Glide across Boston Harbor aboard a private crewed sailing yacht, taking in the city skyline, historic harbor islands, and the storied waterfront from the water. An utterly civilized and unforgettable perspective on one of America's great port cities.
What to expect
Step aboard a beautifully maintained sailing vessel right from the Boston waterfront and cast off into the harbor. Your experienced captain narrates the history of the port — from colonial maritime trade to the tea ships of 1773 — as the city's glittering skyline unfolds astern. Spot harbor seals on the outer islands, raise a glass of Champagne as you pass Logan Airport's flight path, and feel the salt breeze of Massachusetts Bay. The return glide into the Inner Harbor with the Bunker Hill Monument lit above Charlestown is genuinely breathtaking.
Good to know
Charter departures are from Fan Pier Marina, a 10-minute walk from the Black Falcon Cruise Terminal. Pre-book 4–6 weeks ahead in summer. Allow a generous buffer before all-aboard — harbor traffic can slow returns. Bring a light layer; sea breeze on the harbor is cooler than the city.