12 Boston Sunset & Cocktail Cruises Worth Booking

1.Boston Harbor Sunset Cruise

★★★★★★★★★★4.5 · 888 reviews · 1h 30m · from $31Our pick

Review of Boston’s 90-minute sunset harbor cruise, with skyline views, USS Constitution, history, onboard bar, pricing, and practical tips.

“I highly recommend this harbor cruise!! I took my husband for his 60th birthday. The boat was nice with outdoor seating. The captain’s narration was interesting and fun. Seeing the city go from sunset to nighttime was amazing. You can’t beat this experience! Reserve your parking ahead across the street at the 55 Purchase Street/International Place garage. We paid $15 altogether booking it ahead. Don’t miss this! We loved it!!”

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2.Boston Harbor Sunset Cruise

★★★★★★★★★★4.5 · 632 reviews · 2 hours (approx.) · from $54

Watch Boston’s sunset from the harbor, hear the USS Constitution’s cannon, and enjoy skyline views, light commentary, and onboard drinks.

“Unfortunately for us, we had a rainy sunset cruise. However, still had a wonderful time, through some mist and rain, we were still able to see the city and learn some key features. We enjoyed a light bite and enjoyed the seasonal drink menu as well.”

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3.Harbor Sunset Yacht Cruise

★★★★★★★★★★4.6 · 570 reviews · 2 hours · from $54

Cruise Boston Harbor at sunset aboard the Northern Lights, with skyline views, light commentary, a full bar, and cannon fire from USS Constitution.

“The cruise was very nice. The food and drinks were good. But we have to wait for our food more time than we expected.”

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4.Narrated Sunset Cruise of Boston Harbor

★★★★★★★★★★4.0 · 532 reviews · 1 hour 30 minutes (approx.) · from $29Best value

See Boston Harbor at sunset, hear live history, and watch the skyline light up on this relaxed 90-minute cruise from Rowes Wharf.

“very little fact narration, most of the time spent identifying other cruise ship and hearing about the encore shuttle. not much distance covered. took an extra 20 minutes for them to even be able to dock the boat. don’t waste your money.”

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5.Sunset Sailing Cruise on a Tall Ship in Boston Harbor

★★★★★★★★★★4.5 · 414 reviews · 2 hours (approx.) · from $68

Review of Boston’s two-hour sunset tall-ship cruise, with skyline views, drinks, crew tips, pricing, weather rules, and booking advice.

“Absolutely loved this experience aboard the Liberty Star. We had gorgeous city views from the water. The captain and deck hands were professional and informative yet extremely funny. Price was fair and we enjoyed the drink selection aboard.”

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6.City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

★★★★★★★★★★4.5 · 411 reviews · 1 hour 30 minutes (approx.) · from $56

Watch Boston’s skyline turn gold on a 90-minute narrated harbor cruise with sunset views, historic sights, and the USS Constitution’s cannon salute.

“The boat tour was great. Great views & the tour guide made it very enjoyable & funny. Only bad part was the annoying family that was being very loud & listening to music the whole time on their phone. Would have liked to throw them overboard. Would still highly recommend though!”

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7.City Cruises Sunset Skyline Cruise with Commentary

★★★★★★★★★★4.6 · 381 reviews · 1h 30m · from $55

See Boston Harbor at sunset, hear lively history, and watch the USS Constitution fire its traditional cannon salute on a 90-minute cruise.

“lots of fun! Get to the meeting place early because a long line will form. The first in line will get the best spots on the boat. The guide (Holly) was fantastic. The boat had a cash bar! Would absolutely do again and recommend to anyone visiting Boston.”

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8.Harbor Champagne Sunset Sail from Rowes Wharf

★★★★★★★★★★4.8 · 299 reviews · 2 hours · from $82

Sail Boston Harbor at sunset aboard a classic schooner, with skyline views, historic landmarks, friendly crew, and drinks available onboard.

“This experience was so relaxing and beautiful. The staff was so attentive it made for a perfect evening. Thank you.”

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9.Boston Harbor Sunset Sail Tour

★★★★★★★★★★5.0 · 132 reviews · 2 hours (approx.) · from $82Top rated

Review of Boston’s two-hour sunset sail, with skyline views, harbor islands, helpful crew, onboard drinks, costs, and practical tips.

“Beautiful cruise in the harbor. Great backdrop of the city at sunset and planes landing over your head. Great and helpful staff.”

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10.Sunset Tall Ship Harbor Cruise

★★★★★★★★★★4.8 · 115 reviews · 2 hours · from $68

Sail Boston Harbor at sunset aboard a classic tall ship, helping raise the sails, enjoying skyline views, and buying local drinks onboard.

“A perfect way to relax after a busy day in Boston. The view is spectacular and the crew was so friendly.”

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11.Charles River Sunset and Cocktail Cruise

★★★★★★★★★★4.4 · 50 reviews · from $36

Watch Boston and Cambridge glow from the Charles River on a 90-minute sunset cruise with music, cocktails, and covered seating.

“Disappointing. No narrative or explanation was given of what we were seeing along.”

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12.Holiday Sunset Cruise in Boston Harbor

★★★★★★★★★★5.0 · 11 reviews · from $70

Cruise Boston Harbor at sunset aboard a heated 1920s-style yacht, with skyline views, holiday music, hot drinks, and historic sights.

“I had a fantastic time. I will go back next year for the holiday hot chocolate cruise. The reason I gave it 4 stars is because at first we were given the seat next to the bar two steps down from the main floor where all the fun was happening. Our tRead more”

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