Top 15 Sailing Trips in San Diego

1.Small-Group San Diego Sunset Sailing Excursion

★★★★★★★★★★5.0 · 592 reviews · 3 hours (approx.) · from $127Our pick

Join Sail San Diego for a three-hour sunset sail from Shelter Island, limited to six passengers. Look for Point Loma Lighthouse, USS Midway, Coronado Island, the bridge, sea lions, and dolphins while enjoying beer, hard seltzers, soft drinks, snacks, blankets, and your own music.

“I was solo and am grateful that Captain Chris has a great personality and is willing to converse. It was my first time on a sail boat and I loved every second. Everything was smooth sailing!”

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2.Small-Group San Diego Afternoon Sailing Excursion

★★★★★★★★★★5.0 · 531 reviews · 3 hours (approx.) · from $116

Spend three hours aboard a 40-foot Catalina-style sailboat with up to six passengers. Captain Dave, Greg, Breezy, Chris, Frank, or another crew member may guide your route past Point Loma, Coronado, naval vessels, and the USS Midway. Beer, seltzers, soft drinks, snacks, blankets, and Bluetooth music are included.

“Just an absolute great time sailing for the first time . Planning my next sail. Captain Chris was wonderful!!”

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

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

Join Captain Phillip aboard Liberty, a hand-restored yacht modeled on a 1904 sailboat, for a 2.5-hour San Diego Bay cruise. With space for six passengers, beer, white wine, soft drinks, snacks, and views of Navy ships, the Coronado Bridge, sea lions, and the skyline, this is a calm, personal evening on the water.

“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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4.2.5-Hour Small-Group Catamaran Sunset Sail with Drinks

★★★★★★★★★★5.0 · 223 reviews · 2 hours 30 minutes (approx.) · from $119

Spend 2.5 hours sailing San Diego Bay aboard a spacious catamaran limited to six people. Captains such as Ryan, Matt, and Kaya share local facts, serve beer, wine, soft drinks, and water, and may let you take the wheel while you watch the sunset near Point Loma.

“We enjoyed the whole experience. Our captain, Kaya, was wonderful. The evening sail was relaxing and beautiful. We made new friends, and everyone was so pleasant to be around.”

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

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

Join Captain Mike or Captain Peter aboard a Catalina 34 sailboat for a relaxed two-hour cruise around San Diego Bay and nearby coastal waters. Choose a morning, afternoon, or sunset departure, ask questions as you sail, and bring your own drinks if you are 21 or older.

“Capitán Mike, was amazing perfect weather, my husband and my enjoy the experience, the sunset was perfect”

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6.San Diego Bay Sunset & Daytime Sailing Experience

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

Sail from Sunroad Resort Marina on Harbor Island with an English-speaking captain such as Patrick, Nick, Rick, or Bri. Expect a relaxed two-hour trip past the USS Midway, downtown skyline, and North Island Coronado Naval Station, with wine, water, soft drinks, and a chance to spot sea lions or dolphins.

“Fabulous evening, guide was engaging and fun and so knowledgeable!”

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7.2-Hour Private Sailing Experience in San Diego Bay

★★★★★★★★★★5.0 · 168 reviews · 2 hours (approx.)

Join Captain Liz aboard the clean, spacious Mojave for a private two-hour sail from Harbor Island. Your group of up to six can shape the route around the USS Midway, sea lions, Coronado, the skyline, sunset views, or a relaxed cruise with snacks, drinks, and champagne.

“My sisters and I took my mom for Mothers Day for a cruise on Harbor island Bay. Liz was sweet and patient! We all had such a great time!”

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8.Daytime Sailing Along San Diego’s Skyline

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

Set sail from Safeharbor Sunroad Marina for a two-hour cruise around San Diego Bay. Captain Adam, Nick, Rick, Bree, Patrick, and other local skippers guide the yacht past the Midway, naval ships, skyline views, and possible sea lions or dolphins. Bring snacks, settle into a bean bag, and enjoy the bay at an easy pace.

“The captain was fantastic!! I don’t remember her name but she was very sweet to all of the passengers and was great at including us, I even had the chance to sail the boat myself and she said I did perfect. I highly recommend, if you’re reading this thank you so very much. You made my birthday so so very fun :)”

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9.Luxury Catamaran Sailing Charter of San Diego

★★★★★★★★★★5.0 · 87 reviews · 2 to 8 hours (approx.)

