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San Juan Gate (Puerta de San Juan) Tours

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San Juan Gate (Puerta de San Juan)
Named in honor of Saint John the Baptist, San Juan Gate (Puerta de San Juan) was originally one of five doorways to the city used to protect its streets from invaders and each gate has its own unique function. Today, this towering red and white entryway that’s tucked into the city’s surrounding stonewall offers a truly magical way to enter and explore Puerto Rico’s capital city.

Travelers who pass through this historic entrance will find energetic vendors selling traditional snacks and ice-cold piragua along walkways heading towards the historic old town. Ancient trees stretch high into the sky and provide cool shade for lovers on romantic strolls. Narrow cobblestone streets lined with restored Spanish colonial homes and ornate balconies add to the charm of this favorite San Juan attraction. 

Practical Info

Travelers who start their walk to the gate from Paseo la Princesa will find the most picturesque views of San Juan Bay.
Address: Paseo de la Princesa, San Juan, Puerto Rico
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22 Tours and Activities to Experience San Juan Gate (Puerta de San Juan)

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details
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San Juan Catamaran Sunset Sail

San Juan Catamaran Sunset Sail

star-5
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$90.00
From
$90.00
Taking safety measures

Flavors of Old San Juan Food Tour

Flavors of Old San Juan Food Tour

star-5
Get a taste for the flavor and culture of Puerto Rico on this small-group Old San Juan food tour featuring several local eateries. Join your guide for a culinary exploration of island staples like plantains and sofrito, all with the cobblestone streets and colorful facades of the city’s oldest neighborhood as your backdrop. Your tour includes an alcoholic beverage or non-alcoholic substitute if you prefer. 
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$111.61
From
$111.61
Taking safety measures

Old San Juan Walking Tour

Old San Juan Walking Tour

star-5
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$41.03
From
$41.03
Taking safety measures

Old San Juan Segway Tour

Old San Juan Segway Tour

star-5
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'.
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  • 2 hours
  • Free Cancellation
From
$108.98
From
$108.98

Small Group Tour to Old San Juan and Rum Barrilito Destillery

Small Group Tour to Old San Juan and Rum Barrilito Destillery

star-4
Tour the colorful streets and winding alleys of the UNESCO World Heritage-listed Old San Juan, the second-oldest city in America. This guided small-group tour, capped at 11 participants, ensures a comfortable and personalized introduction to the city's major attractions and historical areas. Continue your tour at the Bacardi Rum Factory, an integral San Juan icon, before concluding with hotel drop-off at your accommodation.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$94.81
From
$94.81
Taking safety measures

Private Old San Juan Walking Tour

Private Old San Juan Walking Tour

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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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$151.29
per group
From
$151.29
per group
Taking safety measures

Fountain of Youth Tour of Old San Juan

Fountain of Youth Tour of Old San Juan

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Travelers who want to stay forever young will love this fountain of youth tour of Old San Juan. Learn about the colonial Gilded Age and discover the stories and history of Ponce de Leon's city and people. Listen in as your friendly guide shares stories about riots and revolutions and find out why the colony was known as "Gold Island". Wander through burial sites where greats like Ponce de Leon and other founding fathers of Puerto Rico are buried and get an up close look at history, culture and traditions that define this destination.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$46.16
From
$46.16
Taking safety measures

Private Old San Juan Momentos & Pictures discovery experience

Private Old San Juan Momentos & Pictures discovery experience

star-4.5
Experience San Juan, Puerto Rico; one of the Americas’ oldest cities on a slow paced tour specialy oriented to having you create your own ever lasting momentos and capture pictures while discovering how us, fellow american citizens lived 400 years of struggles with Spain, how we have flourished after becoming part of USA and how you can help us stop inequality a d keep being considered an alien race and uncivilized by the territorial clauses of the 1930's wich still rule us as a Comonwealth of the USA. Learn about the city’s history and must see buildings like San Cristobal and El Morro Forts, El Convento, Saint John's Cathedral and monuments like Ponce de Leon square and La Rogativa by the hand of our historians while driving it's narrow streets. After that visit new San Juan's main touristic areas of Condado where you will get to know historic landmarks and buildings in a relaxed and fun way. 
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  • 4 to 5 hours
  • Free Cancellation
  • Taking safety measures
From
$194.86
Price varies by group size
From
$194.86
Price varies by group size
Taking safety measures

