Top San Diego Sailing

Go whale watching from San Diego aboard a replica of a historic sailing schooner that won the world’s first America’s Cup sailing competition in 1851. Throughout your cruise, your expert guide shares informative commentary about gray whales, dolphins, and other marine animals, along with details about the US Navy sites you pass as you head out on the Pacific Ocean.

Watch the sun set over San Diego during an all-inclusive small-group cruise aboard a classic sailboat. Pass landmarks such as the Maritime Museum, Coronado Bridge, and USS Midway, and look for sea lions, dolphins, and other wildlife around San Diego Harbor on the 2.5-hour cruise.

Set sail from San Diego on your own private sailboat cruise that can accommodate up to 12 people. Depart from the Hyatt Regency Mission Bay and glide out to the Pacific Ocean, passing landmarks like Sunset Cliffs Natural Park, Pacific Beach, La Jolla, and Ocean Beach Pier. Get great views of southern California’s landscape and wildlife, and feel free to bring your own refreshments and music to customize your cruise.

Enjoy a sailing adventure on a Catalina-style sailboat with just six people for a comfortable, semi-private experience (or, find five friends and fill up the whole boat). Sail in San Diego Harbor during the day. Sit back and relax to enjoy the water views while enjoying complimentary beer, wine, soft drinks and snacks.

This is a personal tour from one to six passengers that is engaging and diverse tailored to the specific selected tour option(s) Both private and mixed tours are available.

Cruise around San Diego bay aboard an authentic 1992 America’s Cup racing yacht and travel at twice the speed of the average sailboat. The Stars and Stripes USA-11 is one of the fastest and best known America’s Cup racing yachts. It was designed and built to be raced in San Diego, and has been restored to pristine condition. Take a turn at the helm and join in grinding the winches to raise and trim the sails.

Sail Liberty offers the unforgettable experience of a beautiful sailboat touring adventure aboard a traditional sailing yacht. Our replica 1904 Yacht, offers excellent sailing for small group harbor tours and a remarkable sunset cruise all the while using traditional sailing techniques aboard a classic vessel unlike any other in San Diego.

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailing charters and boat tours take you on an exciting tour of San Diego Bay. Book a sunset sailing boat charter and stretch out in the San Diego sunshine with a trusty skipper at the helm, A sunset sailing boat tour on San Diego Bay with Pacifica Sailing Charters is the perfect sailing experience for you and your guests. With over 20 years of boating on San Diego Bay and the waters surrounding the San Diego harbor, our sunset boat charters and sunset sailing boat tours are rated #1 on Google, Yelp, and TripAdvisor.

A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sailing charters and boat tours. Sail San Diego with us. Our sailing charters and boat tours take you on an exciting tour of San Diego Bay. Book a sailing boat charter and stretch out in the San Diego sunshine with a trusty skipper at the helm, Choose from several types of yacht charters, catamaran cruises, sailboats, and powered luxury yachts. A sailing boat tour on San Diego Bay with Pacifica Sailing Charters is the perfect sailing experience for you and your guests. . With over 20 years of boating on San Diego Bay and the waters surrounding the San Diego harbor, our boat charters and sailing boat tours are rated #1 on Google, Yelp, and TripAdvisor...

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea life including Sea Lions, Dolphins and Whales. Whether you need a classic sailboat or catamaran for your Bachelorette Party, we can provide a private catamaran that is roomy, comfortable and stable. Much heavier than traditional boats today, Sea Esta will provide a steady, smooth sail no matter what the conditions. This large and stable catamaran is perfect for sightseeing around San Diego Bay and the perfect bachelorette party yacht for you and your guests.

Sail the magnificent San Diego Bay on this private cruise aboard a restored 1934 sailboat. A personalized alternative to crowded group outings, the cruise can be tailored to you; help sail the boat, or just relax on deck enjoying included drinks and snacks. With service from a captain and two crew members, you’ll cruise past San Diego landmarks from the Coronado Bridge to the Embarcadero.

A fully restored 70 foot private sailing ship for your own private group of upto 12. We can comfortably accommodate 12 passengers, we have a bluetooth stereo, and a immaculate interior belowdecks. There is a clean restroom belowdecks and we have a tremendous crew. You will have a Captain and two crew on board to assist with all the sailing, answer any questions, and to assist you in anything needed. If you would like you can assist in hoisting and trimming sail, or, you can sit back and enjoy a cold beverage and some salami, cheese, and crackers.

Sail into the setting sun aboard a Catalina style sailboat during this intimate cruise with a small group. Feel like you have the ship all to yourself on this trip that’s limited to just 12 total guests, watching as the last rays of the sun drop into the glistening waves. Enjoy the included beer, wine, soft drinks and snacks during the ride, as well as jackets and wind gear in case you get cold. You can even plug in your own music to add to the fun. Departure times vary throughout the year. Guest must contact Sail San Diego after purchase for the exact departure time.