7 Sailing Yacht Charters in the USA Worth Flying For

1.Sailing on Historic Schooner Yacht in Salem, MA

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

Set sail from 10 Blaney Street in Salem aboard the classic schooner Malabar for about two hours. You’ll cruise Salem Sound, Marblehead, and nearby islands while the crew explains the vessel and may invite you to help raise the four sails. Captain Seth and crew members such as Kos and Kate bring the boat’s story to life. Drinks are available for purchase onboard.

“Very nice and relaxing experience! The crew were very helpful and welcoming! A very romantic setting for couples as well.”

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

★★★★★★★★★★4.8 · 152 reviews · from $53 a seat Best value

Spend 90 minutes aboard Stars & Stripes, the 12-meter yacht Dennis Conner raced in the 1980 America’s Cup. Your English-speaking crew explains the boat, invites you to help raise sails or take the helm, and points out Hilton Head sights in Calibogue Sound. Captain Peter and crew members such as Luke and Taylor have earned praise for their friendly, hands-on approach.

“We had a perfect day- sunny but not too hot- with a nice wind- the captain and crew were so nice! Very informative re the boat and the surrounding islands. I enjoyed chatting with everyone on board. I could have stayed out there twice as long!”

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3.Daytime Sailing Along San Diego’s Skyline

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

Spend about two hours aboard a sailing yacht with a captain such as Adam, Nick, Rick, Bree, or Corinne. You’ll cruise calm San Diego Bay, pass the USS Midway from the water, watch for sea lions and dolphins, and relax on bean bags with wine, cushions, and blankets. The boat carries no more than six people.

“Nick was a great Captain! It was very relaxing and fun! I would definitely recommend adding this to your to do list when in San Diego.”

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

★★★★★★★★★★5.0 · 55 reviews · 2 to 4 hours (approx.) · whole boat $760, up to 6

Set sail from 17 Lockwood Drive aboard the 50-foot yacht Fate for a private Charleston sunset cruise. Captain Scott and crew members such as Will, Sam, Grace, Maddie, and Adam have hosted sailings featuring the Battery, Ravenel Bridge, USS Yorktown, USS Laffey, and sometimes Fort Sumter. Soft drinks are included, while you bring alcohol and snacks or arrange catering.

“We had the absolute perfect sunset sail. We had Captain Scott with Will as his first mate. The boat is spacious and comfortable. I would highly recommend this trip!!”

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5.San Diego: Classic Yacht Sailing Experience

★★★★★★★★★★5.0 · 47 reviews · 2h 30m · from $109 a seat

Spend 150 minutes aboard Liberty, an early-1900s replica Friendship sloop, with Captain Phillip at the helm. Sip beer, white wine, or soft drinks as you pass the USS Midway, Coronado Bridge, Point Loma, and the Star of India. The small-group cruise can include hands-on sailing, wildlife viewing, and a private option when you book all six seats.

“We absolutely loved the sunset sail. It was a great way to start our vacation and the best GYG tour we’ve ever done.”

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

★★★★★★★★★★5.0 · 42 reviews · 2 to 4 hours (approx.) · whole boat $599, up to 6

Sail privately aboard the 50-foot yacht Fate with Captain Scott, Will, Adam, or another experienced local captain and a first mate such as Sam or Monique. Bring your own alcohol, enjoy complimentary soft drinks, and cruise past the Battery, Ravenel Bridge, USS Yorktown, and sometimes Fort Sumter.

“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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7.San Diego Bay Private Sailing Experience Aboard Classic Yacht

★★★★★★★★★★5.0 · 4 reviews · 2 hours 30 minutes (approx.) · whole boat $625, up to 6

Join Captain Philip aboard the restored wooden sailboat Liberty for a private 2.5-hour sunset cruise on San Diego Bay. Your group of up to six can help sail, spot sea lions, and pass the USS Midway, Coronado Bridge, Point Loma, and historic ships. Beer, wine, soft drinks, water, and snacks are included.

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