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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.

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Authentic San Diego Sailing Adventures
Aboard a Classic Yacht

Discover San Diego Bay's Most
Beautiful Sailing Experience

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.

Our Sailing Experiences

Three Ways to Experience the Liberty

Book Your Cruise
Sunset Cruise
2.5 Hours | Golden Hour Magic


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:

  • 2.5 hours of sailing on San Diego Bay
  • Packaged snacks 
  • California white wine 
  • Soft drinks and local craft beer
  • Guests may not bring red wine or hard alcohol
  • Maximum 6 guests for an intimate atmosphere
  • USCG-licensed Captain Phillip with over 45 years of experience at the helm
  • Hands-on sailing opportunities.

Highlights:

  • Golden hour photography opportunities
  • Downtown San Diego skyline views
  • Coronado Bridge and naval vessels
  • Point Loma and Pacific Ocean views
Book Your Afternoon Sail
Afternoon Sail
2.5 Hours | Best Wind & Sun


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:

  • 2.5 hours of peak wind-powered sailing
  • Packaged snacks are included in your fare
  • California white wine
  • Soft drinks and local craft beer
  • Guests may not bring red wine or hard alcohol
  • Maximum 6 guests  for personal attention
  • USCG-licensed Captain Phillip with over 45 years of experience
  • Educational sailing instruction and opportunities to steer and trim sails

Highlights:

  • Optimal afternoon wind conditions
  • Learn traditional gaff-rig sailing techniques
  • Family-friendly atmosphere
  • Active participation encouraged
  • Beautiful San Diego Bay views
Book Your Private Charter
Private Charter
2.5 Hours | Private Exclusive 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:

  • Private sailing experience for up to 6 guests.
  • 2.5 hours exclusive sailing charter
  • Packaged snacks 
  • California white wine
  • Soft drinks and local craft beer
  • Guests may not bring red wine or hard alcohol
  • Personalized service from USCG-licensed Captain Phillip (45+ years experience)
  • Hands-on sailing opportunities or relaxed cruising — your choice

Highlights:

  • Complete privacy and exclusivity
  • Ideal for meaningful celebrations
  • Authentic classic sailing experience
  • Beautiful San Diego Bay and coastal views
  • Refined and intimate onboard atmosphere

San Diego Sailing
Adventures is Different

Genuine Sailing Aboard a One-of-a-Kind Classic Yacht

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Sailing the Way It's Meant to Be

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.

Historic Maine Built Friendship Sloop

The Liberty is a meticulously crafted Friendship sloop. She preserves traditional maritime craftsmanship while meeting modern safety standards.

Small Groups Maximum 6 Guests

The maximum number of guests allowed on board is six. This ensures personalized attention, comfortable seating, and an intimate atmosphere.

Traditional Gaff Rigging

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.

Hands-On Experience

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's Expertise

Captain Phil has over 45 years of experience on the water as a licensed captain.

The Liberty: San Diego Bay's Only Classic Friendship Sloop

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.

Learn More About the Liberty

What to Expect on Your San
Diego Bay Sailing Adventure

From Departure to Return: Your Journey Aboard the Liberty

Before You Sail

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.

Departure & Raising Sail

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.

Under Sail on San Diego Bay

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.

Return to Harbor

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.

  • What You'll See
  • Downtown San Diego skyline
  • Coronado Bridge
  • Naval vessels and aircraft carriers
  • Point Loma and the Pacific Ocean
  • Harbor Island and Shelter Island
  • Sea lions basking on buoys
  • Spectacular sunset views (sunset cruises)
  • Your Sailing Experience
  • Hands-on steering opportunities (if desired)
  • Traditional sail trimming instruction
  • Maritime history and stories from Captain Phil
  • California white wine and craft beer served
  • Packaged snacks included.
  • Photography opportunities
  • Peaceful, relaxing atmosphere

Meet Captain Phil & the
Liberty

A Decade of Excellence on San Diego Bay

 

San Diego Adventures|Home

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. 

12 Years in Business

Since 2014

10,000+

Guests Hosted

500+ Five-Star

Reviews

Family-Run Excellence

  • Captain Phil is a USCG-licensed captain and owner
  • Restoration expertise passed through generations
  • Traditional sailing techniques preserved and taught
  • Personal attention to every guest's experience
Learn More About Captain Phillip & Our Story

Gallery

Frequently Asked Questions

Everything You Need to Know Before You Sail

How many people can sail on the Liberty?

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 Phillip 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.

What happens if there’s bad weather?

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 Phillip 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 Phillip 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 Phillip will provide detailed meeting instructions when you book.

What Our Sailors Are Saying

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

Ready to Experience San Diego Bay's Most Beautiful Sailing Adventure?

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.

Choose Your Experience:

Sunset Cruise

Golden hour romance and spectacular views (2.5-3 hours)

Afternoon Sail

Optimal wind conditions and active sailing (2.5-3 hours)

Private Charter

Complete exclusivity for your group (flexible duration)

Pricing:

Sunset Cruise

shared experience, max 6 guests

$115–$135 per person

Afternoon Sail

shared experience, max 6 guests

$115–$135 per person

Private Charter

entire boat, up to 6 guests, flexible duration

$750–$810

Book Your Adventure:

  • (619) 889-5988
  • info@sandiegosailingadventures.com
  • 955 Harbor Island Drive, San Diego, CA 92101
  • Online Booking:
Check Availability & Reserve Your Spot

Gift Certificates Available!

Give the gift of authentic sailing on San Diego Bay. Perfect for birthdays, anniversaries, holidays, or any special occasion.

Purchase Gift Certificate