Multi-Day Trips in Boston

Discover the rich history, vibrant culture, and captivating beauty of Boston over a series of memorable multi-day trips! Here’s your essential guide to planning an unforgettable journey through America’s “Cradle of Liberty.”

Day 1: Explore Boston’s Iconic Landmarks

Start your adventure at the heart of the city: Freedom Trail. This 2.5-mile-long path connects 16 historic sites, including the Paul Revere House, the Bunker Hill Monument, and the Old North Church.

Next, pay a visit to Boston Common—America’s oldest city park—and stroll around Beacon Hill, admiring its charming Federal-style rowhouses. Don’t forget to check out Faneuil Hall Marketplace for some shopping and dining experiences!

Day 2: Museum Hopping & Waterfront Exploration

Dedicate the second day to Boston’s world-renowned museums, beginning with the Museum of Fine Arts, boasting an extensive collection spanning 5,000 years of art. Afterward, head over to the Isabella Stewart Gardner Museum for a glimpse into Boston’s cultural past.

In the afternoon, explore Boston’s Waterfront. Visit USS Constitution Museum, learn about the city’s maritime history at The Boston Tea Party Ships & Museum, and take a leisurely walk along the Freedom Wharf Pier.

Day 3: Fenway Park, Harvard University & Beyond

Spend your third day immersed in sports and education. Catch a Red Sox game at iconic Fenway Park (be sure to check the schedule in advance) or take a tour of this historic ballpark.

Next, head to Cambridge to explore Harvard University. Walk around Harvard Yard, visit the John F. Kennedy Presidential Library and Museum, and don’t miss the beautiful Longfellow Bridge.

In the evening, unwind at the Charles River with a picturesque sunset view—a perfect end to your multi-day journey through Boston!