Boston Sailing Tour: compare 6 options from US$ 51

The verdict

Our pick

Sunset Sailing Cruise Boston Harbor: Classic Tall Ship

›

‹

Sunset Sailing Cruise Boston Harbor: Classic Tall Ship★ 4.59 (491) · 2hfromUS$ 71View ›

Best price

Boston Harbor: Day Sail Cruise on Classic Schooner Boat

›

‹

Boston Harbor: Day Sail Cruise on Classic Schooner Boat★ 4.80 (640) · 1h 30m–2hfromUS$ 54View ›

Top rated

Boston Harbor: Sunset Sail Tour & City Landmarks Cruise

›

‹

Boston Harbor: Sunset Sail Tour & City Landmarks Cruise★ 4.82 (187) · 2hfromUS$ 82View ›

Sort

Boston Harbor Cruise: USS Constitution & Waterfront Yacht Tour

›

‹

Boston Harbor Cruise: USS Constitution & Waterfront Yacht Tour★★★★★★★★★★ 4.75 (12)1h 30mYou board at the Ferry Terminal, settle into comfortable seating on a restored 1920s-style yacht, and spend 1.5 hours cruising Boston Harbor. The daytime option includes live narration from a local guide pointing out the USS Constitution, Bunker Hill Monument, and historic waterfront neighborhoods; the sunset cruise skips the narration and ends with cannon fire at dusk. Either way, you get unobstructed water views and a break from the city's pace, with no need to arrange your own transport or figure out which landmarks matter.Is it for me?Pick this if you want to see Boston's waterfront landmarks without renting a boat or navigating the harbor yourself—the fixed route and included narration (on the daytime cruise) mean you get context and views in a single afternoon or evening, and the small-boat intimacy beats the larger harbor tour crowds.Free cancellationKids −17%fromUS$ 51View ›

Boston Harbor Private Sunset Cruise on Yacht Trinacria

›

‹

Boston Harbor Private Sunset Cruise on Yacht Trinacria★★★★★★★★★★ 5.00 (1)2hA private sunset cruise on Boston Harbor aboard Yacht Trinacria carries only your group and the crew on a 10 to 12 mile loop past the skyline, Logan Airport, Charlestown, the Seaport and East Boston. Water and soft drinks are provided; you're welcome to bring your own food and beverages. The boat travels at a slow pace, giving you time to photograph the bridges and architecture as the sun sets. Departure times shift with the season to catch sunset, and the cruise ends 30 minutes after sunset in August and September.Is it for me?Book this if you want the sunset and the skyline to yourself — the private boat means no crowd between you and the view, and the slow pace gives you time to actually frame the shots instead of watching the moment pass.Instant confirmationfrom · per groupUS$ 1,200View ›

Boston: Private Yacht Harbor Tour & Boston Light Cruise

›

‹

Boston: Private Yacht Harbor Tour & Boston Light Cruise★★★★★★★★★★ 5.00 (1)3h–5hYou get a private yacht with Captain Riccardo, no shared passengers, and the freedom to choose your route — Inner Harbor sightseeing, a full cruise to Boston Light, or autumn foliage. Stops include the USS Constitution, Bunker Hill Monument, Charlestown Navy Yard, and the harbor islands. Bring your own food and drinks; the boat provides water, soda, and fishing gear. Tours last 2 to 5 hours depending on what you pick, with flexible pickup around Boston Harbor.Is it for me?Book this if you want to see Boston Harbor and Boston Light without arranging a shared tour or managing a group schedule — the private boat and flexible timing mean you move at your own pace, and bringing your own food keeps the day exactly how you want it.Instant confirmationfrom · per groupUS$ 2,000View ›

Boston Sailing Tour — what to know before booking

This guide compares 6 bookable options for Boston Sailing Tour, with up-to-date prices and real traveler reviews. Prices start at US$ 51. The average rating is 4.8 out of 5, based on 1,332 traveler reviews.

4 of the 6 options offer free cancellation. 2 private experiences are also available for closed groups. The verdict at the top highlights the travelers' favorite, the best price and the top-rated option, updated with live data.

Frequently asked questions

How much does Boston Sailing Tour cost?

Prices start at US$ 51. There are 6 options to compare, and the final price depends on the date, group size and the option you choose.

Can I book with free cancellation?

Yes: 4 of the 6 options offer free cancellation, so you can book now and confirm your plans later.

Which one is the travelers' favorite?

Sunset Sailing Cruise Boston Harbor: Classic Tall Ship is the travelers' favorite, rated 4.6 out of 5 across 491 reviews.

Are private options available?

Yes, 2 private experiences are available if you prefer a closed group.

More things to do in Boston

Freedom Trail Tours19 optionsMuseums9 optionsBoston City Tour10 optionsBoston Food Tour26 optionsBoston Airport Shuttle7 optionsBoston Ghost Tour13 optionsBoston Trolley Tour7 optionsBoat Tour Boston16 optionsBoston Walking Tour79 optionsNorth End Tours43 optionsNorth End Food Tour9 optionsConcord Tours8 optionsBike Tour Boston5 optionsBeacon Hill Walking Tour23 options