Top Experiences in San Juan Gate (Puerta de San Juan)

Get ready to go back in time on this walking tour of Old San Juan. Sometimes I will bring a van and we drive a bit. The City of Old San Juan was founded in the year 1521, making it the Oldest City in Puerto Rico and the second oldest city in The Americas. Yes, its that old! We will be walking and stopping at all the main sites, like castles, forts, cobblestone streets, colorful buildings, monuments, and plazas learning of their history. This tour does not go inside the forts. Every picture you take in Old San Juan is beautiful and unique, so make sure you bring your camera. We will also learn everything there is to know about the city and the island. You will be with a certified tour guide, so you can ensure you're getting the correct information everywhere you stop. My main goal is for you to fall in love with the island and keep coming back. I'm excited to meet you - book your tour and I will see you soon!

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Bring Good Vibes Only

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.

Glide through Old San Juan’s 500 years of history on this 2-hour Segway PT or scooter tour, exploring the scenic route on a Segway Kickscooter. Known as ‘The Walled City,’ Old San Juan was founded as a military stronghold and remains the oldest city under the American flag. This small-group tour is limited to 6 riders for Segway PT and 6 riders for Segway Kickscooter, allowing you to zoom around effortlessly and see more than 15 attractions. Learn from an informative guide about the city’s role during the Spanish empire, World War II, and as a US territory. Capture stunning views of San Juan Bay and Castillo San Felipe Morro along the way.

*Please note* tour schedules per vehicle type and weight restrictions are listed in the 'additional information section'.

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.

Old San Juan is so beautiful and has tons of amazing places that just makes the perfect background for an amazing picture. Whether or not you are an influencer, have tons of followers on the IG, or just want to show off your awesome trip to PR to family and friends, these spots we selected are worth stopping by for a picture.

Our guide will take you to the coolest places to snap a photo, while giving you some historical content.

We Take You to the historic, colonial city of Old San Juan, carrying over 500 years of history in one small islet. Many of the roads in the city contain the original cobblestone pavement that matches the same hues of blue as the ocean. The streets are full of colorful and european-style architectural buildings in vibrant pastel colors that clearly show the influences the city takes after. Visitors can enjoy themselves in the local stores, restaurants, and experiences in all corners of the streets. You will be able to see parts of the original wall that was built to protect the city from Spain’s enemies. Old San Juan combines a vintage charm with Caribbean sunshine. Our tour highlights parts of the city and its history that our expert guides are very knowledgeable of. We'll show you all the hidden gems within the streets of the city. Let us take you through history on this walking tour!

Step into history, enjoying the beauty of the “walled city” of Old San Juan. Our guides will cover 500 years of puertorican History and Culture, helping you explore one of the oldest cities in the hemisphere via its beautifully preserved architecture dating all the way back to the founding of what will eventually become Old San Juan. The tour is designed to have photo opportunities and water breaks along the way, lasting two and a half hours.

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying bottomless mimosas, house rum punch, and more complimentary drinks. Take in the panoramic views on this pleasure sightseeing tour of San Juan Bay and adjacent waters. Relax on a romantic sail with your loved one or have a fun getaway with a group of friends. Take a break from the city and step out into the ocean with your professional captain on call.

Join your host for a 3 hour culinary exploration of staples like single-origin Puerto Rican coffee, Caribbean sourced chocolate, street food and mojitos or piña coladas. Try the iconic dish "mofongo"...all with the cobblestone streets and colorful facades of the city’s oldest neighborhood as your backdrop. Your tour also includes historical and cultural information of Old San Juan.  

Everything is included in the ticket price - food, 1 cocktail and a historical walking tour. Get a taste for the authentic flavor and culture of Puerto Rico while dining across a handful of local mom & pop restaurants (alcohol/dietary subs accommodated).

Experience the ultimate exploration of Old San Juan in a masterfully curated sightseeing and walking tour to the 90 most important landmarks of the city. A feat like this easily take at least 8 hours if done just walking, but we cover it all in eithier 2, 3, 4 hours or even a full day. by stolling in our premium vehicles providing a sanctuary of cool comfort, as you avoid sweating under the sun or geting wet under the unexpected rain showers in the tropics. You'll appreciate the ease of moving up and down the historic hills without exertion, ensuring your energy is reserved for enjoyment and discovery.

Your guide, an expert in the city's rich heritage, will lead you through Old San Juan's storied streets and facades, revealing the hidden tales behind each significant site.

Customize it adding Puerto Rico's finest rum distillery, Barrilito, our African Heritage Village, the Rainforest or all of the above for the ultimate full day San Juan Experience.

