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    5. 2.5-Hour Private Sailing Charter in San Diego Bay
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    2.5-Hour Private Sailing Charter in San Diego Bay

    Private sail on San Diego Bay with snacks and drinks for up to six

    5.0 stars• 94 reviews
    From$795incl. taxes and fees

    Duration

    2 1/2 hours

    Ideal For

    Up to 6 people

    Includes

    Drinks, snacks, restroom

    Highlights

    Reserve a classic yacht for a private sail on San Diego Bay with your group of up to six. Enjoy a relaxed on-the-water tour with an experienced captain.

    • Reserve a private sail for up to six passengers
    • Meet at 955 Harbor Island Drive in San Diego
    • Enjoy a 2 1/2-hour cruise on the bay
    • Bring your own snacks and drinks if you like (no red wine)
    • Use the onboard restroom during your sail

    What's Included

    • Craft beer
    • White wine
    • Water
    • Packaged snacks
    • Bluetooth speaker
    • Blankets
    • Restroom on the boat

    Things to know

    A liability waiver signature is required for all passengers. Children are welcome and pets are not allowed. Gratuity for the captain and parking are not included.

    Cancellation Policy

    Cancel up to 24 hours before departure at no charge. Cancel within 24 hours or no-show and you pay the full amount. Weather cancellations are decided by the captain; if canceled due to weather and you cannot reschedule to your satisfaction, you will not be charged.

    FAQs

    Arrive 15 minutes before departure so you can leave the dock on time.

    Parking is not included and costs approximately $12. Gratuity for the captain is not included.

    Wear rubber-sole shoes (no high heels or black soles). Bring a jacket, sunscreen, a hat, and a camera.

    Meeting details

    955 Harbor Island Drive, San Diego, CA

    Experience provided by Sail Liberty
    Experience provided by Sail Liberty

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Report an issue

    Reference #6885YP

    Private Charter

    $795

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    94 reviews•Google Maps

    Captain Phil has clearly created something special with his replica 1905 wooden sloop. Reviewers consistently praise his welcoming personality, impressive craftsmanship, and deep knowledge of San Diego Harbor's history and landmarks. The boat itself gets nearly as much attention as the captain, with guests admiring the beautiful vessel he personally renovated. What stands out most is the intimate, personal atmosphere he creates as a privately-owned operation, often accommodating small groups that allow for a relaxed, conversational experience rather than a crowded tour. The sunset cruises seem to be the popular choice, and guests love the complimentary beverages and snacks Phil provides. Multiple locals mention this is the best harbor experience they've had despite trying other options. Families appreciate that kids can explore the boat, and there's often wildlife like dolphins and sea lions to spot. If you're looking for a more sophisticated, intimate sailing experience over a large party boat atmosphere, this comes highly recommended by everyone who's sailed with Captain Phil.

    What people are saying

    Review 1 of 5
    5/5

    Caption Phill was super awesome and so welcoming. We were on our way to the air port and had baggage that he offered to store for us . Made everything super convenient and just super easy. We enjoyed learning about how captain phill renovated the boat and his craftsmanship is first class. His tour around the harbor is amazing and he knows a lot about the history of the harbor and the navy in the harbor. He made our last night in San Diego epic!

    Photo of James Schroeder

    James Schroeder

    January 25, 2026

    Review 1 of 1
    5/5

    Caption Phill was super awesome and so welcoming. We were on our way to the air port and had baggage that he offered to store for us . Made everything super convenient and just super easy. We enjoyed learning about how captain phill renovated the boat and his craftsmanship is first class. His tour around the harbor is amazing and he knows a lot about the history of the harbor and the navy in the harbor. He made our last night in San Diego epic!

    Photo of James Schroeder

    James Schroeder

    January 25, 2026

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