Top Puerto Rico Private Sightseeing Tours

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! ⛵️🌴☀️

Me and my family booked the 2 hour ride and it was amazing the view was so beautiful and we experienced scenes where movies were produced the horses was easy to handle some People in our group it was their first time riding and they enjoyed anytime we come back we will be sure to book again thanks for the amazing experience and our tour guide was the best he was very detailed and patient with us

We had an incredible experience with Carlos as our captain! He was amazing from start to finish, taking us to several beautiful islands where we got to watch sea turtles, snorkel, and enjoy the water. Carlos went above and beyond to make the day special. He prepared lunch for us, had drinks ready, and made sure everyone in the family was having a great time. He was personable, knowledgeable, and an excellent captain. Communication was also fantastic. Carlos was quick to respond whenever we reached out, and all of his directions were clear and easy to follow. Most importantly, we always felt safe and well taken care of throughout the entire experience. We couldn’t have asked for a better day on the water and would absolutely recommend Carlos to anyone looking for a fun, safe, and memorable boat experience in Puerto Rico. We would definitely book with him again!

Absolutely loved our Culebra snorkeling experience! 🐠🌊 The water was beautiful and crystal clear, and we got to see so many colorful fish and amazing marine life. The whole experience was well organized, and the crew was friendly, helpful, and made us feel comfortable throughout the trip.

The salsa class with Juan was excellent! I would honestly give it more than 5 stars if I could. Juan is a great instructor and did an excellent job of balancing different skill levels. I first heard about his classes through a YouTube video while looking for things to do in Puerto Rico. It was very clear that his salsa lesson was the highlight of the youtuber's trip because of how much she learned during the class. I was so happy to see that he had availability during my visit to Puerto Rico. Juan also went out of his way to help me cross a busy street, which I greatly appreciated. (I parked on the opposite side of the park, but there are parallel parking spots right next to the park if you're able to grab one of those.) Thank you again, Juan! I highly recommend this class to anyone visiting Puerto Rico, whether you're a complete beginner or have some salsa experience.

Our walking tour with Antonio was easily one of the highlights of our time in San Juan. Well paced, wonderful energy, and incredibly insightful. I’m grateful to have learned the things that he shared with us. Highly recommend to anyone visiting! Be sure to book this, you won’t regret it. Thank you so much for this experience, and for going above and beyond by walking us to see the Bad Bunny mural! ❤️

Angel and Annie helped make our visit to San Juan special. Angel is a walking encyclopedia on Puerto Rican history and culture, and he customized the entire tour around our interests — Old San Juan and the forts, the modern city, and a great stop at Plaza del Mercado where we grabbed fresh local fruit and a smoothie. Annie kept us safe and comfortable, with minimal walking involved. Professional, warm, and genuinely passionate about their island.

Amazing experience! The captain is fantastic. Friendly, fun, knowledgeable, makes you feel safe. Follow the provided instructions and you won't have a problem. Put "San Juan Bay Marina" in your uber app/gps. Meet at the green gate, next to the building. Arrive a few minutes early because the boat leaves at the scheduled time. It's not a party boat (in the best way). Highly recommend and would absolutely book this tour again.