5 of the Best San Diego Sailing Tours

by Paul Joseph  |  Published May 24, 2022

Whether it’s gentle cruising in the harbour or heading out to the Pacific Ocean for wildlife watching, San Diego is a magical place for a sailing adventure.

(Photo: Imagine Sailing San Diego / Courtesy Viator)

The city’s deep harbour is home to a large active naval fleet, with the USS Midway, an aircraft-carrier-turned-museum, open to the public, all of which are visible from the frequent tour boats that navigate the calm waters. Head further out into the deep ocean, and you open the possibility of spotting exotic marine life such as sea lions, seals, dolphins and whales. Whatever your preference, there are San Diego sailing experiences for you. Here are five of the best.

Luxury Sailing Tour of San Diego’s Bay and Coastal Waterways

Sail out into the San Diego Bay and take in great views of the city’s skyline with this small-group 2-hour tour aboard a 34-foot Catalina sailboat. Led by a captain from renowned local company Imagine Sailing, guests can choose from morning, afternoon, or evening departures. During the tour, your captain will regale you with tales and facts about San Diego  as you pass along the beautiful bay and costal waters. Snacks and bottled water are included and guests are welcome to bring their own beers if they desire. From $121 per person.

Book at Viator

America’s Cup Sailing

(Photo: Sail Stars and Stripes USA-11 / Courtesy Viator)

Cruise around San Diego bay aboard an authentic 1992 America’s Cup racing yacht and travel at twice the speed of the average sailboat on this adrenaline-fuelled tour. The Stars and Stripes USA-11 is one of the fastest and best known America’s Cup racing yachts and has been restored to pristine condition. During the tour, guests can take a turn at the helm and join in grinding the winches to raise and trim the sails. Photos and videos of the experience are included in the tour price. From $67 per person.

Book at Viator

Classic Yacht Sailing Experience

Enjoy a traditional sailing yacht experience off the scenic San Diego coastline complete with complimentary wine, beer and light snacks. Over 2.5 hours, you’ll set sail on a hand-restored 1914 replica sailboat from the Sunset Resort Marina, stopping to spot marine wildlife such as sea lions and dolphins, as well as the world famous USS Midway Aircraft Carrier. During the tour there’ll also be the chance to learn how to helm a sailboat yourself. From $99 per person.

Book at GetYourGuide

Sunset Sail

(Photo: GetYourGuide)

Experience an awe-inspiring sunset on this 3-hour tour. Departing from one of the closest marinas to the Pacific, guests get the maximum time on the water to take in the breathtaking scenery as the sun melts into the sea. During the tour, there’ll also be the chance to marvel at huge military ships and enjoy the sights and sounds of ocean wildlife such as sea lions, seals, dolphins, and whales. Complimentary, unlimited beer, white wine, and non-alcoholic drinks and snacks are complimentary is also provided. From $95 per person.

Book at GetYourGuide

Sunset sail by catamaran

This small-group tour invites you to sail the San Diego waters by catamaran, with special bow nets designed for sunbathing, and lounging around watching sea life. The stable ocean design ensures a comfortable ride without the rolling and leaning that often causes seasickness on other boats. After boarding, you’ll head out to the harbour and hoist the sails. With the motor off, and a cool drink in your hand, you can kick back, relax, and watch the beautiful sunset go down over the bay. During the 2.5-hour tour you’ll explore the harbour and other notable landmarks before returning. From $121 per person

Book at Viator