6 Coastal Sailing Tours in San Diego Worth Casting Off For

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, for a 2.5-hour evening cruise on San Diego Bay. The small group, usually limited to six people, keeps the outing personal. You can help with the sailing, watch for sea lions and dolphins, and enjoy beer, white wine, soft drinks, water, and light snacks.

“The boat is very nice but definitely just fits 6 plus Captain Philip. It does get chilly on the water as the sun is starting to set but we came prepared so we were quite comfortable. There was plenty of refreshments on the boat and everything was clean and shiny. I think the Captain knows a lot about the area and could share a lot of info about what you're seeing but he pretty much read his audience and did tell us about a lot of things and was very knowledgeable and always answered our questions but as we were girlfriends (plus my lucky husband) of close to 60 years…”

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

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

Spend about two hours sailing San Diego Bay on a 34-foot Catalina sailboat with a local captain. Depart in the morning, afternoon, or evening for skyline and coastal views, bay stories, snacks, and water. Groups are limited to six, and guests over 21 may bring their own alcohol.

“This was a great time on the water with a beautiful ship, relaxing bay, very informative captain, very interesting sites. I would do this tour again and highly recommend to those interested in getting on the water in San Diego.”

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3.San Diego Bay Sunset & Daytime Sailing Experience

★★★★★★★★★★5.0 · 181 reviews · 2 hours · from $89Best value

Join a captain such as Patrick, Nick, Rick, or Bri for a two-hour small-group sail from Harbor Island. You’ll pass the USS Midway, downtown, and North Island Coronado Naval Station, with white wine, soft drinks, and water provided. Bring food, watch for sea lions and dolphins, and reserve all six seats for a private sail.

“What a beautiful day and a beautiful time, very intimate. Well worth it.”

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4.2-Hour Private Sailing Experience in San Diego Bay

★★★★★★★★★★5.0 · 168 reviews · 2 hours (approx.) · from $625 whole boat, up to 6

Join Captain Liz of Sterling Sails for a private two-hour cruise from Harbor Island. Your group of up to six can shape the route around the USS Midway, Maritime Museum, Cabrillo National Monument, Coronado, sea lions, skyline views, or sunset. The clean yacht includes a bathroom, snacks, beverages, champagne, and space to sit or stand on deck.

“Captain Liz and her sailboat were much fun. There is something magical about being on a small sailboat powered by the wind, and Liz demonstrated it. She was great with our kids, allowing them to steer the ship and hoist sails. She was also very happy to share her knowledge, has great pride in her ship, and clearly wanted us to have a great time. I think it will be a forever memory that will bring a smile to our faces. Thanks, Captain Liz.”

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5.San Diego Bay: Signature 2-Hour Sailing Tour

★★★★★★★★★★4.5 · 4 reviews · from $130

Spend two hours aboard a classic sailing yacht from Harbor Island, taking in San Diego’s skyline, Coronado Bridge, aircraft carriers, and harbor wildlife. Captain Alan may add lively stories about the city, Navy, and local animals. The six-person limit keeps the outing personal, though the experience may feel more like a narrated boat ride than active sailing.

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6.San Diego Bay Sailing Tour

★★★★★★★★★★5.0 · 2 reviews · from $650 whole boat, up to 6

Join captain Liz aboard a private 42-foot yacht for two hours on San Diego Bay. You can cruise past the USS Midway, Star of India, Coronado Bridge, and Point Loma, or head toward the sea lions and sunset. Champagne, snacks, drinks, a restroom, music, and blankets are included.

“My group and I had the absolute best time with Liz! The complimentary champagne was amazing and there was plenty of space in the fridge for our extra drinks and snacks. Liz was so knowledgable about San Diego and the whole bay area and answered all our crazy questions. It was the perfect sunset cruise listening to music, taking in the views, and chatting. 100% recommend for any occasion!”

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