San Diego Yacht Charters: the 11 Best Boats to Book

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

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

Join Captain Phillip aboard Liberty, a hand-restored reproduction of a 1904 sailboat. This intimate 2.5-hour cruise carries no more than six passengers and includes beer, white wine, soft drinks, water, and snacks as you pass Navy ships, the Coronado Bridge, the Star of India, and the San Diego skyline.

“Captain Phillip’s sailing tour was beautiful! My husband and I went out along the bay with our two other friends and it was an incredible experience! The views, the sailboat, everything was top tier. Will definitely be doing this again in the future and I recommend if you want an intimate personal experience, this is the tour to do! Thank you again!”

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2.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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3.Daytime Sailing Along San Diego’s Skyline

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

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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4.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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5.San Diego Sunset or Afternoon Sail on Classic Yacht

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

Spend about 2.5 hours aboard Liberty, a restored replica of a 1904 sailboat, with Captain Philip at the helm. You’ll cruise San Diego Bay past the Star of India, USS Midway, Coronado Bridge, Rady Shell, and downtown, with snacks, soft drinks, beer, and white wine included.

“Captain Phillip was incredible! Extremely knowledgeable about the San Diego Bay, it’s history, the sights and the area in general. The boat is super cool. The trip was idyllic. Highly recommend!”

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6.San Diego: Classic Yacht Sailing Experience

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

Spend 150 minutes aboard Liberty, a hand-restored classic Friendship sloop, with Captain Philip at the helm. Sail past the USS Midway, Coronado Bridge, Point Loma, and naval base while enjoying beer, white wine, snacks, and possible sightings of dolphins and sea lions.

“So awesome! Me and my boyfriend loved it. It was a beautiful day outside and got to see a dry docked submarine, sea lions barking and tons of other people enjoying the bay. Captain Phil was extremely knowledgeable and funny. Highly recommend:)”

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7.Private Sailing Charter on San Diego Bay

★★★★★★★★★★5.0 · 41 reviews · 3 hours (approx.)

You’ll sail San Diego Bay aboard the Lucky Sol with a private captain, usually Jason or Brett, for up to six people. Expect snacks, bottled water, bay landmarks, naval views, and flexible sightseeing, with morning and afternoon departures available.

“We had an awesome time with Jason! The boat was clean, well-maintained, comfortable, and stocked with snacks and beverages. We all felt at ease with Jason who was very knowledgable and professional. The ride was smooth and we got some beautiful views of San Diego. It was the perfect way to celebrate my sister’s bachelorette. I couldn’t recommend this experience enough!”

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8.San Diego: Whale Watching Cruise on the Yacht America

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

Spend four hours off San Diego aboard the sailing yacht America, watching for gray, humpback, blue, fin, and minke whales, plus dolphins and sea lions. The English-speaking crew shares more than 50 years of whale-watching experience, with snacks, soft drinks, free parking, and whale and seasickness guarantees included.

“Sadly no whales but lots of dolphins. The captain and crew were fun. Ship was roomy. Beautiful day at sea. Beverages available. Seas were calm and we saw a lot of sea creatures.”

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9.San Diego Bay Private Sailing Experience Aboard Classic Yacht

★★★★★★★★★★5.0 · 4 reviews · 2 hours 30 minutes (approx.)

Join Captain Philip aboard the restored Liberty, a traditional wooden sailboat limited to six people. This 2.5-hour private sunset cruise includes beer, white wine, soft drinks, water, snacks, and views of the USS Midway, Coronado, Point Loma, and sea lions.

“If you want to feel the wind in your hair and the sun on your face, all while enjoying the ease of sailing with a captain who’s both professional and can bring a dad joke, Sail Liberty is for you. During our recent vacation to San Diego, we decided to do something on the water, and decided on a sunset sail with Sail Liberty. Captain Philip was a delight. Communications were on point, including detailed texts the day of our cruise ensuring we had the location and time handy. Once on board, we felt immediately at ease…glasses of wine, beer, and soda were offered along with a light snack. The…”

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10.59′ Paradise Party Yacht – Adventure Cruises San Diego com

★★★★★★★★★★5.0 · 2 reviews

You’ll cruise San Diego Bay aboard a private 59-foot yacht for up to 15 people, led by a captain and first mate. Expect USS Midway and Coronado Bridge views, a powerful Bluetooth sound system, BYOB service, karaoke, and swimming with floats on cruises of three hours or more.

“The captain and the crew member was amazing and we had the most amazing experience. We will deff go again !!!! I recommend anyone to do it!”

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11.Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests

★★★★★★★★★★3.5 · 2 reviews · from $600

You’ll cruise San Diego Bay for about two hours with a private captain and up to five companions. Choose a catamaran, sailboat, or powered yacht, and look for sea lions, dolphins, aircraft carriers, submarines, and sunset views. Captain Mick is one possible guide.

“Due to a race in the San Diego harbor our captain decided not to put up the sails because he felt we would get in the way. We ended up motoring most of the time, not our idea of a sailing cruise, a bit disappointing. There were many other Read more”

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