Top 12 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.Luxury Private Boat Charter in Big Island Hawaii

★★★★★★★★★★5.0 · 56 reviews · 4 hours (approx.)

Start at 8:30 a.m. in Kailua-Kona for a four-hour private charter with Captain Koichiro and a rotating first mate. Snorkel at Kealakekua Bay, watch for dolphins, whales, turtles, or manta rays, and shape the morning around your group.

“We had a fantastic time on our tour, captain and first mate were awesome and let us decide what we wanted to do. We got lucky and were able to see whales and two different species of dolphins . The snorkeling was fantastic and we would definitely recommend this trip!”

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6.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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7.Waikoloa Catamaran Snorkel & Sail Adventure with Lunch

★★★★★★★★★★4.8 · 39 reviews · 3 hours · from $189

Sail from Anaeho‘omalu Bay aboard the Spirit of Aloha for a relaxed three-hour snorkeling trip along the Kohala Coast. You’ll get gear, safety help, reef time, a sandwich lunch, tropical drinks, shaded seating, and views of Mauna Kea and Hualalai.

“Honestly that was 100% worth it, and totally awesome. The whole crew aboard the Spirit of Aloha made the experience extremely special for my girlfriend and I (neither of us had been snorkeling and didn’t know what to expect). Everything was straightforward, easy, and the crew was accommodating every step of the way (drinks, snacks, food, help with the gear). I highly recommend taking this trip with Hawaii Nautical — we will definitely be back the next time we come here!”

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8.Private Charter: Customizable Big Island Boat Adventure

★★★★★★★★★★5.0 · 23 reviews · 4 hours (approx.)

Spend four private hours off Kona with Hang Loose Boat Tours. Your captain can shape the trip around snorkeling, dolphins, whales, or the black volcanic coast. Snorkel gear, wetsuits, snacks, water, and sandwiches are included. Simon, Kenney, and Adam are among the guides named in guest feedback.

“Awesome crew. Awesome time. Highly recommend! Our family age range was 11-76 and all had a blast. Go go go.”

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9.Goodland, FL: The 10,000 Islands Private Sailing Tour

★★★★★★★★★★4.8 · 8 reviews · 2 hours

Join Easy Breezy Charters in Goodland for a two-hour private catamaran sail around Marco Island and the 10,000 Islands. Captain Nick may point out dolphins, sail toward a sunset, or stop at a quiet island for shell collecting. The spacious boat has a restroom, lounging space, and bottled water.

“The highlight of our vacation! Friendly captain, a beautiful sunset, and lots of dolphins. Would highly recommend!”

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10.Private Boat Charter for Masonboro Island and Wrightsville Beach

★★★★★★★★★★5.0 · 8 reviews · 5 hours (approx.)

Captain Reggie takes your private group of up to six from Carolina Beach through the Intracoastal Waterway, Banks Channel, and Wrightsville Beach to Masonboro Island. Expect beach time, house and waterway views, onboard restroom, WiFi, fuel, and a flexible five-hour outing.

“We had a wonderful time with Captain Reggie on his beautiful boat! We loved Masonboro Island it was such a gorgeous beach and he treated us like family. We will definitely recommend and be back to explore more!”

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11.Sail Bainbridge Island & Seattle Waters – Classic Sailboat

★★★★★★★★★★5.0 · 3 reviews · 2 hours

Meet Captain Ben at Harbour Marina on Bainbridge Island for a private two-hour sail aboard a classic 44-foot ketch. Learn basic sailing, take the wheel, and watch for sea birds, seals, orcas, distant Mount Rainier, and the Seattle skyline.

“I loved this sail so much the first time that we brought our kids along for the second experience, and they absolutely loved it too! As a returning customer, I can honestly say it’s totally worth the cost, and don’t think twice—do this, you won’t regret it! We saw a rare elephant seal, which was incredible to witness, and Captain Ben also saw orcas with clients the day before—something I didn’t even know we might see! Going to have to go a third time. Be sure to grab a coffee from the adorable, Instagram-famous Pegasus Coffee at the marina before heading out—it's the perfect start—and they also offer amazing sunset…”

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12.Stock Island Wind & Wine Sunset Sail aboard classic Schooner

★★★★★★★★★★5.0 · 2 reviews · 2 hours · from $133

Meet your captain at Perry Hotel & Marina, then board a historic schooner for a two-hour sunset sail. Expect eight wines, five premium beers, charcuterie, and a relaxed English-guided evening on the water. The $133 price suits travelers seeking a polished, intimate alternative to a basic sunset cruise.

“Apps were light but good! Wine and drinks were also nice. Gorgeous evening! We really enjoyed it.”

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