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.
“Be aware, the entire sailing adventure stays in the bay. If you want to go out into the ocean, this is not the trip you want. However, it was very relaxing and romantic!”
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.
“Very fun three hours. Captain Dave was so in tuned to the guests on board. And we had some decent breezes, dolphins, sea lions, Navy ships, sun… perfect”
Experience San Diego’s stunning sunset from a vintage sailboat, with wine, wildlife sightings, and iconic landmarks onboard a small, intimate cruise.
“Had an amazing time! The small group made the cruise feel really cozy and personal. Drinks and snacks were great, and the sunset views were beautiful. Definitely recommend captain Philip is a good dude”
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.
“This was an awesome trip in the bay. Very peaceful and relaxing. Captain Ann was very accommodating and knowledgeable.”
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.
“We had a private cruise around the harbor with Captain Matt. It was a wonderful experience, very relaxing with a beautiful sunset! Highly recommend!”
Experience San Diego’s stunning skyline and coastal waterways on a luxurious 2-hour sailing tour with personalized service, expert guides, and beautiful views.
“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!!!!”
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 Patrick was a wonderful host and Skipper. This trip was the perfect end to our California vacation. A peaceful, quiet sail with excellent company. Patrick was accommodating and knowledgeable. It was well worth the price for a nearly private cruise. We’re both still smiling…”
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.
“Liz made the final night of our family vacation the best night! My family cannot stop talking about the boat ride and how much fun Liz was! We did so many things together this week, and this won the week! Liz was very knowledgeable, professionally…”
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.
“A wonderful sailing experience with an experienced and knowledgeable Captain Ryan. A very personable fellow who made this adventure quite memorable. Catamaran was clean and ship shape.”
Enjoy a 2.5-hour vintage sailing experience in San Diego's harbor, with drinks, snacks, and stunning views on a restored 1904 yacht.
“Phil was very helpful explaining the safety features and what to expect to keep everyone safe. He was knowledgable about the bay and the surrounding points of interest. His hospitality was generous and the boat comfortable even for older bones. Definitely a field trip worth…”
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.
“Captain Corey was great! Beautiful and lots of great history - wonderful experience Thank you so much”
Sea caves, sails and a zoo that set the standard, all in shirtsleeve weather.