Discover Boston together: Fun experiences for every group
Full of history and culture, Boston is an ideal destination for friends, couples, and families of all ages.
Edited by Sarah Kuta | December 18, 2025
Boston’s neighborhoods are full of character, history, and activities that make exploring with a group a delight. From the cobblestone streets of the North End to the bustling energy of the Seaport, the city offers something for everyone. No matter the season, Boston’s vibrant culture and iconic landmarks create the perfect backdrop for making memories together. Here’s how to plan a group trip to some of Boston’s best neighborhoods, so everyone can enjoy the city’s sights and experiences together.
In this article: Where to stay in Boston for your next group trip
Seaport made simple for families
Game days and nights near Fenway
Seaport made simple for families
The Seaport is a parent’s dream for car-free days with kids. Many families begin at the Boston Children’s Museum, then meander the stroller-friendly Boston Harborwalk for breezy waterfront views and snack stops at local bakeries. On rainy days, swap in the New England Aquarium or Museum of Science. From May through October, hop a ferry to the Boston Harbor Islands or book a whale watching cruise to see these majestic marine mammals gliding through the water. From April through September, ride the iconic swan boats in the Public Garden and make a Boston memory of your own. Homewood Suites by Hilton Boston Seaport District keeps families close to the action with spacious suites, full kitchens, free hot breakfast, and easy access to Seaport highlights.
Game days and nights near Fenway
For friend groups chasing game-day energy, Fenway is the city’s lively heart. Take a guided tour of Fenway Park by day, then catch a game or concert at night. Pre- and post-event, try a favorite local bar or join a brewery tour. Spring and fall weekends are especially popular, so booking early can help secure your ideal seat in the stadium. Hilton Boston Back Bay is one of the top hotels near Fenway Park, with easy public transit access for nights out across the city. After the final inning, walk the three blocks back to the hotel to gather at the lobby bar and relive the game’s most exciting plays.
Harbor lights and North End nights
Couples will find classic romantic things to do in in Boston’s North End and waterfront, where golden-hour harbor walks lead to sunset cruises and candlelit dinners. . Begin your day with coffee and a stroll on the Rose Kennedy Greenway, then explore art and architecture at the Museum of Fine Arts, Boston or the Isabella Stewart Gardner Museum. Evenings are for strolling narrow streets, sampling Italian pastries, and watching the city light up across the water. Canopy by Hilton Boston Downtown is a boutique-style base tucked between downtown and the North End, with free bikes and a welcoming vibe that’s perfect for couples.
Easy-access days around Boston Common
Boston Common and the Public Garden are ideal destinations to explore as a group. Follow the Freedom Trail for history at your own pace, with plenty of benches and green spaces for when you need to take a rest. Enjoy the Swan Boats in spring and summer, or plan a foliage walk if you’re visiting in the fall. For winter, pivot to museums or cozy theater nights. DoubleTree by Hilton Hotel Boston – Downtown is steps from Boston Common and the Theater District, with amenities and a convenient location that make it easy for everyone to explore.
Disclaimer: We used AI assistance to generate this content. All information was reviewed by Hilton's team to ensure it meets our standards for accuracy and ethics, allowing us to better match your travel needs and connect you with the right stay.
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