Top California Sailing Tours

Set sail on the San Francisco Bay aboard the historic brigantine Matthew Turner, the largest sailboat in the area. Experience the beauty of the bay as you glide past iconic landmarks like the Golden Gate Bridge, Alcatraz, and Angel Island. Keep an eye out for playful seals and porpoises, while sea birds soar overhead. Enjoy the tranquil ambiance as the sun sets behind Sausalito's hills, casting a golden hue across the water. Whether you choose to assist the crew with raising the sails or simply relax, this sailing adventure offers a unique glimpse into maritime history on a spacious and stable vessel. - Sail on the largest resident sailboat in San Francisco Bay - Witness stunning views of the Golden Gate Bridge, Alcatraz, and more - Spot local wildlife, including seals and porpoises - Comfortable seating available both on deck and inside the chart house

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!

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.

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.

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.

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

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.

Admire views of San Diego that many other visitors miss—and help keep your sightseeing personal—on this small-group sailing excursion that's timed for sunset. Travel aboard a Catalina–style sailboat, and soak up the peaceful ambiance, plus a photo-worthy perspective on the city skyline, Old Point Loma Lighthouse, Coronado Island, and other highlights. Along the way, enjoy beer, soft drinks, and snacks, plus blankets in case you get cold.

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 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

San Diego looks spectacular from the water and with this sailing tour, you can sit back, relax, and enjoy having a crew to take the lead. During your sailing trip, you can enjoy onboard perks, such as alcoholic and soft drinks as you enjoy the panoramic views of San Diego Bay.

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!

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)

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco Bay. While our boats are coast guard licensed for 34 passengers, we are limiting to groups of 24 or less for comfort and class. Price includes entire boat, captain and crew as well as a customary gratuity. You can stick with our standard route or tell us where you want to go. Its your boat and your party.

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!

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.

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.

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.

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.

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.

We are a small charter company we offer a personal experience that is flexible to our guests needs. Sailing Is our speciality and we will try to sail our best to shut down the engine and sail by wind power.

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.