Sail PR

31/05/2024

We mean it when we say you’ll have the best sailing experience with us. Our crew actively race in sailing competitions internationally and over Memorial weekend participated in US Sailing’s Multihull Championship on Hobie 16’s. Sailing against the best sailors in the class in the US, our captain Francisco claimed 1st place with his crew Faith while Pedro sailed with his captain, also Pedro and placed 5th!
Book your sail with us today :)
Link in bio.

31/12/2023

Wrapping up 2023 we thank everyone who sailed with us and trusted us to help create lifetime memories aboard Ohana. Cheers to 2024 and to keep providing the absolute best sailing experience in Puerto Rico. 🥂 🎉
Many blessings and best wishes to all.
The Sail PR Team

📷 by as Ohana sails by Castillo San Felipe del Morro back into San Juan Bay on our last sunset sail of the year.

02/11/2023

Full time Captain position available in the San Juan,PR area. Join our growing team of the best sailing experience in Puerto Rico! Interested send resume to [email protected]

18/03/2023

A great shot of a beautiful proposal aboard!



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Swipe to see how this afternoon started !
If you’re getting engaged you must read this! 🚨
This is not an ad, only a recommendation from a photographer’s point of view: if you’re looking for a romantic location for a proposal, you cannot go wrong with .

Everything from the nice ocean breeze to the silence of a sailboat in the sunset to free drinks; you will love every bit of this trip!

23/02/2023

A great picture of
“winter” sailing experience in beautiful San Juan Bay. It’s always sunny in PR!


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morning sail in Puerto Rico with ☀️
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13/09/2022

It has been a great year so far and we must now take a short break. We will be closed until October 3rd for maintenance and some time off. Bookings are available live online at www.sail-pr.com . Reserve your spot to make memories like these! 💙We look forward to welcoming you aboard!

14/08/2022

22/06/2022

The are in 🏆And our Daysails were named as one of the best experiences in Puerto Rico! 🎉
The Viator Experience Awards recognize top experiences based on average review ratings, share of bookings with a review, and number of bookings from adventure-seekers around the world during the 2021 calendar year. This initial round of awards celebrate the top 20 products per geographical region.

Book our Morning Mimosas or Afternoon Sail to try out this for yourself!

14/04/2022

Our famous rum punch or a local Medalla beer? That is the question. Which would you have on a sail with us?
☀️ ⛵️

06/03/2022

Lucky #7 🍀! It’s our 7th anniversary and we couldn’t feel more lucky being still open and providing the best sailing experience in PR. It’s been a complicated past few years for everyone and we want to thank all of our guests, past and future, for choosing us for your sailing experience in Puerto Rico and helping us stay open.
But as the old saying goes: “A smooth sea never made a skilled sailor”.
See you aboard!

01/03/2022

Our Morning Mimosas Sail and Afternoon sails are great to take in the sights of historical Old San Juan from a unique viewpoint.
Book yours now online
www.sail-pr.com

23/02/2022

We will be temporarily closed until next Monday 28th as we take a short break and our boat undergoes preventive maintenance to keep it in top shape for our guests!

Live availability for bookings on our website www.sail-pr.com

06/02/2022

Say hello to our new logo incorporating the new color Puerto Rico Sunshine!
Because sailing with our amazing sunshine and sunsets is what we do best.

What do you think? 🌅⛵️

02/02/2022

Amazing pictures taken aboard Ohana 2 for a love story. ❤️💙
Thank your for sharing !!

26/12/2021

As 2021 comes to a close we want to thank all our guests who sailed with us helping us overcome the effects of a pandemic on the tourism industry. We are closed until beginning of next year and look forward to a great 2022!

Dates are available to book online from January 3rd on www.sail-pr.com

Happy Holidays and Happy New Year from the Sail PR Team!!

30/10/2021

🤩🐬

103 Likes, 5 Comments - Sail PR () on Instagram: “This morning's weather conditions provided the best encounter we've ever had with our dolphin…”

26/10/2021

Just another Tuesday out in San Juan Bay 😍.
Sunset sails are filling up quick for the remainder of the year!

Book yours at www.sail-pr.com

20/10/2021

San Juan Bay after sunset is a sight to see especially with a full moon and cruise ship at port.

Book your sail with us at www.sail-pr.com and see it for yourself!

30/08/2021

Light winds today means the dolphins come out to play and they love swimming of our bow!
🐬🤩

17/08/2021

"Reviews from millions of Tripadvisor travelers place this in the top 1% of things to do worldwide" 😲

Words can't describe the feeling of having our dedication to provide the absolute best sailing experience recognized as one of the 1% BEST IN THE WORLD!

We will continue to push ourselves and provide even better service and experiences in the years to come.

Thank you to all our guests who have sailed with us and left their reviews to get us here.

Book your sail with us today at www.sail-pr.com

19/07/2021

We wish we could sail every day for sunsets like this one in PR!

For now, we will be taking some time off and will be closed from today until August 3rd as our catamaran "Ohana 2" is scheduled for a haul out and maintenance to keep her top shape for our guests. Our calendar with live availability is on our main website www.sail-pr.com for future bookings.

See you in 2 weeks!

27/06/2021

🚨We are hiring mates and USCG licensed captain in the San Juan, PR area!🚨 Send us your resume by email if you qualify the basic requirements and are interested:

[email protected]

14/06/2021

A sunset pic within a pic. 🌅⛵

Thanks for sharing

17/05/2021

Enjoy your sailing experience with us aboard Ohana 2 in total comfort with extra space to spread out. Book your sail at www.sail-pr.com

12/04/2021

The forward net on Ohana 2 is a favorite for laying out and getting some great pictures to remember your sailing experience in PR.

Book your sail with us to enjoy this setup and sail in total comfort. www.sail-pr.com





Thanks for sharing your pic!

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San Juan, Puerto Rico

Main character 🌺

06/04/2021

Ohana 2 looking beautiful with her new sails passing by UNESCO World Heritage Site Castle San Felipe del Morro. 😍