Ultimate Guide for a Friends Squad Day in Boston
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Boston is the perfect city for a fun-filled trip with your friends. From exploring historic neighborhoods and quirky landmarks to enjoying vibrant nightlife and delicious food, there’s something for every squad in this exciting city. Whether you’re adventuring together during the day with outdoor activities or winding down at a local brewery or rooftop bar, Boston offers endless opportunities for memorable moments. Get ready to bond with your friends over unforgettable experiences in one of America’s most dynamic cities!
1. Explore the Freedom Trail
Location: Starts at Boston Common, 139 Tremont St, Boston, MA
A must-do for any first-time visitor, the Freedom Trail offers a 2.5-mile walk through Boston’s historic sites. As you stroll through iconic landmarks like the Massachusetts State House, Paul Revere’s House, and Old North Church, your squad can enjoy a mix of history, culture, and fun photo opportunities.
Squad Tip: Split up into teams for a fun challenge—take a selfie at each landmark and see who gets the best shot by the end of the day!
2. Hop on a Duck Tour
Location: 4 Copley Square, Boston, MA
For a quirky, all-in-one tour of Boston, jump on one of the famous Boston Duck Tours. These amphibious vehicles give you a chance to see the city by land and water, cruising through historic neighborhoods and then splashing into the Charles River for a unique view of the skyline. It’s a fun and interactive experience, perfect for a group.
Squad Tip: Make sure to sit near the front for the best views and engage with the guide—they love to have fun with the group!
3. Picnic at Boston Common and the Public Garden
Location: Boston Common, 139 Tremont St, Boston, MA
Take your squad to Boston Common, the oldest public park in the U.S., and nearby Public Garden, known for its iconic Swan Boats. Pack a picnic or grab some takeout from a nearby deli, and enjoy the green spaces while people-watching and chatting. It’s a great place to relax and soak in the vibe of the city.
Squad Tip: Rent the Swan Boats for a fun group ride on the pond or play a casual game of frisbee on the open grass areas!
4. Visit the Museum of Science
Location: 1 Science Park, Boston, MA
The Museum of Science is perfect for a fun and educational squad adventure. Explore interactive exhibits on everything from space to the human body, and check out the planetarium for an out-of-this-world experience. Your group can challenge each other with science-based games or take in a live show at the IMAX theater.
Squad Tip: Plan a visit to the museum’s live animal exhibits or get competitive with trivia quizzes in the hands-on science areas.
5. Eat Your Way Through the North End
Location: North End, Boston, MA
Boston’s North End is famous for its Italian food, so it’s the perfect place to indulge in a food crawl with your friends. From classic pasta dishes to the best cannoli in town, there’s something to satisfy everyone’s cravings. Make your way from one restaurant to another, sampling pizza, pastries, and fresh seafood.
Squad Tip: Challenge your friends to a cannoli taste test at the North End’s two iconic pastry shops—Mike’s Pastry and Modern Pastry—and see which one comes out on top!
6. Bar Hop in the Seaport District
Location: Seaport District, Boston, MA
If your squad is into nightlife, the Seaport District is home to trendy bars, rooftop lounges, and craft breweries. Start with a drink at one of the stylish rooftop bars for stunning views of the harbor, then hop from one cool venue to the next. The district’s vibrant atmosphere makes it perfect for a night out with friends.
Squad Tip: Download a map or list of the best bars in the Seaport and create your own “bar hop” challenge to see who can pick the most unique cocktail or craft brew.
7. Take a Boat Tour of Boston Harbor
Location: Long Wharf, Boston, MA
A boat tour around Boston Harbor is a relaxing yet fun way to take in the city from the water. Whether you’re looking for a daytime tour or a sunset cruise, you and your squad can enjoy stunning views of the skyline, historic landmarks, and the Boston Harbor Islands. Some boat tours even include a lively narration or live music!
Squad Tip: Grab some drinks or snacks for the ride and enjoy chatting while taking in the breathtaking waterfront views.
8. Brewery Tour in Jamaica Plain
Location: Jamaica Plain, Boston, MA
Jamaica Plain, one of Boston’s coolest neighborhoods, is home to several craft breweries. Take a brewery tour to taste some of the best local beers and learn about the brewing process. Many breweries also have taprooms with fun games like cornhole, which makes it easy for your squad to hang out and enjoy some drinks.
Squad Tip: Make it a friendly competition and vote on your favorite brews at each stop!
9. Visit the Isabella Stewart Gardner Museum
Location: 25 Evans Way, Boston, MA
If your squad enjoys art and history, the Isabella Stewart Gardner Museum is a unique and beautiful place to visit. The museum is housed in a stunning Venetian-style palace and features a collection of European, Asian, and American art. Its central courtyard garden is a peaceful escape, and you can also enjoy the art exhibits scattered throughout the museum.
Squad Tip: Take your time exploring the exhibits and chatting about your favorite pieces. The museum's eccentric atmosphere makes it a memorable group experience.
10. Catch a Game at Fenway Park
Location: 4 Yawkey Way, Boston, MA
There’s nothing like a Red Sox game at Fenway Park. It’s one of the oldest and most iconic stadiums in the U.S., and the energy from the crowd makes it a fun and exciting experience for your squad. Even if you're not a huge baseball fan, the electric atmosphere and historic setting are sure to impress.
Squad Tip: Get a group of tickets in the same section for an even more exciting experience. You can also take a tour of Fenway if there’s no game on that day!
11. Visit the Skywalk Observatory
Location: 800 Boylston St, Boston, MA (Prudential Center)
For some of the best views of the city, head up to the Skywalk Observatory. Located on the 50th floor of the Prudential Center, this observatory offers 360-degree views of Boston and beyond. Whether it’s daytime or sunset, the panoramic vistas provide an amazing backdrop for group photos and moments of awe.
Squad Tip: Capture the breathtaking views and make a group photo album to remember your squad’s adventure in Boston!
Disclaimer
The information above is accurate as of January 2025. Activities, hours of operation, and availability may vary depending on the season, weather, or special events. Always verify the details with each location before planning your outing. nearbywonders.com is not responsible for any changes to events or schedules. Plan ahead to ensure a fun and smooth experience with your squad!