Top Puerto Rico Private Sightseeing Tours

We had such a wonderful time on our private charter to Icacos! Having the boat to ourselves made the day feel relaxed and special, and the island and water were absolutely beautiful. It was one of the highlights of our Puerto Rico trip. We’d happily do it again and highly recommend it to anyone looking for a memorable day on the water!

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! ⛵️🌴☀️

Our tour guide Ian was wonderful! It was such a great experience to ride these gentle animals. Get ready for trotting and just know you might lose your sunglasses or phone along the way. So please make sure you secure them properly. So glad I did this with my daughter for her 21st birthday!