PUERTO RICO SAILING TOURS & CHARTERS

Sunset sail was a great experience! Very smooth sailing on the bay, but a little choppy out on the ocean. Captain Willie and First Mate Hector were such excellent and fun guides, I would definitely do it again! We learned a lot, enjoyed great drinks, and had the best time. Highly recommend!!

The view was terrific. captain and 1st mate were great. A1 experience. Catamaran experience was great.

Great boat ride around the bay with delicious rum and pineapple drinks! The crew was very friendly and knowledgeable and gave just the right amount of information about the points of interest you can see from the boat. My husband and I were on the trip with two other couples and there was plenty of room so everyone could have a great seat.

Wonderful boat tour of old San Juan! We explored the city during the day and was wonderful to see it from the water at night. Pedro and Francisco were wonderful and very knowledgeable.

A great value for an enjoyable boat ride around the harbor. Easy to find. Experienced captain. Accommodating and helpful mate. Plenty of drinks. Doesn't take up the whole day either. Well worth it.

Amazing time! Worth every penny - the views and explanations about the landscape were perfect. And the sunset was incredible! Would absolutely go again!

Wonderful outing! Willie and Hector did an awesome job taking us and another couple on a sail of San Juan bay. We were impressed by their focus on safety and making sure that we were all comfortable and enjoying ourselves. They did a great job pointing out landmarks and educating us on the history of the area. I highly recommend this tour. The drinks were great too.

Easy walk from our airbnb to the marina. The crew were very friendly and pointed out the sites on the cruise. Mimosas were excellent!!

Hector and Willie were incredible! They made us feel very secure, they put up with my father-in-law’s humor, and they were extremely knowledgeable. We had a lot of fun, it was an absolutely beautiful experience on a lovely vessel. It was a beautiful experience to see Old San Juan from the water. I’d recommend this to anyone, I just wish it was longer than 90 minutes because I didn’t want to get off the boat!

The crew made sure we had an amazing time. They were very knowledgeable and made the experience worth it.

This was a great experience. It’s a small boat and he only takes 6 people but it was a lot of fun. You get to see San Juan from a different perspective. I would definitely recommend.

We enjoyed the boat ride with amazing views of Puerto Rico from the water. The drinks were great too. Very attentive crew.

Willie and Hector are amazing! The tour was super fun and the drinks were even better. We will definitely be coming back!

It’s a must do when in PR. You will not be disappointed. There was a sprinkle of rain and the team navigated around it making for an exceptional sunset cruise.

So nice and the view was gorgeous! Lovely crew and a very nice boat too Would absolutely do it again

The day sail was very enjoyable thanks to the Captain and Mate. The drinks were good as well. I highly recommend this sail. They were very friendly and professional. We had a wonderful time.

The staff was personal and great to sail with. They gave history on Puerto Rico and San Juan. They also talked about history of Puerto Rico culture and gave great recommendations for the rest of our trip.

The sunset cruise was the highlight of our Puerto Rico trip! My girlfriend and I had such a blast, and the crew was extremely attentive and friendly! They offered to take photos, gave history facts of PR, checked on us to see if we needed another drink, and were very fun! You get to see views all across San Juan. Very romantic activity - highly recommend!

This was such a relaxing way to see Old San Juan from the water. Captain Francisco and First Mate Hector were awesome! The instructions seem a little intense, but it's necessary because there isn't much signage to direct you where to go. They send you a picture of where to go the day of your trip to make their location on the dock easier to find. If I could give them more stars I would. Will definitely do this again if we ever come to San Juan again!

Very friendly crew. The boat was clean and we left on time. Enjoyable sail in the San Juan bay. Recommend! Good for a family too!

My wife and I went to PR for our honeymoon as I'm a PR native raised on the mainland. The staff upon arrival were very kind and very comedic. I was hesitant because I'm bigger and nothing mentioned a weight limit. A team member (I believe they're cousins) (I'm blanking on his name now) assured me, and was very patient as I overcame my anxiety. During the entire trip we had drinks, laughs, and we're educated more on PR after this. Thank you and we will be back!

We had an AMAZING cruise....the crew were very friendly and nice to us and the other couple on the boat with us. The made sure our drinks were refilled and gave a nice history of the island and recommendations of others areas to go. Please if you come through give them a try. AMAZING company and customer service

A must for anyone wishing to explore the beautiful city of San Juan. The tour group was intimate, engaging, and informative which allowed for a VIP experience. Such a WONDERFUL tour!!

