San Diego Sailing Adventures
Experience intimate sunset cruises, afternoon sails, and private charters on San Diego Bay — limited to just 6 guests. Sail aboard the Liberty, a meticulously crafted 41-foot Friendship sloop. She’s more than a boat — she’s a boat with soul.
Book Your Sail Today
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Welcome aboard San Diego Sailing Adventures — a small-group sailing experience designed for those who want something better than a crowded tour boat. Since 2014, we’ve shared the magic of San Diego Bay aboard the Liberty — a classic Friendship sloop.
This is not a party boat or a booze cruise — it is a true, traditional sailing experience. Feel the wind fill the gaff-rigged sails, hear the creak of the rigging, and experience the splash of water against the hull. This is true sailing — peaceful, beautiful, and powered by the wind.
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. Our sunset sail combines steady evening winds with breathtaking golden hour light, creating an unforgettable journey aboard the Liberty — a 41-foot Friendship sloop. This is authentic wind-powered sailing — not a party boat. All sails are exactly 2.5 hours.
Perfect for:
Couples, anniversaries, proposals, romantic celebrations, photographers
What’s Included:
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Book Your Afternoon Sail
Sail during San Diego Bay’s optimal wind conditions for the most engaging and active sailing experience. Afternoon breezes fill the Liberty’s traditional gaff-rigged sails beautifully, offering the true feel of classic seamanship aboard a 41-foot Friendship sloop. This is authentic wind-powered sailing — not a party boat. All sails are exactly 2.5 hours.
Perfect for:
Families with children, sailing enthusiasts, active adventurers, first-time sailors
What’s Included:
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Book Your Private Charter
Book the entire Liberty for your group and enjoy a completely private sailing experience aboard a classic 41-foot Friendship sloop. This is authentic sailing — not a party boat atmosphere — designed for meaningful celebrations and relaxed gatherings. Private charters are exactly 2.5 hours.
Perfect for:
Proposals, corporate events, family celebrations, milestone occasions, photography sessions
What’s Included:
Highlights:
Genuine Sailing Aboard a One-of-a-Kind Classic Yacht
Unlike motorized ‘sailing’ tours, the Liberty primarily sails under wind power. The engine is used only when entering and exiting the harbor or when wind conditions are very light, ensuring a safe and smooth experience.
The Liberty is a meticulously crafted Friendship sloop. She preserves traditional maritime craftsmanship while meeting modern safety standards.
The maximum number of guests allowed on board is six. This ensures personalized attention, comfortable seating, and an intimate atmosphere.
Liberty carries original gaff-rigged sails — a traditional working rig you rarely see on modern charter boats. This is wind-powered sailing, not a motor cruise with scenery.
Want to steer? Trim a sail? Learn traditional sailing? You’re invited to participate as much or as little as you’d like. This is your experience.
Captain Phil has over 45 years of experience on the water as a licensed captain.
Our sailing experiences take place aboard the Liberty, a meticulously restored Friendship sloop, that’s unlike any other charter vessel on San Diego Bay. With her traditional gaff-rigged sails, mirror-finish teak woodwork, bronze fixtures, and graceful classic lines, S/V Liberty is captain Phil’s floating work of art.
From Departure to Return: Your Journey Aboard the Liberty
Arrive at Harbor Island Marina 20minutes before departure. Meet Captain Phil, get settled aboard, and receive a safety briefing. Store your belongings, grab a beverage, and get comfortable as we prepare to cast off.
Watch as Captain Phil raises the Liberty’s gaff-rigged sails using traditional techniques. Feel the boat come alive as wind fills the canvas and the engine goes silent—replaced by the sounds of the wind and the water.
Glide across San Diego Bay’s protected waters, powered only by wind. Relax on comfortable cushioned cockpit seating, sip premium beverages, and take in spectacular views of the downtown skyline, Coronado Bridge, and Point Loma.
As your adventure concludes, Captain Phil guides the Liberty back to Harbor Island Marina. Disembark with memories of a genuine sailing experience and the peaceful satisfaction of having traveled by wind power alone.
A Decade of Excellence on San Diego Bay
Captain Phil’s love affair with sailing began decades ago and culminated in a dream: to share the magic of authentic wind-powered sailing with others aboard a genuine classic yacht. That dream became reality in 2015 when he launched San Diego Sailing Adventures.
The Liberty herself is the result of a painstaking multi-year restoration that brought this 41-foot Friendship sloop back to her original glory. A boat with soul. From Maine to California, every detail—from the hand-stitched sails to the bronze fittings—reflect a commitment to preserving maritime heritage.
Since 2014
Guests Hosted
Reviews
Learn More About Captain Phil & Our Story
Everything You Need to Know Before You Sail
The Liberty accommodates a maximum of 6 guests . This intimate group size ensures everyone has comfortable seating, personal attention, and space to move around freely. We never overload the boat—your comfort and safety are our priorities.
We provide packaged snacks, California white wine, and all required safety equipment (life jackets in all sizes). Guests are welcome to bring beer or white wine if they wish. Please note that red wine and hard alcohol are not permitted onboard.
