Specials & Events

Nights of Lights - Sailing Charter

November 17, 2018 – February 3, 2019 / Leaving the Dock at 6PM, 7:30PM, and 9PM daily.

St. Augustine, Florida, USA city skyline and Bridge of Lions.

Beginning November 17, 2018 experience the Nights of Lights from the water’s points of view and let our Captain sail you and your guests on one of our beautiful sailing vessels along the Historic St Augustine Bayfront.  Over the duration of the your 75 minutes sailing charter you will be able to watch the sunset over city’s landscape and enjoy seeing the million of holiday lights.

Prices range from $39.95 to $59.95 per person for 75 minutes sailing charter.  Choose from one of our newer luxury sailing yachts ranging from 35 feet to 45 feet, both mono-hull and catamaran.  Each vessel can accommodate a maximum of 6 guests.

Daily charters at 6:00 PM, 7:30 PM and 9:00 PM.

Pricing for private charters begins at $200 (not to exceed 6 guests).

Choose from any of our Sailing Vessels

Esprit De Corp
French Kiss
Monkey's Uncle


  • Located in Comachee Cove Yacht Harbor Marina.  As you turn into the marina, continue straight past the security guard building.  We are located in the fifth structure on the right, facing the water.
  • Please arrive 15 minutes early to check in.
  • The weather is generally cool this time of year.  Please dress accordingly.  Blankets will be available on board if needed.
  • Feel free to bring whatever you wish to eat or drink.
  • Please advise if there will be any children under the age of six so we may properly fit them for life jackets.
  • All sales are final.  No refunds for cancellations except in the case of inclement weather.  We will happily attempt to reschedule your cancelled charter for another day or time.
  • Please provide contact information (email and mobile number) in case we need to contact you in case of inclement weather.

Valentines Sailing Charter

For the month of February 2019 – Romantic Sailing Charters begin at 5:00 PM – 7:00 PM

Sail away to a world of romance as you watch the sunset against the beautiful and historic backdrop of Saint Augustine’s city landscape.  Enjoy the intimate atmosphere as you treat your loved one to an evening of rest, relaxation and romance.  All you have to do is sit back and enjoy as we cast off from Camachee Cove Yacht Harbor for your romantic sailing charter.  Allow your skipper to ensure smooth sailing buy keep an eye out for dolphins as you sail by porpoise point. Then the sail continues making way along the shoreline of Matanzas Bay to historic Saint Augustine Bay Front where you will see Saint Augustine Light House, the oldest U.S. masonry Fort Castillo de San Marcos, numerous historic buildings and of course the Bridge of Lions.

Price beginning at $499.00 for 2 hour sailing charter and includes:

  • 1 bottle of Sparkling Wine,
  • 1 Dozen Red Roses, and
  • 1 Dozen Chocolate Covered Strawberries

Additional $160.00 per couple sharing the same charter

Gift Certificates

For any special occasion, consider a Gift Certificate for that special someone who would enjoy time on the water… charters with Captains, bare-boat charters for those already-a-sailor on your list, or an ASA sailing class. We also do private instruction 🙂 We have something for every sailor or would-be sailor! Simply give us a call. We can mail or email a gift certificate to you!


About Us

We are St. Augustine's Sailing Connection!

We've been teaching Sailing for decades from St. Augustine's premier marina and we're a certified American Sailing Association Training Facility.

Our well-maintained fleet of sailboats from 19 to 41 feet is here at the docks by our harbor-front office. Our Captains/Instructors are certified by the American Sailing Association and are USCG licensed... you'll find us to be a Friendly, Supportive Staff of Fellow Sailors!

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