SAN DIEGO
San Diego’s best days out.
A short guide to the 15 best sailing tours, with what each one costs, how long it runs and who you book it through.
Small-group sunset sailing from Shelter Island with views of Point Loma, USS Midway, and Coronado—plus drinks, snacks, and your own music.
Most Popular“Great scenic tour to experience San Diego, on time departure and pleasant ride, not rough, we were a family of 4, had the boat to ourselves…”
Six-person San Diego Harbor sailing with beer, snacks, jackets, binoculars, and your own music on board.
“Beautiful!! Dave was an amazing captain and made the experience even better. So much to see and enjoy.”
Vintage yacht sunset sail on San Diego Bay with beer, wine, snacks, and a small-group cruise under full sail.
“Beautiful, peaceful sail. Phil was so informative of the bay. Delightful sunset. Totally would recommend.”
2.5-hour San Diego sunset catamaran with beer, wine, and soft drinks, minimal motor use, and views of USS Midway and Point Loma.
“We’ve been in SD for 3 days, sight seeing and having a great time in a beautiful city, but we definitely saved the BEST for the last experience here. This sunset sail was absolutely breathtaking beautiful and the Captain of our boat was so friendly and full of knowledge he shared with us on this…”
Small-group sail on a 34-foot Catalina from Harbor Island for skyline and coastal views, with local captain stories, snacks, and BYO drinks.
“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”
San Diego Bay sunset or daytime sailing from Harbor Island with included wine, soft drinks, sea lion spotting, and skyline views.
“The sunset sailing experience was amazing. It was so beautiful before, during and after the sunset. Captain Nick was so welcoming and knowledgeable. He gave us options when it came to where we were going based on what we were interesting in seeing (we got very close to some adorable seals and sea lions). The…”
Private 2-hour sail in San Diego Bay with Captain Liz. Up to 6, custom route, snacks, drinks, and champagne.
“Liz was a fun and insightful captain. We had great winds and weather making our experience amazing. We toasted with champagne to a beautiful trip to see family living in the area.”
A 2-hour daytime sail in San Diego Bay with onboard wine, comfy deck seating, and skyline views plus a pass by the USS Midway from water.
“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 the gate and walked us down to the sailboat. From…”
Private luxury catamaran sailing from Mission Bay with smooth cruising to La Jolla Cove or Sunset Cliffs, crew service, and BYO snacks.
“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.”
Small-group catamaran sailing from San Diego’s Harbor Island with drinks, blankets, and wildlife sightings for about 2.5 hours.
“Prepaid for high steps. Nice cool breeze on the water.beautiful sites for pictures. The Captain was great and very knowledgeable about the Harbor.”
Small-group San Diego sunset or afternoon sail on the classic Sail Liberty, passing Star of India and USS Midway, with snacks and drinks.
“We had a perfect day aboard the Liberty. With knowledgeable and capable Captain Philip at the helm, we got to see many of the sights of San Diego Bay - all without the noise of a motor. Philip is a wealth of knowledge about the area and about sailing. The trip as a wonderful afternoon,…”
A private 2.5-hour San Diego sunset sail for up to 12, with blankets, snacks, and close views of the Midway, Seaport Village, and 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!”
Private 2.5-hour sailing in San Diego for up to 12 guests, with options for Point Loma sea lions or Downtown sights and a sail under Coronado Bridge.
“It was one of the if not the most memorable experience the group had on a long weekend spent in San Diego! Captain Gus was full of energy and fun facts. Loved the attention to detail and the atmosphere he had that was welcoming and professional. Thank you for an amazing experience!!! Be ready for…”
Sunset sailing from San Diego Bay with wine, beer, and local stories. Spot dolphins, sea lions, and skyline landmarks.
“We had a lovely sail with a very considerate and competent skipper. We will do this again soon.”
2-hour small-group sailing from Harbor Island with snacks and wine/beer, wildlife spotting, and Coronado views across San Diego Bay.
“The captain was good entertainer !!! Got me interested in staying in touch w him . Will always recommend them .”
Every neighborhood, every stretch of coast, and every way to get out on the water.
