CATAMARAN SAILING TRIPS IN THE USA

15 Catamaran Sailing Trips in the USA Worth Casting Off For

39 sailings  ·  from $35 a head

The 15 best catamaran sailing trips in the USA you can get aboard today, with what each costs, how long it stays out and who it suits. Number one is first for a reason; start there.

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

1.Waikiki Turtle Snorkel and Sail on Hawea Catamaran

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

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

2.Sunset Dolphin Sail Aboard the Privateer Catamaran

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

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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Ko Olina Catamaran Sail and Snorkel with Lunch - The sailing portion is more than transportation
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Ko Olina Catamaran Sail and Snorkel with Lunch

3.Ko Olina Catamaran Sail and Snorkel with Lunch

★★★★★★★★★★5.0 · 630 reviews · 3 hours (approx.) · from $195

Sail Oahu’s west coast aboard a 53-foot catamaran, then snorkel over a reef known for tropical fish and possible sea turtles, dolphins, and whales. The 3-hour trip includes gear, a turkey or vegetarian sandwich lunch, three complimentary cocktails for adults, and juice or soda. Ko Olina pickup is easy, while Waikiki transport costs extra.

“This excursion was by far the best experience we had. For the price it is so worth it. They gave us three free drinks, an amazing sandwich for lunch, and let us snorkel and jump off the boat. We saw wildlife and lots of fish. You won’t regret booking!”

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Sightseeing and Sunset Catamaran Sailing Excursion - Swimming and shelling at a secluded beach
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Sightseeing and Sunset Catamaran Sailing Excursion

4.Sightseeing and Sunset Catamaran Sailing Excursion

★★★★★★★★★★5.0 · 617 reviews · 2 hours 30 minutes (approx.) · from $80

Board the 20-passenger catamaran Cool Beans in Naples for a 2.5-hour day sail or 2-hour sunset cruise. Expect Gulf sailing, dolphins and birds, drinks, and crew members such as Dan, Patrick, Kyle, Toni, or Jack. Day sails may include swimming and shelling at a secluded beach, while sunset trips include a champagne toast.

“Best Sunset sailing in the area. Have tried them all and this is without a doubt the best one. The crew was fantastic.”

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Oahu: Waikiki Sunset Catamaran Sail and Swim - The swim stop before sunset
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Oahu: Waikiki Sunset Catamaran Sail and Swim

5.Waikiki Sunset Catamaran Sail and Swim

★★★★★★★★★★4.7 · 519 reviews · from $44

Spend two hours on Pink Sails Waikiki’s catamaran, leaving Waikiki for a sunset cruise with views of Diamond Head and the shoreline lights. You can jump into the ocean before sunset or stay aboard. English-speaking crew members such as Jamie, Alexio, Peter, and Morgan have earned praise for friendly service, music, photos, and good humor.

“AWESOME! best thing i did in waikiki!!!!! the crew (alex, nici and mo) was amazing and the vibes were GREAT!”

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Sunset Dolphin Sail Aboard the Footloose Catamaran - The Footloose catamaran and where to sit
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Sunset Dolphin Sail Aboard the Footloose Catamaran

6.Sunset Dolphin Sail Aboard the Footloose Catamaran

★★★★★★★★★★5.0 · 442 reviews · 1 hour 30 minutes (approx.) · from $40

Join Paradise Adventures at the Bluegreen Bayside Golf & Spa Resort for a 90-minute sunset sail aboard the 40-foot Footloose catamaran. You’ll cruise the Gulf of Mexico, look for dolphins, enjoy tropical music, and receive one complimentary beverage. Recent crews have included Ryan, Lamar, Gordon, Dale, Mike, and Trevor, though staff may vary.

“We had such a great time. It was absolutely beautiful! Saw several dolphins. The staff were amazing!”

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Waikoloa Signature Catamaran Sunset Sail - Starting at Anaehoomalu Bay
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Waikoloa Signature Catamaran Sunset Sail

7.Waikoloa Signature Catamaran Sunset Sail

★★★★★★★★★★4.5 · 396 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $159

Board a 53-foot power catamaran from Anaehoomalu Bay for a relaxed 90-minute sunset sail along the Kohala-Kona coast. You’ll cruise barefoot, enjoy premium cocktails, beer, wine, snacks, and live commentary, then pause offshore for sunset and a possible green flash. The boat holds up to 49 people.

