Top California Sailing Tours

Admire San Francisco and its surrounding sights from the water on a San Francisco Bay sailing cruise. Onboard a catamaran, sail past the iconic Golden Gate Bridge, legendary Alcatraz Island, and the hamlet of Sausalito. Take advantage of great photo ops while you soak up the sea breeze during this scenic tour.

Book this small group tour to get out on the San Diego Bay on a comfortable Catamaran at sunset. Your captain will make sure you are comfy with a glass of white wine, beer, and soft drinks onboard. Just relax as you sail along with your small group, checking out the San Diego skyline while looking out for friendly sea lions and sometimes dolphins.

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 6 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.

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.

Drive down one of the most scenic roads in California on this full-day tour from San Francisco. Cruise along the coast-hugging Highway 1, passing Pebble Beach on the iconic 17-Mile Drive. Enjoy free time to explore Monterey, where you can stroll down Steinbeck’s Cannery Row or visit the Monterey Bay Aquarium. Browse the ritzy boutiques of Carmel-by-the-Sea and get a glimpse of Silicon Valley’s tech campuses on the return drive to San Francisco.

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.

Discover the natural and manmade beauty of 17-Mile Drive on an electric bike tour from Pacific Grove. The e-bike allows you to cover more ground without getting worn out. The tour is great for the whole family, with the option to ride tandem with children weighing up to 120 lbs (54 kgs). Along the way, learn about the area from your guide and make stops at impressive viewpoints.

Sail across San Francisco Bay at twilight to admire the skyline as it begins to light up for the night, and enjoy a perspective on the skyline that few other visitors get to see. With an experienced captain at the helm, you’ll glide past Alcatraz Island and cruise underneath the Golden Gate Bridge. As you go, you can also enjoy one complimentary beverage to accompany your sightseeing, or purchase additional drinks from the on-board bar.

Look for whales as they migrate through the waters of the Pacific Ocean off of California on this half-day whale-watching cruise from Monterey. Your naturalist guide shares commentary about the whales and their habitat as you search for gray whales (most common), humpback and blue whales, and other marine life such as dolphins and sea lions during your cruise. Get tips for great photo ops and learn all about the mighty creatures at one of California's most famous whale-watching destinations.

See the sights of Hollywood on this tour by open-top Mercedes minibus or Ford Van with a canopy, which allows you to enjoy unobstructed views as you go. Traveling with an on-board guide, you'll pass by attractions such as the Dolby Theatre, Hollywood Sign, Rodeo Drive, and movie studios. Plus, get a look at some of the mansions where past and present stars have lived.

See what lives in the Pacific waters surrounding Catalina Island on a 45-minute underwater cruise. As you sit comfortably in a climate-controlled cabin on board a large boat, you'll glide five feet (1.5 meters) below the surface to look for marine life in their natural habitat out of your own porthole. Along the way, listen to live commentary from a guide.

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other tour boats which take 50+ passengers, our sailing yacht, "Blue", limits our capacity to 18 passengers. If you care to enjoy the beauty of propulsion by Mother Nature without the sound and smell of an engine, come sail with us!

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.

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.

Take a relaxing afternoon sailing cruise aboard a traditional sailboat on the San Francisco Bay. Cruise past landmarks such as Alcatraz Island, Angel Island, the Sausalito waterfront, and Golden Gate Bridge, and see the San Francisco skyline on your way back to Pier 39. Includes two drinks, and personalized attention from the crew and captain.

Come aboard the Privateer, your sailboat for the evening, for a a scenic cruise along the San Francisco Bay. As you set off on the water, you'll enjoy sightseeing at the most beautiful time of day—sunset. Coast along and look out for local landmarks like Alcatraz, the Sausalito shoreline, and the Golden Gate Bridge, all with a drink (or two) of choice in your hand.  

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.

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.

Set sail on the San Diego Harbor without spending a fortune on this dreamy 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.

Live the Mediterranean dream in Southern California on a sailing adventure in the Santa Monica Bay. We are a boutique luxury sailing charter with gourmet cuisine and a love of the sea. We take our guests on a safe, fun and memorable sailing past the mountains of Malibu, the famous Santa Monica pier and Venice Beach boardwalk. Let us share the joy of sailing with you!

Experience Los Angeles' best kept secret, the waters of Marina del Rey by coming on board one of our boats (boat depends on group size - we have 2 options). Bring your own food or beverage , your friends, and have a relaxing time on the water. Guests will take a tour around the marina, see the ocean, wild marine life such as sea lions and dolphins. The luxury yachts of the rich and famous are also on full display. Our tour guide is very knowledgeable about the area, and you'll often get more information than you bargained for - our ears our definitely on the ground and are up to date with all the cutting edge happenings of the location.

Relax in the sun aboard a catamaran in San Diego Bay on this small group sailing excursion. Your captain will welcome you aboard with beer, wine, and soft drinks. You can relax, sunbathe, look at the sea life, and help sail if you like. You’ll also be keeping costs down with this small group tour.

Experience the stunning beauty of San Diego Bay at sunset! Our boat charter mono hull is the perfect vessel for a sunset sail, with space for up to 6 passengers. As we sail through the calm waters of the bay, keep your eyes peeled for the possibility of seeing playful dolphins, majestic sea lions, and colorful seabirds. The experienced crew will be on hand to point out these incredible creatures. You'll have the opportunity to witness the wonder of sea life against the backdrop of a breathtaking sunset. As we set sail towards Point Loma, greeting the rolling waves of the ocean or going towards the heart of the San Diego Bay, seeing the city towards the famous Coronado bridge, don’t miss out and anchor these memories for a lifetime. Book your sunset sailing excursion today and discover the magic of San Diego Bay!