Top San Diego Sailing

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, soft drinks and snacks.

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, 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.

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.

Set sail at one of the best times of day—sunset—during this San Diego Bay cruise. Board a comfortable sailing yacht and cruise along San Diego's coastline, taking in views of the scenic waterfront, military vessels, and historical landmarks. Catch sight of marine life and enjoy spectacular photo ops. Gorgeous sunset views and Wine makes this tour a great choice for couples or travelers celebrating a special occasion.

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.

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.

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.

A boat ride in San Diego Bay offers the perfect vantage point from which to view the city’s Skyline. This luxury sailing adventure on a 40-foot yacht lets visitors take in the sights in comfort and privacy, the perfect activity for those seeking an extra special addition to their San Diego trip.

Sailing is an art, an adventure, and a great way to relax. Weather you're throwing a special event or you just want to get back to nature, the sea is the place to be. Sailing yacht 'Mojave' is the perfect place for birthday parties, anniversaries, honeymoons, family vacations, engagements, or just a tour of the bay with friends. The boat is clean, luxurious, and very spacious. Join me, Captain Liz, on a trip to see the icon sites of San Diego such as The USS Midway aircraft carrier, The Star of India, The Coronado Bridge, or just say hello to the sea lions. There are complementary snacks and beverages on board or you can bring whatever you would like. I can even make the party special for your event with balloons, party decorations or whatever your needs may be.

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure you'll see many types of sea life as well as learn a little about the many features of San Diego that truly make it "America's Finest City".

Sail the lovely waters off San Diego on a private yacht charter. The itinerary is up to you, or your captain can suggest some places to go. You can opt for a whale watching tour (seasonal), or lay anchor and go for a swim. If you prefer, choose a bay tour; seeing the sights like the Hotel del Coronado, Point Loma Lighthouse, Tijuana, and the San Diego skyline.

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.

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll make sure your time on the sailing vessel RIVIERA is the highlight of your visit. During the warm summer months, we'll anchor off of Coronado Island and you and your friends can dive into the bay for a swim. In late winter and spring, we can take to the Pacific Ocean and watch for whales, dolphins and seals off the coast of San Diego. Our Captain and crew are fun, experienced and knowledgeable. The yacht is flawless, comfortable and very well appointed. When we return to the dock, you won't want to leave.

Claire Sailing offers a new, luxury Beneteau sailing yacht. She has a spacious comfortable cabin with new cushions, clean blankets, pillows, and bean bags on the bow. We also welcome special requests so don’t hesitate to ask!

This is a personal introduction to big boat ocean sailing. For those who have never sailed before we will introduce you to ocean sailing by wind power, with our guests being a private group of no more than 6 people we will sail at our guests comfort level. All guests are welcome to participate in the sailing activities. Guest can treat this sailing experience as a hands on adventure, we happily place the tiller (steering-wheel) in the hands of those willing so they may steer the boat. We are always aware of current conditions and aim to provide an enjoyable sail for all ages and personalities. Children are welcome and as this is a private charter adults may bring personal beverages and snacks.

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.