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“Great host and boat captain, beautiful views of the bay and the downtown city scape! Had a great time!”
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.
“Very much worth it! Loved our experience. The complimentary drinks and snacks were a great touch. Our guide was amazing and provided great music for our time on the boat. Would book this again with a group of friends!”
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.
“The entire trip was so fun! Captain. Dave was great and made our trip so much fun! Can’t wait to do another sailing!”
Experience San Diego’s stunning sunset from a vintage sailboat, with wine, wildlife sightings, and iconic landmarks onboard a small, intimate cruise.
“Beautiful, peaceful sail. Phil was so informative of the bay. Delightful sunset. Totally would recommend.”
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.
“Absolutely incredible night. Matt our captain was wonderful, helpful, and informative. The boat was safe and comfortable.”
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 sailing trip was excellent, and our captain, Patrick, was amazing as well! Even though the sunset wasn’t as vibrant as usual due to weather, we were still able to see some very pretty views of the shoreline lit up after the sun went down.…”
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.
“Lovely morning out on the waters with Captain Liz! She was professional, yet friendly and highly attentive to any requests. She got us up close and personal with the sea lions sunbathing on the buoys. HIGHLY recommend an excursion with her out on the waters.…”
Experience San Diego from the water on a 2-hour small-group yacht sail, with stunning views, a glass of wine, and personalized service.
“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…”
Experience San Diego’s stunning coastline on a private luxury catamaran, enjoying personalized service, wildlife, and breathtaking views tailored for your group.
“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!”
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.
“Prepaid for high steps. Nice cool breeze on the water.beautiful sites for pictures. The Captain was great and very knowledgeable about the Harbor.”
Enjoy a 2.5-hour vintage sailing experience in San Diego's harbor, with drinks, snacks, and stunning views on a restored 1904 yacht.
“Very comfortable yet relaxed vessel, well stocked with snacks and drinks. Captain Phillip has a great personality that topped everything off.”
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.
“I'll give you 3 1/2 stars. Captain Charlie was very good. Sailing duration was 1hr 35 minutes not 2 hours as advertised. I am not sure I would take this sailing again. Price versus value received requires a max rating of 3 1/2 stars. Good…”
Sea caves, sails and a zoo that set the standard, all in shirtsleeve weather.