“This cruise is accessed by a tender boat right off the beach. You have to leave your shoes off, and step up a couple steps to board the tender. It was pretty easy. It is a little bit of a walk from the parking area at Lava Lava beach club, which was fine on the walk there....coming back after dark was more challenging, make sure your phone has a flashlight! The lighting is horrible at the beach club, even with our phone light it was tricky finding our way back safely.”

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From Ma'alaea: 'Alihilani Sunset Sail Catamaran Tour - The Au’Au Channel and Maui’s changing light
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From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

8.From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

★★★★★★★★★★4.8 · 348 reviews · from $114

Set sail from Ma’alaea Harbor aboard the 49-passenger catamaran *‘Alihilani* for two hours in Maui’s Au‘au Channel. Enjoy included drinks and cold hors d’oeuvres while the crew handles the details. Stretch out on the forward trampolines, use the covered seating, and watch for dolphins or humpback whales from December through March.

“The catamaran sunset cruise was amazing from start to finish. The crew was attentive and highly competent. The sunset was breathtaking! I would highly recommend this activity.”

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2.5-Hour Small-Group Catamaran Sunset Sail with Drinks - Meeting at Harbor Island
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2.5-Hour Small-Group Catamaran Sunset Sail with Drinks

9.2.5-Hour Small-Group Catamaran Sunset Sail with Drinks

★★★★★★★★★★5.0 · 223 reviews · 2 hours 30 minutes (approx.) · from $119

Meet Captain Ryan, Matt, Kaya, or Ty at Safe Harbor Sunroad for a relaxed 2.5-hour sunset sail on San Diego Bay. The six-person catamaran passes the USS Midway, downtown, Coronado Bay Bridge, Embarcadero, and Point Loma. Beer, wine, soft drinks, water, blankets, and a bathroom are included, with motor use kept to a minimum.

“Absolutely incredible night. Matt our captain was wonderful, helpful, and informative. The boat was safe and comfortable.”

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Kona Signature Catamaran Sunset Sail - Kailua-Kona views from the water
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Kona Signature Catamaran Sunset Sail

10.Kona Signature Catamaran Sunset Sail

★★★★★★★★★★5.0 · 218 reviews · 1 hour 30 minutes (approx.) · from $109

Sail the Kona Coast aboard a spacious catamaran for about 90 minutes, with Captain Michael and crew members such as Caesar, John, or Kevin often helping on board. You get sunset views, possible dolphins or whales, light bites, a casual dinner, and a full bar with cocktails, beer, wine, soda, and juice.

“A great time with an excellent crew! Food and drinks were delicious and the music was on point. Highly recommend.”

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Catamaran Sailing Dolphin/Manatee Watch in Daytona Beach - Comfort on the Howling Owl
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Catamaran Sailing Dolphin/Manatee Watch in Daytona Beach

11.Catamaran Sailing Dolphin/Manatee Watch in Daytona Beach

★★★★★★★★★★4.5 · 179 reviews · 1 hour 15 minutes (approx.) · from $64

Join Captain Randy and the crew of the Howling Owl for a 75-minute catamaran sail on Daytona Beach’s Halifax River. With room for only six people, the ride feels personal and calm. You’ll have shaded and sunny seating, bottled water, soft drinks, a bathroom, music, and a chance to spot dolphins, manatees, and pelicans.

“Great relaxing boat ride! Captains were very nice. We saw a few dolphins and got to just relax and enjoy the beautiful weather out on the water.”

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Sunset Catamaran Sail in Cocoa Beach - What the two-hour itinerary feels like
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Sunset Catamaran Sail in Cocoa Beach

12.Sunset Catamaran Sail in Cocoa Beach

★★★★★★★★★★5.0 · 176 reviews · 2 hours (approx.) · from $56

Sail from Merritt Island through the Banana River Lagoon and Thousand Islands on a two-hour Cocoa Beach catamaran trip. Captains such as Andrew, Kris, Don, and others share local stories while you watch for dolphins, manatees, turtles, pelicans, and ospreys. Soda and water are included. Bring your own alcohol if desired.