We had a great time with Captain Willy and Raf. Raf was very knowledgeable and gave us a brief history lesson on Old San Juan.

We had a great tour of the area, our guides gave us so much history of the area. Later, their info helped give us a better understanding as we walked around old San Juan

Everything was simply amazing! Beautiful. Intimate. Educational. Serene. And let’s not talk about the drinks. Whewwwww! The rum punch and mimosas were divine! The Captain was great! And so was our guide.. the views were breathtaking! Thank you again for a beautiful tour

This was a fantastic sailing trip and I highly recommend it. The water was calm, and the air was soothing. I left the cruise so relaxed. The captain and first mate were friendly, accommodating and very knowledgeable of the island. It was a little tricky getting to the boat, bet we’ll worth the adventure. Unfortunately I can only rate this up to a 5.

Fantastic experience with a wonderful crew! There were only 4 of us (plus the 2 man crew) - it was peaceful/relaxing, informative and drinks a-plenty! Seriously - thank you!

This was a fantastic trip for us - very welcoming guides/hosts, and a lovely sail around to Old San Juan, complimented by history and fun facts about what we could see. Provided plenty of instructions to find the boat, and offered tasty drinks and refills throughout the trip. We didn't get a great sunset, but it was still well worth it - I wish I could go out again!

The trip was great... Very informative, everyone was nice and made the experience very enjoyable especially Willy.... and not to mention the bottomless mimosas & rum punch! 😁 I definitely recommend

Awesome experience! Loved the route and information given! Beautiful tour, would definitely recommend

My wife and I took a sunset cruise with SailPR last night. What a great decision it was! We were joined by two other couples and were all in great hands with the crew of Francisco, Rafa, and Willie. The boat was very nice and comfortable. They offered a variety of alcoholic and soft drinks. Refills were plentiful. Seeing the San Juan harbor from the boat was a great perspective. There was plenty of space for all three couples, and we all had great views. It's very windy on the water, which nicely counteracted the Puerto Rico heat. Everyone was in short sleeves or no sleeves, yet no one appeared to be cold even after the sun went down. Rafa regularly appeared at the bow to either refill our drinks or point out notable sights of San Juan. It was quite relaxing to just sit there and be carried by the winds over the tiny waves. We had a great time and would absolutely return on our next trip to San Juan. Highly recommended!

Second time booking with Fransisco, it’s so beautiful and an amazing experience every time. Have to do this every time I come back to PR it’s a must. The drinks are great, they explain as you go so you know what your looking at but not the whole time so you can sit and enjoy. Bathroom you can use, very clean boat and smooth ride. Don’t forget to tip I’ve seen people each time not tip and they run around so much for us to get drinks it’s only right

This was easily the highlight of my quick trip to San Juan. We departed and returned on time (the latter was especially important for me, as I had dinner reservations and then my flight home right after); the drinks flowed freely (rum punch and sparkling wine, but also water and sodas), the crew were wonderfully kind and hospitable, and though I was traveling alone there was a great group also on the tour and we ended up getting along fantastically. Bonus points to the company for rescheduling my trip from Friday to Monday when Friday ended up being too overcast for them to be able to provide the full sunset experience—though I was somewhat disappointed it also showed how much they cared that tour guests got the experience they paid for, and Monday's rescheduled trip absolutely was worth it. They were also fully glad to provide a refund if Monday wasn't possible for my schedule, which thankfully it was. Highly recommend this tour whether solo, couples or small groups. Thank you for a great final night in San Juan!

Nice sail around San Juan harbor. Captain and first mate were super nice and knowledgeable. The only downfall is we wish it was longer - An hour and a half goes by quick. However we were lucky enough to see dolphins 🐬 and had our share of pineapple mimosas. Would recommend for a quick afternoon activity.

Great time on catamaran Ohana. Francisco and Rafael were awesome hosts sharing information on the local area, sites and the beautiful boat we were aboard. Rafael kept our drinks filled well sharing historical facts. The couple we cruise with was awesome! All in all a great experience.

We had such a great time on this sunset catamaran! There were only 6 passengers on board plus Captain Francisco and his first mate. They were so friendly, taught us about all of the landmarks we sailed by and gave us such a relaxing and memorable time. They always made sure our drinks were full and it really was a great experience that I would recommend to anyone!

