Sail the blue waters and experience the beauty of Puerto Rico!

We aim to make your sailing experience as fun, relaxing and memorable as possible. We want to create lasting memories that you will remember forever and want to relive again.

We believe sailing should be enjoyed by everybody, no matter your age or skill level. With our expert staff and easy-going atmosphere, we're confident that you'll have a great time on board!


Meet our guide

Captain Francisco

Captain Francisco

A licensed US Coast Guard Master Captain, Francisco has been sailing since he was 4 years old. A sea lover at heart, he will truly provide you with the sail you will 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. Along the way, he specialized in multihull Hobie Cat 16’s and has claimed important placings in major championships, including:

  • 14th Overall at 2019 Hobie 16 World Championships
  • 3 North American Championship titles (2008, 2011 & 2016)
  • 2-time Runner Up North American Championship title (2012 & 2015)
  • 2-time Puerto Rico Olympic Committee Sailor of the Year
  • 10th place at the 2007 Hobie 16 World Championships
  • Bronze medal at 2005 Youth World Championships
  • An experienced racer and all-around sailor, he has a natural feel for any boat with a sail on it. Book your sail with Francisco today and enjoy an experience to remember!


Our Boats

A catamaran sailboat offers superior comfort and stability while still offering a true sailing experience. A fast boat capable of 14kt speeds she can provide a smooth relaxing sail or a faster exciting sail with enough wind! Equipped with a forward net area to layout and lounge, a front cushioned area to sit on the deck and take in the sights and a shaded cockpit area in the back with seating for protection from the elements you can make yourself comfortable where you please. Ohana 2 is also equipped with Bluetooth radio for streaming your music and full bathroom inside for added comfort. All sails aboard Ohana 2 include complimentary alcoholic and non-alcoholic drinks to choose from. While snacks or food are not provided during our sails, guests are more than welcome to bring along their own and enjoy them aboard. There are sturdy, cockpit tables and inside cabin aboard to sit with no worry of it being tipped over.

Why choose us?

Top-rated San Juan sails!

We offer the best sailing experiences in Puerto Rico! We have been consistently top-rated in multiple review sites and earned various recognitions. We provide personal attention and top notch service with our crew of expert sailors and hosts. With 3 different sail times to choose from daily, it's easy to fit a great sail into your day. Let us take care of everything aboard so you can unwind and relax.

Environmentally Friendly

In an effort to reduce plastic waste in our seas, we do not serve single-use plastics such as straws and water bottles. We provide 100% Britta filtered water. You are welcome to bring along your reusable bottle and we will fill it up for you. We use compostable cups aboard for included drinks.

Catamaran Sailboat

Our Ohana 2 is defined as “a yacht or other boat with twin hulls in parallel (imagine two separate big canoes joined together by a platform)” it is the most stable sailing experience you can get while still having a full 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 in case of rain and full bathroom inside your comfort needs are met for a great sail!

Special Sailebrations

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.


A slice of paradise San Juan, Puerto Rico

Sail PR is located in San Juan, Puerto Rico. It is the most populated city in the island and has a tropical climate. It is known for its beautiful beaches and historic buildings.

Here are some facts about the area:

  • San Juan's weather is almost always sunny and warm, with temperatures ranging from the mid-70s to the low 90s Fahrenheit.
  • It is home to the largest marine life conservation in the Caribbean.
  • There is no wet season and the dry season lasts from December to April. This means that you can enjoy sailing all year long!

Frequently asked questions

Most frequent questions and answers

We are a convenient 5-10 minute drive from the major hotels in the San Juan, Condado and Isla Verde area in Puerto Rico. We are located in San Juan Bay Marina at Slip A72. If you are taking a cab, ask your driver to take you to San Juan Bay Marina and reference where the Sizzler Restaurant is at. Once at the Marina, walk through the boatyard towards the lower part of Sizzler Restaurant. Once at sea level, go past a Jetski rental kiosk towards the long dock with boats on either side. Our slip is on the left past the white gate that leads to the dock. Slip numbers are marked on the floor.

You may book online here, or by clicking any of the “book now” buttons. We ask that you call, text, or email us for same-day bookings to ensure availability even if the calendar doesn’t show it. Online bookings are handled through a secure and encrypted provider accepting most major credit cards.

For daysails we recommend cool, light clothing, hat, sunglasses and sunblock. While San Juan Bay has very calm waters and you will usually not get wet, there is always the possibility of some small splashes of water. Sunset sails have usually calmer breeze and cooler temperatures so you may dress more comfortably, however we do recommend light clothing. If you choose to go out into the ocean, the possibilities of getting wet are more likely as we will be sailing in bigger seas. No shoes allowed on-board.

We ask that you arrive at least 15 minutes before your sail for a proper safety briefing and preparations. Sails depart sharp on time. Plan to be on time as in consideration to others that may be present we can not delay departure time. Failure to be on time for departure will result in forfeiting full fare or a $50 rebooking fee.

We can accommodate 2-6 passengers for a personal, intimate experience. If you wish your sail to be private you may opt for the Private Charter or reserve the boat for your group. If you are sailing alone we ask that you contact us so we may schedule you with a current group.

Your crew will take care of all the boat handling maneuvers so you may sit back and relax, but you are welcome to take part if you want a more hands-on experience.

As we usually sail in very calm waters, the possibilities of getting seasick are almost zero. However, if you have gotten motion sickness at other times, we do recommend taking some remedies beforehand.

We offer complimentary soda, water, local beer, rum & coke and special rum punch for adults over 18 years of age. Sunset sails also include Spanish Cava or Prosecco.

We welcome everyone to enjoy the wonderful experience of sailing! However, US Coast Guard requires children under 13 to wear a lifejacket at all times. There is also certain level of physical exertion that may take place to board and move around so we advise caution for the elderly and persons with mobility issues and serious medical conditions.

Of course! We encourage you to do so. Our speaker is bluetooth ready so you may connect your own device and use your personal playlist. We use Spotify and Pandora and may look up your favorite station.

While the times shown are our standard offerings we are always available for special requests. Give us a call or email us to make special arrangements

We have a 48 hour cancellation notice policy for full refund. 48 hours or less cancellations forfeit 50% fare. 24 hour cancellations forfeit full fare. No shows, late to departure time or same-day booking cancellations will forfeit 100% fare.

We want you to enjoy a great experience while sailing with us so we would reschedule your sail for another day when the weather is ideal. If this would not be possible due to your travel plans, we would offer a full refund. The decision to cancel due to weather rests solely on the Captain. Tropical weather can change quite rapidly so some decisions to cancel might be last minute, however we always take into consideration your time and alternate plans so we try to always cancel at least an hour in advance from our scheduled departure time.

Just be ready for a great sailing experience! If you do have any additional questions, please feel free to call, text or email us and we will gladly clear up any doubts.

Book your next trip.

Come aboard and let us show you the best of Puerto Rico!