Sailing trips · SAN DIEGO SAILING TRIPS
This is the shortlist you would send a friend: 11 san diego sailing trips worth the money, each with its price, its traveller verdict and the one thing to know before the lines come off.
Sail San Diego Bay for about two hours with up to six people, passing the USS Midway and Maritime Museum as the sun sets. Captains such as Aaron, Patrick, Adam, and Derek keep the outing friendly and informative. Bean bags, blankets, cushions, and an onboard bathroom add comfort.
“Fun and scenic activity. Good value. About an hour and a half. Parking at marina $20-$30 in addition.”
Set sail from Shelter Island for about three hours with a maximum of six passengers. Expect sunset views of Point Loma, Coronado, the USS Midway, and the skyline, plus beer, hard seltzers, soft drinks, snacks, blankets, binoculars, and Bluetooth music. Captains such as Dave, Greg, and Rhys keep the trip friendly and informal.
“Getting to know the 4 other people on board. Sunset cruise was just what I needed to decrease my asthma symptoms.”
Sail San Diego takes up to six passengers on a three-hour daytime cruise from Shelter Island. Expect Point Loma lighthouses, Coronado Bridge, naval ships, wildlife, snacks, beer, soft drinks, and Bluetooth music. Captains such as Dave, Greg, Bree, and Chris add local color.
“Captain Bree was amazing. She made all of us very comfortable, single-handedly sailed the boat, and was pleasant and positive throughout. We caught some super fun wind outside the harbor then came back inside to see some sights. Highly recommend Captain Bree to all and sail San Diego as well.”
Spend about 2.5 hours aboard Liberty, a hand-restored reproduction of a 1904 sailboat. Captain Phillip guides a maximum of six passengers past the USS Midway, Coronado Bridge, Navy ships, sea lions, and the glowing San Diego skyline. Beer, white wine, soft drinks, water, and snacks are included.
“We had a wonderful time. Captain Philip is very nice and knowledgeable. The pleasures of the bay were fully experienced. From the other ships and boats ( private and commercial and military) to the seals and sea lions and birds and to the aircraft overhead, we enjoyed the quiet sailing and the panoramic views of the San Diego skyline. The gorgeous sunset put the whole experience into another level of spectacular. I’d recommend this trip unconditionally!”
Spend about two and a half hours sailing San Diego Bay with no more than six people aboard. Captains such as Ann, Colin, Billy, and DJ share harbor stories, point out sea lions and dolphins, and guide you past the USS Midway, Coronado Bridge, Seaport Village, and other waterfront sights. Drinks are included, and the cruise returns to the marina.
“The views were amazing, Captain Collin was awesome, and the drinks were complimentary! This was my fiance and I's favorite activity in San Diego, cannot recommend it enough!”
Spend 2.5 hours sailing San Diego Bay with no more than six people aboard. Captains Ryan, Matt, and Kaya mix local stories with easygoing hospitality as you pass the USS Midway, Coronado Bay Bridge, Point Loma, sea lions, and seabirds. Beer, wine, soft drinks, water, and blankets are included.
“Captain Ryan is very knowledgeable, both about the area and his boat. The sail was a quiet and relaxing few hours with my kids, husband, and friend, with plenty of room to spread out. It is big enough for kids to wiggle around safely, but I wouldn't recommend a catamaran for kids who don't listen well to directions (for safety reasons). We will definitely use this company again next time we come to San Diego!”
Join Captain Patrick, Nick, Rick, Bri, Stu, Corinne, or another English-speaking skipper for a relaxed two-hour sail from Harbor Island. Expect skyline views, the USS Midway, Coronado Naval Station, included wine and soft drinks, and a chance to spot sea lions or dolphins.
“Captain Bri was amazing 👏🏾 the sunset sailing was great, with sites to see, the sunset was nice. Definitely bundle up, it did get a little cold, but Captain Bri offered us a blanket. Seen a few dolphins 🐬 which was a plus. we had a very good experience.”
Spend 150 minutes sailing San Diego Bay with a captain such as Colin, DJ, Anna, or JC. Sip beer, wine, soft drinks, or water while watching for dolphins, seals, pelicans, and sunset views of Coronado Bridge and downtown.
“We really enjoyed it. We learned about sailing. It was relaxing. Captain DJ answered all our questions. Our daughters enjoyed it. We would recommend it.”
Spend 150 minutes aboard Liberty, a hand-restored 1904 gaff-rigged Friendship sloop, with Captain Philip at the helm. Sail past USS Midway, Coronado Bridge, Point Loma, and naval landmarks while enjoying wine, beer, soft drinks, snacks, and chances to spot dolphins and sea lions.
“Our time on Phil’s boat was relaxing and fun. We never sailed on an actual traditional sail boat and we will do it again. Phil was a character and made trip enjoyable. Thanks Phil”
Spend four hours aboard the 139-foot sailing yacht America, watching for gray, humpback, blue, fin, and minke whales, plus dolphins and sea lions. Your English-speaking crew shares decades of whale-watching experience, with snacks, non-alcoholic drinks, free parking, and whale-sighting and no-seasickness guarantees included.
“Sadly no whales but lots of dolphins. The captain and crew were fun. Ship was roomy. Beautiful day at sea. Beverages available. Seas were calm and we saw a lot of sea creatures.”
Sail San Diego Bay for two or three hours aboard a 40-foot yacht with a US Coast Guard-certified captain. Pass the USS Midway, Coronado, Point Loma, and airport runways while enjoying drinks, snacks, blankets, and a small group limited to six.
“Captain Dave was super! A lover for local knowledge particularly all the naval bases and aircraft’s. Super insightful and a joy! From the UK!”
Pick the boat, the hour on the water or the country.
