San Diego Sailboat Charters — Private & Ticketed Sails

Celebrate your special day aboard a luxury sailboat in San Diego with Sail San Diego’s Bachelorette Sail. Enjoy sun, sea, and stunning views on a 3-hour cruise customized for unforgettable moments with friends.

Discover the thrill of exploring California's stunning coastline on a private all-day sailing trip. Perfect for personalized adventures, this experience offers scenic views, wildlife encounters, and luxurious comfort—all on the open water of San Diego Bay.

Join Sail San Diego for an unforgettable evening aboard a private vessel, drifting through shimmering waters as the sunset paints the sky. Perfect for celebrating or unwinding, this trip offers a personal perspective on the coast’s natural beauty. Embark on a serene journey along San Diego’s coastline, where vibrant colors fill the sky and gentle waves lapping against the hull create a soothing soundtrack. This experience is designed for those seeking a peaceful yet inspiring escape, featuring complimentary drinks and snacks to enhance the moment. From sipping local craft beers to enjoying the cool ocean breeze, guests can relax and soak in views of landmarks like the Coronado Bay Bridge and downtown San Diego. What sets Sail San Diego’s sunset sail apart is its intimacy and focus on guest comfort. The boat’s attentive crew combines safety with local insights, making each trip educational and enjoyable. Whether celebrating a romantic milestone or gathering with friends, the vessel’s private setting offers a tailor-made adventure—in a location renowned for its coastal splendor. As daylight fades, the spectacle of colors unfolding over the Pacific creates perfect photo opportunities, making memories that last. For outdoor enthusiasts and tranquility seekers alike, this sail offers a refreshing perspective on California’s captivating shoreline.

Discover the stunning coastal beauty of San Diego on a private day sail with Sail San Diego. Experience personalized service, breathtaking vistas, and the thrill of sailing on California's Pacific waters—all tailored to your preferences.

Discover the beauty of San Diego from the water with a private morning sail. Enjoy stunning coastal views, peaceful seas, and personalized service on this unforgettable adventure.

Set sail into the evening with Sail San Diego’s sunset cruise, providing breathtaking views and a peaceful escape on the Pacific. Discover why this is a favorite for those seeking a memorable coastal experience in San Diego.

Discover the beauty of San Diego's coast on a private midday sailing adventure with Sail San Diego. Perfect for relaxing, sightseeing, and creating memorable moments on the water.

Set out early on San Diego's waters for a private sailing experience that combines stunning coastal views with personalized service. Perfect for relaxation, sightseeing, and unforgettable memories on the Pacific Ocean.

Celebrate the groom-to-be with a private sailing adventure in San Diego. Experience stunning views, personalized service, and a memorable day on the water with Sail San Diego.

Enjoy a one-of-a-kind Easter celebration on the water with Sail San Diego's private Easter Sunday Sail. Discover breathtaking views, marine wildlife, and the joy of sailing along the San Diego coast.

Set sail on a serene 3.5-hour journey from San Diego and watch Grey Whales migrate along the coast. Enjoy quiet sailing, stunning views, and expert wildlife insights for an unforgettable adventure.

Treat your dad to an unforgettable sailing adventure on the waters of San Diego this Father’s Day. Enjoy quality time, stunning views, and a relaxing day at sea with Sail San Diego’s private sail experience.

Join an exclusive investor tour of the historic Fiddlers Green in San Diego followed by a stylish 2-hour yacht sail. Network, explore innovative designs, and enjoy coastal views with Sail San Diego.

Experience a private 4th of July sail in San Diego with drinks, snacks, and a prime view of the Big Bay Boom fireworks. Celebrate Independence Day in style on the water!

Join Sail San Diego for a 3.5-hour sailing adventure and witness the awe-inspiring grey whales during their migration. Glide silently through the Pacific and learn fascinating whale facts from your captain, creating memories you'll never forget.

Set sail on a private evening adventure with cocktails and coastal views along San Diego’s stunning shoreline. Discover why the Sunset Sail Soiree is the perfect blend of relaxation and fun!

Celebrate Mother's Day with a stunning private sail in San Diego. Choose a Midday or Sunset Sail for breathtaking views and unforgettable moments on the water.

Set sail on a private yacht in San Diego Bay with your group of 15-22 guests. Customize your trip for swimming, sunset views, and local brews guided by expert captains.

Master the art of sailing with private lessons in San Diego’s beautiful harbor. Led by certified captains, this three-hour experience is tailored for all levels to learn sailing skills with expert guidance.

Discover San Diego’s coastline aboard the private Sailing Vessel Maile. Customize your trip from a relaxing bay cruise to ocean swims, enjoying local brews and expert captains for a coastal adventure unlike any other.

Set sail on San Diego Bay with a private 3-hour day or sunset cruise that blends serene waters, iconic views, and personalized service. Celebrate special moments with drinks, snacks, and the city skyline as your backdrop.

Celebrate your birthday with a sailing adventure in San Diego! Enjoy stunning views, sea life, and personalized service on a memorable cruise. Read on for all the details.