Sail privately from San Diego for 2 to 8 hours, heading toward La Jolla Cove or Sunset Cliffs. Your crew handles the boat while you relax, watch for dolphins, and enjoy bottled water plus two coolers for your own food and drinks. Confirm the exact departure dock before sailing.

“Captain and staff were very friendly and knowledgeable. Taught was newer and in top condition. The head and galley were very clean. Definitely will see y’all next year.”

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10.2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

★★★★★★★★★★5.0 · 86 reviews · 2 hours 30 minutes (approx.) · from $119

Sail San Diego Bay for about 2.5 hours with a maximum of six people, a captain such as Kaya, Ryan, Matt, or DJ, and complimentary beer, wine, and soft drinks. Expect skyline views, the Coronado Bay Bridge, sea lions, seabirds, and sometimes dolphins, with the motor off whenever conditions allow.

“Incredible experience with a knowledgeable captain. This catamaran is smooth and so peaceful. Perfect small group size. Would love to do it again! It really is so relaxing!”

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11.San Diego Sunset or Afternoon Sail on Classic Yacht

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

Join Captain Philip aboard Liberty, a restored replica of a 1904 sailboat, for a relaxed 2.5-hour cruise around San Diego Bay. Expect views of the Star of India, USS Midway, Coronado Bridge, and downtown skyline, plus snacks, soft drinks, beer, and white wine for up to six people.

“Very comfortable yet relaxed vessel, well stocked with snacks and drinks. Captain Phillip has a great personality that topped everything off.”

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12.2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests

★★★★★★★★★★5.0 · 73 reviews · 2 hours 30 minutes (approx.) · from $260

Sail from Harbor Island on a private 2.5-hour sunset cruise for up to 12 people. Captain Gus guides your group past the USS Midway, Seaport Village, The Rady Shell, and beneath the Coronado Bridge. Blankets, drinks, and snacks are included, with parking and gratuity extra.

“Great experience to see the harbor and the San Diego Skyline! Beautiful views and lots of fun! We had a group of 13 girls on the sail for a bachelorette party and we were well taken care of!”

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13.Private Day Sailing Experience in San Diego up to 12 guests

★★★★★★★★★★5.0 · 67 reviews · 2 hours 30 minutes (approx.) · from $235

Set sail from Harbor Island with your private group of up to 12, choosing Point Loma sea lions or downtown San Diego. Your captain handles the boat while you enjoy harbor views, USS Midway, Seaport Village, Coronado Bridge, snacks, drinks, and warm blankets.

“It was one of the if not the most memorable experience the group had on a long weekend spent in San Diego! Captain Gus was full of energy and fun facts. Loved the attention to detail and the atmosphere he had that was welcoming and professional. Thank you for an amazing experience!!! Be ready for some waves and a great time!”

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14.Sunset and Day Sailing Excursion with Drinks

★★★★★★★★★★4.9 · 55 reviews · 2h 30m · from $101

Spend 150 minutes sailing San Diego Bay with a local captain such as Colin, DJ, Anna, or J.C. Sip beer, wine, soft drinks, or water while passing Coronado Bridge and harbor sights. Small-group and private options are available, with sunset sailing and marine-life spotting along the way.

“I had an amazing sunset cruise. DJ our Captain was awesome. I wanted to have a turn sitting up front but because I'm unsteady on my feet to move about the boat. DJ would not let me miss the opportunity. He took me by the hand and carefully walked me to the front of the boat. And took amazing pics of me taking it all in. Thank you Capt DJ for your kindness and hospitality. The wine was also good lol. Will definitely book again whenever I'm in San Diego.”

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15.Small-Group San Diego Sailing Trip

★★★★★★★★★★5.0 · 49 reviews · from $130

Spend two hours aboard a classically restored yacht with a skipper and no more than five other passengers. From Harbor Island, you’ll see Downtown, Point Loma, Shelter Island, and Coronado Island while enjoying cheese, salami, crackers, and drinks.

“Captain Boat Daddy Bruce was genuinely the nicest guy! We went for a bachelorette party and had a great time on the water. The snacks and drinks were such a nice touch. We brought a Bluetooth speaker to play music and had a blast.Thank you Bruce for hanging out with a loud group of girls for the day!”

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