San Diego
The sailing options: small-group trips on a bay that behaves itself, from vintage wooden yachts to modern cats. Most pours include local beer and wine once the sails are set.
Experience San Diego’s stunning sunset from a small, intimate sailing yacht with great views, knowledgeable guides, and comfortable amenities for $112.50.
Most Popular“A beautiful cruise on a comfortable boat. Friendly and knowledgeable captain. An enjoyable way to end a day visiting San Diego.”
Enjoy a private, 3-hour sunset sailing in San Diego with limited groups, stunning views, drinks, snacks, and your own music for a personalized experience.
“Excellent experience. We had a private charter and Captain Dave was a great host! In addition to being an excellent sailor, he was very knowledgeable about the area. We will be doing this again!”
Experience San Diego’s stunning harbor on a small-group sailing trip. Enjoy personalized service, scenic views, and complimentary drinks for an authentic day on the water.
“Six of us went on the boat tour for a bachelorette party. We had a wonderful afternoon! There were assorted chips and snacks provided as well as drink options, such as beer and seltzers. We were able to connect our phone to the boat’s speaker…”
Experience San Diego’s stunning sunset from a vintage sailboat, with wine, wildlife sightings, and iconic landmarks onboard a small, intimate cruise.
“A wonderful anniversary sunset cruise with Captain Phillip. The scenery including two aircraft carriers, The Coronado Bridge, a yacht confiscated from a Russian Olegard, and the gorgeous San Diego skyline was truly magical”
Discover San Diego’s coastline on a small-group sunset or day sail. Enjoy stunning views, marine life sightings, onboard drinks, and an authentic sailing experience.
“Amazing views, experienced professional and fun captain, the experience was as described, perfect sunset sailing cruise”
Enjoy a 2.5-hour sunset sail on a spacious catamaran in San Diego, with drinks, stunning skyline views, and chances to spot sea lions and dolphins.
“Suited to small groups. Totally worth it and then some!! Kaya was an amazing captain. Great views of the city!!”
Experience San Diego’s stunning skyline and coastal waterways on a luxurious 2-hour sailing tour with personalized service, expert guides, and beautiful views.
“Captain Mike was wonderful, knowledgeable about the area and complimented our sail. I recommend this trip 100%”
Experience stunning San Diego views on a 2-hour daytime or sunset sailing cruise. Relax with wine, spot sea lions, and enjoy personalized guidance.
“The sunset cruise was very relaxing, a great experience. Our guide was knowledgeable and low key. which was very appropriate for that setting. We enjoyed it very much.”
Enjoy a 2-hour private sailing tour in San Diego Bay for up to six people. Relax, see iconic sights, wildlife, and enjoy personalized commentary from Captain Liz.
“Captain Liz is an excellent host, with a gorgeous and well-kept boat. She was welcoming and knowledgeable and made our sail a treat! The sunset was spectacular and the sights were beautiful!”
Experience San Diego from the water on a 2-hour small-group yacht sail, with stunning views, a glass of wine, and personalized service.
“Very pleasant and relaxing experience, sailing in a marina, music and wine provided. Me and My husband really enjoyed it.”
Experience San Diego’s stunning coastline on a private luxury catamaran, enjoying personalized service, wildlife, and breathtaking views tailored for your group.
“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.”
Experience 2.5 hours of sailing in San Diego Bay aboard a spacious catamaran, enjoying scenic views, drinks, and the chance to help steer the boat.
“Amazing. Highly recommend Relaxing. Informative. Very worth while saw sea animals. Navy fighters take off”
Enjoy a 2.5-hour vintage sailing experience in San Diego's harbor, with drinks, snacks, and stunning views on a restored 1904 yacht.
“Total Relaxation!! Captain Philip was very knowledgeable of the area and an entertaining host. Tour of the harbor and sights were fantastic!! This yacht was in great shape and very comfortable!! We were in such a cool place and enjoyed ourselfs on this wonderful tour!…”
Discover San Diego on a private sunset sailing tour with stunning bay views, friendly crew, snacks, and the chance to see iconic landmarks up close.
“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!”
Experience stunning San Diego sunsets aboard a private sailboat with drinks, snacks, and scenic views—perfect for a romantic evening or special outing.
“Great captain, beautiful sunset. Calm waters. Enjoyed the sail, learned a lot about the area. Captain shared but not too much.”
Sea caves, sails and a zoo that set the standard, all in shirtsleeve weather.