THE USA

The 15 Best Coastal Sailing Trips in the USA

30 sailing trips  ·  from $35 a head

San Diego bays, Charleston harbour, Newport under the bridges and the Hudson past the skyline. These 15 are flat-water afternoons, priced and timed, with the shortest first.

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - Sunset views, city lights, and changing weather
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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - The 8:30 a.m. start and check-in routine
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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

San Francisco Bay Sailing Cruise - Pier 39 departure and the first views
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San Francisco Bay Sailing Cruise

3.San Francisco Bay Sailing Cruise

★★★★★★★★★★5.0 · 629 reviews · 1 hour 30 minutes (approx.) · from $72

Review of San Francisco’s 1.5-hour Adventure Cat sailing cruise, with Golden Gate Bridge views, Alcatraz, Sausalito, tips, and honest value advice.

“We were blessed with a small group of travellers. Got to chat to our operators, have great photos taken and really enjoy the experience of the wind in our hair and no engine noise sailing under the famous Golden Gate Bridge.”

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Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor - Fort Sumter and the story of Charleston Harbor
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Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

4.Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

★★★★★★★★★★4.5 · 620 reviews · 1 hour 30 minutes (approx.) · from $45

Review of Charleston’s 90-minute Schooner Pride dolphin cruise, with Fort Sumter, harbor views, sailing tips, pricing, and honest drawbacks.

“Was an amazing experience will do that again, the ship and the crew was amazing and so helpful allowing people to help raise the sails. What a great service and experience.”

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Classic Tall Ship Cruise in Boston Harbor - Setting Sail on the Liberty Star
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Classic Tall Ship Cruise in Boston Harbor

5.Classic Tall Ship Cruise in Boston Harbor

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

Sail Boston Harbor aboard a classic schooner for skyline views, helpful crew, drinks, and a relaxed 90-minute outing.

“It was a great trip, plenty of wind for a good sail. The crew was informative, attentive and lots of fun!”

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Sightseeing Day Sail around Boston Harbor - Fan Pier, Moakley Courthouse, and Harpoon Brewery
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Sightseeing Day Sail around Boston Harbor

6.Sightseeing Day Sail around Boston Harbor

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

Sail Boston Harbor aboard a classic schooner, with skyline views, island landmarks, a cash-free bar, and flexible 1.5 or 2-hour trips.

“Was a very fun boat ride! The bartender Marcus was incredible he had great energy and made delicious drinks!”

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Kauai’s Na Pali Coast Snorkel and Sail Tour - Seeing the Na Pali Coast from Leila
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Kauai’s Na Pali Coast Snorkel and Sail Tour

Seattle Sailing Harbor Tour - What the two-hour sailing feels like
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Seattle Sailing Harbor Tour

8.Seattle Sailing Harbor Tour

★★★★★★★★★★4.5 · 473 reviews · 2 hours (approx.) · from $39

Review of Seattle’s two-hour tall ship sail, with skyline views, Mount Rainier sightings, practical tips, pricing, and honest drawbacks.

“My friends and I took a trip on s beautiful sail boat in the Puget Sound. The captain and crew were very hospitable.”

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Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling - Biscayne National Park by Sail
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Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

9.Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

★★★★★★★★★★5.0 · 441 reviews · 3 hours 30 minutes (approx.) · from $129

Sail Biscayne Bay on a small wind-powered catamaran with snorkeling, sandbars, wildlife, snacks, and an intimate Miami eco-adventure.

“Amazing time with JP. No extra fees he added on like all the other tour reviews say. We were even late due to Uber and he kindly waited on us. He took us to his fav spots, we saw conch, fish and a crocodile. Had snacks. And he took pics for us. I specifically told him we would write a review for him - very much worth it. Book it!”

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Sunset Sailing Cruise on a Tall Ship in Boston Harbor - Boston Harbor at sunset, from the deck
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Sunset Sailing Cruise on a Tall Ship in Boston Harbor

1.5-Hour San Francisco Bay Sailing Tour - Alcatraz, Angel Island, and the Bay Bridge
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1.5-Hour San Francisco Bay Sailing Tour

11.1.5-Hour San Francisco Bay Sailing Tour

★★★★★★★★★★5.0 · 393 reviews · 1 hour 30 minutes (approx.) · from $99

Review of San Francisco’s 90-minute sailing tour from Pier 39, with Alcatraz, Golden Gate views, drinks, costs, tips, and honest drawbacks.

“Great staff; very pleasant & accommodating. Would recommend it as it was both relaxing and enjoyable”

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2-Hour Sunset Sail on the San Francisco Bay - Sunset views toward the Bay Bridge
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2-Hour Sunset Sail on the San Francisco Bay

12.2-Hour Sunset Sail on the San Francisco Bay

★★★★★★★★★★5.0 · 392 reviews · 2 hours (approx.) · from $129

Review of San Francisco’s two-hour sunset sail, with Golden Gate views, two drinks, group size, weather tips, itinerary, and value advice.

“Well worth it! The crew was very chill, friendly and knowledgeable. The sailing was much smoother than I’d expected.”

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San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included - Meeting Liberty at Safe Harbor Sunroad
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San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

Boston: Harbor Champagne Sunset Sail from Rowes Wharf - Boarding the Adirondack III or IV
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Boston: Harbor Champagne Sunset Sail from Rowes Wharf

Boston: Tall Ship Harbor Sail - The first minutes under sail
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Boston: Tall Ship Harbor Sail

15.Boston: Tall Ship Harbor Sail

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

Review of Boston’s 90-minute tall ship harbor sail, with skyline views, friendly crew, onboard drinks, practical tips, and honest value advice.

“Lots of fun for my family celebrating my husband's 75th birthday.”

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