Unique Experiences

St. Augustine Sailing is northeast Florida’s premier destination for unique sailing experiences, in-depth sailing lessons, diverse sailing membership options, and sailboat ownership expertise. We are your one-stop-shop for everything sailing! We are St. Augustine’s sailing connection where you’ll find a friendly, supportive staff of fellow sailors! Have a look through the site for details, and call us anytime for more information at 904-829-0648. We look forward to seeing you dockside soon!

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Fun and Adventure Awaits




We have traveled a lot and been on many charters and sails all over the world, but never anything so great as this.

Mikesroadtrip.com - Professional Travel video blogger and publisher of the award-winning travel blog

Mike Shubik
Mike Shubik

I’ve always seen friends going for a sunset cruise but We are glad we went with this one! The sailboat was beautiful. Once our party boarded, there was a champagne welcome for the party! The crew was top notch. We can’t wait to sail again with friends.

Harry and Dianne Brut
Harry and Dianne Brut

Tripadvisor’s Reviews

  • star rating  The original plan was to sail on a monohaul sailboat and the staff at St Augustine sailing had worked delightfully with my request especially last min, and then they double... read more

    avatar thumb Msyaya1
    January 21, 2023

    star rating  Beautiful 7:30 evening cruise with Captain Finn. Only 4 guests (including us) on this 35 ft sail boat. Amber prepared a lovely charcuterie board for us. Great way to ring... read more

    avatar thumb LABDRB
    January 1, 2023

    star rating  We thoroughly enjoyed our sailing experience although we didn't really travel far. I was disappointed that no beverages or snacks were provided, not even bottled water. We had... read more

    October 26, 2022
  • star rating  This was the highlight of our vacation in St. Augustine. Beautiful boat, expertly handled. This is not some party cruise where you power around the harbor with the sound and... read more

    October 21, 2022

    star rating  Captain Finn was amazing! We had an incredible experience! Definitely will be doing this again in the near future!

    September 14, 2022

    star rating  Our captain, Captain Finn, was very knowledgeable, friendly, and accommodating. Captain Finn explained all the pertinent details of the boat, especially the emergency points and procedures. The boat was immaculate,... read more

    September 12, 2022
  • star rating  Incredible experience, worth every penny—and way more. Beautiful beautiful. And to top it all off, Captain Finn answered all my questions from his deep knowledge of history. He is 100%... read more

    August 28, 2022

    star rating  Absolutely was the bet experience! My girlfriends and I had a blast on the boat as part of my bachelorette weekend! The crew was very nice and boat was super... read more

    August 2, 2022

    star rating  Our sunset charter was a wonderful experience! The booking process was a breeze, and the staff was friendly and professional (especially our captain, Finn!). Finn was not only professional and... read more

    July 13, 2022

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