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2019 Top Sailing Charters In San Diego 


Aolani Catamaran Sailing

Winner of the San Diego A List’s Best City Tour in 2014 and 2016 and winner of the number one Activity in San Diego by Lifestyle Magazine, Aolani Catamaran Sailing is the first private yacht charter company business in San Diego, California. Their comfortable, well-appointed catamaran vessel is certified by the Coast Guard to sail with up to 48 passengers, including in the open ocean. 


Boat Bed & Breakfast

With an impressive fleet of the Agavero, Mea Culpa, Elegante, Czech Mate, Ode to Our Joy, Seas the Day, and Slipaway, Boat Bed & Breakfast has outstanding ratings and reviews on Yelp and VRBO. Boat Bed & Breakfast is a bed and breakfast yacht hotel offers charter and dockside accommodations. This establishment owns seven beautiful boats that have been converted into an extraordinary bed and breakfast experience. 


California Cruisin’ Yacht Charters

California Cruisin’ Yacht Charters is a boat rental service located in San Diego, California. Their yacht charters include sailboats, powerboats, weddings, dinner cruises, and overnight stays. California Cruisin’s San Diego yacht charters and bay cruises are an exciting way to see the city’s spectacular skyline and world-famous harbor, or to just soak up the sunshine while cruising the San Diego Bay.


Cast Off Sailing

With prices starting from $85 per person for three hours, a whale watching adventure for $85 per person for three and a half hours, and a private sailing adventure for $499 for three hours and up to six guests, Cast Off Sailing is a great option. This boat rental business is located in the heart of the San Diego Bay, California which means you can take full advantage of the climate and steady winds. 


Chere Amie Yacht Charters

Chere Amie Yacht Charters is a cruise agency and boat charter business founded in 2008. They host birthdays and private parties, weddings and formal events, and business meetings. Their crew has already served 217,000 passengers on 2,100 cruises for more than 8,700 hours and counting. Chere Amie Yacht Charters is where luxury meets affordability.


Coletta Sportfishing

Coletta Sportfishing is a fishing charter service. Their Captain, Christopher “Chris” Coletta, has more than 35 years of fishing experience.Their charter boat, Wanu, is a custom 32′ Marshall flybridge sport fisher powered by a 250 HP Cummins Turbo Diesel with the latest in digital controls. Wanu was specifically designed and built to fish the coastal waters of Southern California. Coletta Sportfishing was voted as the Top Charter Boat in San Diego for 2015 by ReelReports.com.


Harbor Yacht Clubs

Harbor Yacht Clubs is a boat charter company with locations in San Diego and Long Beach, California that has been in business for over 20 years. They offer a sailing club, sailboat rentals, and sailing lessons. Their sailboat fleet is composed of 11 boats, and their sailing school is award-winning.


Mai Tai Yacht Charters

Mai Tai Yacht Charters is a yacht charter business with a 41’ sporting yacht harbored in Harbor Island. Clients can experience the beauty of San Diego Bay from the deck of their yacht charter. Customers are free to bring their cameras, as the photo opportunities are plentiful. This yacht charter offers beautiful sunset cruises, corporate outings, special events, private celebrations, and snorkeling tours. Luxury is the name of the game here. 


Next Level Sailing

Next Level Sailing is a boat tour agency founded in 2003 that specializes in corporate and private charters. Their charter services include corporate entertainment, groups of up to 76 can enjoy, corporate whale watching, catering/dining, and weddings. Next Level Sailing is the official partner of the San Diego Maritime Museum and special discounted offers are available on numerous sites for those who are searching for a bargain. 


Sail JADA Charters, LLC

Sail JADA Charters, LLC is a boat tour agency established in 1938, making it one of San Diego’s oldest chartering services. Their sail charters include corporate charters, private charters, memorials at sea, sunset cruises, whale watching, weddings at sea, and public charters. Sail JADA Charters, LLC has a public charter as well and is the only authentic classic wooden sailing yacht available for charter in San Diego.


Sail San Diego

Sail San Diego is a charter boat company that provides 12 different sailing and fishing options for 2 people to up to 50. Services include yacht brokerage, private fishing trips, and sailing lessons. Their crew has over 80 years of experience in the chartering business. Winner of Trip Advisor’s Certificate of Excellence six years in a row and Hall of Fame Award, number one Charter company by Fishing Booker in 2016, and 4th place winner and 1st place captain in the Make-a-Wish Tuna Challenge 2016, Sail San Diego is used by concierges of top hotels throughout the San Diego metro area. 


San Diego Bay Cruises

San Diego Bay Cruises is a private yacht charter that provides sailing yachts, sport fishing boats, motor yachts, mega yachts, small boats and sport crafts, and boatels, (boat hotels). Their featured yacht is the Antonina. San Diego Bay Cruises is a proud sponsor of the San Diego Brews Cruise.


San Diego Luxury Sailing

San Diego Luxury Sailing’s charter options include sunset sail, day sail, whale watching, romantic sunset sail for two, overnight at anchor, engagement proposal, and more. They also offer fun yachting activities such as stand-up paddleboarding and kayaking, a dock and dine at one of San Diego’s finest restaurants, the Humphreys and Summer Pops concert series, and swimming and snorkeling. In 2015, San Diego Luxury Sailing received the Trip Advisor Certificate of Excellence. 


Stars & Stripes Sailing Tours

Whether you’re a sailing fanatic or just enjoy the view of floating sails on the water, I think we can all agree that sailing on an International America’s Cup Class yacht would be an amazing, unforgettable experience. Luckily, you can! Docked up at the Kona Kai Resort and Marina in San Diego California, the Stars & Stripes USA-11 is one of the fastest racing sailboats in the world, and you can charter it for a day on San Diego Bay! Great fun for all ages, a three hour harbor cruise in the San DiegoBay on the Stars & Stripes is sure to make the top of your list of fun group activities.


SV Sweet Angel

SV Sweet Angel, a sailboat charter business, boasts over 42 years of sailing experience. This establishment has one of the newest and best-looking 42-foot charter sailboats available in the Bay at the moment. With highly competitive pricing, and an extremely experienced captain, the SV Sweet Angel should be the first choice for those wanting to sail in style.


Waterhorse Charters

Waterhorse Charters is a SCUBA tour agency that provides trips to Wreck Alley, Coronado Islands, Kelp Beds, and various points in between. Their custom vessel, the Humboldt, was designed especially for scuba diving with an overall length of 45′ and a 16′ beam. They can carry 22 passengers on board at a top speed of 30 mph and a cruising speed of 26 mph. Waterhorse Charters offers SCUBA diving with ample space, a friendly crew, good food, and all the details that make for an unforgettable dive.


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