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March 7, 2026
Family-owned since 2015, offering authentic sailing on San Diego Bay aboard the classic 1904-style Friendship sloop replica, Liberty.
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Everything You Need to Know Before You Sail
San Diego Sailing Adventures was established in 2015 after an 18-month restoration of the Liberty. Captain Phillip has over 55 years of maritime experience and has been sailing San Diego Bay since 2015.
Yes! As the owner and only captain, Captain Phillip personally guides every sailing experience. You’ll never get a substitute captain or seasonal employee—you’ll sail with the person who built this business and restored the Liberty.
Captain Phillip is a USCG Licensed Captain, and the Liberty is fully certified by the United States Coast Guard for passenger operations. We maintain all required safety equipment, insurance, and inspection certifications.
The Liberty is a replica of a 1904 Friendship sloop—a classic American sailing design. She’s handcrafted with traditional woodwork, bronze fittings, and period-appropriate details. She’s the only vessel of her kind operating on San Diego Bay and is 100% wind-powered (no motor-sailing).
Absolutely! We’ve coordinated dozens of proposals, hosted corporate events, celebrated anniversaries, and accommodated special dietary needs. Contact us to discuss your specific needs—we’re happy to help make your sail perfect.
Perfect! Most of our guests are first-time sailors. Captain Phillip explains everything, answers questions, and can teach you basic sailing techniques or let you simply relax and enjoy the ride. No experience necessary.
Yes! We’ve welcomed guests from age 2 to 92. The Liberty has stable, comfortable seating, safety equipment in all sizes, and San Diego Bay’s calm, protected waters make for gentle sailing. Captain Phillip adjusts the experience to your group’s comfort level.
Three Ways to Experience the Liberty
Experience San Diego Bay at its most spectacular as the sun sets over Point Loma and the Pacific Ocean. Golden hour magic, premium beverages, and unforgettable views.
Ideal for: Couples, anniversaries, proposals, romantic celebrations
Sail during optimal wind conditions for the most engaging and active sailing experience. Perfect for learning traditional sailing techniques or enjoying beautiful weather.
Ideal for: Families, sailing enthusiasts, first-time sailors
Book the entire Liberty for your group and create a completely customized sailing experience. Choose your departure time, design your route, and enjoy exclusive access.
Ideal for: Proposals, corporate events, celebrations, photography
Book Your Sail Aboard the Liberty Today
Whether you’re celebrating a special occasion, seeking a unique family adventure, or simply want to experience authentic sailing on San Diego Bay, the Liberty provides the perfect platform for unforgettable memories.
Golden hour romance and spectacular views (2.5 Hours)
Optimal wind conditions and active sailing (2.5 Hours)
Complete exclusivity for your group (flexible duration)
shared experience, max 6 guests
$115–$135 per person
shared experience, max 6 guests
$115–$135 per person
entire boat, up to 6 guests, flexible duration
Give the gift of authentic sailing on San Diego Bay. Perfect for birthdays, anniversaries, holidays, or any special occasion.