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Sail PR

Sailing Tours & Activities in Puerto Rico

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Established in 2015, Sail PR is a young, modern experience provider. Our captain is a semi-pro racing sailor currently ranked #14th in the world sailing his specialty, Hobie Cat 16 sailboats. Our 37ft Lagoon Catamaran sailboat will take you sightseeing Old San Juan and San Juan Bay in a small group with complimentary drinks included!

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Your licensed US Coast Guard Master Captain, Francisco, has been sailing since he was four years old. A sea lover at heart, he will truly provide you a sail you’ll always remember. A currently active, competitive sailor, Francisco has traveled the world representing Puerto Rico for regattas to destinations like South Africa, Fiji, France and more.

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Our Lagoon 37′ Catamaran offers superior comfort and stability while still providing a true sailing experience- feeling the wind in your face and the fluid motion of the ocean. Equipped with a forward net to lay out, shaded area, spacious cabin, Bluetooth radio, and full bathroom, your comfort needs are met for a great sail!


Loved This Cruise

This cruise was fabulous. It was nice to see the city from a different perspective and during the day and evening. The captain and his first mate were great! Very knowledgeable and personable!

– Patricia H. | TripAdvisor
Great Time

Our San Juan Sunset Cruise was beautiful and relaxing. Sail PR did a fantastic job. The drinks, crew, and sights were amazing. I'd highly recommend a sail with them to anyone!

– Steve A. | TripAdvisor
Wonderful Trip

My fiancé and I recently took the sunset catamaran cruise on a recent stay in Puerto Rico. Great hosts- knowledgeable about the history and very welcoming to all of us on board. Highly recommend!

– Michelle B. | TripAdvisor
Vacation Highlight

The captain and his assistant were very friendly and professional. They had a variety of drinks for us and let us play our own music. Highly recommend to anyone looking for a great time with friends!

– Laura A. | TripAdvisor



What better way to celebrate a special occasion than on a great sail with your loved ones or friends? We’ll make your engagement proposal, birthday party, anniversary, etc. even more special. Let us know of any special requests you may have such as helping to arrange a surprise birthday cake (additional cost), candid pictures, recording of your proposal, or anything else we can do to make your sail memorable.


Sailing a boat with your crew requires a team effort, communication skills, and a positive outlook to reach a common goal. This is why many companies choose sailing outings as a great team-building activity. Whether you’re rewarding your team for a job well done or having them work on communication skills, actively taking part in the boat handling will make it happen! We will cater to your needs. Pricing per cater.

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