Sail Away: Private Scenic Excursion From San Juan

Captain jimbo was fantastic he was knowledgeable not just about sailing but also about the area. He took his time explaining how the sail boat worked and it truly was a wonderful experience. My husband, myself and a family friend enjoyed our day even more than expected.

Jim provided such an interactive, relaxing, and well rounded experience for me and my family! We were able to swim, take a turn at the wheel, and see beautiful sites of San Juan, old and new. Would definitely recommend for groups, there's enough space on multiple sides of the boat for everyone to enjoy.

We enjoyed our sailboat excursion so much! Captain Jimbo was great in communicating with us before the trip, as well as with our young children. He gave them a sailing lesson! Highly recommend!

My parents and I chartered Jimbo’s sailboat out of San Juan for my 30th birthday, and it was easily one of the highlights of our trip to Puerto Rico! Our 3-hour charter ended up being about 3.5 hours, because Jimbo was in absolutely no rush to get us off the boat. He even offered us complimentary, completely optional sailing lessons. You could either sit back, relax, and enjoy the ride or get hands-on and learn how to sail. My stepdad especially loved the unexpected opportunity to learn how to steer and help sail the boat! We started in the bay and headed out toward the Atlantic, passing some incredible sights along the way, including the Governor’s Mansion, the red-door entrance into Old San Juan, Castillo San Felipe del Morro, Castillo San Cristóbal, the historic cemetery along the oceanfront, La Perla, and the Puerto Rican Capitol. Jimbo had a cooler full of ice ready for the food and drinks we brought onboard, let me control the Bluetooth radio with my own phone and playlist, and even had a bathroom below deck. We spent the afternoon with our feet in the water, soaking up the sun, enjoying drinks, listening to music, and taking turns helping with the sails and steering while Jimbo guided us the entire time. The 3 hours flew by, and honestly, I wish I had the option to book a longer charter! Jimbo was knowledgeable, laid-back, attentive, and made the entire experience feel personal rather than rushed or touristy. He also mentioned that he offers sunset and evening sails for anyone who wants to see Old San Juan lit up at night — which is definitely on my list for next time! If you’re visiting San Juan, I highly recommend booking with Jimbo. We had an amazing time and would absolutely do it again! ⛵️🌴☀️

What an incredible adventure! Thank you, Captain Jimbo! You made my 7-year-old daughter, who was absolutely terrified at the thought of sailing, fall in love with it. At first, she was in tears, and I honestly never imagined she’d calm down, let alone be smiling and laughing while the boat was heeling over. By the end of the trip, she was having an absolute blast! Thank you for your patience, encouragement, and for creating such an unforgettable experience. We’ll definitely be back!

Jimbo was a great host and captain! My husband and I enjoyed this trip and Jimbo was pleasant and very knowledgeable.

On vacation but with a toddler, so the excursions were limited. Party boat/rum cruise, so I chose this private experience. We arrived at the outdoor restaurant and met Jimbo at the docks. He helped get us on board and brief us on safety and boat information. We set sail! It was a nice breeze sailing and learned about PR. He gave my son the opportunity to to steer the boat which was a whole other experience . I would highly recommend this excursion especially for families who want to enjoy the water without the party vibe.

We booked this excursion for a friend's birthday, and we had a blast! Captain Jimbo was an absolute pleasure and very accommodating. We had the perfect amount of time. If you're looking for a "yacht-like" luxury feel, this isn't that but the sailboat was still decent for 5 women.

Such a beautiful experience! We absolutely loved every minute of the sailing trip. The scenery was breathtaking, everything was well organized, and our guide was incredibly friendly, knowledgeable, and made the experience even more enjoyable. We would definitely recommend this tour to anyone looking for an unforgettable day on the water!

We had a great time on this family-centered excursion. Highly recommend! The boat was beautiful, Captain Jimbo was a great guide and teacher, and our kids (ages 7-15h had an absolute blast. We learned the basics of sailing, battled “pirates,” snorkeled amidst the shores of Old San Juan and even got to inspect starfish and sea urchins. It was the perfect mix of fun, adventure, and learning for the whole family. A highlight of our trip to Puerto Rico!