Great boat & crew… relaxing way to see old San Juan from the sea, sipping rum punch and capturing the beautiful afternoon light! Only 6 guests so lots of space to spread out & enjoy.

Awesome experience!!!! Captain Francisco and 1st mate were fantastic and welcoming. They provided us with historical information, along with delicious drinks to enjoy this sunset cruise!! We would recommend to anyone in San Juan!

Such an amazing experience. Captain Francisco & Raphael were great tour guides and made our experience so memorable and relaxing. I will definitely be recommending this tour to all of our friends and family.

We had a great time, enjoyed all of the sites and its history, the Crew was excellent, very professional, friendly and Always making sure we were having a good time and taken care of. Recommend this tour 100% you are in for an awesome trip.

Amazing information on San Juan and 100% relaxing. The captain and 1st mate were great. Well worth it, a must for a nice, relaxing and romantic trip. My girlfriend and I loved it.

Relaxing, drinks included and informative on old San Juan. Highly recommend especially if you want to do multiple excursions in one day.

This was a wonderful way to start our vacation in San Juan. Along with my wife and I, our 19 and 17 year old boys also loved it. Highly recommended.

This cruise was everything we expected! The crew members were very friendly and provided interesting historical information. The captain shared some great suggestions and tips on places to go and eat in the area. HIGHLY recommend,

It was the view and history about Old San Juan that really made the cruise interesting as well as fun. You can also create your own fun with a small party.

The crew awesome and we saw dolphins! Definitely try the punch. 100% recommend this sunset cruise to anyone

Everything about the trip was amazing. The boat is beautiful and I loved sitting right up front. Winds were good and we really sailed. Crew was knowledgeable and friendly. Drinks kept us all relaxed and happy :-)

Crew was very friendly and made sure we were comfortable and taken care of. The tour route could be improved, we spent most of the time going back and forth in the same bay but we did see dolphins and again, the crew was wonderful.

Just being out on the water on a sunny day with the wind in your hair and a rum punch in your hand made this outing soooo relaxing! Add to that the warm and welcoming personality of both the Captain (Francisco) and his First Mate (Rafe) -- and their interesting explanations of points of interest along the way -- and you've got yourself a wonderful experience! (Francisco even helped us find a reputable and reasonably-priced jet ski rental place before we left). The marina, itself is full of interesting boats and yachts to peruse while you wait for your departure, so that was an added bonus. Overall, I highly recommend this experience!

Excellent attention and a beautiful sailing tour. Fantastic seating and view. I highly recommend this tour.

It was a nice relaxing sail. The captain and first mate were very friendly and knowledgeable. We didn't see dolphins or turtles which was advertised, but still a good time.

I had such a good relaxing time . The host were amazing and the rum punch was everything! The sail was very informative .

The day sail around the harbor offered an unsurpassed view of the city while Captain Francisco and his First Mate filled in some of the details about the landmarks and history of San Juan. Both were extremely kind, attentive, and fascinating hosts making the experience and view a must for couples seeking romance or families wanting a relaxed tour of old San Juan, the harbor and more.

Super friendly family-operated business. Great experience, best part of our trip to the island. Highly recommend to anyone who visits San Juan.

Wonderful tour of San Juan from the bay. Captain and mate were friendly and knowledgeable. Drinks were good and plentiful. A highly enjoyable and relaxing tour, would definitely recommend.

Small group on my sailing 6 pax on the trip, both captain and mate are friendly and knowledgeable during the sailing. Complimentary drinks on board. We enjoy the the almost semi private setting of small group. It was a interesting experience to see old San Juan bay differently from a sailboat. Cool experience!

We learned a lot and the captain and mate we’re both very fun and good energy! They were very attentive and showed the most beautiful parts of San Juan. Thank you for having us!!

The whole sail was gorgeous! Definitely would recommend for the first few days visiting the island. Pedro and the captain were both so informative and friendly. My boyfriend and I loved every single moment of the experience and the rum punch was great

Excellent experience! Would definitely suggest to anyone visiting San Juan. The sailor and the guide were both great!

We had a spectacular and lovely sailing in the sunset. The captain and first mate told us the history of San Juan while providing drinks. It was a romantic carriage ride of the sea.

