California

5 of the Best San Diego Sailing Tours

by Cedric Pentonville  |  Updated July 31, 2024

With its deep harbor, naval bases and long Pacific shoreline, San Diego is among the best places in the USA for thrilling sailing experiences.

(Photo: Getyourguide.com)

Sailing cruises depart daily from numerous marinas and piers all around San Diego Bay and beyond. From private charters to whale- and dolphin-watching tours, there are many different ways to get out onto the Pacific Ocean, in many different types of vessels, but sailboats and yachts remain the most elegant way. We’ve reeled in all the tours we could find and condensed the choice down to the very best five sailing experiences from San Diego available today.

San Diego Sailing Aboard a Classic Yacht

The Liberty is a beautiful pine green yacht, with pretty triangular sails, and it offers a really unique way to explore San Diego Bay in style. The yacht, modelled on a 1914 Friendship sloop from Maine, will take you past all the city landmarks during the two-and-a-half-hour trip. You’ll even get a chance to take over the wheel for a while. But don’t forget to keep an eye out for marine life as you go, with seals, dolphins and whales usually nearby. From $99 per person.

Book at Getyourguide.com

(Photo: Getyourguide.com)

San Diego 3-Hour Sailing Tour

Spending three hours out on San Diego Bay, white sails to the breeze, is a memorable way to explore this city’s maritime side. Pass by the USS Midway, which dwarfs your little sailboat, and see San Diego’s downtown in a new light from the water. Binoculars, sunscreen and blankets are provided, so that you’re covered no matter how the weather turns out. Unlimited alcoholic beverages and snacks are also provided on board for guests. From $95 per person.

Book at Getyourguide.com

San Diego 3-Hour Sunset Sail

As the sun sets over the Pacific Ocean, San Diego’s downtown and other neighborhoods are painted varying shades of orange and magenta, a sight that is best witnessed from the water. This sunset sailing tour departs from a marina close to the ocean. You captain, who is U.S. Coast Guard-certified, will take you past many of the city’s best landmarks, providing narration along the way. See the Maritime Museum and the downtown area, along with other landmarks during the trip. From $95 per person.

Book at Getyourguide.com

(Photo: Viator.com)

Sunset Sailing Experience on San Diego Bay

For an alternative sunset sailing experience aboard a more modern yacht, there’s this two-hour trip. Taking in everything from the best waterfront views, the historic sights and the best spots for marine life, such as sea lions, this is a great choice for getting good photos as the sunset adds to the atmosphere. White wine, water and chocolate are also provided as part of the ticket price. Daily departures throughout the year. Times vary between 3 and 6pm to coincide with the sunset. From $119 per person.

Book at Viator.com

San Diego Dinner Cruise

For a boat trip on San Diego Bay that feels a little less exposed to the elements and the waves, there are plenty of alternatives. One of the classiest options is this dinner cruise, which includes a buffet meal – ribs, salmon and vegetarian options are usually all available – followed by a DJ providing the entertainment. Look back to shore from the upper deck as you pass landmarks such as Coronado Bridge, and the Cabrillo National Monument. From $155 per person.

Book at Getyourguide.com