HeliTour of Old San Juan and Bayamon with Mixology Class

HeliTour of Old San Juan and Bayamon with Mixology Class

star-5
Join us in this unique and VIP experience for you and 2 friends!! You will soar the skies to see some of the island's historical monuments such as the Capitol House, La Fortaleza-The Governor’s Mansion, Fort San Cristobal and catch a postcard view of our Fort San Felipe del Morro, all this from a new and incredible perspective flying over 500 feet in height. Afterwards, learn the history behind Puerto Rico's finest rum "Ron del Barrilito" in his original distillery "Hacienda Santa Ana" located in Bayamón City and improve your bar tending skills with an interactive class taught by superstar mixologists who will show you how to make show-stopping cocktails. We’ll use Ron del Barrilito to craft some of today’s most elegant drinks, such as Old Fashioned, Presidente, and Hemingway Daiquiri. By the end of the class, you’ll be able to easily impress your guests with your bar tending moves at your next party.
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  • 3 hours
  • Free Cancellation
From
$675.00
per group
From
$675.00
per group

The Best Old San Juan Walking Tour

The Best Old San Juan Walking Tour

This tour is perfect for those looking for a quick yet informative tour with lots of fun facts about the island's history. In just 2 hours you will experience life in our beautiful colonial city of Old San Juan. You will capture views of our unique colorful buildings, Spanish and European architecture, and the oldest cathedrals created in the new world. Explore 500 years of history in approximately just one mile. Our certified tour guide will answer all your questions and will provide you with the most valuable information about all the places you will be visiting. Be amazed by all our old city has to hide. This is a must-do tour for history lovers and those with tight schedules. Learn and tell about your experience in Puerto Rico.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Old San Juan's Colonial Heritage

Old San Juan's Colonial Heritage

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During the tour, we will explore the colonial quarters of San Juan, the capital of Puerto Rico, founded by the Spanish conquistadors in 1521.  Old San Juan is not only the oldest city in the United States but one of the two oldest European cities in Latin America. Old San Juan has preserved its historical identity and architectural integrity.    See the historical allure of this city through the eyes of Sir Francis - Drake, whose attempt to wrestle San Juan from the Spanish crown cost him dearly, as you visit fine examples of the military architecture of those times.   Today’s urban legends, modern folklore, and a lively discussion of Puerto Rico’s ambiguous political status will help you connect past with presents and emerge from the tour with a new understanding of this unique Caribbean island and its people.   
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  • 2 hours
  • Free Cancellation
From
$65.00
From
$65.00

HeliTour of Old San Juan and Bayamon with Distillery Rum Tasting

HeliTour of Old San Juan and Bayamon with Distillery Rum Tasting

You will soar the skies to see some of the island's historical monuments such as the Capitol House, La Fortaleza-The Governor’s Mansion, Fort San Cristobal and catch a postcard view of our Fort San Felipe del Morro, all this from a new and incredible perspective flying over 500 feet in height. Afterwards, get ready for the best and most exclusive rum tasting experience in the Caribbean. Learn the history behind Puerto Rico's finest sipping rum "Ron del Barrilito" in his original distillery "Hacienda Santa Ana" located in Bayamón City. A unique opportunity to sip and enjoy all of their rums, from the cult-classic Three Stars to the extremely limited-edition Five Stars.
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  • 3 hours
  • Free Cancellation
From
$675.00
per group
From
$675.00
per group

Barrilito Rum Distillery and Old San Juan Half Day Tour

Barrilito Rum Distillery and Old San Juan Half Day Tour

A guided tour where you will learn the history of the founding of Ron del Barrilito and visit different areas within the factory. Includes a welcome cocktail. Duration 30 minutes. Starting from 9:15 a.m. and repeating every half hour until 4:00 p.m.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$80.00
From
$80.00
Taking safety measures

Unique Walking Tour through Old San Juan

Unique Walking Tour through Old San Juan

star-4.5
Discover the historic delights of Old San Juan as you pound its ancient cobblestones on a 5-hour walking tour. Take a comprehensive look at the wealth of colonial landmarks in this former Spanish colony, visiting ‘La Fortaleza’ (Governor’s House), the imposing San Felipe El Morro Fort, 16th-century San Jose Church, the Ballaja Barracks and much more. As you stroll, your expert guide provides additional insight into the design and famous personalities that once inhabited this charming area.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$66.99
From
$66.99
Taking safety measures

