12 Sailing Yacht Charters in the USA Worth Booking

1.Fort Lauderdale Sailing Charter

★★★★★★★★★★5.0 · 387 reviews · 4 hours (approx.) · from $150Our pick

Captain Dan takes your private group from 937 Mandarin Isle through Fort Lauderdale’s New River, past grand homes and yachts, then toward the Atlantic. Bring your own food and drinks, learn basic sailing, swim if conditions allow, or simply relax aboard the Wind Pirate.

“Captain Dan is knowledgeable about local history of the water and real estate. The best investment of time for our week. You could not have a better host and hostess.”

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2.4-Hour Fort Lauderdale Sailing Charter

★★★★★★★★★★5.0 · 311 reviews · 4 hours (approx.) · from $148

Sail Fort Lauderdale aboard Daffy with Captain Charlie for four hours, passing mansions, yachts, Port Everglades, and the Atlantic coast. Bring your own food and drinks, take a turn at the wheel, and choose between a relaxed dockside stay or a trip out to sea. The boat holds up to six people.

“Captain Charlie was very amusing. A sense of humor is a must on this adventure cause the Captain is a character in his own right. He was very understanding when my husband got sea sick and puked on the side of the boat. Please take his advice and take the motion sickness meds if you are not familiar with sailing. He warned us and we didn’t listen.”

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3.Luxury Sailing Tour of San Diego’s Bay and Coastal Waterways

★★★★★★★★★★5.0 · 187 reviews · from $119

Spend two hours aboard a Catalina 34 sailboat with a local captain such as Mike or Peter. You’ll see downtown San Diego, the bay, coastal waters, and possibly the Coronado Bridge. Choose morning, afternoon, or sunset sailing, and bring your own alcohol if you’re over 21.

“Let me start by saying, I booked this experience specifically because so many reviews spoke so highly of Captain Mike. They were right! Couldn’t have asked for a better captain. Sunscreen, sodas, waters, and a variety of chips weRead more”

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4.Sailing Charters in Wilmington

★★★★★★★★★★5.0 · 184 reviews · 2 hours (approx.) · from $89

Join Captain Oliver for a private two-hour sail from 5 N Water St in Wilmington. Your group of up to six can see the Riverwalk and state ports, help steer or raise the sails, and bring drinks and snacks for a sunset cruise.

“That was so awesome first time on a sailboat and was so relaxing and calming and the Captain was so nice and detailed.”

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5.Sailing on Historic Schooner Yacht in Salem, MA

★★★★★★★★★★5.0 · 172 reviews · 2 hours (approx.)

Spend about two hours aboard a beautifully maintained classic schooner, sailing from Salem toward Marblehead and the islands of Salem Sound. Captain Seth and crew members such as Kos and Kate may invite you to help raise the sails, explain the vessel, and point out lighthouses. Drinks are available for purchase onboard.

“My husband and I had the most fun not only relaxing on the sail boat, but also participating with lifting the sails and just being a part of the crew. We will do this again when we are back in the area. The crew was fantastic too!!”

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6.Hilton Head Island: America’s Cup Sailing Yacht Cruise

★★★★★★★★★★4.8 · 152 reviews · from $53Cheapest seat

Spend 90 minutes aboard Stars & Stripes, the 12-meter yacht raced by Dennis Conner in the 1980 America’s Cup. Your English-speaking crew may let you raise sails or take the helm while sharing local history around Calibogue Sound. Captain Peter and crew members such as Luke and Taylor have earned warm praise.

“The Captain was great with letting us take the helm and also making sure we got great pictures. He let us know when there would be great shots and they were! The crew were fantastic. It was the highlight of our vacation!”

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7.Daytime Sailing Along San Diego’s Skyline

★★★★★★★★★★5.0 · 145 reviews · 2 hours (approx.) · from $89

Sail San Diego Bay aboard a yacht limited to six people. Expect a relaxed two-hour cruise, an included glass of wine, bean bags, blankets, and views of the Midway, naval ships, skyline, sea lions, and dolphins. Captains such as Adam, Nick, Rick, Bree, and Patrick keep the outing easygoing and personal.

“Very pleasant and relaxing experience, sailing in a marina, music and wine provided. Me and My husband really enjoyed it.”

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8.Luxury Catamaran Sailing Charter of San Diego

★★★★★★★★★★5.0 · 87 reviews · 2 to 8 hours (approx.)

Book a private 2 to 8-hour catamaran charter from San Diego for your group. The crew takes you from Mission Bay toward La Jolla Cove or Sunset Cliffs, with bottled water, two ice-filled coolers, and time to bring your own food and drinks. Maddie and Jake are among the crew members praised for friendly service.

“The whole experience was enjoyable. We plan on doing another trip again. The crew was awesome. They took us out and we saw dolphins up close and personal.”

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9.Luxury Catamaran Sailing Charters in Maine

★★★★★★★★★★5.0 · 85 reviews · from $135

Captain Nils and first mate Nick take you from Saco River past Wood Island Lighthouse and Old Orchard to Biddeford Pool and Cape Porpoise. This two-hour catamaran sail carries no more than six people, offers indoor and outdoor seating, and lets you bring your own food and drinks.

“Beautiful day, calm seas, great crew. Surprisingly it was a very relaxing sail. We’d do it again, although the weather is probably not under control of the company.”

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10.Private Sailing Charter with Captain, BYOB

★★★★★★★★★★5.0 · 64 reviews · 2 hours 30 minutes (approx.)

You and up to five companions sail Charleston Harbor for about 2.5 hours with a captain at the helm. Bring wine, beer, snacks, or a picnic, then watch the Battery, Fort Sumter, Ravenel Bridge, USS Yorktown, and St. Michael’s Church slide by. Sunset departures offer the best light for photos.

“Nice relaxing trip and a great sailing day overlooking all areas of Charleston and surrounding areas”

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11.Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

★★★★★★★★★★5.0 · 55 reviews · 2 to 4 hours (approx.)

Reserve the 50-foot sailing yacht Fate for a private Charleston Harbor sunset cruise for up to six people. Captain Scott and rotating first mates such as Maddie, Sam, Will, Grace, or Adam guide you past the Battery, Ravenel Bridge, USS Yorktown, and sometimes Fort Sumter. Bring your own alcohol and snacks.

“We so enjoyed sails up, sailing. The weather was beautiful, the yacht beautiful, and our captain and assistant wonderful. Thank you. Book - you’ll love every second.”

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12.Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

★★★★★★★★★★5.0 · 42 reviews · 2 to 4 hours (approx.)

Spend two to four hours on Fate, a private 50-foot sailing yacht for up to six people. Captain Scott, Will, Adam, or other crew members may guide you past the Battery, Ravenel Bridge, USS Yorktown, and possibly Fort Sumter. Soft drinks and water are included, and you may bring alcohol.

“Great trip! Definitely worth it!! Amazing crew and captain! They were very knowledgeable about the area and they are experienced sailors.”

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