San Diego Sailing Adventures is a family-owned sailing charter company operating since 2015 on San Diego Bay. Tours and private charters run aboard the Liberty — a 41-foot 1904 Friendship Sloop replica built with a wooden mast, gaff-rigged canvas, teak decking, and bronze deck hardware. The maximum is 6 guests per sail. Captain Philip has been a USCG Licensed Master for more than 50 years. Tickets start from $95 per person.
San Diego Bay Has Dozens of Charter Companies. None of Them Sail a 1904 Friendship Sloop.
Most tours on San Diego Bay fall into two categories: a catamaran carrying 40 passengers where the engines run from departure to return, or a motorized sightseeing cruise that lists “sailing” in its title while the sails stay furled. Neither of these is what San Diego Sailing Adventures offers.
San Diego Sailing Adventures has run small-group sailing tours and private charters on the bay since 2015, aboard the Liberty — a 41-foot Friendship Sloop replica with a wooden mast, gaff-rigged canvas, and teak decking. She is the only vessel of her type on the bay. The maximum is 6 guests, the engine is shut off when the sails fill with wind, and Captain Philip — with more than 50 years at the helm — is present for every departure without exception.
That is the operation. Simple, deliberate, and without equivalent on San Diego Bay.
Liberty holds 6 guests — sunset departures book 2–3 weeks out in summer → Check availability at sandiegosailingadventures.com | (619) 889-5988 | From $95/person
Built Around One Boat: A Family Operation Since 2015
Captain Philip and his family purchased the Liberty in 2014 and spent 18 months restoring and preparing her for charter operations before her first departure in 2015. The rebuild focused on the details that define the boat’s character: mirror-finish teak woodwork, polished bronze deck hardware, gaff-rigged sails maintained to traditional working specifications, and a below-deck cabin with cushioned seating.
The business has operated continuously since. It is personally run — Captain Philip is at the helm for every sail, not a rotating seasonal crew. That continuity is not a branding decision. It is the mechanism that maintains the standard.
San Diego Sailing Adventures departs from Safe Harbor Sunroad Marina, 955 Harbor Island Drive, San Diego, CA 92101 — on Harbor Island, five minutes from San Diego International Airport and ten minutes from downtown.
S/V Liberty: The Vessel
The Liberty was built as a replica of a 1904 Friendship Sloop — a vessel type developed by New England fishermen for stability and seakeeping in cold Atlantic waters, named for Friendship, Maine, where the design was refined. Liberty carries that design forward with a wooden mast, gaff rigging, teak decks, and bronze deck hardware, while meeting current USCG safety standards.
She measures 41 feet and is consistently described by guests as the most photographed sailboat on San Diego Bay. The gaff boom and canvas draw attention from other vessels. Guests who have chartered boats in other cities often describe Liberty as unlike any vessel they have been on. That reaction reflects a deliberate design standard — every piece of hardware and every plank of teak was chosen for the version of this boat Captain Philip intended to maintain for the long term.
See the Liberty before you book — photos at sandiegosailingadventures.com/about-our-boat/ Private charters available — book all 6 seats for an exclusive experience
What San Diego Sailing Adventures Offers
Sunset Sail — 2.5 Hours
The most-booked tour. Afternoon winds build reliably on San Diego Bay from the thermal differential between the Pacific and the warm inland desert. Captain Philip raises the gaff-rigged sails by hand as the Liberty clears the harbor mouth. The engine goes off. For the next two-plus hours, the boat moves under canvas alone — past the USS Midway Aircraft Carrier Museum, the Star of India at the Maritime Museum, Seaport Village, and the Coronado Bridge. The sky over Point Loma turns orange as the tour crosses back to Harbor Island. All-inclusive — craft beer, California wine, soft drinks, snacks.
Afternoon Sail — 2.5 Hours
San Diego Bay’s afternoon sea breeze peaks between noon and 4 PM, producing the most active sailing conditions of the day. The afternoon departure gives guests a sail with a full canvas throughout. Same landmarks, same all-inclusive inclusions, more wind.
Morning Tour — 2 Hours
A shorter, discounted departure. Includes mimosas in place of the craft beer and wine of the afternoon and evening tours. Fewer vessels on the bay, cooler temperatures, an earlier return for guests with afternoon plans.
Private Charters
Book all six seats and the Liberty is yours entirely — no shared passengers, a route shaped around what the group wants, the option to bring additional food or a special bottle. Private charters run 2.5 hours at the same rate as booking six individual tickets. Popular for proposals, anniversaries, milestone birthdays, retirements, and small corporate outings.