Explore the captivating charm of Old San Juan in just one hour as you stroll through its historic streets lined with colorful colonial buildings and discover the stories of this centuries-old city. Follow our tour guide as we wander the streets of Old San Juan on this concise walking tour of the most iconic places in this beautiful city. We will explore the landmarks on Tetuán and Cristo Streets and provide details about the Chapel, the Governor's Mansion, as well a the Cathedral of San John the Baptists.

Professor Nat aims to provide a truly authentic experience in a one-of-a-kind destination of the Viejo San Juan. Old San Juan-the oldest city in the United States, has reached its 500th anniversary. This intense and rich with sites and experiences tour is designed for history savvy, a cultural buff, or a sightseeing enthusiast! Attendees will get to know Puerto Rican culture on a tour of most iconic historical sites in Old San Juan complemented with cultural experiences. Within the tour, there will be 32 narrated by professional guide landmarks for participants to see(not all are mentioned in the description ).For the Opulent experience I'll treat your taste buds to a one of a kind secret cocktail that you can only taste on this tour! Culminated with the tasting of 'Coffee of the Popes and the Kings' and crafting of a memorable souvenir with a certified artisan, for an ultimate cultural immersion!

Discover Puerto Rico in a 3 day luxury vacation that has a hand picked variety of locations and activities that will get you craving for more. This package gives you the best of the Metropolitan touristic zone, our historic city and our most amazing natural wonders.

The first day you will visit America's oldest city, Old San Juan, our african heritage capital, Pinones, and our finest Rum Distillery at El Barrilito. It will be a day filled with stories, legends and stories about our history

The second day is a nature exploring one in which you will hike a rock formation in Mar Chiquita with amazing views, visit our hiden gen Toro Negro Rainforest and experience perhaps the most beautifull waterfalls in all Puerto Rico.

The last day is special because you wil visit our finest cays at La Parguera, snorkel it's crystal clear waters, and then do the most unique thing you can do in our island: swim in the warm waters of La Parguera Biobay and make it glow and sparkle at your will!

(Cruise Port Walking Distance)
Dare to Explore a New Adventure Way! Embark on a wonderful tour aboard a one-of-a-kind high-performance Chiliboats water bike. Enjoy easy and smooth pedaling, combined with stability and safety. Take in unique and amazing views of Old San Juan Bay, featuring over 500 years of the city's rich history. Highlights include Puerto Rico's most iconic attraction: San Felipe del Morro Fort. Marvel at impressive views of La Fortaleza (Santa Catalina Palace/Governor's residence), San Juan Gate (original city entrance), "Baluarte de San Agustín," Santa Elena Battery, El Morro Wall, the "Garitas," and more. A must-do adventure!

Our tours are guided and certified by the Puerto Rico Tourism Company, the Department of Natural and Environmental Resources, and the Ports Authority of Puerto Rico. We prioritize quality and safety! Whether you're an individual adventurer or part of a family or friend group, you can enjoy this experience to the fullest.

If there is a tour every cruiseship visitor and traveler must do before even trying to walk our old city’s street, this will be it!

This tour was curated with comfort and as little walking as posible in mind, and it is the single tour every and anyone should do to avoid wasting hours looking for the landmarks, buildings and walking under the scorching sun trying to discover it’s history.

In it your driver and guide will take you in a route through the main buildings and landmarks and a journey in time telling you about the city’s history the city’s story in short and precise way as he drives you slowly driving through the narrow and colorful streets of our historic walled city.

You will have 4 to 6 stops to take pictures and get a closer look of the main landmarks of the city. Among them San Cristobal and El Morro Forts, El Convento, Ballaja, Saint John’s Cathedral, La Rogativa, Del Cristo and San Jose chapels and Colombus and Ponce de Leon square.

A cultural delight unlike any other! Experience life from centuries ago on an unforgettable walk through Old San Juan. With stops at the original gate to the city, her oldest fort- Castillo San Felipe del Morro, two 16th century cathedrals, and La Fortaleza mansion, to name a few! We will navigate both the streets of Old San Juan and tales of conquest and perseverance which are woven into the fabric of this great city!

After visiting the many highlights and landmarks of Old San Juan, we will venture through the Calle Fortaleza shopping district. Calle Fortaleza is home to shops, restaurants, and souvenirs galore! Guests will have a chance to secure memorabilia to remind them of this amazing day for years to come!

We will end our time in Old San Juan with lunch at an authentic Puerto Rican restaurant. Enjoy locally inspired drinks and dishes while taking in the sites, sounds, and atmosphere of Old San Juan!

"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.

Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran sailboat completely powered by the wind is the perfect setting for a romantic moment with your loved one or a fun time with friends. Complimentary beer, rum & coke, rum punch, and sparkling wine will be available to celebrate that special occasion or just because you're on vacation. Your veteran captain will point out sights along the way as you enjoy the views and the company aboard.

