Boston is one of the great American cities — compact, walkable, historically layered, and possessed of the specific civic confidence that comes from being the place where a country decided it was done taking orders from England. When VV’s New England and Canada itineraries call at Boston, Sailors get access to the Freedom Trail, the best lobster rolls on the planet, the USS Constitution, Fenway Park, and one of the most genuinely enjoyable food scenes in the northeastern United States.
Getting Around Boston
Boston is one of the most walkable major American cities. The cruise terminal is at the Black Falcon Cruise Terminal in South Boston — about 2 miles from Downtown, easily accessible by water taxi, Uber, or the MBTA (the “T”). Once downtown, almost everything worth seeing is walkable or a short T ride away.
The Freedom Trail
A 2.5-mile walking trail through the heart of historic Boston connecting 16 significant historic sites: the Massachusetts State House, Park Street Church, the Granary Burying Ground (Paul Revere, Samuel Adams, John Hancock), King’s Chapel, the site of the first public school in America, the Old South Meeting House, the Old State House, the Boston Massacre site, Faneuil Hall, Paul Revere’s House, the Old North Church, Copp’s Hill Burying Ground, and USS Constitution. A self-guided walk takes 2–3 hours. Guided tours depart from Boston Common.
The Food: Lobster, Chowder, and More
Boston’s food scene anchors on seafood and does it better than almost anywhere in the country. The priorities:
- Lobster rolls: The debate between warm butter (Connecticut style) and cold mayo (Maine style) is eternal. Both are exceptional. Neptune Oyster in the North End and Row 34 in the Fort Point neighborhood are the benchmarks.
- Clam chowder: New England clam chowder in a sourdough bread bowl at Faneuil Hall Marketplace is the platonic ideal of tourist food that is also genuinely excellent.
- North End: Boston’s Italian neighborhood has been here for over a century and is still producing some of the best cannoli and espresso in the city. Mike’s Pastry or Modern Pastry for the canonical cannoli debate.
Fenway Park
If the Red Sox are playing on your port day, go. Fenway Park is the oldest ballpark in Major League Baseball (opened 1912), the Green Monster is real and extraordinary, and watching a game there with a Fenway Frank and a beer is one of the great American sports experiences. Check the schedule before sailing.
The North End and Waterfront
The North End is a short walk from the cruise terminal through the Waterfront. The combination of the Old North Church, Paul Revere’s House, Christopher Columbus Park, and the Italian restaurant corridor on Hanover Street makes for an excellent half-day loop.
Insider Tips from Joel and Erin
- The water taxi is the fastest way from the terminal to Downtown. Runs from near the Black Falcon terminal to Long Wharf downtown in about 10 minutes. Faster and more scenic than a cab.
- Book Fenway before sailing if there’s a game. Day-of tickets exist but good seats go fast. Check the Red Sox schedule before you book your itinerary.
- Allow the full day for Boston. The Freedom Trail alone is 3 hours. The North End lunch, Fenway, and the Waterfront together make for a full and genuinely excellent port day.
Ready to Explore Boston?
Joel and Erin are certified First Mates. Let them help you build the perfect Boston port day and book the New England sailing that includes it.
Related Reading
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