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“It’s a very relaxing and scenic adventure. We had a pleasant want experience! Saw the most beautiful sunset. Knowledgable captain!”
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 relaxing and informative excursion! Captain Dave runs a tight ship, spotless clean, all the convenient but relaxed environment!”
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.
“We had an awesome time sailing! Will definitely return to sail again 😊 It’s a fun intimate experience on a sail boat”
Experience San Diego’s stunning sunset from a vintage sailboat, with wine, wildlife sightings, and iconic landmarks onboard a small, intimate cruise.
“Lovely evening with Capt. Phillip and two other couples, sailing through the bay! The captain is a wealth of knowledge… just ask him questions!”
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 probably THE BEST thing we did while visiting San Diego! We had a great sail! Our captain, Colin was super interesting to talk with and was a very gracious and attentive host. Highly recommend this experience!!!”
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.
“SHOUT OUT TO MY MAIN MAN STEW!!!! he really knows how to be a captain, and i would follow this man thru the gates of Point Nemo.”
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.
“Nick was a great Captain! It was very relaxing and fun! I would definitely recommend adding this to your to do list when in San Diego.”
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.
“Relaxing Day on the water. Celebrated my anniversary sailing this was the relaxing day that we needed to take time out Of our lives to truly take in the beauty of San Diego”
Enjoy a 2.5-hour vintage sailing experience in San Diego's harbor, with drinks, snacks, and stunning views on a restored 1904 yacht.
“Philip was great. The itinerary wasn't well described and only included a couple slow laps around the bay, no ocean sailing/sunset or sailing description/instruction.”
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.
“Had a wonderful cruise around San Diego Bay with Sal as our captain. Sal was a lot of fun and very knowledgeable about sailing. We learned a lot. Seeing San Diego from the water both day and night was spectacular…almost forgot to watch the sun…”
Sea caves, sails and a zoo that set the standard, all in shirtsleeve weather.