We really enjoyed ourselves on the sunset sail. The weather was perfect, it was a relaxing, calm ride. I loved that they keep it small to only 6 people. The captain and mate were super friendly and helpful. Absolutely beautiful.

Francisco and Pedro were wonderful!Best part of your trip!Highly recommended!!! Everything was perfect !

Perfect night. The night was beautiful and Pedro kept us entertained with fun facts about Old San Juan and kept the drinks flowing. Captain did a fantastic job keeping us safe and entertained.

Our first mate and captain were amazing! Very informative and a fun time. Views were incredible! Would definitely recommend.

Highly recommended for those that enjoy a low-stress, relaxing cruise and have an appreciation for sunsets! Captain Francisco and first mate Pedro nailed it! Promptly departed at 5 pm with six passengers (max capacity - nice!) and plenty of rum punch to be had! Thank you guys for an amazing two hours on the water! And thanks to our fellow passengers - Neil, Alexis and Cynthia - for making it such a great time!

Top notch Ohana 2 sailing experience. Francisco and Pedro were fantastic! Super safe, super fun. We had an option for drinks (adult and virgin), and there's a boat/over-hammock in the front where passengers can sit and lay on over the water as you sail. Seating is limited to 6 passengers per outing, so it's intimate and interactive. We had a fantastic time and would absolute recommend!

Both the Captain (Franceso?) and First Mate (Pedro) made the catamaran trip very enjoyable and informative! A must do while in the San Juan area.

Such an amazing experience, the host were very friendly and informative. I would 100% recommend to anybody visiting.

Thank you Captain Francisco for another memorable sailing. this was my 2nd sailing which was exactly 4 years apart. My wife Sylvia and I did this for our 13th anniversary unfortunately I lost her in may of 21 to cancer. I made her a promise that I would still go on this journey. I cannot thank you enough for being understanding and for another wonderful memory. when I return in the future this sailing will always be a part of my trips to San Juan.

My Hubby and I really enjoyed the tour..I was celebrating my birthday and Pedro made it really fun!!! We will definitely refer this tour to our family and friends…

This sail is a must do for anyone coming to PR. Pedro and Francisco were such good guides and were extremely personable & welcoming! Pedro took amazing pictures for everyone on the boat, which we really appreciated, and was always ready to get us more drinks when we needed them. Definitely a top favorite memory from all of my times coming to Puerto Rico.

This sunset sail is a MUST DO in Puerto Rico. It is a small group (6 or less) that sets sail around the island. We had a great time enjoying cocktails and the sunset. The crew was absolutely wonderful. We would most definitely recommend this cruise and do it again in a heartbeat!

A must do when traveling to San Juan! The captain and tour guide were so knowledgeable and provided us with so many drinks and facts through the tour. I would highly recommend this to anyone visiting!

Great service. Great information. So much fun!! I wish it it was twice as long because we enjoyed every minute of our morning sail!

It was such a beautiful experience. Our mate, Pedro was very helpful and equipped with facts. He was also the bartender and photographer. The rum punch was 10/10 and so were the pictures. Both Pedro and the captain made the experience as great as it was! A must do while in Puerto Rico.

A full moon, a beautiful sunset, good company, and an excellent and accommodating crew made our Valentines Day cruise extraordinary! Shout out to Pedro for providing interesting facts and refilling our drinks and showing us how to skillfully balance while sailing! We’ll never forget the yellow-footed boobies… Book this trip, you will love it!

This was the first vacation for my husband and I without kids (in 12 years) so it was important to us! With that said, don’t give this decision another thought, just book it! Captain Francisco and Pedro were professional and brilliant! Captain Francisco told us all about San Juan from the beauty of the water and he was so sincere and the most gracious host! He has been sailing since he was four years old and it showed. He could have sailed the catamaran with his eyes closed.Follow the instructions they give when you book. It’s so smooth and easy! There is a restroom on the boat. You don’t need to worry about a thing! Pedro has you covered with drinks and photos - we didn’t lift a finger which was so nice as parents of 4.I only wish we would have started our trip on the Ohana 2. We tried to book the morning mimosa sail the next day, it was so worth it for us both!! They book up fast!

Our host were nothing less than amazing! We had a great time leaening more about Old San Juan! Would defly recommend to everyone!

Wonderful sail, beautiful views and very relaxing! Captain and crew were truly attentive. Highly recommended!!!

