Puerto Rico Sailing Trips
salvi wk horizontal
hawksnest wkF
Meet Our Fleet 2 final
Janise Gennaker
janise little lameshur cactus
janise salinas
janise interior2
Piñeros Janise Best 1
wk best interior
ivan sunset
Piñeros Janise Best 3
Lily Pad Palomino
Cockpit 380
Janise Yeah Lameshur

Sail with us in the beautiful

Caribbean Sea!

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Welcome to Puerto Rico Sailing Trips’ website. We specialize in offering the first-class service in our sailing charter business.  As the #5 company in Tripadvisor, we integrate our nautical expertise, commitment to the best service and culinary talent into our sailing charters so that you sit back and enjoy a lifetime of amazingly memorable moments.


Puerto Rico Sailing Trips offers the exclusive Why Knot Private Charter in a awesome sailboat. We also offer our Janise Sailing Day Charter and Janise Sailing Afternoon Charter in a comfortable catamaran. Our expert team strives to provide the best customer service and a memorable sailing experience on the beautiful Puerto Rico sea coasts. Come sail with us to the pristine nature reserve of Piñeros Island, the best-kept secret in the Caribbean.

Our positive testimonials have made us earn the top positions in TripAdvisor as well as being recognized with TripAdvisor’s 2021 Travelers' Choice Award for our nautical boating expertise and terrific customer service. Come and experience why we are in the very top positions on Tripadvisor out of 70 companies in Fajardo!


Unlike the large boat charters, we have small private groups which make for a wonderful experience on the water. We take a limited amount of guests to be in compliance with our USCG boat permits and our COVID-19 Safety Protocols. Our crew includes the USCG-certified licensed captain and 1 first mate.

An impeccable boat fleet, the expertise in nautical tourism, and personalized service come together for a uniquely amazing sailing charter experience. Our vessels are meticulously maintained and outfitted for comfort and performance. 


We meet in Puerto del Rey Marina, Fajardo which is a 45-minute drive from San Juan. There's plenty of free parking and state-of-art facilities in the marina. The GPS address for the location is ‘PUERTO DEL REY MARINA FAJARDO’.


Puerto Rico Sailing Trips
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