“⭐️⭐️⭐️⭐️⭐️ Amazing Catamaran Experience Had an awesome time out on the catamaran! Captain Andrew and his deckhand Deb were top-notch—friendly, knowledgeable, and made the whole trip smooth and fun. We got to see some incredible wildlife, and there were tons of great photo opportunities. The boat was comfortable, the views were unreal, and the whole experience was one to remember. Highly recommend this trip if you’re in the area.”

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Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans - What the sailing portion feels like
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Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

13.Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

★★★★★★★★★★5.0 · 166 reviews · 2 hours 30 minutes (approx.) · from $79

Set out from Capri Boulevard on the 42-foot Mainecat Cool Beans for a 2.5-hour Naples sailing trip. You can swim to a shell-covered beach, watch for dolphins, and enjoy beer, white wine, soda, and water. Captains Patrick, Dan, and the first mates keep the small group moving safely, though tides and weather can change the beach stop.

“Captain Dan and Magic Mike are Awesome!! This is the second year we have done this cruise and it was so fun!! They are very personable and the group of people on board is small, so it doesn't feel crowded and you get to know each other. 💯 Recommend. The shells on the beach they drop you off near are awesome also!”

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Panama City Beach: Sunset Sail on the Privateer Catamaran - Two hours toward Shell Island
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Panama City Beach: Sunset Sail on the Privateer Catamaran

14.Sunset Sail on the Privateer Catamaran

★★★★★★★★★★4.7 · 138 reviews · from $49

Spend two hours aboard the Privateer catamaran, sailing from Panama City Beach toward Shell Island as the Gulf turns gold and pink. You get one complimentary drink, music on some evenings, and access to a cash bar for more drinks and snacks. Keep watch for dolphins, then return to 4114 Jan Cooley Drive after sunset.

“This was the perfect ending to our vacation. We loved the cruise and the crew was fantastic.”

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Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran - What the Hāwea catamaran feels like
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Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran

15.Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran

★★★★★★★★★★5.0 · 134 reviews · 1 hour 30 minutes (approx.) · from $55

Board the 50-foot Hāwea catamaran near the Duke Kahanamoku Statue at 3:00 pm for a 90-minute sail along Waikiki toward Leahi, better known as Diamond Head. Enjoy included alcoholic drinks, mocktails, music, ocean breezes, and a relaxed crew. Sightings may include dolphins, turtles, flying fish, or seasonal humpback whales.

“Very enjoyable experience. The crew is very friendly and works hard to ensure all passengers are comfortable. I also felt very safe in their care.”

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Newest in Catamaran Sailing Trips in the USA

★ 4.5Key West Dolphin Watch and Sunset Sail on CatamaranFrom $11733 reviews
★ 5.0Bimini Charters – Private Luxury Catamaran 3-hr Sunset SailsFrom $1373 reviews
★ 5.0Bimini Charters – Private 3hr Catamaran Charters, Sail & Snorkel26 reviews
★ 5.0Waikoloa Turtle Catamaran Snorkel SailFrom $1492 reviews
★ 5.0Kona Luxury Catamaran Yacht Snorkel & SailFrom $44940 reviews
★ 5.0Kona Tradewind Catamaran Day SailFrom $8942 reviews
★ 4.5Kona Deluxe Catamaran Whale WatchFrom $10955 reviews
★ 5.0San Diego Bay: 2.5 hour Pure Catamaran Sailing CruiseFrom $11916 reviews
★ 4.7Ocean City: Sailing Catamaran Cruise with CrewFrom $1109 reviews
★ 4.6Orange Beach: Dolphin & Sailing Cruise Aboard 52′ CatamaranFrom $5515 reviews
★ 4.8Monterey Bay: Sunset Catamaran Sailing CruiseFrom $9531 reviews
★ 4.6Monterey: Catamaran Sailing CruiseFrom $6514 reviews
★ 4.7Ma’alaea Catamaran Sunset Sail with AppetizersFrom $13716 reviews
★ 5.0Luxury Catamaran Whale Watch & SailFrom $1192 reviews
★ 5.0Maalaea Harbor: Sunset Sail on a Charming Hawaiin CatamaranFrom $1295 reviews

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