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.

Sail out into the San Diego Bay and take in great views of the city's skyline with this small-group tour aboard a 34-foot Catalina sailboat led by a local captain. You can choose from morning, afternoon, or evening departures and you will be welcome to bring your own drinks on board.

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.

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.

Spend a few hours relaxing, sunbathing and sightseeing in the placid waters just off San Diego during this 1 or 2 hour San Diego Harbor cruise. Sit back and relax as you take in a fully-narrated tour, offering top-notch sight lines of the San Diego skyline, a cruise under Coronado Bridge, a look at the bustling US Naval fleet and a chance to spot some of the harbor’s resident sea lions. Choose between 1 and 2 hour cruise options, offering you two trips to fit your schedule and interests.

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.

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 along the San Diego Bay on this relaxing 1-hour cruise. While aboard, enjoy views of the city, as well as US naval vessels, the Star of India, and the Coronado Bridge. Catch sight of the Hotel del Coronado, and spot sea lions in their natural habitats. Along the 1-hour route, you can pick up a snack and drink at the snack bar (own expense), and relax as you cruise the water.

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.

Set sail on the San Diego Harbor without spending a fortune on this affordable small-group sailing tour. Climb aboard a replica 1904 yacht that's unlike any other in San Diego, and enjoy several hours of cruising the bay and harbor, from Seaport Village past the USS Midway Museum and other shoreline attractions. No sailing experience is required, as a captain handles the navigation so you can enjoy the voyage.

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.

Tour San Diego Bay by boat with this small-group sailing activity for up to six passengers. You'll sail past the downtown and alongside aircraft carriers and submarines with a professional captain to take the helm. You may even spot marine life such as sea lions and dolphins along the way. Opt for a daytime departure to get time in the sun or choose an evening departure for the best shot at sunset views.

Experience San Diego Bay the way it was meant to be seen, from the water on a private yacht. A dedicated captain handles the navigation so your group can sit back, relax, and enjoy the sights and sounds of the bay, from the USS Midway to Seaport Village and harbor seal hideouts. With room for up to six passengers, it's a great value for families, special occasions, and small groups.

Get out into the waters of Mission Bay on a 34 foot sailing boat with a guide. You can be beginners or experienced, and everyone will get a chance to steer and maneuver the vessel. You’ll set the mainsail, and then get into the ocean and feel the cool breeze to power your sail. The boat can take a group of four of you and your family and friends.

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride without the rolling and leaning that often causes seasickness on other boats. When you are welcomed aboard, you'll feel comfortable right away because we really do like people, and with such small groups, you've escaped the crowds. We always say it's great to be a tourist, but better to not feel like a tourist. With cushioned seating with back rests, our catamarans are comfortable for all ages of guests from young kids to seniors. A perfect way to spend a lazy day, unwinding and relaxing, no cares in the world.

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!

With over 35 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride without the rolling and leaning that often causes seasickness on other boats. When you are welcomed aboard, you'll feel comfortable right away because we really do like people, and with such small groups, you've escaped the crowds. With cushioned seating with back rests, our catamarans are comfortable for all ages of guests from young kids to seniors. A perfect way to spend a lazy day, unwinding and relaxing, no cares in the world.

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...

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. The San Salvador is a replica of Juan Rodriguez Cabrillo’s ship that arrived at the port we now call San Diego on September 28, 1542. These 4-hour Sailing Adventures are for people who love history, and sailing. Very few people have sailed aboard galleons of the 16th century and now you can!

Enjoy perfect views of the San Diego Bay with a 2-hour private sailing experience aboard a 37 foot (11.2 meter) yacht that accommodates up to six passengers. Relax on deck with a bottle of champagne and cold drinks as the captain steers the boat along the coast, and watch for dolphins and sea lions in your wake. Take the helm and learn to sail, see San Diego’s iconic skyline from the water, or just soak up the sun and serenity of a trip under sail.

Take your bachelorette party up a notch--by renting a private catamaran. With this package for up to 12 guests, you'll get the chance to sail out on the San Diego Bay aboard the sturdy Sea Esta for fantastic views of the cityscape. Snacks and bottled water will be provided on board and you're welcome to bring your own additional food and alcohol.

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by all of the amazing San Diego harbor monuments while enjoying the smooth sailing of San Diego's largest catamaran! Let our captain and crew guide you through the calm waters of San Diego Bay while our friendly bartenders whip up our famous custom cocktails and mocktails!

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984 Summer Olympic Games in Los Angeles. In July 2003, the Governor signed a bill into law designating the Californian as the official tall ship of the State of California. She is the only ship to carry this prestigious title. Since her launching in San Diego the Californian has played host to thousands of adventure travelers, sailing enthusiasts, students and history buffs up and down the West coast. She has also made voyages to Hawaii, Mexico and the East coast of the United States. Californian casts a distinctive and instantly recognizable silhouette and has become one of the most well known tall ships in America. Sailing the Californian and experiencing a tall ship adventure with the Maritime Museum sail crew on San Diego Bay is a Top Thing To Do when in San Diego!