Top La Jolla Sailing

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.

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.

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.

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.

We are based in San Diego and we are designed for families. Our whole mission is to bring families closer together. We want to put smiles on everyone’s faces; parents, children, and grandparents alike. Our vessel, the Sea Monkey, is a 35 foot yacht. On board you will have a designated captain , at your service, making sure you have a safe and memorable sail. You will have 2 options for your sail. Head to Coronado Bridge: In this option, we will sail along the US Midway, see landmarks like the Kissing statue, the Rady Shell, seaport village, view Coronado island and we will go under the Coronado bridge. Go see the Seals: This option is best in the morning when the winds are calmer. Here we will be sailing for around an hour there, circle the seals a few times, and head back. In some rare scenarios, you might view a dolphin or two.