San Diego · SAILING
31 tours
The bay is protected, the breeze is reliable from midday, and the skyline lines up perfectly at golden hour. These 15 sailing trips compare on boat, group size and whether drinks come with it, from small-group afternoons to a vintage yacht with beer and wine on board.
Small-group San Diego sunset sailing for up to 6. Enjoy Point Loma, USS Midway, Coronado, snacks, drinks, blankets, and your own music.
“The boat is so clean! I crawled on my knees, in my dark navy pants from the bean bag on the bow to the stern and not one speck of white dust was on my knees as I had feared.”
Small-group 3-hour San Diego Harbor sail with snacks, beer, and onboard gear, plus your own music. See Coronado Bridge and USS Midway.
“Great time on the sail boat. Dave was an awesome captain and shared a lot of knowledge with us along the way. Highly recommend to couples just looking to relax and soak in San Diego’s views.”
Sail on the hand-restored Liberty at sunset with beer, white wine, and snacks. Small group, serious views, and real seamanship.
“Great tour. And worth the money. Tour guide is very personable. We had a lovely and relaxing evening. Thank you.”
San Diego sunset catamaran for up to 6 with beer, wine, and soft drinks. Motor off fast for quiet sailing and sea lions.
“Well worth the money as memories were made that will last a life time. The catamaran was a joy to cruise on! Don't pass on this adventure.”
Small-group Catalina 34 sail from Harbor Island for skyline and coastal views, with snacks, water, and local captain stories.
“Capt. Mike was awesome! We had so much fun and his knowledge about the area was incredible. The best part was when we sailed back from the Coronado bridge. It was so peaceful and relaxing! I would absolutely do it again!!!!”
Sail San Diego Bay for two hours from Harbor Island, with downtown skyline views, sea lions, and included wine.
“Excellent sailing tour! Rick was a fantastic captain. Highly recommended this tour.”
Sail San Diego Bay on a private yacht with Captain Liz. Customize your route, spot sea lions, and enjoy snacks, drinks, and champagne.
“Liz and The Mojave sailboat were amazing!!! A great, overall experience. I don’t know how it could be better.”
San Diego skyline sailing for 2 hours with a glass of wine, cozy bean bags, and water views near the Midway carrier. Small group.
“Relaxing, lovely and fun experience. Captain was pleasant and knowledgeable. Beautiful views and interesting things to see.”
Private luxury catamaran cruise from Mission Bay to La Jolla or Sunset Cliffs, with attentive crew and coolers included.
“We loved this whole experience! We were a group of 6 and the crew was beyond accommodating and we had an amazing time on the water. Would highly recommend!”
Small-group San Diego catamaran sail with beer, wine, soft drinks, sea life sightings, and quiet motor-off sailing.
“It was a beautiful and peaceful day on the water and Captain Matt was wonderful. The boat was comfortable and clean. Loved all the sea life and all that we got to see during our time on the water.”
Classic yacht sail in San Diego Bay with vintage style, small group vibes, and iconic passes like Star of India, Midway, and Coronado.
“Very comfortable yet relaxed vessel, well stocked with snacks and drinks. Captain Phillip has a great personality that topped everything off.”
Private 2.5-hour San Diego sunset sail for up to 12, with blankets, drinks, and snacks, passing Seaport Village and sailing under Coronado Bridge.
“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!”
Private 2.5-hour San Diego sailing for up to 12, blankets and snacks included, choose Point Loma or USS Midway, sail under Coronado Bridge.
“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!”
150-minute San Diego sunset sail from Harbor Island with wine and beer, skyline views, and real wildlife spotting like dolphins and sea lions.
“Captain DJ was awesome and the route around San Diego was perfect - all the best sites and sunset sites were spectacular”
A 2-hour small-group sail on San Diego Bay. Classic yacht, wildlife spotting, and snacks with wine or beer included.
“Our guide made sure that we had an amazing time. He made us feel as if we were old friends. My wife and I were on an anniversary trip and just happened on the ad lucky us.”
