Top California Sailing Tours

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!

Looking for the perfect way to wind down after a busy day in Monterey? Skip the crowds on land and set sail into the sunset on this relaxing evening cruise. Enjoy a drink as you travel across the bay, and soak up unparalleled ocean views. There's even the chance to spot marine life such as sea lions, otters, dolphins, and whales. With great music and a laidback captain at the helm, it’s the perfect way to end your day on a high note.

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!

Experience the beauty of the San Diego coastline on a peaceful sunset sailing tour, avoiding the crowds at popular viewing spots. Relax aboard your vessel as you take in stunning sunset views, along with possible sightings of dolphins, vibrant seabirds, and sea lions. Along the way, enjoy scenic views of the Coronado Bridge, Point Loma, and San Diego Bay.

See San Francisco’s most famous waterfront landmarks from the water on a bay cruise that combines iconic views with onboard flexibility. Sail beneath the Golden Gate Bridge, pass Alcatraz Island, and take in panoramic views of the city skyline while listening to stories and insights through an app-based audio guide. With skip-the-line boarding and indoor and outdoor viewing areas, it’s an easy way to experience the bay from a different perspective.

An interactive adventure, this tour is time-efficient and takes you on a sailing adventure on the San Francisco Bay. Hop aboard a private yacht with a USCG licensed captain. Sail beneath the Golden Gate Bridge, cruise along the San Francisco waterfront, and marvel at Alcatraz and Angel Islands up close. Take the helm for a hands-on sailing experience and capture scenic views, encounter local wildlife, and create memories.

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 comfortable bean bag seating makes this tour a great choice for travelers celebrating a special occasion.

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of the harbor, look out for sea lions, sea otters, and harbor seals. Once you pass the breakwater, the sailing fun begins and you can relax with a beverage while your captain takes care of you. Be sure to be on the look out for whales and dolphins while you sail! Our spacious and comfortable catamaran is the perfect vehicle for exploring the bay and searching for wildlife! You have a chance to see sea otter, sea lions, harbor seals, dolphins and whales!

Take an unforgettable boat ride in Monterey Bay to spot local marine wildlife, from humpback whales to Great white sharks to dolphins. This whale-watching adventure takes you to one of the best spots in the state to spot some of these majestic creatures. Sail over Monterey Bay Canyon, which is a nutrient-rich area known for attracting all kinds of underwater wildlife.

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.

See San Diego from a marine vantage point on this 90min harbor cruise, including a look at the marina, seabirds and potential sea lion sightings. Listen to live narration from your captain and enjoy for-purchase snacks from the onboard snack bar.

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.

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.

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.

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

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. Whether you choose an afternoon sail or stay for sunset, the experience is calm, unhurried, and genuinely personal — less like a tour, more like being invited onto a private yacht. Take in the San Diego skyline, Coronado Bridge, and USS Midway from the water — no narration script, no rushing, just the bay at its best. Afternoon sail — open skies, warm sun, and the city in full view. Sunset sail — watch the sky change over the water as the city lights come on. Ideal for couples and travelers who want an authentic, uncrowded San Diego sailing experience. All sails are 2.5 hours. Included: craft beer, California white wine, soft drinks, and packaged snacks. Paid marina parking available. Gratuity for the captain is appreciated and not included.

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica Bay and beyond. Founded by Captain & Chef Matthew Mancini—a USCG-licensed master mariner and culinary artist—we’re backed by a tight-knit crew of lifelong ocean lovers who live for the sea. We move with the currents, plan by the tides, and chase the sun across the SoCal Riviera. Deeply passionate about exceptional food and the profound harmony of the ocean Committed to sharing the transformative peace that comes from syncing with the rhythms of the waves Overjoyed to pass on our lifelong love for sailing, gourmet cuisine, and the healing magic of the water—turning every guest into part of the crew (and often lifelong friends)

Set sail on the tall ship Matthew Turner and soak in the stunning sunset views of San Francisco Bay, including iconic sights like the Golden Gate Bridge, Alcatraz, and Angel Island. This unique experience combines adventure with the opportunity to learn about nautical history aboard a beautifully crafted 132’ wooden brigantine. Enjoy the gentle sway of the ship and take in the rich maritime atmosphere. Perfect for families, friends, and anyone looking to enjoy a memorable evening on the water. - Sail on the historic Matthew Turner, launched in 2017 - Experience breathtaking views of San Francisco Bay's famous landmarks - Bring your own food and drinks (beer and wine allowed) - Ensure to arrive 15 minutes early for a prompt departure from Sausalito

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.

Head out onto the San Francisco Bay for an approximately 2-hour sail, where you watch a beautiful sunset with the Golden Gate Bridge in the background. This is an intimate group with a maximum of six, so you have plenty of space to spread out and enjoy the views. Sip on bottled water while you sail. The tour is offered in English and Spanish to accommodate more guests.

Enjoy a sailing adventure on a Catalina-style sailboat with just six people aboard for a comfortable, small-group experience (or, find five friends and fill up the whole boat). Sail in San Diego Harbor, and look out for top city attractions, from Coronado to the USS Midway. Sit back and relax, and enjoy the views, all while enjoying complimentary beer, hard seltzer, non-alcoholic beverages, and snacks.

Skip the crowded cruise ships and watch the sunset over San Diego Bay from the water on your very own private yacht instead. With just your party on board, enjoy unobstructed panoramic views as you pass by Coronado Bridge, Sunset Cliffs Natural Park, Shelter Island, and more. Travel further out into the bay and admire the changing faces of San Diego, from city skyscrapers and busy marinas to natural parklands and rugged sea cliffs.

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.