Top California Sailing

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.

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.

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.

Enjoy a different perspective and 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.

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.

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.

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.

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.

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.

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.

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)

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an unforgettable evening with contagious laughter and panoramic views of the Newport Bay. Bring your plus one or your three closest pals as four is the maximum on this cruise with close proximity. Please BYOB (bring your own drinks and tapas/ food as we will have an area to facilitate provisions). The cruises we offer are described below- We are now offering a sunrise cruise to start your day off the right way! We offer early to late afternoon cruises to enjoy some sun rays and the beautiful views of Newport Harbor! Then we have our sunset time cruise, so you can enjoy the entire sunset! Finally, we offer romantic twilight cruises for those who love to see the beautiful lights that come out when the sun goes under the sea! Let us know if you have any questions and we look forward to meeting you soon!

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.

With this San Diego harbor cruise, you can check off views of a selection of San Diego’s most important monuments, without encountering crowds or traffic. Simply enjoy a stress-free sail through the water in a large catamaran, and benefit from a full bar on board, so you can purchase drinks along the way.

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.

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.

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.

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.

Guarantee your seat aboard the Privateer, your sailboat, when you prebook 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 two drinks of your choice in your hand.

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.

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.