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    1. Local experiences
    2. /Things to do in San Diego…
    3. /Water Activities
    4. /Sailing
    5. /Private Sailboat Cruise & Wine Tasting in San Diego
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    Private Sailboat Cruise & Wine Tasting in San Diego

    Sail San Diego Bay, then savor local wine on a private outing

    3.4 stars• 217 reviews

    Duration

    5 hrs

    Ideal For

    Up to 10 people

    Includes

    Private sail, wine tasting

    Highlights

    Bring your group together for a private San Diego outing suited to celebrations and relaxed time on the water. Enjoy personalized hosting and time to take in the waterfront atmosphere.

    • Celebrate a date night, birthday, proposal, or group outing
    • Travel with a professional captain or host
    • Capture photos along San Diego's waterfront
    • Pack a jacket or sweater for the sea breeze
    • Wear comfortable footwear

    Itinerary

    3:00 PM – Meet & Welcome at San Diego Marina Meet your guide or captain at the boarding point. Brief introduction and safety overview.

    3:15 PM – Private Sailing Experience in San Diego Bay Board a private sailboat for a 90-minute scenic cruise. Enjoy panoramic views of Downtown San Diego, the Coronado Bridge, USS Midway, and the Pacific coastline.

    4:45 PM – Disembark & Transfer to Urban Winery After the cruise, you will be comfortably transferred to a local urban winery to continue the experience.

    5:00 PM – Wine Tasting with Light Pairing Enjoy a guided tasting of local wines paired with a cheese or charcuterie board (subject to availability). This is a private and personalized experience.

    6:30 PM – Free Time to Explore or Purchase Wines Take time to shop, capture photos, or relax with an additional glass of wine (optional).

    7:00 PM – Return Transfer or Hotel Drop-Off (if arranged) Conclude the experience with a comfortable transfer back to the starting point or continue your evening in the city.

    8:00 PM – End of Tour

    What's Included

    • Professional host or guide
    • Bottled water
    • All taxes and port fees

    Important details

    • Arrive at least 10 minutes before departure for check-in
    • Wine tasting is for ages 21+ only; bring valid photo ID
    • No outside alcohol is allowed
    • Light snacks are allowed with prior notice
    • No swimming is allowed during the sailing portion

    Cancellation Policy

    All bookings are final and nonrefundable. Receive a full refund if weather or minimum requirements prevent the tour from operating. No refund if you miss the boat departure.

    Product ID: Y66GCD

    FAQs

    Wear comfortable flat shoes and bring a jacket or sweater for the sea breeze. Bring a camera if you would like photos.

    No sailing experience is needed. A professional captain guides the private sailboat cruise.

    Outside alcohol is not allowed. You may bring light snacks with prior notice.

    Meeting details

    San Diego San Diego, CA US

    Experience provided by Five Star Tours

    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

    2 Person Private Tour

    $528.94

    0

    4 Person Private Tour

    $1,057.88

    0

    6 Person Private Tour

    $1,586.82

    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

    What people are saying

    Review 1 of 5
    5/5

    We booked a tour hiking Torrey Pines Nature Preserve with Five Star Tours (Alfonso) while in San Diego. Alfonso was an excellent tour guide; he provided lots of information about the area, but most importantly, he was personable and made us feel instantly at ease. In fact, we liked Alfonso so much that we booked another tour later in the week. We asked Alfonso to put together a tour of some beautiful coastal areas, and he did not disappoint. He took us to several sites that were exactly what we were hoping to see. We highly recommend Five Star Tours, and especially Alfonso. He made our trip to San Diego truly memorable.

    Photo of Lynn Ruedinger

    Lynn Ruedinger

    July 24, 2026

    Review 1 of 1
    5/5

    We booked a tour hiking Torrey Pines Nature Preserve with Five Star Tours (Alfonso) while in San Diego. Alfonso was an excellent tour guide; he provided lots of information about the area, but most importantly, he was personable and made us feel instantly at ease. In fact, we liked Alfonso so much that we booked another tour later in the week. We asked Alfonso to put together a tour of some beautiful coastal areas, and he did not disappoint. He took us to several sites that were exactly what we were hoping to see. We highly recommend Five Star Tours, and especially Alfonso. He made our trip to San Diego truly memorable.

    Photo of Lynn Ruedinger

    Lynn Ruedinger

    July 24, 2026

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