Best Sailing Yacht Charters in the USA: Our Top 6 Picks

1.Sailing on Historic Schooner Yacht in Salem, MA

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

Sail Salem Sound aboard a classic schooner, help raise the sails, see Marblehead and islands, and enjoy a relaxed two-hour coastal outing.

“My fiancé and I had such a wonderful time. Everything was perfect. The entire crew were absolutely wonderful. They were so informative, friendly, and made the experience a very memorable one. The schooner was very well taken care of. They provided non alcoholic beverages and also had a bar available as well. They made us feel right at home. Would highly recommend!”

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

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

Sail Hilton Head on the historic Stars & Stripes yacht, help work the sails, spot dolphins, and enjoy a practical 90-minute cruise.

“This sailing trip on the Stars & Stripes was amazing and we felt very fortunate to be on an "America's Cup" boat. Staff was super friendly! A couple of suggestions: 1.You might mention on your website that most of the seating is literally on the boat deck (could be difficult for older, larger people to sit down and then get up); 2. Didn't see anything on your website about you selling beer & wine. Was a pleasant surprise to have the availability. Would recommend this cruise!”

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3.Daytime Sailing Along San Diego’s Skyline

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

Sail San Diego Bay for two hours with wine, skyline views, sea lions, dolphins, naval ships, and a six-person maximum.

“Relaxing, lovely and fun experience. Captain was pleasant and knowledgeable. Beautiful views and interesting things to see.”

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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.)

Review the private 50ft Fate sunset sail in Charleston, with harbor views, BYOB freedom, crew service, pricing, and practical booking advice.

“What a fantastic voyage for sunset! The sailing yacht and crew were wonderful and made it a fun experience for the entire family.”

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5.Classic Yacht Sailing Experience

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

Sail San Diego Bay aboard the restored Liberty, with harbor landmarks, wildlife, drinks, snacks, and hands-on sailing for up to six.

“Awesome boat ride in the San Diego bay! The boat was beautiful!”

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

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

Review of Charleston’s private BYOB harbor sail aboard the 50-foot yacht Fate, with sights, pricing, crew tips, timing, and practical advice.

“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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