USA SAILING TOURS

Sailing the US Coasts: 15 Trips Worth the Ticket

306 sailings  ·  from $11 a head

Key West schooners, Waikiki catamarans, Maine sloops with a ten-week season and Virgin Islands reef days. The 15 below sort them by what they cost, how long they run and which months they actually sail.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - Fort Zachary Taylor and the open-water turn
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Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Sail from Key West for about two hours aboard a spacious catamaran with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and hors d’oeuvres. Local musicians provide live music as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Arrive 30 minutes early and bring a sweater for cool or windy evenings.

“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”

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Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - What the Moana Catamaran feels like underway
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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

2.Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89Top rated

Board the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a two-hour sunset sail along Waikiki and past Diamond Head. Your captain and crew serve a complimentary first drink from the premium bar, with more available for $8. Look for dolphins, and humpback whales from November through May. Shoes are collected before boarding.

“A really wonderful expierence, we did the VIP which we liked to board early and get the free drinks included. Lovely hosts and weather was amazing!”

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Waikiki Turtle Snorkel and Sail on Hawea Catamaran - The Hawea Catamaran and the Sailing Return
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Waikiki Turtle Snorkel and Sail on Hawea Catamaran

3.Waikiki Turtle Snorkel and Sail on Hawea Catamaran

★★★★★★★★★★5.0 · 1,655 reviews · 2 hours 30 minutes (approx.) · from $89

Meet at the Duke Paoa Kahanamoku Statue for a 2.5-hour catamaran trip to Turtle Canyon. The crew provides snorkel gear and guides you to turtles, tropical fish, reefs, octopus, and starfish. Morning and afternoon departures are available, with snacks, drinks, and a sailing ride along Waikiki included.

“The crew made this an awesome, safe, and fun experience! The bar onboard was a great bonus after snorkeling :-)”

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Key West Afternoon Snorkel Sail with Unlimited Cocktails! - Snorkeling over shallow coral reef
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Key West Afternoon Snorkel Sail with Unlimited Cocktails!

4.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef, about 7.5 miles offshore. The crew supplies masks, fins, instruction, and safety guidance. Expect roughly 45 to 60 minutes in the water, then beer, wine, soft drinks, and cocktails on the ride home. Captain Brett has led some departures.

“The crew is great! They explained how to use the equipment and worked to make the experience a great one!”

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Setting sail with wine and small plates
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Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

5.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125

Spend about two hours sailing from 255 Front Street with a group capped at 26 people. The crew serves up to eight wines, five beers, soft drinks, and easy-to-eat hors d’oeuvres while sharing stories and tending to the boat. Recent sailings have featured crew members including Mary, James, Connor, Lexi, Tony, and Molly.

“Our sunset sail was perfect from start to finish. We absolutely loved the wine tasting and appetizers — you never know what you’re going to get on these types of excursions, and sometimes you brace yourself for cheap wine and sad snacks… but this was the total opposite. The wines were genuinely great bottles, and the cheese apps were delicious and beautifully done. We also adored our all-women crew. They were fun, warm, and made the whole experience feel extra special — the perfect vibe for a girls trip celebrating our 40ths. Would 100% recommend this sail to anyone looking for something elevated, relaxing, and unforgettable.”

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Key West Sunset Sail with Live Music, Drinks and Appetizers - A 65-foot catamaran with room to move
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Key West Sunset Sail with Live Music, Drinks and Appetizers

6.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Spend about two hours aboard Fury’s 65-foot catamaran, with live local musicians, unlimited margaritas, champagne, beer, wine, soda, and seasonal appetizers. You can dance, sit on the sundeck, or watch the sunset from shaded decks. The cruise returns to Greene Street in time for dinner.

“Sunset was amazing. Staff were great and very engaging. Service was great. Lots to eat & drink. It was a beautiful night.”

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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure - Turtles, fish, and the luck of the day
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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

7.Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

★★★★★★★★★★4.5 · 936 reviews · 2 hours 30 minutes (approx.) · from $76

Sail from Kewalo Harbor to Turtle Canyon for a guided family snorkel with provided gear, certified lifeguards, and a secured raft for children and beginners. You may see turtles, tropical fish, starfish, octopuses, dolphins, or even a monk seal. The first drink from the premium bar is included.

“Such a great experience even with 2 kids.We saw 2 turtles and tons of fish. Everyone who worked the boat was very knowledgeable and sweet. One even swam down and brought up a sea urchin for my son to hold. Great adventure!!”

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Sunset Sail in Key West with Beverages Included - Watching Key West’s Sunset Celebration from offshore
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Sunset Sail in Key West with Beverages Included

8.Sunset Sail in Key West with Beverages Included

★★★★★★★★★★5.0 · 907 reviews · 1 hour 30 minutes (approx.) · from $79

Sail from the Hyatt Centric Key West Resort aboard Floridays for about 90 minutes, with champagne, wine, margaritas, beer, and soft drinks included. The crew, including Eric, Carlo, Hunter, Chuck, Lori, and Janet on various departures, keeps the mood relaxed while you watch the sunset and the nightly waterfront celebration from the water.

