Unique Experiences

St. Augustine Sailing is northeast Florida’s premier destination for unique experiences, in-depth lessons, diverse 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  My husband and I went on the Thirsty Thursday sailing from 4:30 to 6:30pm. It was an absolutely delightful experience. The booking was easy, the customer service was... read more


    star rating  I can't say enough good things about this company, its owners and team. I have taken two ASA sail courses and have done a private half-day sailboat charter with STA... read more


    star rating  We went on the ‘Tuxedo Tuesday’ cruise with St Augustine Sailing and it was an incredible experience. Everyone from St Augustine Sailing was very friendly and made us feel... read more

  • star rating  Had a glorious evening 3 hour sail on the Rendezvous with Destiny captained by Libby. From phone call start to return to dock after a spectacular sail this was a... read more


    star rating  We have traveled extensively locally in out of the country and I have written over 1200 reviews and I have over 2500 contributions on Tripadvisor. I am a retired travel... read more


    star rating  These people know what they are doing. Ships are Great Condition. Staff very helpful. You will have a learning and fun time. The Management of the company know what... read more

  • star rating  Rose Ann and Chuck Points, owners of St. Augustine Sailing Enterprises, Inc. in St. Augustine, Fla. hosts students from Florida School for the Deaf and the Blind with on-board time... read more

    Bonnie H

    star rating  First they lost our reservation, Even though we confirmed two days ahead of time. They seemed surprised to see us. The lady that supposedly runs the business, took us out... read more

    emmett s

    star rating  Could use more experienced personnel. Some are quite good while others need more training. Prices are a bit high but average for the area.

    James D

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