SAN JUAN
Ranked by traveller popularity
The 10 most popular historical tours in San Juan. Here's what they actually deliver, who runs them, and what they cost.
Intimate San Juan Bay sunset sail with a local captain, prime Morro photos, and included drinks in a small-group cruise.
“It was a great sunset tour. Had a nice sangria to celebrate my husband’s 60th birthday trip. The captain and crew were amazing.”
Walk Old San Juan at sunset in 2 hours: colonial squares, churches, fort views, and local food and nightlife tips for $39.
“I talked to the tour leader asking him to slow down, he did not. There were 10 of us and 6 were young and could walk fast with him. 4 of us were 50 plus old and needed him to slow down. He ignored the need to do this, and went with the young part…”
Old San Juan in half a day: guided history walk, air-conditioned transport, time on Calle Fortaleza for shopping, plus a lunch stop.
“Awesome Tour of Old San Juan with very knowledgeable & friendly guide Michelle !!!”
A 2-hour Old San Juan walking tour for up to 18 people, with free-entry stops, expert guide stories, and a great first-trip orientation.
“Learn a lot about San Juan, our guide was knowledgeable and informative. Just wish we could've visited the forts”
Small-group tour linking Old San Juan, Loíza culture, and Santurce murals with A/C comfort, local food chances, and clear guide storytelling.
“A wonderful tour with Stephanie. Our small group of 7 had a great time learning about the history and culture of Puerto Rico. Stephanie was knowledgeable and friendly. We enjoyed it very much.”
Wind-powered sail in San Juan Bay to Old San Juan forts, with a small crew, sideways sailing, and drinks on a 2-hour ride.
“Informative, relaxing, great communication. We had a nice time. It was just two couples and the captain and first mate”
Half-day small-group trip from San Juan into central Puerto Rico for mountain views, local history, and an optional authentic lunch.
“Historically very interesting , and the town & outlying areas are so beautiful & photogenic!Our guide Manuel was fun & very informative. We enjoyed our morning with him very much🤩”
Skip ticket lines at Hacienda Santa Ana for a small-group Ron del Barrilito tour, a welcome cocktail, and a close-up look at rum-making.
“Great place to visit with amazing rum! The tour guide, bartenders, and all staff were very friendly!”
A 2-hour Old San Juan walking tour with Dr. José Morales, covering forts, churches, plazas, and colonial Caribbean strategy for $45.
“Jose's wealth of historical information was very interesting. He offered many insights to the history and culture of Puerto Rico. We enjoyed a stop for a limber! Jose was open to questions and even offered a few a lof his favorite local eateries at the end of the tour. We could have listened to him…”
Private Can-Am UTV tour of Old San Juan with guided stops, beach-to-fort views, and a real chance to drive, priced per group.
“Eddie was amazing. One of the best things we did in Puerto Rico. He showed us all the good spots and gave us plenty of time to take pictures. Would recommend to everyone.”
