Puerto Rico · HISTORICAL TOURS

13 Puerto Rico History Tours That Hold Up

13 tours  ·  from $34 a head

Five hundred years of Spanish walls, two forts and a governor’s house still in use. These 13 are compared on what they get you inside, how long the walking is, and whether the fort tickets are included.

Historical San Juan Bay Sunset Sailing Tour - What the two-hour route feels like
Cruises & Boat Tours, Cruises & Boat Tours in San Juan, Evening Experiences, Historical Tours, Historical Tours in San Juan, Sailing, San Juan Tours, Tour Reviews, Tours

Historical San Juan Bay Sunset Sailing Tour

1.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115Our pick

Review of San Juan Bay’s two-hour sunset sail, with fort views, drinks, captain commentary, meeting tips, value, and honest drawbacks.

“This was our 26th anniversary trip and captain Joe and Carlos did not disappoint! This was such a peaceful experience and would highly recommend to anyone visiting Puerto Rico!”

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Historic Old San Juan Sunset Walking Tour - Plaza Colón starts the story
Evening Experiences, Historical Tours, Historical Tours in San Juan, Old San Juan Walking Tours, San Juan Tours, Tour Reviews, Tours, Walking Tours, Walking Tours in San Juan

Historic Old San Juan Sunset Walking Tour

2.Historic Old San Juan Sunset Walking Tour

★★★★★★★★★★5.0 · 634 reviews · from $39Top rated

Explore Old San Juan at sunset with a two-hour history walk covering plazas, churches, forts, architecture, and local food tips.

“Antonio was an excellent guide and genuinely seemed like a great person. We learned a lot about the city and the history of the island, and got to know the area. Highly recommend!”

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Old San Juan Historical Walk, Shopping, and Dining w/ Transport - Starting at Plaza Colón and getting oriented
Dining Experiences, Dinner Experiences, Historical Tours, Historical Tours in San Juan, Old San Juan Walking Tours, Private Drivers, Private Drivers in San Juan, San Juan Tours, Shopping Tours, Tour Reviews, Walking Tours, Walking Tours in San Juan

Old San Juan Historical Walk, Shopping, and Dining w/ Transport

Old San Juan Historical Walking Tour - Casa Estrecha and the city’s smaller stories
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Old San Juan Historical Walking Tour

4.Old San Juan Historical Walking Tour

★★★★★★★★★★5.0 · 331 reviews · from $46

Review of Old San Juan’s 2-hour historical walking tour, with expert guides, key sights, practical tips, price value, and honest drawbacks.

“Carola was very friendly, funny, and informative. Wear good shoes, even though there are plenty of stops/breaks. The streets and sidewalks have bumps, holes, and cracks. Old San Juan is amazing and has a lot of history. This your does not take you inside of any buildings and costs more than other ones that may be similar.”

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Discovering Puerto Rico: Lifestyle, Art, and Cultural Tour - Loíza: the part of the tour with the strongest local flavor
Historical Tours, Historical Tours in San Juan, San Juan Tours, Tour Reviews, Tours

Discovering Puerto Rico: Lifestyle, Art, and Cultural Tour

San Juan Historical Bay Daytime Sailing Tour - Meeting the crew at San Juan Bay Marina
Cruises & Boat Tours, Cruises & Boat Tours in San Juan, Historical Tours, Historical Tours in San Juan, Sailing, San Juan Tours, Tour Reviews, Tours

San Juan Historical Bay Daytime Sailing Tour

6.San Juan Historical Bay Daytime Sailing Tour

★★★★★★★★★★4.5 · 173 reviews · from $99

Sail San Juan Bay on a small wind-powered boat, see Old San Juan forts, enjoy drinks, and get practical tips before booking.

“Excellent cruise. Not a big boat, it was just myself, wife and daugher along with the captain and mate. Our captain was extremely friendly and knowledgeable on PR history, restaurants, sailing, etc. I highly recommend for a relaxing and fun two-ish hours on the bay.”

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Half-Day Center of Puerto Rico Cultural Tour - San Juan and the metro-area introduction
Half-Day, Historical Tours, Historical Tours in San Juan, San Juan Tours, Tour Reviews, Tours

Half-Day Center of Puerto Rico Cultural Tour

7.Half-Day Center of Puerto Rico Cultural Tour

★★★★★★★★★★5.0 · 172 reviews · from $80

Explore Puerto Rico beyond San Juan on a small-group mountain tour with local history, scenic stops, authentic food, hotel pickup, and coffee.