Old San Juan, a cultural delight unlike any other. Experience life from centuries ago on an unforgettable walk through Old San Juan. With stops at the original gate to the city, its oldest fort - Castillo San Felipe del Morro, two 16th-century cathedrals, and La Fortaleza mansion, to name a few! We will navigate both the streets of Old San Juan and tales of conquest and perseverance woven into the fabric of this great city.

After visiting the many highlights and landmarks of Old San Juan, we will venture through the Calle Fortaleza shopping district. Calle Fortaleza is home to shops, restaurants, and souvenirs galore! Guests will have a chance to buy memorabilia to remind them of this amazing day for years to come.

We will end our time in Old San Juan with lunch at an authentic Puerto Rican restaurant. Enjoy locally inspired drinks and dishes while taking in the sights, sounds, and atmosphere of Old San Juan!

Forget stiff smiles and awkward posing! This tour is all about letting loose, having fun, and creating authentic memories you can see in your photos. I'll be your photographer, blending in to capture candid laughter, heartwarming embraces, and playful shenanigans – the real moments that tell your family or couple story far better than any staged pose.

We will walk through the charming pedestrian promenade which is beautifully decorated with trees, old street lamps, benches, gardens, sculptures and fountains, all while taking wonderful photographs.

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.

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.

Experience our Private Local Food Tour in San Juan!

Embark on a serene journey through the picturesque landscapes of Puerto Rico as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting food tour of San Juan.

Experience the flavors and culture of Puerto Rico on a private food tour in Old San Juan. Explore local eateries and sample island staples such as plantains and sofrito, all while taking in the charm of the city's oldest neighborhood. Your tour also includes a choice of an alcoholic beverage or non-alcoholic substitute.

We'll greet you directly at the city center or hotels and ensure you return with ample time to relax and relish your day.

Leave the details to us as we escort you on an extraordinary adventure, crafting memories that will stand the test of time!

Note: Participants must be capable of walking long distances.

Discover the beauty of Old San Juan with writer David Rodríguez, author of "The Rise and Fall of the Great Barbate." Explore Old San Juan's most significant historic sites, delve into Puerto Rican culture, and immerse yourself in the places and activities that authentically depict the stories and people of Puerto Rico's past and present.

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.

Immerse yourself in Puerto Rico’s culture, history, and some of the best spots in the city with our guided walking tour through Old San Juan’s beautiful streets. This family-friendly 2.5-hour tour will let you discover the old city’s magical corners and sight-see its wonderful architecture.

If you're looking for a unique, locally immersive experience in Puerto Rico, our magical sunset tour in San Juan is the ideal choice for your short vacation. Explore our walled city, enjoying its stunning architecture dating from the 16th century to the present day. This two-hour tour, for adults only, allows you to discover the most emblematic and spectacular sites of the city, including plazas, the impressive San Felipe del Morro Fortress facing the Atlantic Ocean, churches, colorful narrow streets, and local bars with a great atmosphere that will make our sunset tour a unique and magical experience as you learn about Puerto Rico's historical and cultural roots alongside a local guide. This will be a relaxing experience where you can take panoramic sunset photos by the sea and enjoy local flavors, good music both inside and outside the walls of Old San Juan.

Note: Participants must be able to walk long distances

Discover the Beauty of Old San Juan with writer David Rodriguez, The Rise and Fall of the Great Barbate. From San Juan’s colonial Golden Age to the Gilded Age summer colony, discover the transformation of Ponce de Leon's city and people. Riots and rebellions, enemies and allies! Learn about Puerto Rico’s role in the revolution. See where scoundrels lived, pirates profited and criminals were punished. Find out why this colony was known as “Gold Island.” Explore the burial site of Ponce de Leon, Puerto Rico's founding father. Learn about the stone carvers, their art and the diverse people buried there who helped shape Ponce de Leon’s homeland.

This is a 1-hour photo session tour in historic Old San Juan!

First, we will meet up at Hotel El Convento in Old San Juan for an introduction and a quick chat, to get to know each other and to better understand your photo style. Then we will proceed to walk along a specific route to make sure we hit some of the most iconic photo spots in Old San Juan.

We will start at El Hotel Convento and then go down a street that looks like a jungle right in the city, Caleta de San Juan! Then, as we past by the historic Door of San Juan and the surrounding fortifications, we will make our way to Caleta de las Monjas, which is famous for it's variety of colorful houses. From there, we will go down a small alley with a garden in the center - a real hidden gem of Old San Juan! After that, we will head towards two iconic Puerto Rican flag doors.

Up to 5 days later, you will receive 30 professional images that capture the memories of your experience in Old San Juan!