Seasonal Whale Watching
Pacific gray whale migration runs December through March as the whales move between Arctic feeding grounds and Baja California breeding lagoons. Captain Philip operates whale watching tours during migration season, drawing on more than 50 years of local knowledge of where and when to position the boat.
Why Captain Philip Built This Operation
Captain Philip has spent more than 50 years sailing — offshore races, coastal passages from Alaska to Mexico, open-ocean crossings. He has also watched San Diego Bay’s charter market fill with motorized tours that use the word sailing as decoration, and catamarans where 45 people share a deck and the engines never stop.
The Liberty was purchased and rebuilt because nothing on the bay matched what a genuine small-group, wind-powered sail should be. The 6-guest cap costs revenue. The insistence on shutting the engine off when the sails fill requires reading weather rather than just scheduling departures. The all-inclusive pricing model removes the upsell dynamics that erode trust on other operators. Every one of these decisions reflects the same principle: deliver the experience as described, without compromise.
Who Boards the Liberty
First-time visitors to San Diego: Couples and groups on a 3–5 day trip who have covered the USS Midway, Old Town, and Balboa Park and want one experience that does not come from a guidebook. The most common post-sail description: “best thing we did on the trip.”
Couples marking a milestone: The Liberty’s 6-person cap makes every departure feel personal. Anniversary sails, proposals, and birthday charters book regularly. Captain Philip handles special occasions with discretion and attention — contact (619) 889-5988 to discuss logistics for any event.
First-time sailors with motion sickness concerns: San Diego Bay’s protected harbor produces flat-water conditions regardless of wind strength. There is no oceanic swell inside the bay. Guests who arrive nervous about sea sickness routinely describe the Liberty as the smoothest, most comfortable boat they have ever been on.
Experienced sailors: A gaff-rigged Friendship Sloop maintained to this standard, with a captain who has 50 years of offshore and coastal sailing, is a different conversation than most charter experiences allow. Taking the helm and feeling the boat loaded under a full gaff rig is available on every departure.
Location and Booking
San Diego Sailing Adventures departs from Safe Harbor Sunroad Marina, 955 Harbor Island Drive, San Diego, CA 92101. Parking is available at the marina. Guests are asked to arrive 15 minutes before departure.
Tickets start from $95 per person for shared departures. Private charter rate equals six individual tickets. Book online at sandiegosailingadventures.com or call (619) 889-5988 for dates, group questions, or special occasion planning. Cancellations more than 24 hours before departure receive a full refund. Weather cancellations by Captain Philip come with a full refund or complimentary reschedule.
Frequently Asked Questions
Is this worth booking if none of us have sailed before?
Yes — and first-time sailors make up the majority of Liberty passengers. The experience does not require any prior sailing knowledge, and the 6-guest format means Captain Philip has time to explain what is happening and why throughout the sail. Guests who arrived expecting a passive sightseeing ride consistently describe it as one of the most engaging two and a half hours of their San Diego trip.
What is included in the ticket price?
All tours include a selection of craft beers from San Diego’s local breweries, California wine, soft drinks, water, and snacks. The morning tour substitutes mimosas. Guests are welcome to bring additional food, a special bottle, or a birthday cake — Captain Philip has no objection to supplementing what is already on board.
How is the Liberty different from a catamaran sailing tour?
Three specific differences. Vessel: the Liberty is a 1904 Friendship Sloop replica with a wooden mast and teak decking — there is no equivalent on the bay. Scale: a maximum of 6 guests versus 20–45 on a typical catamaran departure. Propulsion: the Liberty’s engine is switched off when the sails fill; a catamaran tour maintains engine use throughout to hold departure schedules regardless of wind. These are not variations of the same experience.
We are a group of 8 — can we all sail together?
The Liberty’s USCG-regulated maximum is 6 passengers. Groups of 7 or more cannot sail together on a single Liberty departure. Options: split into two separate bookings on different dates, or contact (619) 889-5988 to discuss alternatives. San Diego has capable catamaran operators (Ocean Spirit is well-reviewed) that can accommodate larger groups if keeping everyone together on the same sail is the priority.
Can guests take the helm?
Yes. Every departure includes the option to take the wheel and steer the Liberty under Captain Philip’s instruction. This is not a two-minute photo rotation — it is active participation in sailing the boat, calibrated to each guest’s comfort and interest. Some guests spend a significant portion of the sail at the helm.
Six guests. One captain. Engine off when the sails fill. From $95/person → Book at sandiegosailingadventures.com | (619) 889-5988 | Free cancellation 24hrs prior