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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• 96 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.

    Split the cost with your group

    This booking is for the whole experience, which fits up to 6 guests.

    From$132per person
    Split with

    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

    Related locations

    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 1-877-GREET-WELL

    Report an issue

    Reference #6885YP

    Private Charter

    $795

    Fits up to 6 guests · 2 1/2 hours

    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
    96 reviews•Google Maps
    95
    0
    0
    0
    1

    Captain Phil is the real draw here, and it shows in nearly every review. Guests consistently rave about his warmth, humor, and deep knowledge of San Diego Bay, its naval history, and the boat itself. The vessel is a beautifully restored replica of a 1905 sloop, and Phil did much of the restoration work himself, which adds a genuinely interesting layer to the experience. The sunset cruise format lends itself to small, intimate groups, which most guests seem to appreciate. Snacks and complimentary drinks are included, and Phil has even been known to store luggage for guests catching flights. Wildlife sightings like dolphins and sea lions come up more than once, which is a nice bonus. Across the board, reviews reflect a relaxed, personal atmosphere that feels a world away from the typical tourist boat tour.

    What people are saying

    Review 1 of 5
    5/5

    An absolutely amazing evening!!!! Captain Phil with his knowledge and skill made the experience of a sunset cruise magical! The boat he has restored is top notch and beautifully done. If you are looking for an intimate experience to see the sunset please book!

    Photo of Missy Hein

    Missy Hein

    April 20, 2026

    Review 1 of 1
    5/5

    An absolutely amazing evening!!!! Captain Phil with his knowledge and skill made the experience of a sunset cruise magical! The boat he has restored is top notch and beautifully done. If you are looking for an intimate experience to see the sunset please book!

    Photo of Missy Hein

    Missy Hein

    April 20, 2026

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