Puerto Rico · HISTORICAL TOURS
Five hundred years of Spanish garrison, then a century of something else. The 14 below take in El Morro, San Cristóbal and the streets between them, priced, with a note on which include the fort entry and which leave you to buy it.
Review of San Juan Bay’s intimate sunset sail, with fortress views, local history, drinks, practical meeting tips, and honest value advice.
“Had a great time with our Captain. Talked about the history of the area and sailed out to the fortress at the mouth of the inlet and back. Was an enjoyable experience and would recommend to my friends and familly.”
See Old San Juan glow at sunset on a two-hour history walk with local guides, grand plazas, colonial buildings, photo stops, and practical tips.
“Very informative & helpful with giving suggestions for the rest of our trip in San Juan. I enjoyed learning about the history .”
Walk Old San Juan’s fortified streets with a local guide, then enjoy free time for shopping and lunch, with air-conditioned transport included.
“Nathan was lovely and very knowledgeable. It was definitely a bit of a walk but 100% worth it. I would recommend this tour to everyone!”
Explore Old San Juan on a two-hour small-group walk covering churches, colonial streets, Casa Estrecha, Ballajá, and local tips.
“Daniel was incredible. This was one the best tours I have ever had. He knows everything about everything in San Jaun and if he doesn’t he knows the person who does. This tour made my trip.”
See Old San Juan, Afro-Puerto Rican Loíza, and Santurce murals on a small-group cultural tour with local food and expert guidance.
“Stephanie was an awesome tour guide. She was very informative and flexible since we were the only two people on the tour. She educated us on the history of Old San Juan. She gave us time to get out the van and take pictures. The trip to Loíza was nice! We got to see a bomba class and ate some delicious alcapurrias! My favorite part was the walk in Santurce. The art was beautiful. She showed us quite a few murals and told us about the artists. We took lots of pictures! 10/10 I highly recommend this tour! Stephanie knows her stuff and is cool peoples!”
Sail San Juan Bay in a six-person boat, with Old San Juan forts, local history, wind-powered sailing, beer, sangria, and rum drinks.
“Captain Joe and Marie were fabulous! They were very good at paying attention to every detail, safty and shared their knowledge of the area.”
Explore Puerto Rico beyond San Juan on a small-group mountain tour with local food, history, scenic views, hotel pickup, and expert guides.
“I thought I had reviewed this right after the tour, but it keeps popping up. This was one of the most enjoyable things we did in Puerto Rico. Our guide even took us to a local restaurant (we paid of course) to eat traditional Puerto Rican food.”
Review of Ron del Barrilito’s 30-minute heritage tour in Bayamón, with historic buildings, a welcome cocktail, rum-making stories, and practical tips.
“Marjorie our tour guide was very enthusiastic, friendly and knowledgeable. What made this tour good is that it felt very personable, rustic, and familiar. We did not have to do a lot of walking and it was a good mix of history, family lore, and rum!”
Walk Old San Juan with historian Dr. José Morales, visiting forts, churches, and plazas while learning Puerto Rico’s layered past.
“Jose was an outstanding guide. Extremely knowledgeable and shared unique facts about and sites in Old San Juan. Highly recommend Jose!”
Explore Old San Juan, El Morro, beaches, and Santurce by private Can-Am UTV, with a guide, one driving turn, and room for three.
“We did not see historical old San Juan We road on the beach for a moment and on the road and that was it”
Review of San Juan’s haunted history walk, with ghost legends, colonial landmarks, practical route advice, guide details, and honest value notes.
“Leo was the best! A very informative and hands on tour that took us to many sights of past and present hauntings. I enjoyed the history portion of the tour, especially in the cool evening. Leo went above and beyond to introduce us to a loRead more”
Explore Santurce street art, Afro-Puerto Rican culture, Samuel Lind’s studio, local snacks, and a beach paint-and-sip from San Juan.
“Yuma, our tour guide was knowledgeable and so enthusiastic about sharing that knowledge as she drove us around the different sites. She showed respect for her country and it's variety of culture and art. Each stop brought an entirely unique aspect to PR that we never knew and motivated us to want to return to the island to learn more.”
Explore Old San Juan after dark on a two-hour ghost tour featuring forts, haunted stories, local legends, and Puerto Rico’s spooky past.
“Had a great time on the Spooky History tour! It was a great way to see the old city and learn a lot about the history. Our guide was excellent and so helpful! Highly recommend this tour :)”
Explore Old San Juan on a 2.5-hour bilingual walk covering forts, gates, churches, and colonial streets for $65.
“We absolutely loved our tour of Old San Juan. Our tour guide was amazing knowledge, funny and well cultured.”
Start from a coast, a mountain road or a table.
