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.
“The staff were really great! They walked us right to our dock and helped us get aboard. Once onboard Happy Captain Greg was wonderful at explaining everything we needed to know about the boat. We enjoyed some hard seltzers and cuddled up on the front…”
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.
“Amazing sailing trip with Captain Kinley! We could not have been happier with our experience. We sailed out in the beautiful sailboat past the lighthouse at point Loma. We saw dolphins and sea lions and even followed them as they sailed along!”
Experience San Diego’s stunning sunset from a vintage sailboat, with wine, wildlife sightings, and iconic landmarks onboard a small, intimate cruise.
“Philip was knowledgeable about the Bay, sailing, and was very kind and funny. We went when it was cloudy and missed the sunset, but I would still recommend it!”
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.
“We took a sunset cruise. Captain Billy was so helpful and kind. The kids were in a trance on the beanbag in the front of the boat, just enjoying the peace and tranquility of the water. This is a mellow and beautiful boat ride. Great…”
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.
“Very relaxing, private and friendly experienced captain Matt! We had a great time with perfect weather. Free wine was a bonus!”
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.
“Captain Bri was amazing 👏🏾 the sunset sailing was great, with sites to see, the sunset was nice. Definitely bundle up, it did get a little cold, but Captain Bri offered us a blanket. Seen a few dolphins 🐬 which was a plus. we had…”
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.
“We had a wonderful time sailing around San Diego Bay with Liz and her first mate Sydney. The boat is clean and comfortable and they are friendly and knowledgeable about the water and wind conditions and kept us informed. Highly recommended for small groups of…”
Experience San Diego from the water on a 2-hour small-group yacht sail, with stunning views, a glass of wine, and personalized service.
“We were very lucky to have Eric all to ourselves ! He was so pleasant & informative. Delightful 2 hours .”
Experience San Diego’s stunning coastline on a private luxury catamaran, enjoying personalized service, wildlife, and breathtaking views tailored for your group.
“Our group of 11 had a great time on the Malarky. The crew was friendly and very accommodating. We brought everything for a sunset wine and cheese and it was perfect watching the sun set over the horizon. The catamaran has been the highlight of…”
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.
“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.”
Enjoy a 2.5-hour vintage sailing experience in San Diego's harbor, with drinks, snacks, and stunning views on a restored 1904 yacht.
“Phillip our Captain was incredible! We sailed, listened to music, conversed, and I was even the Captain for a short period of time.”
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.
“Fabulous cruise with a fabulous Captain! A wonderful experience I would certainly recommend.”
Sea caves, sails and a zoo that set the standard, all in shirtsleeve weather.