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“Aaron was AMAZING! He took us out for the best sunset cruise. The views were spectacular! Definitely worth every penny!!!!”
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.
“Captain was spectacular and worked hard to please the group with sights, enjoyment, great stories and beverages He was incredible”
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.
“Great time on the sail boat. Dave was an awesome captain and shared a lot of knowledge with us along the way. Highly recommend to couples just looking to relax and soak in San Diego’s views.”
Experience San Diego’s stunning sunset from a vintage sailboat, with wine, wildlife sightings, and iconic landmarks onboard a small, intimate cruise.
“Captain Phillip was incredible! It was an amazing experience! I would absolutely recommend this experience to anyone visiting San Diego!”
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.
“If you've never sailed before, this is a perfect introduction to sailing. We took the sunset sailing tour of Mission Harbor. We saw so many things from from sea lions to naval ships, Coronado Island in the distance and the San Diego skyline at sunset.…”
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.
“My parents and I had a beautiful time sailing the San Diego Bay through Viator. Our captain Peter was wonderful! He had years of sailing experience, was very knowledgeable (and easily answered my parents million questions hahRead 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.
“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.
“We had a beautiful sunset cruise with Captain Liz. Her boat is fantastic and she was so accommodating and fun to spend time with. Loved Captain Liz’s stories and wide knowledge of everything was saw. We will be back.”
Experience San Diego from the water on a 2-hour small-group yacht sail, with stunning views, a glass of wine, and personalized service.
“Relaxing, lovely and fun experience. Captain was pleasant and knowledgeable. Beautiful views and interesting things to see.”
Experience San Diego’s stunning coastline on a private luxury catamaran, enjoying personalized service, wildlife, and breathtaking views tailored for your group.
“Captain and staff were very friendly and knowledgeable. Taught was newer and in top condition. The head and galley were very clean. Definitely will see y’all next year.”
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 relaxing ride through the SD harbor! Beautiful views, smooth sailing, and a peaceful atmosphere—highly recommend.”
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.