San Juan Done Right! - Driving Tour

San Juan Done Right! - Driving Tour

star-5
San Juan Done Right! Experience Old San Juan in a delightful ode to its seat of honor within the history of the New World’s conquest. Receive insight into the life of the common city dwellers, as well as the military origins of the Spanish stronghold that is the City of Saint John the Baptist. Our licensed tour guide will impart on a walking tour along the Paseo de la Princesa (Princess Promenade) to enter the old city through the historic San Juan Gate. Believed standing since approximately 1540. Once inside see Plazuela La Rogativa. Then it’s on to visit the Basilica Manor Cathedral San Juan Bautista, full of devotion, architecture, and art. Our guide walks you through its history and mystique. Later learn about La Fortaleza, today it remains the official residence of Puerto Rico’s governor. Close by, take pictures of Cristo Chapel, Pigeon Park and La Casa Estrecha (the Narrow House), one of the skinniest houses in the world. Finish with a Piña Colada at Barrachina Restaurant.
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  • 3 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$75.00
From
$75.00
Taking safety measures

Ruta San Juan Bautista (church tour)

Ruta San Juan Bautista (church tour)

Old San Juan is considered the "crib" of Christianity in America. There is a lot of history (art, culture, architecture, etc. ) in the Old City. Alonso Manso (the first Bishop of San Juan) is also the first Christian Bishop to come to America (1512). That means that all the churches in America had to report to San Juan. Within the city walls, we have one of the highest concentration of temples per square mile in the world. Some of the structures are considered as UNESCO World Heritage sites. The Route of San Juan Bautista shows the most important religious attractions in Old San Juan. You can discover the origins of Christianity in the New World for the past 500 years. You will discover some of the oldest churches in America, some located inside forts and palaces; also catacombs, religious ceremonies, saint persons, miracles, religious art, relics and a unique architectonic legacy. I love to feel the energy of every church (different congregations).
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$151.80
per group
From
$151.80
per group
Taking safety measures

Helicopter Tour and Restaurant with Puerto Rican Cuisine

Helicopter Tour and Restaurant with Puerto Rican Cuisine

If you want a unique, festive and VIP experience we can offer you our “Tasting Puerto Rico Experience”. On this tour we will fly over the areas of San Juan, Cataño, Bayamón and Naranjito, flying over spectacular buildings for amazing pictures. Then we will take you to 1 of 6 restaurants (all serving Puertorrican cuisine) with up to 2 hours waiting on land free of cost. This offers a truly local experience in which we will reserve the table and order your food so that when you arrive, everything is ready. Here is a list of the restaurants: Asador San Miguel, Naranjito Salitre, Arecibo Toro Verde, Orocovis Roka Dura, Orocovis The Sand and The Sea, Cayey La Vecindad Bar & Grill, Barranquitas
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  • 3 hours
  • Free Cancellation
From
$1,200.00
per group
From
$1,200.00
per group

The Enchanted Shore HeliTour

The Enchanted Shore HeliTour

star-5
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.
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  • 10 to 12 minutes
  • Free Cancellation
From
$153.85
From
$153.85

Let’s Roam’s Old San Juan Scavenger Hunt: Find the Fountain of Youth!

Let’s Roam’s Old San Juan Scavenger Hunt: Find the Fountain of Youth!

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.
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  • 2 hours
From
$12.31
From
$12.31

Old San Juan: Let the city's buildings tell you their stories on an audio tour

Old San Juan: Let the city's buildings tell you their stories on an audio tour

"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.
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  • 1 hour 20 minutes to 1 hour 40 minutes
From
$5.00
From
$5.00

San Juan Bay Day Sail

San Juan Bay Day Sail

star-5
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.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$78.00
From
$78.00
Taking safety measures

San Juan Done Right! - Walking Tour

San Juan Done Right! - Walking Tour

Experience a delightful ode to unmatched Old San Juan. With half a millennium of groundwork on hand, allow us the privilege of presenting you our history in the context of the New Worlds’ conquest. We provide complimentary pick-up and drop-off. Our interest is serving you and we therefore will contact you regarding the time and location. We ask that you are considerate of other guests. Please be there when we arrive at your scheduled pick-up.
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  • 3 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$60.00
From
$60.00
Taking safety measures

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What's the best way to experience San Juan Gate (Puerta de San Juan)?