On the water · BOSTON HARBOR CRUISES

Boston Harbor Cruises: the 15 Worth Booking

29 tours  ·  from $27 a head

Boston runs tall ships alongside the big sightseeing boats, and the season closes when the weather turns. The 15 below cover the schooners, the historic harbour loop and the sunset sailings, with prices and departure points.

City Cruises Boston Historic Sightseeing Harbor Cruise - Boarding at 1 Long Wharf
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City Cruises Boston Historic Sightseeing Harbor Cruise

1.City Cruises Boston Historic Sightseeing Harbor Cruise

★★★★★★★★★★4.5 · 1,388 reviews · 1 hour (approx.) · from $46Our pick

Set out from 1 Long Wharf for a one-hour narrated cruise through Boston’s inner and outer harbor. You’ll see the USS Constitution, Boston Tea Party ships, Old North Church, Boston Light, Fort Independence, and the Harbor Islands area. Guides such as Kevin and Holly bring the history to life, while indoor and outdoor seating helps in changing weather.

“The tour itself was great - especially the narration and history shared. I was a little surprised by the interior of the boat. Definitely aged with torn upholstery. Seemed a bit beat up. Overall still a worth while tour.”

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Boston: Boston Harbor Sunset Cruise - Meeting at Rowes Wharf without missing the boat
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Boston: Boston Harbor Sunset Cruise

2.Boston Harbor Sunset Cruise

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

Meet at Rowes Wharf for a 90-minute English-language cruise around Boston Harbor. You’ll see the skyline, USS Constitution, Logan Airport activity, and the city changing from daylight to evening. A guide provides history and local stories, while the onboard bar sells snacks and drinks. Indoor and outdoor seating are available.

“The weather😂. Everything else was as advertised. The narrator was knowledgable, friendly and really nice to listen to. Thoroughly enjoyed learning all about Boston and its harbour.”

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Boston Harbor Sunset Cruise - Rowes Wharf makes the start fairly simple
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Boston Harbor Sunset Cruise

3.Boston Harbor Sunset Cruise

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

Cruise Boston Harbor for about two hours as sunset colors the skyline and historic waterfront. You will pass the Old North Church, Charlestown Navy Yard, USS Cassin Young, and USS Constitution, whose cannon marks sundown. Choose the open-air deck or heated cabin, and buy drinks or light snacks onboard. Commentary is brief, not a full guided tour.

“Very nice ride around the harbor. The Christmas decorations wade the trip very pleasant. The entertainment was nice too.”

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Classic Tall Ship Cruise in Boston Harbor - Raising the sails with Captain Fredo, Jess, and Max
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Classic Tall Ship Cruise in Boston Harbor

4.Classic Tall Ship Cruise in Boston Harbor

★★★★★★★★★★4.5 · 615 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $35

Board the Liberty Star at Marina Overlook for a relaxed 90-minute sail around Boston Harbor. Captain Fredo and crew members Jess and Max may invite you to help raise the sails, while you enjoy skyline views, snacks, drinks, and fresh air. The route depends on wind and conditions, so this is a sailing experience, not a guaranteed trip to the harbor islands.

“Just loved the sailboat — not your usual tourist attraction, but definitely something worth doing! Pure zen time: peaceful, beautiful, unforgettable.”

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Sightseeing Day Sail around Boston Harbor - Fan Pier, the courthouse, and Harpoon Brewery
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Sightseeing Day Sail around Boston Harbor

5.Sightseeing Day Sail around Boston Harbor

★★★★★★★★★★5.0 · 541 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $66Top rated

Step aboard the Adirondack III or IV at Rowes Wharf for a 1.5 or 2-hour sail past Boston’s Seaport, Fan Pier, Fort Independence, Spectacle Island, and Long Island. This is not a fully narrated cruise, but the captain and crew answer questions, explain sailing details, and point out landmarks. Bring a snack, dress warmly, and pay for drinks by card.

“Great time on Boston Harbor. The sailing was great and we enjoyed watching the aircraft coming into Logan International.”

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Narrated Sunset Cruise of Boston Harbor - Rowes Wharf and the first look at Boston Harbor
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Narrated Sunset Cruise of Boston Harbor

6.Narrated Sunset Cruise of Boston Harbor

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

Sail from Rowes Wharf for 90 minutes of live Boston Harbor narration, passing Fish Pier, Logan Airport, East Boston, Charlestown, the USS Constitution, and the North End. You’ll see Boston change from daylight to city lights, with outdoor and indoor seating plus a bar and snacks for purchase. Arrive early for the best upper-deck seats.

“It was super good! Get a seat in the front of the boat and bring a jacket for night cruises. Such a fantastic time!! The microphone was a little quiet in some parts of the ship.”

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Boston: City Cruises Harbor Codzilla High Speed Thrill Boat - The first burst of speed
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Boston: City Cruises Harbor Codzilla High Speed Thrill Boat

7.City Cruises Harbor Codzilla High Speed Thrill Boat

★★★★★★★★★★4.6 · 318 reviews · from $40

Join Boston Harbor City Cruises at One Long Wharf for a 45-minute high-speed ride on Codzilla. Two turbocharged diesel engines power sharp turns, wave crashes, and 360-degree spins while the crew adds a loud soundtrack, comic narration, and safety guidance. Expect strong wind, salty spray, and a real chance of getting soaked.

“as advertised...definitely wear your poncho...we got soaked...”

