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Sailing Charters in Fajardo, PR

Come sail in our favorite place in the World! Fajardo, Puerto Rico is the perfect winter getaway, an amazingly beautiful and especially friendly place that offers unparalleled sailing in the tropical Caribbean. The raw beauty of the place is breathtaking.

Select A Time

Two - Six People | 3.5-Hour Sailing Yacht Cruise | 25% Deposit

Full Day Sail

$895/$795 | 7-8 Hours | 25% Deposit


Ready for an all day Caribbean sailing adventure? Sail in the beautiful Vieques Sound with a private full-day sailing charter, departing from Fajardo with Classic Sail Charters. Enjoy tropical views and breezes as you create an unforgettable adventure on one of our world-class yachts. 

Fajardo, PR

Welcome to Classic Sail Charters

Fajardo is our favorite place in the Caribbean, and anything but stressful. We call it “water therapy.”

Charters Feature:

  • Friends and family adventures
  • Romantic sunset cruises
  • Half-day sailing manna
  • Full-day sailing/snorkeling​

Or let us help you design your own custom outing. (For example: Captain for a day – introduction to sailing).

Bienvenidos a Classic Sail Charters

Fajardo es nuestro lugar favorito en los Caribbean. Contrario al nombre, es un pueblo donde se respira paz y armonía. Le llamamos terapia en el agua.

Ofrecemos viajes:

  • Aventuras para la familia y amigos.
  • Atardecer romántico
  • Medio día navegación
  • Navegación día completo y snorkeling

O podemos diseñar el viaje de sus sueños. También puede ser el capitán por un día y/o tomar un curso de introducción a la vela.

Annapolis, Maryland

Annapolis Landing Marina

980 Awald Road 
Annapolis, MD 21403


Fajardo, Puerto Rico

Puerto Del Rey Marina