SAN DIEGO SAILING TOURS
Wind, season and head-count decide more about a day afloat than the brochure does. These 15 san diego sailing tours are set out with the hours, the price and the swim stops so the choice takes a minute.
Sail San Diego Bay for about two hours with up to six people, passing the USS Midway and Maritime Museum as the sun drops behind the skyline. Captains such as Aaron, Patrick, Adam, Derek, and Maggie keep the mood friendly and safe. Bring drinks or snacks, and pack a jacket for the cool ride home.
“Great service, beautiful and relaxing. Bring a jacket… even if it’s warm when you set sail. Gets cold quickly.”
Set sail from Shelter Island for about three hours aboard a Catalina-style sailboat limited to six passengers. Your captain handles the boat while you enjoy views of Point Loma Lighthouse, the USS Midway, Coronado Island, and the skyline. Beer, hard seltzers, soft drinks, snacks, blankets, binoculars, and Bluetooth speakers are provided.
“I was solo and am grateful that Captain Chris has a great personality and is willing to converse. It was my first time on a sail boat and I loved every second. Everything was smooth sailing!”
Spend three hours aboard a 40-foot Catalina-style sailboat with up to five other passengers and a captain such as Dave, Greg, Bree, or Chris. Sail past Point Loma lighthouses, Coronado Bridge, Navy ships, and sometimes Seaport Village. Beer, hard seltzers, soft drinks, snacks, blankets, binoculars, and Bluetooth music are provided.
“Wonderful! Awesome captain! Beautiful boat. Awesome thing to do!!!! Totally recommend. Tip at least 20%. Our captain was really cool”
Join Captain Phillip aboard Liberty, a hand-restored reproduction of a 1904 sailboat, for a 2.5-hour evening cruise on San Diego Bay. The small group, usually limited to six people, keeps the outing personal. You can help with the sailing, watch for sea lions and dolphins, and enjoy beer, white wine, soft drinks, water, and light snacks.
“The boat is very nice but definitely just fits 6 plus Captain Philip. It does get chilly on the water as the sun is starting to set but we came prepared so we were quite comfortable. There was plenty of refreshments on the boat and everything was clean and shiny. I think the Captain knows a lot about the area and could share a lot of info about what you're seeing but he pretty much read his audience and did tell us about a lot of things and was very knowledgeable and always answered our questions but as we were girlfriends (plus my lucky husband) of close to 60 years…”
Spend about 2.5 hours sailing San Diego Bay from Harbor Island with a captain such as Ann, Colin, Billy, or DJ. Expect views of the USS Midway, Coronado Bridge, Seaport Village, historic ships, and downtown lights, plus soft drinks and alcoholic beverages. The group is capped at six, making this a relaxed choice for couples, families, and first-time sailors.
“Very capable and personable captain. We were the only ones on the boat so had our own private cruise”
Meet Captain Ryan, Matt, Kaya, or Ty at Safe Harbor Sunroad for a relaxed 2.5-hour sunset sail on San Diego Bay. The six-person catamaran passes the USS Midway, downtown, Coronado Bay Bridge, Embarcadero, and Point Loma. Beer, wine, soft drinks, water, blankets, and a bathroom are included, with motor use kept to a minimum.
“Absolutely incredible night. Matt our captain was wonderful, helpful, and informative. The boat was safe and comfortable.”
Spend about two hours sailing San Diego Bay on a 34-foot Catalina sailboat with a local captain. Depart in the morning, afternoon, or evening for skyline and coastal views, bay stories, snacks, and water. Groups are limited to six, and guests over 21 may bring their own alcohol.
“This was a great time on the water with a beautiful ship, relaxing bay, very informative captain, very interesting sites. I would do this tour again and highly recommend to those interested in getting on the water in San Diego.”
Join a captain such as Patrick, Nick, Rick, or Bri for a two-hour small-group sail from Harbor Island. You’ll pass the USS Midway, downtown, and North Island Coronado Naval Station, with white wine, soft drinks, and water provided. Bring food, watch for sea lions and dolphins, and reserve all six seats for a private sail.
“What a beautiful day and a beautiful time, very intimate. Well worth it.”
Join Captain Liz of Sterling Sails for a private two-hour cruise from Harbor Island. Your group of up to six can shape the route around the USS Midway, Maritime Museum, Cabrillo National Monument, Coronado, sea lions, skyline views, or sunset. The clean yacht includes a bathroom, snacks, beverages, champagne, and space to sit or stand on deck.
“Captain Liz and her sailboat were much fun. There is something magical about being on a small sailboat powered by the wind, and Liz demonstrated it. She was great with our kids, allowing them to steer the ship and hoist sails. She was also very happy to share her knowledge, has great pride in her ship, and clearly wanted us to have a great time. I think it will be a forever memory that will bring a smile to our faces. Thanks, Captain Liz.”
Spend 150 minutes sailing San Diego Bay from Harbor Island with a captain such as Colin, DJ, or JC. Sip wine, beer, soft drinks, or water while watching for dolphins, seals, sea lions, and pelicans. You’ll pass major waterfront sights, hear local stories, and enjoy a relaxed sunset on a private or small-group boat.
“The sailboat was lovely and bigger than expected. We had 6 people and there was plenty of room.”
Sail San Diego Bay aboard Liberty, an early-1900s replica Friendship sloop restored by Captain Philip. Over 150 minutes, you can help sail, spot sea lions and dolphins, and pass the USS Midway, Coronado Bridge, Point Loma, and the Star of India. The tour includes beer, wine, soft drinks, water, snacks, and shared or private booking options.
“The only thing to consider is there is free parking not far away as another option!”
Spend two or three hours aboard a modern 40-foot sailing yacht with a US Coast Guard-certified captain. You’ll pass the USS Midway, Star of India, Coronado Island, Point Loma Lighthouse, and San Diego International Airport. Beer, hard seltzers, soft drinks, snacks, blankets, binoculars, and an onboard bathroom are included. Groups are limited to six.
“Great sailing in a beautiful boat manned by very profesional captain! Very relaxing and high end service”
Spend two hours aboard a classic sailing yacht from Harbor Island, taking in San Diego’s skyline, Coronado Bridge, aircraft carriers, and harbor wildlife. Captain Alan may add lively stories about the city, Navy, and local animals. The six-person limit keeps the outing personal, though the experience may feel more like a narrated boat ride than active sailing.
Spend four hours sailing San Diego aboard the Californian, a replica Gold Rush era revenue cutter and California’s official tall ship. The English-speaking crew invites you to haul lines, take the helm, and watch the sails being set. Your ticket also covers the Maritime Museum, including Star of India and H.M.S. Surprise.
“This was a pirate adventure for my nine year old great grandson. He was enthralled. He especially enjoyed the firing of the cannons and seeing the nuclear submarines. Four generations of my family were aboard. There was something of interest for each generation. It was a wonderful time!”
Spend four hours at San Diego’s waterfront, sailing aboard the wooden San Salvador replica and visiting the Maritime Museum. Hear English-language tales of Cabrillo’s crew, enjoy harbor views, and explore ships such as Star of India and HMS Surprise. Check in at the white ticket booth before the 11:30 AM boarding time.
Sunset, snorkel, or the whole boat.
