Puerta de San Juan

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.

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. 

San Juan is known for its rich history and cultural heritage, but on this private tour, you will discover the spooky side of the city, and hear ghost stories, hauntings and legends when the sun goes down.

On your private ghost tour of San Juan, you will: 

• Start your tour at Columbus square, a place with ghostly apparitions and supernatural occurrences that have been reported in and around the square;
• Learn of the Columbus curse and hear endless tales of deaths, accidents, bankruptcies, and natural disasters all rumoured to be linked to Columbus;
• See the largest fort constructed by the Spanish in the Western Hemisphere and hear tales reminiscent of a Shakespearean tragedy;
• Pass by La Fortaleza, the governor's mansion, which is said to be one of the most haunted places in San Juan;
• Hear the story of the ghost of a former actress who is said to haunt the stage of Teatro Tapia;
• Walk through the old town by prisons and hotels to hear centuries of spectral sightings documented;
• Stay alert for strange noises in the Hotel El Convento, haunted by the ghosts of former nuns who once lived there;
• Hear about many ghost stories associated with the cathedral, including the tale of a former bishop who is said to haunt the building to this day.

Your tour begins in Columbus Square, where your expert private guide will introduce you to the city’s tenuous relationship with the notorious explorer. In June 2016, the 362 foot of Columbus was unveiled 45 miles west of San Juan on a ceremonial site for the Taíno, a culture nearly driven to extinction by Columbus’s exploits.

Learn why islanders are wary of Columbus’s history on their island, and why they attribute centuries of disasters to his name, which they dare not utter in completion.

Next, see Castillo San Cristobal (external only), which was meant to protect the city from attacks by land, and remains haunted by one of the island’s tragic love stories, reminiscent of Shakespeare’s Romeo & Juliet. Other tales include the disappearance of a Spanish soldier whose clothes and gun remained in the remote sentry box; to this day, numerous sightings of the lovers and the soldier are still being reported.

From the Castillo, continue on to several more haunted sites - theatres built on the site of 18th-century gallows, stories of human radiation tests performed in prisons, whose coverups go as high as the White House.

See Hotel El Convento - the oldest member of Historic Hotels of America, and hear the eerie tales known by the locals, of a wealthy widow who turned her home into a convent after her husband was killed, and listen for the faint sounds of robes across the tile floors.

Your private historic hauntings tour of San Juan is two and a half hours and is all done on foot. It is suitable for people of all ages, provided that adults are present with children. Be sure to bring water and stay hydrated throughout your haunted walk. 

The San Juan National Historical Site (Castillo San Cristobal, El Morro, and La Fortaleza) is closed in the evenings and is not visited internally on this tour. If you wish to visit these sites on a ghost tour, please book our day tour instead.