Sail into adventure with the best sailing tours!
Welcome to Sail PR! Come sail with us and experience the beauty of the island from the water. We offer small, intimate sailing experiences that will allow you to see all the best that Old San Juan has to offer, from historical landmarks to stunning natural scenery. Our tours are perfect for families looking to create a unique memory, couples wanting a romantic sail and small groups of friends wanting a private boat for themselves.
Our boat is meticulously maintained and our experienced, professional staff strive to provide the best sailing experience in Puerto Rico. Sit back with a drink in hand and enjoy the sights.
Book your sail online today and enjoy the beauty of Puerto Rico.
Sailing Tours & Private Charters
Morning Mimosas Sail
Enjoy a unique start to your morning, sailing on our spacious catamaran taking in the sights of Old San Juan from the bay.
Make yourself comfortable on the front net and take some sun in or sit back in the shaded cockpit area and sip your drink of choice as we narrate some historical facts along the way.
This one-hour and 30-minute sail includes bottomless mimosas, house rum punch, local Medalla beer, rum and cokes, orange and pineapple juice, soda, and water.
6 spaces are available per sail. To book privately for yourself or a group choose Private Charter.
San Juan Sunset Sail
Our most popular sail! A relaxing cruise around the calm waters of San Juan Bay to enjoy a beautiful sunset and a perfect start to your evening.
See Old San Juan as it changes from daytime to sunset colors and then city lights coming on at night as we are headed back to the marina.
Our two-hour sailing route stays within the calm, protected waters of San Juan Bay for a relaxing experience.
Complimentary refreshments include Prosecco or Cava sparkling wine, our special house rum punch, local Medalla beer, rum and cokes, orange and pineapple juice, soda, or water.
San Juan Bay Afternoon Sail
Soak in the sun with a drink in hand while taking in the sights of Old San Juan and Cataño from a unique point of view.
While the sun is fully out during the time of this sail, the back cockpit area of our catamaran is shaded so you can also enjoy the sail without being subject to the sun.
Bring your lunch and enjoy it aboard; we provide the drinks! Choose from mimosas, house rum punch, local Medalla beer, rum and cokes, orange and pineapple juice, soda, or water.
Our hour and a half sailing route stays within the calm, protected waters of San Juan Bay. Open ocean sail available upon request dependent on weather.
6 spaces available per sail. To book privately for yourself or group choose the Private Charter.
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.
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.
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!
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.
Words from our customers
My family and I took an afternoon sail with Willie and Pedro, and we had the best time. They were friendly, accommodating, and fun to talk to! I highly recommend this to anyone looking for a chill activity.
25th May 2023
Celebrated my birthday in San Juan and decided to do a day sail! Best choice ever, Captain willie and coco was great and drinks made the hot day better!
21st May 2023
20th May 2023
This was my first experience but definitely will not be my last! The Captain and his first mate Hector was amazingly and super informative. Willie and Hector were super encouraging and because of this experience I will definitely try this experience again! My husband who is not a big smiler could not stop smiling!!!
20th May 2023
My gf and I had a great time ! Pedro was amazing. I def recommend sailing with them. It was a beautiful day on the water and we learned a lot of history about San Juan.
16th May 2023
Best way to kick off a trip to PR for SURE!! Pedro and Jonathan were kind, gave us space to chat but also shared fun facts about the city and made sure our drinks were always full! Would love to do again!
16th May 2023
So if you’re looking for a nice tour/sail and you want to look cute while you’re doing it-book them. This was a very nice, chic, classy sail. The guys were laid back but also professional. I could have sailed all day with them and been ok. Loved it!!
11th May 2023
Great trip, not over crowded. Captain and mate were incredibly nice and friendly. I Would recommend.
11th May 2023
This was possibly the best part of our trip. The captain and first mate were kind, relaxed, and made sure we had a ton of fun. I could do this every day I’m in PR and nothing else and be happy.
9th May 2023
The views, the history, and great customer service. Everyone on the boat was very nice and the time for the cruise was perfect.
8th May 2023
Set Sail on a perfect adventure in San Juan, Puerto Rico
San Juan is located in the subtropical region and is the capital of Puerto Rico. It is one of the most visited cities in the world. The main sightseeing attractions include Old San Juan, El Morro, La Fortaleza and Castillo de San Cristóbal. The culture of this City is influenced by its multicultural past and enjoys the reputation of being full of passionate people in music, art and family traditions!
The climate and geography of San Juan, Puerto Rico make it a popular tourist destination. Food is a big part of this place and you won't be disappointed with the local cuisine such as mofongo, a plantain mash or churrasco steak. The flavors of the island are a fantastic combination that you must experience when you visit the city.
Frequently asked questions
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.