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    1. Local experiences
    2. /Things to do in San Diego…
    3. /Water Activities
    4. /Sailing
    5. /Afternoon Sailing Cruise on San Diego Bay
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    Afternoon Sailing Cruise on San Diego Bay

    Sail a classic yacht past San Diego Bay landmarks with drinks and snacks

    4.9 stars• 101 reviews
    From$125/ personincl. taxes and fees

    Duration

    2.5 Hours

    Ideal For

    Up to 6 people

    Includes

    Craft beer, wine, snacks

    Highlights

    Step aboard Liberty, a replica of a 1904 gaff-rigged Friendship sloop, for a relaxed sail on San Diego Bay. Hear local history and find photo spots as you take in harbor views.

    • Explore the Maritime Museum fleet, including the Star of India
    • Glide past USS Midway, Seaport Village, cruise ships, and Navy vessels
    • Look for sea lions, dolphins, and pelicans along the bay
    • Photograph the Coronado Bridge when sailing conditions allow

    What's Included

    • Craft beer
    • White wine
    • Water
    • Packaged snacks
    • Bluetooth speaker
    • Blankets
    • Onboard restroom

    Important details

    • Arrive 15–20 minutes before departure
    • A signed liability waiver is required before boarding
    • Rubber-soled shoes are required; high heels and black-soled shoes are not allowed
    • Pets are not allowed
    • Red wine is not allowed aboard
    • Parking is not included in the listed price
    • Sailing conditions are determined by the captain

    Cancellation Policy

    Free cancellation up to 24 hours before departure. Cancellations within 24 hours and no-shows are charged in full. If the trip is canceled due to weather and no satisfactory reschedule is available, you will not be charged.

    FAQs

    Our Harbor Island location at Sunroad Resort Marina is within a 5-minute walk to three waterside restaurants: C-Level (bistro), Island Prime (steaks and seafood), and Coasterra (modern Mexican). Tom Ham’s Lighthouse is about 1 mile away (20 mins on foot). The Boathouse Restaurant at Harbor Island West Marina is closer with marina-side views.

    You may cancel without charge up to 24 hours prior to departure. If you cancel within 24 hours or fail to show up at boarding, you will be responsible for the full amount. Weather-related cancellations are determined by the captain. If your cruise is canceled due to weather and we cannot reschedule to your satisfaction, you will not be charged.

    Yes, you may bring snacks and beverages. Red wine is not allowed as it can stain the vessel.

    Meeting details

    Safe Harbor Sunroad Marina, 953 Harbor Island Drive, San Diego, CA 92101, Gate #1, Docks A-D

    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 1-877-GREET-WELL

    Report an issue

    Reference #AMZSWT

    Adult

    $125

    0

    Child

    $125

    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

    4.9
    Excellent
    101 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

    Went sailing with Captain Phil on this little classic yacht LIBERTY. Rigged so he can do everything by himself, this vessel performs well in light wind while Phil and the other passengers enjoy every minute on the water. If you even THINK you might want to go sailing on San Diego Bay, book this ride!

    Photo of Dav!d Berg

    Dav!d Berg

    July 2, 2026

    Review 1 of 1
    5/5

    Went sailing with Captain Phil on this little classic yacht LIBERTY. Rigged so he can do everything by himself, this vessel performs well in light wind while Phil and the other passengers enjoy every minute on the water. If you even THINK you might want to go sailing on San Diego Bay, book this ride!

    Photo of Dav!d Berg

    Dav!d Berg

    July 2, 2026

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