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    1. Local experiences
    2. /Things to do in San Diego…
    3. /Water Activities
    4. /Sailing
    5. /San Diego Bay Sunset Sail on a Classic Yacht
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    San Diego Bay Sunset Sail on a Classic Yacht

    Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht

    5.0 stars• 96 reviews
    From$125/ personincl. taxes and fees

    Duration

    2.5 Hours

    Ideal For

    Up to 6 people

    Includes

    Craft beer, wine, snacks

    Highlights

    Sail San Diego Bay at sunset aboard a classic 1904-style gaff-rigged sloop. Sip craft beer or wine with light snacks as the skyline glows.

    • Admire San Diego Bay landmarks at sunset
    • Sip craft beer, white wine, water, and enjoy light snacks
    • Sail aboard Liberty, a classic 1904-style gaff-rigged sloop
    • Hear stories from a captain with over 50 years of experience
    • Relax with blankets, a Bluetooth speaker, and an onboard restroom
    • Choose a shared cruise or make it private by booking six seats

    What's Included

    • Craft beer, white wine, water, and packaged snacks
    • Blankets and Bluetooth speaker
    • Clean restroom on the boat

    Things to know

    Children are welcome; no pets. Liability waiver required for all passengers. You may bring snacks and beverages, but no red wine.

    Cancellation Policy

    Cancel up to 24 hours before departure at no charge. Cancellations within 24 hours or no-shows are charged in full. Weather-related cancellations are at the captain's discretion; if your cruise is canceled due to weather and cannot be rescheduled to your satisfaction, 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 seafood restaurant is at the other end of Harbor Island (1 mile, 20 mins on foot). The Boathouse Restaurant (surf n' turf) at Harbor Island West Marina is a bit closer with marina-side views.

    You may cancel your reservation up to 24 hours prior to departure at no charge. If you cancel within the last 24 hours or fail to show up at boarding, you will be responsible for the full amount. Weather-related cancellations will be 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/or beverages, though red wine is not allowed as it can stain the vessel.

    Meeting details

    955 Harbor Island Drive San Diego, CA 92101 US

    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 1-877-GREET-WELL

    Report an issue

    Reference #YYBAD6

    Adult

    $125

    0

    Child

    $125

    0

    Private Charter for up to 6 guests

    $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
    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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