Top California Sailing Tours

Avoid crowds and traffic in San Diego and have a peaceful adventure on the water with this small-group sailing tour. Keeping the group size small ensures a more personalized experience, without the noise and crowds of large group sightseeing boats. Along the way, pass by lots of great photo opportunities—including the Star of India, Coronado Bridge, and views of the city’s skyline.

Watch the sunset over San Diego and admire the city and ocean views during a small-group cruise on a classic 1904-styled sailboat. Pass landmarks such as the Maritime Museum, Coronado Bridge, and the USS Midway. Look out for sea lions, dolphins, and other wildlife around San Diego Harbor while relaxing and sipping on the provided wine, beer, or non-alcoholic drinks.

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. As an added bonus, enjoy two included beverages, from wine to soft drinks.

See what lives in the Pacific waters surrounding Catalina Island without getting wet on a 45-minute underwater cruise. As you sit comfortably in a climate-controlled cabin on board a large boat, you'll glide below the surface to look for marine life in its natural habitat through your own porthole. Along the way, listen to live commentary from a guide.

Go on a whale-watching expedition in San Diego on a half-day cruise. Get the scoop from a guide who studies the migratory patterns of whales as you keep a lookout for the majestic marine mammals, as well as dolphins, turtles, and more. The yacht offers 360-degree views of the ocean and both indoor and outdoor viewing decks, for an all-round comfortable experience.

Boats that usually take groups out on the San Francisco Bay can be super crowded and it can even be hard to see the views. This San Francisco Bay Private Sailboat Cruise takes just you and your group out on the water, so you never have to worry about missing out on seeing something. See popular spots like Alcatraz Island and the Golden Gate Bridge or customize your time on the bay.

A unique two-hour sailing Experience aboard our 35-foot sailboat, Luna. Limited to six people. Watch for playful dolphins, sea lions, and pelicans. Get hands-on or sit back and enjoy breathtaking views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military vessels and your local Captain shares his knowledge of sailing and San Diego. We invite you to celebrate a special occasion with your partner, family or group and capture the moments in breathtaking photos. No sailing experience is needed for this family-friendly outing, but participation is welcome. We love sharing our knowledge and experience. Choose a public or private tour option when you book. Snacks and bottled water included. Feel free to bring your own easy to handle alcoholic/non-alcoholic beverages and snacks. Free cancellation, 100% refund up to 24 hours before your reservation.

Sail the lovely waters off San Diego in style 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 sights like Hotel del Coronado, Point Loma Lighthouse, Tijuana, and the San Diego skyline.

Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Marina del Rey yacht experience, hosted by our friendly and knowledgeable captains. Whether you’re seeking a laid-back day cruising the coast, curious about hidden gems around the marina, or just want to unwind in style, we’ve got you covered. Ryder Bayo and our trusted local crew will guide you through a safe, smooth, and scenic tour informal, comfortable, yet undeniably luxe. Ask anything, explore everything, and enjoy the California sun aboard your floating getaway. Your day in Marina del Rey starts here, book now and let the harbor become your haven.

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.

Explore the stunning Pacific waters with a private sailing charter in Oceanside, California. Enjoy a customizable sailing adventure tailored to your pace and interests, guided by a friendly, USCG licensed captain. Ideal for families or small groups, this intimate experience allows you to connect with the ocean while creating lasting memories. Sailing trips are designed for up to 6 guests, making it a perfect option for anyone looking to escape the crowded tours. - Private sailing charters for up to 6 guests - Tailored experiences with a local captain - Perfect for families seeking a memorable adventure - Depart from Oceanside Harbor, flexible duration available

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.

Look for whales as they migrate through the waters of the Pacific Ocean off of California on this 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.

Help to steer and sail one of San Diego’s iconic tall ships, the Schooner Califonian, on this group tour. Not many people can say they’ve sailed a tall ship, but you will be able to make that claim. Besides the chance to help sail this ship, this tour also includes a self-guided tour of the Maritime Museum of San Diego to enrich your seafaring knowledge.

Swap crowded ferries and sightseeing tours for a much more intimate alternative—a private boat trip exclusively for your personal group. Set off in the morning for a better chance of spotting wildlife, and benefit from having a captain to take care of the navigating and driving, so you can focus on the views.

Experience Alcatraz from the water while uncovering the stories that made “The Rock” one of America’s most infamous prisons. Rather than simply viewing the island from afar, hear firsthand accounts from former guards and inmates through a smartphone audio guide as you cruise around Alcatraz. Along the way, enjoy views of San Francisco Bay landmarks, including the Golden Gate Bridge, with skip-the-line boarding for a seamless experience.

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.

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.

Step into the 16th century when you board the San Salvador Spanish galleon for a 4-hour sailing. The ship is a replica of Juan Rodriguez Cabrillo's ship that arrived in San Diego on September 28, 1542. For those who love history, or simply want an unforgettable San Diego sailing, this is an unconventional adventure tailor made for you.

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 (own expense). Then enjoy free time to explore Carmel-by-the-Sea before returning to San Francisco.

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 onboard bar.

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the Oceanside harbor. We cater to guests from many of the five star hotels in the area. We serve an upscale experience with Charcuterie and Champagne as an option. Ask about our three and four hour extended experiences. We set sail and begin looking for dolphins and whales. The bow of the boat has been fitted with a special dolphin seat so that you can actually sit over the top of the playful dolphins below. The memories gained abord the Song of David will last a lifetime. Please realize a gratuity of 20 - 30%.

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and the Captain. Enjoy a stunning 1 hr private romantic night cruise and sea life discovery aboard our 42 ft Bertram-Trojan Motor Yacht. Bring your own food and drinks aboard. Consider booking multiple blocks for a longer trip.

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas of San Diego. Watch for playful sea lions, dolphins, and pelicans. Participate or sit back and enjoy breathtaking sunset views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military vessels. We invite you to celebrate a special occasion with your partner, family or group and capture the moments in breathtaking photos. No sailing experience is needed for this family-friendly outing, but participation is welcome. We love sharing our knowledge and experience. Choose a public or private tour option when you book. Snacks and bottled water included. Feel free to bring your own easy to handle alcoholic/non-alcoholic beverages and snacks. Free cancellation, 100% refund up to 24 hours before your reservation.