Category Historical Tours

San Juan · HISTORICAL TOURS

The 11 Best Historical Tours in San Juan

11 reviewed

Historical San Juan Bay Sunset Sailing Tour

Historical San Juan Bay Sunset Sailing Tour - The 2-hour route: calm bay water, then close-in harbor views

1.Historical San Juan Bay Sunset Sailing Tour

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

Small-group San Juan Bay sunset sail past El Morro with captain stories, photo stops, and included beer, sangria, and rum punch.

“Beautiful evening! Ivan was wonderful! Very knowledgeable and friendly! Great drinks! We enjoyed every second! Highly recommend! Thank you Ivan!”

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Historic Old San Juan Sunset Walking Tour

Historic Old San Juan Sunset Walking Tour - Meeting in Old San Juan: Where to Start and What the Route Feels Like

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

Old San Juan Historical Walk, Shopping, and Dining w/ Transport - The 16th-century mansion stops, church sights, and the cathedral focus

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

★★★★★★★★★★4.5 · 381 reviews · from $34Best value

Old San Juan guided walk with Morro and cathedral sights, air-conditioned transport, and time on Calle Fortaleza for shopping and lunch.

“Although Michelle was quite respectful and sweet, I felt that the tour was disappointing. I thought we would really learn about old San Juan and would be able to visit some of the sites shown. I felt it was something I could have really done myself and not paid 139.00”

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Old San Juan Historical Walking Tour

Old San Juan Historical Walking Tour - Meeting point at 206 C. Recinto Sur and how to plan your shoes

4.Old San Juan Historical Walking Tour

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

Old San Juan walking tour in a small group of 18. See Casa Estrecha, the Cathedral and Cuartel de Ballajá in 2 hours for $46.99.

“Pablo was terrific - informative, engaging, enthusiastic and helpful. Wonderful experience.and fascinating history.”

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Discovering Puerto Rico: Lifestyle, Art, and Cultural Tour

Discovering Puerto Rico: Lifestyle, Art, and Cultural Tour - Santurce Murals: 3–4 Blocks with Big Stories

San Juan Historical Bay Daytime Sailing Tour

San Juan Historical Bay Daytime Sailing Tour - What You’ll See During the Route (And Why Each Stop Makes Sense)

6.San Juan Historical Bay Daytime Sailing Tour

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

A small-group, wind-powered daytime sail in San Juan’s bay with Old San Juan views, fort landmarks, and included drinks—about 2 hours.

“Our captain was very engaging, pointing out landmarks and interesting sights within the bay. His crewmanwas also knowledgeable. It was a laid back trip with just our group of 4. A new experience for all of us, which we enjoyed very much”

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Half-Day Center of Puerto Rico Cultural Tour

Half-Day Center of Puerto Rico Cultural Tour - The route gives you a map of Puerto Rico’s day-to-day life

7.Half-Day Center of Puerto Rico Cultural Tour

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

Small-group morning drive from San Juan into central Puerto Rico for history, mountain views, and an authentic meal at local spots.

“Ed Brown and Patty had a great time with Manuel who is an excellent tour guide. Will highly recommend him, always nice to take a tour with a knowledgeable guide. Thanks again Manuel for a fun experience.”

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Ron del Barrilito Heritage Skip-the-Line Tour

Ron del Barrilito Heritage Skip-the-Line Tour - Skip-the-line check-in and the welcome cocktail moment

Discover Old San Juan Rich Heritage

Discover Old San Juan Rich Heritage - Meet Dr. José Morales: The PhD Behind the Stories

9.Discover Old San Juan Rich Heritage

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

A 2-hour Old San Juan walk led by Dr. José Morales, PhD in Puerto Rican and Caribbean history, ending at El Morro with great stops.

“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

Discover Old San Juan: Private Historical Tour by Can-Am UTV - How driving actually works on a Can-Am UTV (and the speed limits)

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

★★★★★★★★★★4.0 · 75 reviews · from $350

Private Can-Am UTV tour of Old San Juan with guided photo stops at El Morro and La Placita, plus a chance to drive.

“So I booked this trip for me and my fiancé on her Birthday, I paid $290 plus $80 additional dollars for motorcycle insurance. So total of $370 to drive maybe a tota of 40 mins they drove the rest, and to be put in a UTV with a fill in so was having himself a grand old time giving us whiplash with his accelerating just to hear the nitrous, my fiancé left sick. The man that worked with the other couple was very nice. I just think it’s so over priced so what we got. Sorry would not recommend to anyone. Save your money.”

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San Juan Haunted History Walking Tour

San Juan Haunted History Walking Tour - The route: 2–2.5 hours, 30 people max, and plenty of uphill

11.San Juan Haunted History Walking Tour

★★★★★★★★★★4.0 · 74 reviews · from $44

San Juan haunted history walk in Old San Juan: 11 eerie stops, Puerto Rican folklore, and night fort views. $44.99, 2–2.5 hrs.

“It wasn't really a ghost tour with this guide. He had a lot of knowledge about history, movies, sports, and the famous people he'd given tours to. Where ghosts had been reported seemed like an after thought. He had no presence for story telling. We went well over time and did a lot of hills. The only great thing about this tour was going to the graveyard.”

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Puerto Rico: Lifestyle, Art, and Cultural Tour

Puerto Rico: Lifestyle, Art, and Cultural Tour - Santurce street art walk: murals, corners, and a canvas moment

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

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

Private San Juan art tour: Santurce murals, Samuel Lind studio, Afro-Caribbean snacks, and beach paint-and-sip in Loíza/Pinones.

“Our tour guide, Sarah, showed us her favorite spots along the streets of Barrio Santurce, where our vision was awash in the urban wonderland of street art. After our foray in the city, we were whisked away to the city of Loíza, where the roads Read more”

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San Juan: Ghosts and Spooky History Walking Tour

San Juan: Ghosts and Spooky History Walking Tour - Teatro Tapia and the Stories Old San Juan Loves to Tell

13.Ghosts and Spooky History Walking Tour

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

A 2-hour San Juan spooky-history walk through UNESCO Morro, haunted Teatro Tapia, El Convento, and two major forts, with local legends.

“Richard was awesome and very informative and we had a beer afterwards it was well worth taking if your in San Juan 10 out of 5 stars”

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