San Diego · SAN DIEGO SAILING TRIPS
Small crews, real sail handling and no engine noise, which is a different afternoon from a narrated cruise. The 15 below cover the America’s Cup yachts, the afternoon charters and the sunset runs, priced by group size.
Sail San Diego Bay at sunset in a six-person yacht, with skyline views, bean bag seating, marine life, and a relaxed two-hour route.
“A beautiful cruise on a comfortable boat. Friendly and knowledgeable captain. An enjoyable way to end a day visiting San Diego.”
Sail San Diego Bay at sunset on a six-person Catalina-style boat with skyline views, complimentary drinks, snacks, blankets, and a relaxed captain.
“Sailing with our family and Captain Dave was so relaxing. Our highlight was seeing a family of dolphins with two youngsters. The weather was beautiful.”
Review of Sail San Diego’s small-group afternoon sail, with harbor views, wildlife, drinks, music, route details, pricing, and practical tips.
“It was fantastic. We opted for the open water excursion. The captain was very chill and professional. The sailboat was much nicer than the photos indicated. I plan on taking this ride on my next trip to San Diego.”
Sail San Diego Bay aboard the restored Liberty with Captain Phillip, sunset views, wildlife, landmarks, beer, wine, and a six-person limit.
“Captain Phillip was awesome. Very entertaining and knowledgeable. Would highly recommend. Great hospitality.”
Review of San Diego’s six-person sunset sail, with bay landmarks, drinks, marine life, captain tips, pricing, and practical booking advice.
“This was an awesome trip in the bay. Very peaceful and relaxing. Captain Ann was very accommodating and knowledgeable.”
Sail San Diego Bay at sunset on a six-person catamaran with beer, wine, sea lions, skyline views, and minimal motor use.
“We had an amazing sunset cruise with Captain Kaya! She was fun, easygoing, and incredibly engaging throughout the trip. Her laid-back personality made us feel totally comfortable, and she struck the perfect balance between being informative and entertaining. We learned so much during the cruise, and the views were absolutely stunning. It was one of the highlights of our trip, and we would absolutely do it again. Highly recommend Captain Kaya if you’re looking for a memorable and relaxed experience on the water!”
Sail San Diego Bay aboard a 34-foot Catalina with a local captain, small groups, skyline views, snacks, and sunset departures.
“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”
Sail San Diego Bay for two hours past the USS Midway, skyline, and Coronado, with wine, sea lions, and sunset views from $89.
“This was the absolute highlight of our trip! The sailboat was gorgeous, Captain Rick was the best, and overall, we were beyond happy with our experience!”
Sail San Diego Bay privately with Captain Liz aboard a clean six-person yacht, with custom sights, sea lions, skyline views, snacks, and champagne.
“Captain Liz is awesome. Very accommodating and knowledgeable about the sea life and area. Such a beautiful and relaxing evening with family and friends. Great experience, we are grateful and blessed. Will return again.”
Sail San Diego Bay for two hours with wine, sea lions, skyline views, and a small group aboard a comfortable six-seat yacht.
“So fun and such great hospitality from Captain Nick and his content creator, Helena. He was so attentive to keeping us comfortable and making sure we had all we needed to enjoy our afternoon on the water. 100% worth every penny because how do you put a value on experiencing San Diego from the water? Would do again!!”
Sail privately from San Diego to La Jolla or Sunset Cliffs on a luxury catamaran with crew service, wildlife views, and flexible trip lengths.
“The whole experience was enjoyable. We plan on doing another trip again. The crew was awesome. They took us out and we saw dolphins up close and personal.”
Sail San Diego Bay aboard a spacious catamaran with a maximum of six people, complimentary drinks, sea life, skyline views, and expert captains.
“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.”
Sail San Diego Bay aboard the restored 1904 Liberty, with skyline views, snacks, drinks, and a small group led by Captain Philip.
“Very comfortable yet relaxed vessel, well stocked with snacks and drinks. Captain Phillip has a great personality that topped everything off.”
Watch San Diego turn gold on a private 2.5-hour sail with harbor landmarks, snacks, blankets, and a close look at the Coronado Bridge.
“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!”
Watch the Pacific sunset from a classic yacht on a small San Diego sail with wine, snacks, marine life, and harbor views.
“I'll give you 3 1/2 stars. Captain Charlie was very good. Sailing duration was 1hr 35 minutes not 2 hours as advertised. I am not sure I would take this sailing again. Price versus value received requires a max rating of 3 1/2 stars. Good time, not a GREAT Time.”
Pick a stretch of coast, a park or a taproom.
