La Fortaleza (The Fortress) Tours and Activities

Explore the colorful buildings and charming streets of Old San Juan in a small group with the help of writer David Rodriguez, author of ‘The Rise and Fall of the Great Barbate.’ During the course of your day, the knowledgeable author helps you discover the area’s key historic sites and gain new insight into Puerto Rican culture. It’s a great opportunity to learn about the many stories of the people who helped to define this unique neighborhood. Your walking trip’s length is flexible based on your needs, and also includes bottled water.

Go sailing and watch the sunset on a cruise from San Juan. Get great photo ops of Puerto Rico’s coastline and enjoy a comfortable sail on the Caribbean Sea. Your captain shares commentary about the region and provides complimentary drinks for your group of no more than six people.

Float past more than 500 years of history and picturesque scenery during this 1.5-hour sailing excursion in Old San Juan Harbor. Climb aboard the ‘Amazing Grace,’ a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area. As you sail you’ll enjoy up-close views of Old San Juan sights such as El Morro fortress, La Fortaleza, and Paseo la Princesa. A guide and complimentary beverages and snacks are all covered.

Experience the old and the new in the atmospheric neighborhood of Old San Juan on this 2-hour small-group tour by Segway. Effortlessly zoom around the 500-year-old colonial architecture of this ancient neighborhood as you visit 25 of the top attractions in the area, and learn about its evolution from Spanish colony to US territory. This intimate sightseeing tour is limited to just 8 participants and also includes all entrance fees, a helmet, secure storage, filtered water and sunscreen. Please note the weight restrictions on this tour, located in the 'additional information section'.

Set sail across the Caribbean on this 1.5-hour cruise from San Juan and enjoy unforgettable views of the Puerto Rican capital. Hop aboard a traditional sailboat and sip complimentary drinks as you cruise along the coast. Keep your camera to hand as you pass landmarks like San Juan Bay Marina and El Morro Fort, and spot dolphins and sea turtles swimming and playing around the boat.

Authentic sailing is culture, having a conversation with a local, with the power of the wind, no engine noise, no crowds, no fake pirates, no straight cats, no crowds, no need to scream . . . we sail sideways, aboard a real racer cruiser (J30), with a toilet and a cabin, just real life sailing. You'll get to see a different perspective of old San Juan, with complimentary drinks, all you can have, feeling save but free, in small groups (no crowds), good for special moment, or turning this moment into an special one. While in contact with nature elements, sometimes you may get surprised by dolphins. 6 people maximum per sailboat Sailboat model: Jboat J30 (racer-cruiser) ** it's not luxury yacht, it's not a catamaran ** Lets Sail, with Sail San Juan Bay

Float past hundreds of years of history and picturesque scenery during this 2-hour sunset sailing excursion in Old San Juan Harbor. Climb aboard the "Amazing Grace," a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area. As you sail you’ll enjoy up-close views of Old San Juan sights like El Morro fortress, La Fortaleza, Paseo la Princesa and more, all set aglow by the fading late afternoon light. A guide and complimentary beverages and snacks are all covered.

If you are looking to experience some of Puerto Rico´s most spectacular views, we recommend the “Enchanted Shore Tour” it offers the best aerial views of our Old San Juan's attractions and a delightful flight above our beautiful coast (beach area) from Old San Juan to the tourist area of Isla Verde.

On this experience you will explore the Old San Juan at the best time of the day. During sunset the sunlight highlights the beautiful historic architecture and the ocean breeze makes the walk pleasurable. Along the way you will learn about the town's historic events and Puerto Rico’s culture from a local’s perspective. By the end of the tour you can stay by El Morro Fort to welcome the night or walk into the old town to enjoy its restaurants and bars. The sunset and the guide of this enjoyable experience transforms the perspective that most people have of Old San Juan and Puerto Rico.

Sail the calm, azure waters of San Juan Bay at sunset during a cocktail cruise. Enjoy a warm welcome aboard from your friendly captain and crew, then settle in for a scenic ride. Watch the island coastline glide by as the sun sinks toward the horizon. Sip a complimentary rum punch or sparkling wine with your family and friends and listen as your captain points out landmarks like El Morro Fort and San Juan Gate. Arrive back at the dock in time to continue your evening in San Juan.

All tours to this magical city are different because Old San Juan is a city filled with history and tales. While we share the history from the books, we also share the tales passed down from generation to generation. When you put the history and tales together, you can feel as you were there present.

Wander the charming colonial facades, ancient forts and cobblestoned streets of Old San Juan during this 4-hour walking tour with a private guide. Feel like a local as you get a personalized introduction to the history of the area with this certified professional guide, exploring its wealth of forts, plazas, churches, museums, cafes and local wildlife. You’ll help choose the day’s itinerary and take breaks whenever and wherever you like. It’s more like a stroll with a friend than a formal tour. Your private walking excursion also includes entrance fees for the forts.

"Talking Buildings" is a first-person account of the historic buildings of Old San Juan. Created by the Saint John's School 6th grade Social Studies class of 2022, this self-guided audio walking tour will take you on a journey through time, from the 16th century to modern-day. If you'd like to donate to the San José Church, as mentioned in the route, please follow this link: iglesiasanjosepr.org The tour is ready whenever you are. Simply download it through the VoiceMap app while in a wifi zone to enjoy the tour with full offline accessibility.

Pirates, ghosts, miracles, the Fountain of Youth, the Bermuda Triangle, and much more! Learn the unique haunted heritage of beautiful old San Juan, Puerto Rico with real ghost stories, local folklore, and recent reports of paranormal activity.

Experience San Juan the best possible way...through a private tour. Focus on your main interest. Discover the untold secrets of San Juan. Get to know the forts, churches, plazas, cafes, museums, and local flora/fauna. A typical tour would start in "Plaza Colon" (our meeting point). We get an overview of the layout of the city, and an introduction to the history of Puerto Rico (and Viejo San Juan). We walk though "Calle San Francisco". We stop at the "San Francisco Chapel" (if open), "Plaza de la Barandilla", "Plaza de Armas", "Calle Cristo" and the vicinity of El Morro Fort. We will see (from the outside) places like The City Hall, the State Department, La Fortaleza (Governor's Mansion), Christ Chapel, El Convento Hotel, San Jose Square, San Jose Church, Plaza del Quinto Centenario, El Morro Fort, The San Juan Gate and the San Juan Cathedral. Feel like a local and walk at your own pace, taking breaks when you want.