“This is a great cruise. We did not want a loud and loaded up party boat. Instead we wanted a nice and quiet cruise. Our boat was a 54 ft sailboat and we had about a dozen people on the boat (I think it holds twice that). The captain and mate were very nice and informative. Plenty of wine, prosecco and beer on board. If you want a peaceful and pleasurable sunset cruise, this is the one.”

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2 Hour Sailing Cruise on Lake Tahoe - Leaving from 900 Ski Run Boulevard
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2 Hour Sailing Cruise on Lake Tahoe

9.2 Hour Sailing Cruise on Lake Tahoe

★★★★★★★★★★5.0 · 886 reviews · 2 hours (approx.) · from $140

Spend about two hours sailing Lake Tahoe from 900 Ski Run Boulevard aboard Blue, a Coast Guard-certified 40-foot yacht. Public cruises are capped at 14 people, with local beer, wine, water, and soft drinks included. Captains such as Justin, Kyle, David, and Nellie share lake details while the route changes with the wind.

“Perfect day on the lake with such great captains! Wind was just enough that it was a nice and steady ride.”

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Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - The marina meeting point and boarding routine
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Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

10.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122

Board America 2.0 at Key West Bight Marina for a two-hour sunset sail past Fort Zachary, Sunset Pier, and Sand Key Lighthouse. Captain Janet, Captain Rae, Captain Dan, and their crews have been praised for friendly service, clear sailing explanations, and hands-on moments such as raising the sails. Beer, wine, Champagne, soda, and plated hors d’oeuvres are included.

“This was our first time sailing on a schooner and it was amazing. Our captain Dan and his crew were all so nice and welcoming. We had such a wonderful evening. We will definitely be back aboard the America 2.0 next year.”

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Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail - Sailing through the Key West National Wildlife Refuge
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Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

11.Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

★★★★★★★★★★5.0 · 767 reviews · 6 hours 30 minutes (approx.) · from $152

Join Danger Charters at Opal Key Resort for a 6.5-hour sail aboard a 65-foot schooner. You’ll snorkel in the Florida Keys National Marine Sanctuary, kayak through mangroves, and explore Key West National Wildlife Refuge. Guides such as Daniel, Brian, Joe, and Captain Janet have helped make the trip friendly, informative, and easygoing.

“We had great experience! The crew was amazing:the capital Evan and his crew was very friendly, helpful and made our trip comfortable and so many ways”

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Afternoon Sail & Snorkel to the Captain Cook Monument - One hour in the marine preserve
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Afternoon Sail & Snorkel to the Captain Cook Monument

12.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 722 reviews · 3 hours (approx.) · from $136

From Keauhou Bay, you ride along Kona's lava coast to Kealakekua Bay, where a guide leads a one-hour snorkel near the Captain Cook Monument. Sea Paradise supplies masks, fins, flotation gear, reef-safe sunscreen, snacks, fruit, and drinks. Expect a powered catamaran, cultural commentary, and a maximum of 44 people.

“The cruise was a lot of fun and supplied all the equipment needed for a great snorkeling adventure. The crew was informative and regarded safety as a high priority for those on board. We had an added bonus to see a pod of dolphins following the boat as we headed back to the harbor. Definitely recommend!”

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Sunset Dolphin Sail Aboard the Privateer Catamaran - Boarding a 52-foot catamaran
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Sunset Dolphin Sail Aboard the Privateer Catamaran

13.Sunset Dolphin Sail Aboard the Privateer Catamaran

★★★★★★★★★★5.0 · 709 reviews · 2 hours (approx.) · from $45Best value

Sail the Gulf of Mexico from Panama City Beach aboard the 52-foot Privateer catamaran for about two hours. You get one drink, tropical music, sunset views, and a chance to spot dolphins, deer, and sometimes sea turtles. Captain Mike, Lamar, Chelsea, Teagan, Jess, and Jeff are among the crew members you may meet, depending on the evening.

“The captain and crew were really hospital and lively. I enjoyed the dolphins and energy during the cruise. The sunset was beautiful and calming.”

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Passing Mallory Square and Key West’s western shore
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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

14.Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

★★★★★★★★★★4.5 · 699 reviews · 2 hours 30 minutes (approx.) · from $89

Sail from Key West’s Historic Seaport on a catamaran with Captain Daniel, John, Jordan, Gracie, and other rotating crew members. Look for wild dolphins, pass Mallory Square, Fort Zachary Taylor, and Sunset Key, then settle in for sunset with wine, champagne, beer, and tapas including shrimp cocktail. Dolphin sightings and sailing under wind are not guaranteed.

“Best couple hours during our entire vacation. Sunset, dolphin, drinks, snacks, romantic,, picture perfect.”

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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - Reaching the Captain Cook Monument
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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

15.Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

★★★★★★★★★★5.0 · 695 reviews · 4 hours (approx.) · from $189

Set sail from Kailua-Kona aboard a 50-foot catamaran with a friendly crew such as Captain Dan and Captain Jacques. Enjoy Kona coffee and pastries, snorkel for about an hour at Kealakekua Bay, then build a deli lunch before sailing home. Instruction, gear, flotation noodles, drinks, and reef guidance are included.

“Amazing snorkeling trip. Friendly and helpful crew, amazing boat and snorkeling gear and the fish and coral are incredible!”

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