Okay! So at first we were skeptical— the location and the host. BUT GUYS, oh how it is important to not be quick to judge. Our host and this experience was such a 10/10!!! I was already appreciative for them waiting a couple of minutes as we were behind due to traffic, but when we got their on the boat he made sure we were educated on the safety features and protocols before sailing, he even taught us the foundations on how to sail, like it was so cool! Unfortunately we didn’t get to snorkel due to the winds and waves, but it was so much fun sitting on the side of the boat and dipping our feet in as we sailed!! I would definitely do this excursion again. Worth the price for a private sail experience and we got bomb photos! Not only that our host Made sure we were good after the excursion and even helped us with local Puerto Rican cuisine dinner options by escorting us to the restaurant and even translated to our server— which he didn’t have to do! 🙌🏾 If you do this tour get Jimbo!!!!

If you want immersive personal tour and learning experience book here. First time sailing a boat . Jimbo walked us through what to expect and is a great communicator.

Jimbo is an excellent captain. He is funny, personable, and professional. We promised we wouldn’t be scared to go full/true sailing (even though I was a bit nervous since I’d never been before) but he described the physics of sailing to me which calmed my nerves immediately…resulting in a full-on sailing lesson for my 20 yo son per his request. Jimbo will take you wherever you’d like to go and caters your sail to you. His boat is clean and fun and he even lets you DJ your own experience if you’d like. Really special experience. I would totally recommend.

Wonderful trip with friends! The captain was a great host and fantastic teacher! Would definitely do it again.

Great experience, great tour guide me and my sisters had an awesome time for my 30th birthday we will be booking again whenever we do come back . Thank you for the best experience this was my first time on a boat and he made it the best experience ever 🙌🏾‼️🇵🇷

Captain Jimbo was very conversational. Several had never sailed before and he explained everything! We even had a pod of dolphins follow us and entertain doing jumps. The whole afternoon was amazing.

This was an amazing tour. Jim was a super friendly and knowledgeable captain, and went out of his way for us to be able to swim. The boat is SO nice and we had the absolute best time!!!

We had an amazing time with Captain Jimbo! It was my birthday and he truly made me feel celebrated from start to finish. My friends and I thoroughly enjoyed the whole experience — especially getting the chance to drive the boat, which was definitely a highlight. Everything was fun, smooth, and memorable. When I come back in the near future, I will absolutely be booking again. 10/10 — highly recommend!

It was easy to find and clean. Direction to the dock where easy to follow. Upon arriving we were greeted by Jimbo. We are given and safety briefing and a brief and informative lesson on sailing. The boat was clean and safe. We had an amazing experience.

Excellent experience and exactly what we were looking for. A relaxing sailing trip around the San Juan harbour with an experienced and knowledgeable Captain. We did this tour as a group of 6 including two younger children (ages 4 and 6) and they both had a blast! I would highly recommend this to anyone while in San Juan.

The captain is extremely experienced, fluent in english, and very helpful with whatever you need. I would highly recommend.

Well worth it! 2-3 hours was just the right amount of time. It rained briefly but was still very enjoyable. I'd definitely do it again!

Cap’t Jimbo made our day really special. He asked before we went out if we understood the conditions (some rain, windy). We were down and so glad we did. Cap gave us some history of PR, we shared personal stories and he gave my fiancé a fantastic sailing lesson. Overall, it was a fantastic experience and we are so glad we got to spend a few hours out on the water.

We had an amazing time!!!! Best boat experience yet. Vibes were great and our captain was great!!!!!!

We had a great time with Captain Jimbo sailing out to see old San Juan from the water. Beautiful day. Great fun was had by all!

Very friendly, very informative, top notch sail with husband and two daughters (ages 22 and 16). Captain Jimbo was professional and fun.

This was one of our favorite excursions well in San juan. Jimbo was amazing and gave us all sorts of information and even allowed our son and daughter to drive the sailboat for a bit. Highly recommend!

We decided at the last minute to take this sailing excursion and it was absolutely worth it. Captain Jimbo took care of our party of five (10y - 76y!) We loved that this was 100% personalized. Some of us are prone to motion sickness but we've also been wanting to try sailing. Captain Jimbo taught us how to sail and allowed us to take the helm as much as we wanted to. Being an active crew was super exciting and enjoyable. We spent most of the time in the calmer bay but also got to experience the chops in the open water. Captain Jimbo is very knowledgeable and has a wealth of experience to share. It made our Puerto Rico trip so much more special!

