Welcome to San Juan's Old Town: Private Half-Day Walking Tour

  • Instant Confirmation
  • Private Tour
  • 3 hr

Explore the colourful streets of Old San Juan with an expert, local guide on this half-day tour. The perfect way to discover the secrets hidden in plain sight, and learn the history of the island!

Itinerary Details

Operated by: Travel Curious

Welcome to our 3-hour walking tour of Old San Juan! On your private half-day tour, learn about the history of San Juan and understand the complex status of the Commonwealth, and the ways this small island has influenced the rest of Latin America. 

On your private walking tour, you will:

  • Start your tour at the beautiful fountain in Jardín Paseo de Ballajá, a historic park filled with beautiful greenery and a popular spot for locals to relax and enjoy the scenery;
  • Discover El Morro, one of the most iconic landmarks in Puerto Rico where you will be able to admire the fortress from the outside and take in the stunning views of the coastline;
  • Walk through Plaza del Quinto Centenario, a beautiful square that commemorates the 500th anniversary of Christopher Columbus's arrival in the Americas with an impressive monument at the centre of the plaza;
  • Cross Puerta de San Juan, a beautiful gateway that leads into the heart of Old San Juan;
  • Visit Capilla del Santo Cristo de la Salud, a historic chapel with beautiful architecture that's been an important part of the community for centuries;
  • Explore Parque de las Palomas, a lovely park and a great photo spot to immortalise your time in San Juan;
  • Pass by Fortaleza, an iconic structure that played an important role in the history of Puerto Rico;
  • Visit a local "Panama Hat" shop, a great spot to pick up a Panama hat or the perfect memento of your time on the island;
  • Sample delicious chocolate at Chocobar Cortés, or enjoy a drink at La Factoria, a popular bar known for its excellent cocktails and lively atmosphere. This will be the perfect spot to end our tour and enjoy a drink or two before saying goodbye.

Whether this is your first trip to San Juan or your 50th, a private walking tour of Old Town with a guide is the perfect way to discover the secrets hidden in plain sight, and learn the history of the island. 

Enjoy a local, professional guide's perspective on what it’s like to live on the island today, and get tips on the island's best-kept secrets. 
With sweeping oceanside vistas, daunting stone forts, steep hills, and intricate stone roads, San Juan oozes a mix of old European charm and vibrant Latin culture. 

On your tour, your guide will give you the best tips for exploring the island. Your guide will be sure to give you a list of their favourite restaurants and introduce you to locals who will make the difference between a tourist holiday to a lifelong love affair with the island and its people. 

Tour duration
3 hours

Type of tour
Walking tour: no transportation is included

Tickets included
No tickets required 

Other inclusions
A coffee and a snack along the route 

Suitable for
Couples, Culture Vulture, Family, History Buffs

Attractions along this route:

La Fortaleza
The powder blue hillside house is the home of the Governor of Puerto Rico and was built five centuries ago.

Castillo San Felipe del Morro
Simply called 'El Morro' by locals, it was built by a fort in the 16th century to protect San Juan from amphibious attacks.

Capilla del Santo Cristo de la Salud
The chapel's origin stories date back to a horse race gone awry, but the legends that arose from that race have brought worshipers seeking petitions of health.

Café Don Ruiz
This coffee shop, attached to a museum, serves only Puerto Rican grown coffee - and the best coffee at that. If you're looking for a pick-me-up, this spot is not to be missed.

Puerta de San Juan
The door served as the entrance to the city during the Spanish colonial era.

Plaza del Quinto Centenario
Built in 1992 to signify 500 years since the Americas were explored by Europeans, the plaza has a totem pole built from clays from across the Americas.

Parque de las Palomas
The quaint park is as much a respite as it is for pigeons, who seem to also revel in the cobblestone charm of the old park.
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