Family-owned since 2015, offering authentic sailing on San Diego Bay aboard the classic 1904-style Friendship sloop replica, Liberty.
San Diego Sailing Adventures began with a dream, a historic sailing vessel, and a captain’s unwavering commitment to sharing authentic maritime experiences on San Diego Bay. Since 2015, we’ve welcomed thousands of guests aboard our meticulously restored 1904-style Friendship sloop, creating memories that last a lifetime.
We’re not a large charter operation with a fleet of modern boats. We’re a family-owned microbusiness dedicated to one thing: providing intimate, authentic sailing experiences that honor maritime tradition while showcasing the natural beauty of San Diego Bay. Every sail is personally guided by Captain Phillip, the owner and heart of San Diego Sailing Adventures.
Why We Do What We Do
We are not a party boat or a booze cruise — our sails are refined, intimate, and rooted in true seamanship., we offer something increasingly rare: genuine wind-powered sailing aboard a historic vessel with a captain who genuinely loves what he does.
We believe sailing should be more than transportation—it should be a journey that engages all your senses, teaches you something new, and leaves you with stories worth sharing.
Your Guide to San Diego Bay’s Best Sailing Experiences
Captain Phillip isn’t just the owner of San Diego Sailing Adventures—he’s the reason guests consistently describe their experience as “unforgettable,” “magical,” and “the highlight of our San Diego trip.”
Captain Phillip holds a valid USCG Captain’s license with a 45-year safety record and zero accidents.
Over 55 years of experience on the water
Personally led the 1.5-year restoration of the Liberty
Deep knowledge of San Diego Bay's history, wildlife, and navigation
Beyond his professional qualifications, Captain Phillip brings something no certification can teach: genuine passion for sailing and connecting with people. Guests frequently describe him as warm, funny, patient, and deeply knowledgeable. He creates an atmosphere where strangers become friends, children feel empowered, and first-time sailors feel completely at ease.
How We Built San Diego’s Most Beautiful Sailing Vessel
Captain Phillip discovered the hull that would become the Liberty in 2014. She was a Friendship sloop design—a classic American sailing vessel dating back to 1904—but required extensive restoration to meet his vision of creating San Diego Bay's most authentic sailing experience.
For 18 months, Captain Phillip and skilled craftsmen rebuilt the Liberty from the waterline up:
In 2015, the Liberty welcomed her first guests on San Diego Bay. From day one, guests were captivated by her beauty, Captain Phillip's warmth, and the authenticity of the sailing experience.
Over the past decade, San Diego Sailing Adventures has:
Why Guests Choose Us Over Other San Diego Sailing Charters
Unlike many “sailing” tours that rely heavily on motors, we’re committed to genuine wind-powered sailing. Feel the difference as the Liberty glides silently across San Diego Bay, propelled only by the wind filling her traditional gaff-rigged sails. This is real sailing—the way it’s been done for centuries.
By U.S. Coast Guard regulations, the maximum number of guests allowed aboard is six, ensuring safety, comfort, and a truly intimate sailing experience. This isn’t about maximizing revenue—it’s about maximizing your experience. With only six guests, everyone gets personal attention from Captain Phillip, comfortable seating, unobstructed views, and the intimate atmosphere that makes our sails feel like a private experience.
The Liberty is not an original 1904 vessel, but a meticulously crafted classic replica yacht built in the style of a 1904 Friendship sloop. She preserves traditional maritime craftsmanship and historic design while meeting all modern U.S. Coast Guard safety standards.
When you sail with San Diego Sailing Adventures, you’re sailing with Captain Phillip himself—the owner, restorer, and passionate steward of the Liberty. This isn’t a corporate charter operation with rotating crew. Captain Phillip is personally invested in every sail, every guest, and every memory created aboard his beloved vessel.
Your fare includes a professionally guided sailing experience aboard the historic Liberty, packaged snacks, all required safety equipment, and Captain Phillip’s expert instruction and storytelling. California white wine is offered, and guests are also welcome to bring their own beverages (BYOB) to enjoy during the sail.
Gratuity is not included in the fare and is greatly appreciated. There are no hidden fees—just an authentic, intimate sailing experience on San Diego Bay.
Guests are asked to tip the captain.
Paid parking is available at the marina.
Whether you want to learn traditional sailing techniques or simply relax and enjoy the ride, Captain Phillip tailors each sail to his guests’ preferences. Interested in helping raise the sails? You’re welcome at the lines. Prefer to sit back with a glass of wine? That’s perfect too. Your experience, your way.
Professional Standards, Meticulous Maintenance, Guest Peace of Mind
The Liberty is fully certified and inspected by the United States Coast Guard for passenger operations. Captain Phillip holds a valid USCG Captain's license with an 45-year safety record with zero accidents
The Liberty is equipped with all required safety equipment including life jackets in all sizes, fire extinguishers, first aid kit, flares, VHF radio, and modern navigation electronics. Captain Phillip conducts a safety briefing before every sail.
The Liberty undergoes continuous maintenance and annual professional inspections. Captain Phillip's background as the vessel's restorer means he knows every inch of the boat and maintains her to the highest standards of seaworthiness.
Your safety is our top priority. We continuously monitor weather conditions and will reschedule if conditions are unfavorable. San Diego Bay is a protected harbor with generally mild conditions, but we never take chances with guest safety.
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.
Consistently rated among San Diego's top sailing experiences with Certificate of Excellence awards every year since 2016.
Guests consistently describe their experience as 'unforgettable,' 'magical,' and 'the highlight of our San Diego trip.'
Proud member of San Diego's maritime community, participating in harbor events and supporting local sailing initiatives.
Committed to sustainable practices including wind-powered sailing, responsible marina practices, and guest education about marine conservation.
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.