We had such a great time sailing today. We're on a cruise so it was so nice to break away from the crowds and have the sailboat to ourselves (family of 6). My husband loved getting to learn more about sailing and the rest of us loved the adventure. Our captain was so informative and relaxed and did a great job of explaining what to expect. Just a warning- you will likely get wet so bring extra clothes. So glad we did this!

We had a great time with our bachelorette party of four. Captain Jimbo was incredibly easy going! We brought champagne, dragged off the side of the boat, and he taught us how to sail. You can decide if you want to sit and relax, or take the wheel (literally)! You’re in good hands. Very cool experience, absolutely recommend.

Jimbo was amazing!!! Great conversation. Told us history of PR. We had a great time out on the boat! Definitely recommend! 😁

Everything was great. The captain was very friendly, and since it was our first time on a sailboat he made the experience very nice!

This was such a great experience! If anyone is contemplating, definitely book. Nice sail and we stopped and swam! Nice view of the bay!

Our sailing excursion was simply AMAZING!!! My husband and I had an absolute blast enjoying the stunning views and being in awe of the beauty of San Juan. Jimbo was an excellent captain was full of information. He was happy to answer our questions and give us any information we asked about. He was an amazing guide and Captain! We had such an amazing experience that we have already booked him for a second time on our trip. Highly, highly, highly recommend!

This a great experience. Jimbo, the captain, was great. Good conversation and great tour. Highly recommended

Fabulous afternoon on the water with James and Nichole! They were awesome! Great, easy conversation, super hospitable, very flexible. Highly recommend!!

We had a nice day on the water with Jimbo. We loved the scenery and the accommodations on the sea. My daughter loved the exhilaration of dragging her feet my mother could have done without the tilt. It was an amazing way to see San Juan from the water and we learned some things about sailing.

It was a great experience! Gorgeous ride, fun atmosphere, captain was laid back, informative, taught us some sailing and let us enjoy the ride. I would do it again!

Wonderful sailing with breathtaking views of San Juan - swimming with a large friendly barracuda was a once in a lifetime. James and Nichole, our skippers, were informative and great fun

Jimbo was excellent. We had a fantastic time. We highly recommend sailing with him. We made a life long memory.

Highly recommend this tour! Captain Jimbo taught my family the basics of sailing and allowed my son to steer the sail boat. It was a fantastic afternoon!!

This was an amazing experience! Captain Jimbo was a fantastic guide, he taught our family the basics of sailing and allowed my 16 year old son to steer the sail boat. Highly recommend this tour!!

We had the most amazing time captain Jimbo was the best. Sailing was great and the young kids loved every minute of it.

Captain Jimbo will be part of our wonderful memories of PUERTO RICO. He was a great host learned a lot of history. Exceptional experience!!!!

The views were beautiful, the weather was lovely, and the boat excursion was so fun! Jimbo is a great captain and teacher. This is definitely a choose your own adventure experience, it can be chill or exciting. Our group had a lot of fun!

Awesome experience. Not only did we sail but we learned to sail and applied his teachings while in the bay! Great communicator, fun and funny, thoroughly enjoyed and was worth EVERY PENNY!!! 10 out of 10

This was a very great experience, Jimbo customize our route for us. He was on a timely manner. He allowed us to bring our own food and drinks and give us the opportunity to get in the water. Would book again thank you!

Captain Jimbo was amazing with our two teenage boys who had never been on a sailboat. The first hour he patiently taught them his three rules of sailing. From then on he let them sail the boat. My son says” I really feel like I can sail a boat now”. His friend agrees “ I never knew sailing was so easy “. Jimbo’s sailing lesson was the highlight of our Puerto Rico vacation for this homeschool Mom! Anne

Our bachelorette party can’t stop raving about our unforgettable sailing trip with Captain Jimbo! He’s an incredible host—fun, knowledgeable, and made everyone feel right at home on the water. Some of us took the chance to learn a bit about sailing (especially my sister, the bride-to-be, who loves picking up new skills), while others kicked back and soaked in the sunshine and ocean breeze. Personally, my favorite part was riding up front as we hit the open ocean and cruised through the waves—absolutely exhilarating! The water was warm, the vibe was perfect, and the timing of the trip couldn’t have been better. I highly recommend sailing with Captain Jimbo to anyone looking for a memorable and unique experience!