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City Cruises Boston: Harbor Buffet Lunch or Dinner Cruise - What you will see from the water
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City Cruises Boston: Harbor Buffet Lunch or Dinner Cruise

8.City Cruises Boston: Harbor Buffet Lunch or Dinner Cruise

★★★★★★★★★★4.3 · 306 reviews · 2 - 3 hours · from $77

Spend 2 to 3 hours aboard the Spirit of Boston with a chef-prepared buffet, table service, city views, outdoor decks, and a live DJ. From Commonwealth Pier, you pass the USS Constitution, Zakim Bridge, North End, and Castle Island. Boarding begins an hour early, and the cruise works best for couples, families, and groups who want dinner with music.

“Excellent views of Boston while on the water! Good food and fun activities!”

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Boston: Tall Ship Harbor Sail - Boston skyline views from the deck
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Boston: Tall Ship Harbor Sail

9.Tall Ship Harbor Sail

★★★★★★★★★★4.6 · 261 reviews · 1h 30m · from $35

Leave Fan Pier Marina aboard a classic Liberty Fleet schooner and spend 90 minutes under sail in Boston Harbor. Expect skyline views, harbor traffic, open water, and a friendly crew who may let you help raise the sails. Drinks are sold onboard, but narration is informal rather than scheduled.

“This was such a fun afternoon activity! We had a long layover in Boston so wanted to get out of the airport and do something fun to kill some time. We’ve been to Boston before and done one of the other Harbor Cruises but this was even more fun! The whole crew is so personable and makes the entire ride interactive. They let anyone who wishes to help with raising and lowering the sails. They chat with everyone but also tell little stories and tell you various facts about the boat you’re on and other Boston fun facts. The whole experience was so much fun. We will definitely save this…”

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Boston: Downtown Harbor Sailing Cruise - Inner Harbor Islands and the Charleston Navy Yard
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Boston: Downtown Harbor Sailing Cruise

10.Downtown Harbor Sailing Cruise

★★★★★★★★★★4.8 · 227 reviews · 90 minutes - 2 hours · from $66

Sail Boston Harbor aboard the classic Adirondack III or IV, a pilot schooner that passes the Fish Pier, Castle Island, Moakley Courthouse, Aquarium, and Inner Harbor Islands. Captain Teresa, Captain Adam, and other crew members have earned praise for friendly service and clear answers. Choose a 90-minute or 2-hour cruise, bring a picnic, and pay onboard by credit card.

“Captain Adam took us on a great cruise around the harbor - lots of fun with an upbeat crew and wind in our sails.”

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Boston: New England Harbor Cruise - Boarding at Rowes Wharf
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Boston: New England Harbor Cruise

11.New England Harbor Cruise

★★★★★★★★★★4.5 · 223 reviews · 1 hour - 90 minutes · from $45

Cruise Boston Harbor for 90 minutes aboard a 115-foot motor yacht styled after 1920s New England steamships. From Rowes Wharf, you’ll see the USS Constitution, Bunker Hill Monument, Fort Independence, the Seaport District, and more. The captain offers moderate narration, while the climate-controlled cabin, open deck, bathrooms, and onboard bar keep the ride easy and comfortable.

“A relaxing cruise on a lovely boat. Helpful staff. Highly recomended.”

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Boston Harbor Brunch Cruise - Boarding at Rowes Wharf
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Boston Harbor Brunch Cruise

12.Boston Harbor Brunch Cruise

★★★★★★★★★★4.5 · 143 reviews · 2 hours (approx.) · from $106

Spend about two hours aboard the Northern Lights, a 1920s-style yacht, enjoying brunch and Boston Harbor views. You’ll see sights including USS Constitution, USS Cassin Young, Bunker Hill Monument, Old North Church, and the inner harbor islands. Captain Jessica has led some departures, with light narration rather than a full sightseeing lecture.

“The boat cruise for a group of Floridians reminded them of home! The food and staff was great! The people we shared the cruise with were extremely nice as well.”

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Boston Harbor Sunset Sail Tour - The Crew Makes the Difference
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Boston Harbor Sunset Sail Tour

13.Boston Harbor Sunset Sail Tour

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

Spend about two hours aboard the schooner Adirondack II or III, sailing from Rowes Wharf around Boston Harbor at sunset. You will pass Fan Pier, Castle Island, Fort Independence, Spectacle Island, and Long Island Head Light. This is not a narrated cruise, but the crew can answer questions, serve drinks, and help you enjoy the changing views.

“We had a great experience on the sunset sail. It was easy to find and the captain and crew were great.”

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Boston: Sunset Tall Ship Harbor Cruise - Raising the Sails With the Crew
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Boston: Sunset Tall Ship Harbor Cruise

14.Sunset Tall Ship Harbor Cruise

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

Spend two hours aboard Liberty Fleet’s classic tall ship, sailing from Fan Pier Marina around Boston Harbor at sunset. You can help hoist the sails, ask the English-speaking crew about landmarks, and possibly take the wheel. Drinks, including Boston-brewed beer, are sold onboard, but food is not included.

“We enjoyed this excursion so much. The crew was absolutely phenomenal. Professional while also being really fun, funny, and entertaining. They're characters for sure in the best way. We loved our time on the ship!”

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City Cruises Boston: Premier Brunch or Dinner Harbor Cruise - Choosing between brunch and the three-course dinner
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City Cruises Boston: Premier Brunch or Dinner Harbor Cruise

15.City Cruises Boston: Premier Brunch or Dinner Harbor Cruise

★★★★★★★★★★4.3 · 74 reviews · 2 hours · from $104

Board the Odyssey at Rowes Wharf for a two-hour Boston Harbor cruise with a private table, buffet brunch or three-course dinner, live DJ, dancing, and open-air views. You’ll pass the USS Constitution, Zakim Bridge, Old North Church, and Castle Island. Arrive one hour early to explore the ship at the dock.

“I had a romantic time with my husband. It was our first dinner cruise in the city and even with the supermoon shining on the water, it made the evening more perfect.”

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