Top Puerto Rico Private Sightseeing Tours

We took the Old San Juan Segway tour on our cruise stop, and it was absolutely beautiful. The listing photos show traditional stand-up Segways, but our tour actually used Segway-brand electric bicycles. That surprised us, but it was still a lot of fun. We rode all around the island, through colorful streets and past historic landmarks and stunning ocean views, and the e-bikes let us cover much more ground than a walking tour. Our guide Jose was outstanding. He's extremely knowledgeable about San Juan's rich history and kept us entertained with interesting stories at every stop. The bikes are a little heavy, and I bumped into a tree at one point, but Jose was right there with a first aid kit, patched up my scrape, and we were off again in no time. He was also happy to give us time at the beach if we wanted it. Our only regret is that we had other tours booked and couldn't stay longer. If we did it again, we'd give this tour more of our day. Highly recommend Jose and Segway Tours of Puerto Rico!

I was just scrolling and came across this one and it didn’t have as many reviews, but they were all really good. The guys were absolutely wonderful. It was me and four of the kiddos ranging 20 to 11 and everybody had an amazing time. They took us to the best spots. They were very patient and knowledgeable. I would absolutely use them again.!!!!!

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! ⛵️🌴☀️