Sailing Boston at a glance
- Our pick: Boston Harbor Sightseeing Cruise: USS Constitution & Islands, US$ 51 per person (1h 30m, 4.52★ · 273).
- Top rated: Boston Harbor Brunch Cruise: 2-Hour Waterfront Tour & Buffet, US$ 106 per person (2h, 4.56★ · 164).
- Private option: Boston Harbor Private Sunset Cruise on Yacht Trinacria, US$ 1,200 per group (2h, 5.00★ · only 1 review).
Price per person across the 5 options priced per person: US$ 51–US$ 106 (median US$ 65). With 100+ reviews: 4 of 7.
Of the 7 options: 7 with live guides in English, 5 with free cancellation, 7 with instant confirmation, 1 with hotel pickup, 3 kid-friendly, 2 private and 5 bookable last-minute.
How we rank: quality, number of reviews, availability, booking conditions and relevance to the topic. In the comparison table, our top 3 comes first. Prices are per person, except options priced per group: that price is for the whole group, and the per-person figure assumes the group is full. “Top rated” = the highest score among options with at least 100 reviews.
Sailing Boston
Based on each operator's calendar. Confirmed when you book.
7 options
Boston Harbor Sail: Classic Schooner with Harbor Islands Sail Boston Harbor aboard a classic schooner past the Seaport District, Castle Island, and harbor islands. Next departure: 1 May 2027 · All ages ★ 4.79 (661 reviews) Duration: 1h 30m–2h Live guide: EN ✓ Free cancellation. from US$ 54 per person
Boston Harbor Sunset Sail: 2-Hour Schooner Tour Sail Boston Harbor for 2 hours aboard a classic schooner at sunset, passing Castle Island, the Seaport District and Harbor Islands. Next departure: 1 May 2027 ★ 4.83 (199 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 82 per person
Boston Harbor Sightseeing Cruise: USS Constitution & Islands Cruise Boston Harbor aboard a 1920s-style yacht with views of USS Constitution, Bunker Hill Monument, and Harbor Islands. Captain commentary, indoor cabin, bar. 1–2 hours. Thu–Sat · 12:30 and 13:00 · All ages ★ 4.52 (273 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 51 per person
Boston Harbor Brunch Cruise: 2-Hour Waterfront Tour & Buffet 2-hour Boston Harbor brunch cruise aboard a 1920s yacht with buffet, views of USS Constitution, Bunker Hill Monument & harbor islands. Captain's narration included. Sat and Sun · 11:00 and 12:00 · All ages ★ 4.56 (164 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 106 per person
Boston Holiday Cocoa Cruise: Sip hot cocoa on the water Cruise Boston's waterfront aboard a heated yacht decorated for the holidays, sipping hot cocoa while passing the Charlestown Navy Yard and Old North. Every day · 12:30, 15:00, 17:30, 20:00 and 20:30 ★ 4.62 (85 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 65 per person
Boston Harbor Private Sunset Cruise on Yacht Trinacria Private sunset cruise on Boston Harbor loops 10 to 12 miles past the skyline, bridges and Seaport in 2.5 hours with water and soft drinks included. Mon, Sat and Sun · No fixed time · Season until 7 Dec ★ 5.00 (1 review) Duration: 2h Live guide: EN · IT ✓ Instant confirmation. from US$ 1,200 per group
Boston: Private Yacht Harbor Tour & Boston Light Cruise Private yacht tour of Boston Harbor featuring USS Constitution, Bunker Hill Monument & Boston Light. Up to 5 hours, flexible pickup. Captain Riccardo's Trinacria. Mon, Sat and Sun · No fixed time · Season until 7 Dec · Pickup available ★ 5.00 (1 review) Duration: 3h–5h Live guide: EN · IT ✓ Instant confirmation. from US$ 2,000 per group
All 7 options, side by side
✓ 2026-11-14| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| Boston Harbor Sightseeing Cruise: USS Constitution & IslandsOur pick | US$ 51 per person | 1h 30m | 4.52★ · 273 | Thu–Sat · 12:30 and 13:00 | English |
| Boston Harbor Brunch Cruise: 2-Hour Waterfront Tour & BuffetTop rated | US$ 106 per person | 2h | 4.56★ · 164 | Sat and Sun · 11:00 and 12:00 | English |
| Boston Harbor Private Sunset Cruise on Yacht TrinacriaPrivate optionPrivate | US$ 1,200 per group up to 6 people · ≈ US$ 200 per person if 6 go | 2h | 5.00★ only 1 review | Mon, Sat and Sun · No fixed time · Season until 7 Dec | English, Italian |
| Boston Harbor Sail: Classic Schooner with Harbor Islands | US$ 54 per person | 1h 30m–2h | 4.79★ · 661 | Next departure: 1 May 2027 | English |
| Boston Harbor Sunset Sail: 2-Hour Schooner Tour | US$ 82 per person | 2h | 4.83★ · 199 | Next departure: 1 May 2027 | English |
| Boston Holiday Cocoa Cruise: Sip hot cocoa on the water | US$ 65 per person | 1h 30m | 4.62★ · 85 | Every day · 12:30, 15:00, 17:30, 20:00 and 20:30 | English |
| Boston: Private Yacht Harbor Tour & Boston Light CruisePrivate · Pickup offered | US$ 2,000 per group up to 6 people · ≈ US$ 333 per person if 6 go | 3h–5h | 5.00★ only 1 review | Mon, Sat and Sun · No fixed time · Season until 7 Dec | English, Italian |
By what you need
- Private (2): Boston Harbor Private Sunset Cruise on Yacht Trinacria (US$ 1,200 per group) · Boston: Private Yacht Harbor Tour & Boston Light Cruise (US$ 2,000 per group)
- With pickup (1): Boston: Private Yacht Harbor Tour & Boston Light Cruise (US$ 2,000 per group)
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