SAILING WORLDWIDE
The best days on the water.
The 15 most popular san diego sailing trips. What each sail costs, how long you are on the water, and which crews run it well.
A small-group sunset sail on a yacht in San Diego Bay with skyline views, wildlife sightings, and easy deck comfort for about 2 hours.
Most Popular“So went on this nice boat ride with David. As we toured the port and I began to ask questions about the surroundings , he did not seem to know anything. He let us know that it was not his boat and that he was filling in for someone. I then asked to go to…”
Small-group San Diego sunset sailing from Shelter Island with beer, snacks, blankets, and big views of Point Loma, USS Midway, and Coronado.
“Excellent, relaxing experience. Boat was well stocked with snacks and drinks. Captain was friendly and knowledgeable. Highly recommended.”
Small-group San Diego harbor sailing with just six aboard a Catalina-style yacht. Beer, snacks, and your music on the water.
“This was one of our top experiences in 30 years of travel around the world! Captain Dave was fantastic! His customer service skills were equal to his sailing skills. One of our many highlights were sailing alongside the USS Carl Vinson as it was leaving port. Don’t forget to ask Captain Dave to give you…”
San Diego Bay sunset sail on Liberty, a 1904-style yacht. Beer, wine, snacks included on a small-group 2.5-hour ride.
“Philip was knowledgeable about the Bay, sailing, and was very kind and funny. We went when it was cloudy and missed the sunset, but I would still recommend it!”
Deluxe Sunset & Day Sail in San Diego Bay. Small-group cruise with drinks, blankets, and landmark views past USS Midway to Coronado.
“The experience was great. I would highly recommend this tour. Colin was an exceptional guide and host. He was very knowledgeable of the waterways, some history of the city and good conversationalist. The ride was comfortable and relaxing.”
A 2.5-hour small-group catamaran sunset sail in San Diego with drinks, warm blankets, and quiet wind time around harbor icons.
“Very relaxing, private and friendly experienced captain Matt! We had a great time with perfect weather. Free wine was a bonus!”
Luxury 2-hour small-group sailing on a 34-foot Catalina in San Diego Bay. Skyline views, snacks, BYO drinks, local captain.
“Capitán Mike, was amazing perfect weather, my husband and my enjoy the experience, the sunset was perfect”
2-hour San Diego Bay sailing from Harbor Island with skyline views, USS Midway sights, and frequent sea lions. Wine included.
“Great captain, very relaxing trip. we had an amazing time enjoying scenery and sunset.”
A private 2-hour yacht sail in San Diego Bay for up to six. Customize your route with Captain Liz, plus snacks, drinks, and champagne.
“I would recommend this experience to everyone. We had a blast , so relaxing and such a wonderful host. Liz is amazing!”
Sail San Diego Bay on a small yacht for skyline views, sea lions, and an easy, intimate 2-hour sunset or daytime cruise with wine included.
“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!”
A 2-hour daytime sail in San Diego Bay with a glass of wine, cozy seating, and skyline views plus views of the Midway from the water.
“Adam is a great captain. He is relaxed, comfortable and friendly. And an awesome sailor. Even solo, I enjoyed myself. It was relaxing and fun.”
Private luxury catamaran sailing from Mission Bay to the Pacific with onboard crew service, coastal sights, and wildlife—2 to 8 hours.
“Our group of 11 had a great time on the Malarky. The crew was friendly and very accommodating. We brought everything for a sunset wine and cheese and it was perfect watching the sun set over the horizon. The catamaran has been the highlight of our trip to San Diego. We highly recommend this experience.”
San Diego small-group catamaran sail with beer, wine, soft drinks, and 2.5 hours of harbor views from downtown to Midway.
“Such a fun experience! Enjoyed being in the sun and on the water. Captain Ryan was a great host. A great way to learn about the city. Would definitely recommend this!”
Sail San Diego Bay on a classic 1904-style yacht with Captain Philip, snacks and drinks, plus close looks at Star of India, Midway, Coronado.
“Captain Phil is amazing! One of the best afternoons of our time here. Can’t recommend this highly enough.”
A private 2.5-hour sunset sail from Harbor Island. Up to 12 guests, warm blankets, snacks, and the best chance at a Coronado Bridge sail-under.
“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!”
The sailing ports worth the trip, grouped by the sea they sit on.
