Charles River looking back onto Back Bay (where we now live!).