Because of our cruise line ( Celebrity) itinerary change we were not able to take our sunset cruise in San Juan . Francisco was friendly and efficient through initial inquiry, booking and cancellation process. We will definitely book another tour with Sail PR when a future cruise finds us in San Juan.

We had so much fun! Pedro and Francisco were awesome, kept us well informed of what to expect on the boat, and kept us safe! There is a lot of beautiful scenery and history to learn about on this trip. The drinks were great as well. 10/10 recommend!

BEST thing we did while in San Juan! Captain Francisco and Pedro were fantastic hosts as we sailed around the San Juan harbor, catching amazing views of Old San Juan, some wonderful fun facts about the castles and history (past and present), and of course, fantastic drinks. 10/10 would recommend this experience for anyone visiting. It was a great way to kick off our weekend in Puerto Rico and really put us in the vacation mindset. Thank you Captain Francisco and Pedro!

Captain Francisco and Pedro were great hosts, they were both quite attentive, knowledgeable of the area and answered all my questions, they both made me feel really comfortable and safe!

Highly recommend! We had an amazing experience. We planned this as a last adventure the night before we left and it was the perfect ending to our vacation and worth every penny.

We enjoyed a lovely sunset sail with Captain Francisco and First Mate Pedro on Jan 13. What a fine, relaxing time we had! Joined by 2 other couples, we had plenty of room to spread out and enjoy. The crew was very knowledgeable and friendly and answered all of our many questions. We enjoyed the beverages available and appreciated having a different vantage point to view Old San Juan and El Morro. We had a spectacular sunset to boot! We were ready to do it again the next night, but we’ll have to wait until our next trip.

We had a great time aboard Ohana2! The crew members were extremely friendly and knowledgeable and the views were beautiful. We even saw dolphins! All while drinking cava. We definitely recommend this experience.

This was an AMAZING experience will do over and over as I visit Puerto Rico the captain and the mate were very personable.

Amazing experience!!! Both tour operators were incredibly kind, helpful, knowledgeable and so much fun!!!

Such a great experience! The guys were so friendly and accommodating. They served drinks, gave us a little tour of San Juan with some history from the water and took great care of us. The boat was very nice and comfortable. Highly recommend!

I give my experience a 10/10. Firstly the captain wnd crew-mate were super friendly and knowledgeable in the information about the landmarks we were passing as sailing. The drinks were great and they weren't watered down. The captain also had a nice updated playlist going. I would Definitely recommend for those looking for a relaxing sail, not necessarily a turn up

We did this trip on our last night in Puerto Rico and so glad we did! The group was a nice small gathering of 6 people and it was all outdoors so it felt super safe in this crazy COVID era we live in. Pedro and the captain were super awesome. We all had a blast. This adventure is a MUST DO for anyone visiting the San Juan area!

It was a nice gentle and informative ride in the bay. Both the captain and mate were friendly and attentive. An intimate ride with more than enough space for everyone.

Francisco and Pedro made sure we had a great sail on our cruise ship stop in San Juan! We took along our 82-year-old mother and she had a blast!

This was my 4th time sailing with Captain Fransisco and sail mate Pedro. I count them as family at this point. Thanks again for the amazing time.

This was the best part of our trip! The catamaran ride itself was incredible, with beautiful views and a relaxing vibe. Seeing Old San Juan from the ocean was well worth it. Captain Francisco and Pedro were awesome, too! Pedro had a lot of information about the sights we were seeing, as well as recommendations on where to go on the island. And he kept the drinks flowing, which my husband loved! Max number of guests is 6, which meant that you weren't crammed in and you could move around the boat easily (we highly recommend sitting up front in the netting!). This company definitely puts quality first!

Beautiful evening to relax & enjoy the views. Pedro was an especially entertaining host! Would highly recommend to anyone wanting to enjoy Old San Juan from the bay.

I don’t usually leave reviews but I definitely have to give a big shout out to Pedro and Capt Francisco! This sailing was awesome. Capt Francisco and Pedro were very clear with instructions and all information provided. The atmosphere is very inviting and if you get a good group the conversation will also be great. We didn’t luck out and see any dolphins but the sky ended up being multicolored. Pedro is awesome as first mate and is a awesome photographer so definitely use him..lol. Will definitely book again next time I’m back in Puerto Rico!

I would highly recommend this Cruise. We were able to see a great sunset and the crew was fabulous! We are so glad we took this tour.