Top 5 Sailing and Yacht Charters in the USA

1.Hilton Head Island: America’s Cup Afternoon Sail

★★★★★★★★★★4.8 · 167 reviews · 1h 30m · from $55Our pick

Board Stars & Stripes at Harbour Town for a 90-minute sail with Captain Peter and crew. You can relax on deck, help trim the sails, or take the helm while watching for dolphins and enjoying views of the lighthouse and Lowcountry coast.

“At first it looked like it was going to be windless and hot. But once we got a little distance offshore the breeze picked up nicely and it was perfect! The captain and crew were amusing and interesting, and my 28 year old daughter and I had a thoroughly enjoyable experience. The youngsters on board all got a turn at the helm (under the very patient eye of the captain) and I'm sure all went home with a life-long memory.”

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2.Private Sailing Tour through the Ten Thousands Islands

★★★★★★★★★★5.0 · 151 reviews · 2 hours (approx.) Top rated

Join Captain Nick, or possibly Captain Kirk, for a two-hour private sail from Goodland through the Ten Thousand Islands. Help handle the sails or relax on a roomy catamaran while watching for dolphins, turtles, mangroves, tropical scenery, and sunset light.

“When the captain let the sails out. Also he took the time to follow the dolphins. My granddaughter really enjoyed that!!!”

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3.2-Hour Sunset Sailing With Wine In Stock Island

★★★★★★★★★★5.0 · 94 reviews · 2 hours (approx.) · from $125

Spend two hours sailing from Stock Island aboard a schooner with eight wines, five beers, sodas, and charcuterie. The crew, including guides such as Tony, Maria, and Lexi on some departures, serves drinks and helps you enjoy a calm sunset on the water. Ages 13 and up.

“This was an awesome experience. The food and wine selection was great! Staff was awesome! And the views of the sunset were top notch! Would highly recommend!”

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4.Waikoloa: Catamaran Sunset Sail with Cocktails

★★★★★★★★★★4.8 · 68 reviews · 1h 30m · from $159

Spend 90 minutes aboard the Spirit of Aloha catamaran, departing Anaeho‘omalu Bay for a sunset sail past Mauna Kea and Hualālai. Your ticket includes a premium bar, island-style snacks, shaded seating, restrooms, and crew service. Boarding requires a short barefoot walk through seawater from the beach.

“Everything about the sunset sail was awesome. Beautiful sailing and sunset; as well as expert/kind/wonderful captain and crew. I couldn’t have enjoyed it more.”

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5.Big Island: Morning Snorkel Sail to Captain Cook’s Monument

★★★★★★★★★★4.9 · 49 reviews · 4h 30m · from $178

Join Sea Paradise aboard the Hoku Nui at 8:30 am for a breakfast sail to Kealakekua Bay, guided snorkeling near Captain Cook Monument, lunch, and a second site near Red Hill. Crew members provide gear, safety help, local history, and reef tips.

“The excursion was awesome. The only thing, I didn’t realize that the alcoholic drinks were not included in the cost. But overall it was lovely and the snorkeling was top notch.”

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