The Liberty’s wide beam and proper ballast create very comfortable motion, and San Diego Bay’s protected waters are typically calm. Seasickness is extremely rare on our charters. If you’re concerned, we recommend taking preventive medication (Dramamine, ginger, or prescription options) 30-60 minutes before departure.
Absolutely! The Liberty’s stability, secure handrails, and low freeboard (distance from water to deck) make boarding easy and sailing comfortable. We have life jackets in all sizes, and Captain Phil adjusts the sailing style to your group’s comfort level. We’ve welcomed guests from age 2 to 92.
Yes! The Liberty has a clean, private marine head (bathroom) below deck—a rare feature on vessels this size. It’s fully functional and well-maintained.
The Liberty accommodates a maximum of 6 guests . This intimate group size ensures everyone has comfortable seating, personal attention, and space to move around freely. We never overload the boat—your comfort and safety are our priorities.
We provide packaged snacks, California white wine, and all required safety equipment (life jackets in all sizes). Guests are welcome to bring beer or white wine if they wish. Please note that red wine and hard alcohol are not permitted onboard.
The Liberty’s wide beam and proper ballast create very comfortable motion, and San Diego Bay’s protected waters are typically calm. Seasickness is extremely rare on our charters. If you’re concerned, we recommend taking preventive medication (Dramamine, ginger, or prescription options) 30-60 minutes before departure.
Absolutely! The Liberty’s stability, secure handrails, and low freeboard (distance from water to deck) make boarding easy and sailing comfortable. We have life jackets in all sizes, and Captain Phil adjusts the sailing style to your group’s comfort level. We’ve welcomed guests from age 2 to 92.
Yes! The Liberty has a clean, private marine head (bathroom) below deck—a rare feature on vessels this size. It’s fully functional and well-maintained.
Safety is our top priority. If weather conditions are unsafe (high winds, storms, or poor visibility), we’ll contact you to reschedule or offer a full refund. San Diego’s weather is typically excellent, and cancellations are rare. Light rain doesn’t prevent sailing if you’re comfortable with it.
California white wine and packaged snacks are included. Guests are welcome to bring additional beverages; however, red wine and hard alcohol are not permitted. Beer and white wine are acceptable. We have a cooler with ice available.
Absolutely! Private charters are perfect for proposals, anniversaries, birthdays, and special occasions. Captain Phil has helped with dozens of proposals and knows how to make your moment perfect. Contact us to discuss your plans—we’ll help create an unforgettable experience.
Yes! Captain Phil loves teaching guests about traditional sailing. You’re welcome to steer the boat, help trim sails, and learn how everything works. Or you can simply relax with wine and enjoy the views—it’s entirely your choice.
We depart from Safe Harbor Sunroad Marina, located at 955 Harbor Island Drive, San Diego, CA 92101. Paid parking is available at the marina. Captain Phil will provide detailed meeting instructions when you book.
Safety is our top priority. If weather conditions are unsafe (high winds, storms, or poor visibility), we’ll contact you to reschedule or offer a full refund. San Diego’s weather is typically excellent, and cancellations are rare. Light rain doesn’t prevent sailing if you’re comfortable with it.
California white wine and packaged snacks are included. Guests are welcome to bring additional beverages; however, red wine and hard alcohol are not permitted. Beer and white wine are acceptable. We have a cooler with ice available.
Absolutely! Private charters are perfect for proposals, anniversaries, birthdays, and special occasions. Captain Phil has helped with dozens of proposals and knows how to make your moment perfect. Contact us to discuss your plans—we’ll help create an unforgettable experience.
Yes! Captain Phil loves teaching guests about traditional sailing. You’re welcome to steer the boat, help trim sails, and learn how everything works. Or you can simply relax with wine and enjoy the views—it’s entirely your choice.
We depart from Safe Harbor Sunroad Marina, located at 955 Harbor Island Drive, San Diego, CA 92101. Paid parking is available at the marina. Captain Phil will provide detailed meeting instructions when you book.
500+ Five-Star Reviews on TripAdvisor, Google, and Yelp
★★★★★
“The most beautiful boat on San Diego Bay! Captain Phil’s passion for sailing is infectious. We learned so much about traditional sailing while enjoying wine.”
Sarah & Michael
Anniversary Celebration
★★★★★
“Perfect family experience! Our kids loved steering the boat and learning about sailing. Captain Phil was patient and made everyone feel comfortable.”
The Martinez Family
Afternoon Sail
★★★★★
“I proposed to my girlfriend on the Liberty at sunset, and Captain Phil helped make it perfect. She said yes! Unforgettable experience.”
David
Private Charter Proposal
★★★★★
“As a lifelong sailor, I appreciated the authenticity. This is REAL sailing—no motor-sailing, proper sail trim. The Liberty is beautifully maintained!”
Robert
Sailing Enthusiast
★★★★★
“Corporate team outing that exceeded expectations. Created a relaxed atmosphere perfect for team bonding. The sunset views were spectacular.”
Jennifer
Corporate Private Charter
Read More Reviews
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 (2.5-3 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
$750–$810
Check Availability & Reserve Your Spot
Give the gift of authentic sailing on San Diego Bay. Perfect for birthdays, anniversaries, holidays, or any special occasion.
