Things To Do
Back Bay
Make your way to the Boston Public Garden to begin your journey down famous Newbury Street — allegedly referred to as the "Rodeo Drive of the East Coast" per Google AI Overview... take that with a grain of salt. See below for a map of the restaurants and shops along Newbury Street!
Charles Street
Spend an afternoon peeking into all the antique stores, boutiques, and cafes along Charles Street in Beacon Hill. And spend some time looking for iconic Acorn Street, renowned for being one of the most photographed streets in the US.
Fenway Park
Head to Fenway to see America's Most Beloved Park! If you're coming in early, catch the Red Sox on Thursday, May 28 at 4:10pm take on the Atlanta Braves!
Freedom Trail
Never been to Boston? This is the perfect way to explore the area and dive into the city's history! Begin at the corner of Park & Tremont on the Boston Common and navigate your way along the 2.5 mile route to the North End (or cross the bridge to Charlestown if you're feeling ambitious!) Depending on how fast you're walking and how much time you're spending at each location, we'd allot anywhere from 2-4 hours to enjoy the trail!
Isabella Stewart Gardner Museum
Explore Isabella Stewart Gardner's stunning palazzo and courtyard filled with her personal art collection, and immerse yourself into the scene of the unsolved 1990 art heist.
North End
Enjoy the food and shops around Boston's "Little Italy"! Set off on a cannoli tasting at Mike's, Modern, and Bova's to decide which pastry really is the best of the North End. Have a refreshing cocktail at Parla, or taste Graham's favorite bite in the city - Trattoria Il Panino's chicken parm! You really can't go wrong in this neighborhood!
South End
Stroll through the South End's brownstone-lined streets to get a feel for Brooke & Graham's every day (hint: they live here!). Try some of our favorite local spots — Coppa, Baleia, and Gigi! Explore the SoWa art galleries, and if you're hanging around on Sunday, pop by the SoWa Open Market from 11am-5pm.
Southie
Not to be confused with the South End, Southie is a neighborhood all its own. And it's where this story all began with Brooke & Graham's first date (RIP Coppersmith)! Walk along M Street Beach (yes, you read that right, Boston has beaches) and head to Castle Island for a bite at Sullivan's, a true Boston landmark. Do a foodie tour of some of Boston's best restaurants according to Michelin — Lenox Sophia, Fox & The Knife, and Bar Volpe. Though you really can't go wrong with any of the shopping and restaurants on Broadway. Play some pickleball at PKL, or try your hand at a New England classic, candlepin bowling at Southie Bowl!