7 San Diego Yacht Cruises to Book This Year

1.San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

★★★★★★★★★★5.0 · 331 reviews · 2 hours 30 minutes (approx.) · from $115 a seat Our pick

Spend 2.5 hours sailing San Diego Bay aboard Liberty, a hand-restored reproduction of a 1904 sailboat. Captain Phillip handles the gaff rigging and shares local stories while you pass the USS Midway, Star of India, Coronado Bridge, and Navy ships. Beer, white wine, soft drinks, water, snacks, and a restroom are included.

“Great tour. And worth the money. Tour guide is very personable. We had a lovely and relaxing evening. Thank you.”

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2.Daytime Sailing Along San Diego’s Skyline

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

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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3.San Diego Sunset or Afternoon Sail on Classic Yacht

★★★★★★★★★★5.0 · 80 reviews · 2 hours 30 minutes (approx.) · from $115 a seat

Spend about 2.5 hours aboard Liberty, a restored replica of a 1904 sailboat, with Captain Philip at the helm. This small-group cruise stays in San Diego Bay, passing the Star of India, USS Midway, Coronado Bridge, and waterfront landmarks. Choose an afternoon or sunset departure, with snacks, soft drinks, beer, white wine, and bottled water included.

“The weather was perfect and Captain Philip was courteous, friendly and skilled in the art of sailing.”

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4.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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5.San Diego: Whale Watching Cruise on the Yacht America

★★★★★★★★★★4.6 · 25 reviews · 4 hours · from $95 a seat

Spend four hours on San Diego Bay and the open Pacific aboard the roughly 140-foot sailing yacht America. The English-speaking crew brings more than 50 years of whale-watching experience, serves free snacks and non-alcoholic drinks, and looks for gray, humpback, fin, blue, and minke whales, plus dolphins, orcas, and sea lions.

“Excellent guides. Great information. And she shared her photos, which was very helpful.”

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6.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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7.59′ Paradise Party Yacht – Adventure Cruises San Diego com

★★★★★★★★★★5.0 · 2 reviews · whole boat $1,400, up to 15

Spend about two hours aboard a private 59-foot yacht for up to 15 people, cruising beneath the Coronado Bridge and beside USS Midway, the downtown waterfront, and Glorietta Bay. Captain Mark and DJ-led entertainment are part of the upbeat setup, with BYOB, food, Bluetooth audio, karaoke, and a restroom onboard. Cruises of three hours or more add swimming and floats.

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