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.
“We had an incredible time! Captain Dave was very knowledgable about the area and engaging! Stunning sunset, fun fellow travelers, and a captain who caught the wind ... couldn't ask for more! Would go sailing with him and Sail San Diego 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.
“It was a great experience overall. My only complaint is the description says there's beer and wine and there was neither. We were looking forward to that. But Captain Greg is really amazing!”
Experience San Diego’s stunning sunset from a vintage sailboat, with wine, wildlife sightings, and iconic landmarks onboard a small, intimate cruise.
“This experience is peaceful, intimate, and serene. The experience is filled with Great San Diego Bay history and amazing views given by Captain Phillip.”
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.
“Nice and personable captain We’ll versed on the city and harbor Boat is clean and in good shape Would book again”
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.
“Captain Ryan was very informative. My grandkids said “I don’t want it to end”. The weather was beautiful and the boat was very clean.”
Experience San Diego’s stunning skyline and coastal waterways on a luxurious 2-hour sailing tour with personalized service, expert guides, and beautiful views.
“Let me start by saying, I booked this experience specifically because so many reviews spoke so highly of Captain Mike. They were right! Couldn’t have asked for a better captain. Sunscreen, sodas, waters, and a variety of chips weRead more”
Experience stunning San Diego views on a 2-hour daytime or sunset sailing cruise. Relax with wine, spot sea lions, and enjoy personalized guidance.
“This was such a beautiful boat ride around San Diego”
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.
“Tour started right on time and ended exactly after 2 hours. We can see the sealions, light house and views of the Coronado Island and San Diego Skyline. Great views, great photos taken by the captain . Best ever sailing experience. Nice boat where you…”
Experience San Diego from the water on a 2-hour small-group yacht sail, with stunning views, a glass of wine, and personalized service.
“This was such a fun experience. My sister and I went on a private sail with just us and Captain Adam and we felt like royalty! Directions to/around the marina were very clear, we found the meeting spot no problem. Adam met us right at…”
Experience San Diego’s stunning coastline on a private luxury catamaran, enjoying personalized service, wildlife, and breathtaking views tailored for your group.
“We had an amazing sunset cruise thru the bay with Maddie and Jake. Our family of 12 enjoyed the evening on the boat. Maddie and Jake were so accommodating and welcoming. Would highly recommend this tour!!”
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.
“We had a small group, so this was very enjoyable, our guide was so informative and very accommodating!”
Enjoy a 2.5-hour vintage sailing experience in San Diego's harbor, with drinks, snacks, and stunning views on a restored 1904 yacht.
“Captain Phillip was low key, interesting and is clearly an experienced navigator of the SD Bay. The restored vintage sail boat was incredible.”
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.