Things To Do
Head of the Charles Regatta
Every October, the Head of the Charles Regatta transforms the Charles River into one of Boston’s most exciting (and scenic) events. Rowers from around the world — from elite athletes to college crews — come to compete in this legendary race. Spectators line the bridges and riverbanks to cheer them on, creating an electric, festival-like atmosphere. In 2026, the regatta will take place October 16–18. It’s one of the busiest weekends in the city, so expect big crowds and plan ahead — but the energy is absolutely worth it! Even if you’re not a rowing fan, it’s an incredible weekend to stroll along the river, grab a cider or hot chocolate, and take in the fall colors, live music, and excitement of the crowd. A true Boston tradition you won’t want to miss!
Explore Beacon Hill & Picnic in the Public Garden
Wander around the Beacon Hill neighborhood and take in its historic charm. If you love to read, stop by the Beacon Hill Bookstore—it’s absolutely adorable! Then, head to Kured and grab a charcuterie board to go. Stroll over to the Boston Public Garden to enjoy the fall leaves and have a cozy picnic.
Boston Freedom Trail Walking Tour
Looking for a historical tour of Boston? The Freedom Trail Foundation's most popular tour highlights the revolutionary history that took place at 11 of the 16 official Freedom Trail historic sites. Purchase tickets in advance! After the tour, head over to Tatte - another Boston classic - for a beautiful pastry and coffee!
Shopping & Dining on Newbury Street
There’s something for everyone on Newbury Street in Back Bay, with plenty of outdoor shopping. You’ll also find even more stores inside the Prudential Center Mall. Notable restaurants in the area: Rochambaeu, Casa Romero, Select Oyster Bar, Krasi & more!
Italian in the North End
Start your evening with dinner (or lunch!) in Boston’s North End — one of the most romantic spots in the city. For a high-end experience, try Mamma Maria (perfect for a special occasion). For something more casual but still delicious, go to Trattoria Al Panino. After dinner, stroll over for cannolis — because no North End night is complete without them! There’s an age-old debate: Mike’s Pastry vs. Modern Pastry. (Will and I are Team Modern!) Why not grab one from each and decide for yourself? Just remember — they’re cash only.
Fancy Night Out in the South End
Head to Barcelona Wine Bar for Spanish tapas, wine, and a lively party atmosphere. Afterwards, cross the street to Kartal, or take a short walk to Wink & Nod for a cocktail. Other notable restaurants in the South End: The Beehive, Kaia and Desnuda cocina & bar
Duck Boat Tours
Looking for a Tour of Boston? Look no further than the Duck Boat Tours! It’s the ultimate way to see the city — both by land and by water — all in one ride. Climb aboard these iconic amphibious vehicles and enjoy fun, lively commentary as you pass Boston’s most famous sights. A total classic and a must-do for visitors and locals alike!
Brookline Booksmith & Mecha
This is our #1 date night! Head over to Mecha, a ramen and pho spot that’s perfect for a chill but delicious evening. They don’t take reservations, so put your name on the list when you arrive. While you wait, pop into Brookline Booksmith right next door and browse their amazing selection — it’s our favorite bookstore in the city! Between the warm noodle bowls and the cozy book browsing, it’s the perfect mix of comfort and charm.