“Jerry was a terrific guide, very informative and relaxed. The tour was well paced and covered a lot of ground. The mountains were particularly impressive .”

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Ron del Barrilito Heritage Skip-the-Line Tour - The welcome cocktail sets the tone
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Ron del Barrilito Heritage Skip-the-Line Tour

8.Ron del Barrilito Heritage Skip-the-Line Tour

★★★★★★★★★★5.0 · 140 reviews · from $45

Tour Puerto Rico’s historic Ron del Barrilito hacienda, enjoy a welcome cocktail, and learn how the island’s oldest rum is made.

“Great staff and great ambient, the guide was extremely well educated about the history of the brand. It could be better if they let you try some pure rum, a shot nothing crazy, the cocktails were great but like I said, it would give them more value.”

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Discover Old San Juan Rich Heritage - Forts, Churches, and Plazas Along the Route
Historical Tours, Historical Tours in San Juan, Old San Juan Walking Tours, San Juan Tours, Tour Reviews

Discover Old San Juan Rich Heritage

9.Discover Old San Juan Rich Heritage

★★★★★★★★★★5.0 · 106 reviews · from $45

Explore Old San Juan with historian Dr. José Morales on a two-hour walking tour of forts, churches, plazas, and Puerto Rican culture.

“If you are thinking about doing a historical walking tour of Old Town San Juan - this is the tour!! Dr. Morales was so knowledgeable and was able to give us a local point of view. There were so many fun stops and detours - my favorite stop was ringing the bell for limbers (popsicles)! I later brought my friends back to that spot because it enjoyed it so much! I would recommend this tour to anyone!”

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Discover Old San Juan: Private Historical Tour by Can-Am UTV - Starting near Ocean Park and Isla Verde
Historical Tours, Historical Tours in San Juan, Old San Juan Walking Tours, Private, Quad Bikes, Quad Bikes in San Juan, San Juan Tours, Tour Reviews, Tours

Discover Old San Juan: Private Historical Tour by Can-Am UTV

San Juan Haunted History Walking Tour - Roots Fountain and the Fountain of Youth
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San Juan Haunted History Walking Tour

11.San Juan Haunted History Walking Tour

★★★★★★★★★★4.0 · 74 reviews · from $44

Explore haunted Old San Juan by night, with ghost legends, forts, cemeteries, history, and practical tips for this 2-hour walking tour.

“He was extremely knowledgeable about Old San Juan, and he was very nice. It seems like he knew about every legend involving the area. Definite potential for spookiness in Old San Juan.”

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Puerto Rico: Lifestyle, Art, and Cultural Tour - Santurce murals: art with no fixed script
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Puerto Rico: Lifestyle, Art, and Cultural Tour

12.Puerto Rico: Lifestyle, Art, and Cultural Tour

★★★★★★★★★★4.5 · 64 reviews · from $145

Explore Santurce street art, Afro-Puerto Rican culture, Samuel Lind’s studio, local food, and beachside painting on this private San Juan tour.

“This was my must do tour after reading the description and the raving 5 star reviews on the website. I was VERY disappointed. In a nut shell, the tour differs significantly from the description. There was no cooking lesson with tasting and the artist wasn't home for the studio tour. The guided art tour was underwhelming. It did not include my favorite photos from the website and the tour guide had limited art knowledge. Lastly, I didn't do the paint and sip as the tour ran long (4.5 w/o the paint and sip) and I didn't want to spend more time on that portion. Note: I did contact the tour…”

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San Juan: Ghosts and Spooky History Walking Tour - Starting at Plaza Colón
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San Juan: Ghosts and Spooky History Walking Tour

13.Ghosts and Spooky History Walking Tour

★★★★★★★★★★4.3 · 57 reviews · 2 hours · from $54

Explore Old San Juan after dark on a two-hour ghost walk covering forts, churches, theaters, legends, and spooky local folklore.

“Richard was our tour guide and he was very knowledgeable and also just had a great personality and really made the tour much more enjoyable. Easy walk, about 2 hours, lots of info. 10/10 recommend.”

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Where to go in Puerto Rico

Pick a coast, a bay or a rum bar.