Top Experiences in La Fortaleza (The Fortress)

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!

Be respectful
Bring Good Vibes Only

(Private exploration) (60-75 minutes approx)
We pride ourselves in providing a unique experience aboard our amazing GOLF CARTS with our friendly and knowledgeable staff, guaranteeing to leave you wanting more. What makes this experience unique is our extreme levels of customer service and our ability to please each end every age group that comes to us looking for a unique San Juan experience, all the while showing you the “3 sides of SanJuan” . Customers should definitely pick this experience because it will end up being the highlight of their day in Old San Juan

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'.

Have the complete San Juan experience by land and sea! There is no other tour in Old San Juan that allows you to walk the city and then cruise the city. This tour commemorates the city's 500-year anniversary.

The tour includes entrance to the fort San Felipe del Morro which is the most visited attraction in Puerto Rico. The tour also includes popular icons of Old San Juan such as its colorful buildings and cobblestone streets. Other landmarks included are the San Juan Cathedral (interior), the Governor's Mansion and the San Juan Gate.

The tour is guided by locals with excellent customer service and vast knowledge about the history, culture and nature of Puerto Rico. Guides are certified by the Puerto Rico Tourism Company and are fluent in both English and Spanish.

This tour covers the most popular landmarks of Old San Juan during the golden hour. At this time you will enjoy beautiful photo-ops of the old town’s beautiful historic architecture. The walk ends in the early evening near restaurants, bars and souvenir shops.

Along the way you will learn about the old town's history and the Puerto Rican culture. The tour is conducted by professional local guides certified by the Puerto Rico Tourism Company.

The sunset and the nice temperature at this time of the day makes the walk memorable and easygoing.

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.

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timeless allure of San Juan Bay, the historical gem of Puerto Rico.

Our Sunset Tour offers a perfect fusion of cultural exploration, awe-inspiring views, and countless photography opportunities. Capture breathtaking images of Old San Juan's iconic landmarks, including Paseo la Princesa, Fortaleza (Governor’s Mansion), Bacardi Distillery, Morro Fortress (San Felipe del Morro’s Castle), Puerto Rico’s Capitol Building, San Juan’s Door, and the formidable 500-year-old San Juan Fortified Walls.

Indulge in the sunshine, relish the vibrant Caribbean atmosphere, and witness Old San Juan from a unique perspective. Treat yourself to delicious light snacks and appetizers, and try our local beer and rum punch, as you soak in the beauty of this unforgettable experience.

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!

See more do more! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a a high performance Powerboat. Enjoy complimentary local drinks. Your personal tour guide and Pro USCG certified Captain will guide you to stunning and interesting historical points of interest full of Caribbean flare in style and with a high quality sound system. Choose between a bay or sunset water tour. For a minimum of 4 guests or pay for 4 and a maximum of 6. Welcome aboard!

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.

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, feeling safe but free, in parties no larger than 6 people. Good for a special moment, or turning this moment into an special one. While in contact with nature elements, sometimes you may get surprised by dolphins. This is not a luxury yacht or a catamaran.

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.

Discover Puerto Rico in a 3 day package 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 history 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, see the tallest Statue of the Americas; the Birth of a New World monument, visit the Camuy Caves and experience perhaps the most beautifull waterfall in our rainforests.

The third day is the special one because you wil visit our finest cays at Guilligan's and Caracoles and then do the most unique thing you can do in our island: swim in the glowing waters of La Parguera Biobay!

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 stray 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, feeling safe but free, in small groups (no crowds.) Good for any special moment, or turning this moment into an special one. While in contact with nature elements, sometimes you may get surprised by dolphins. There are 6 people maximum per sailboat. Sailboat model: Jboat J30 (racer-cruiser.) It's not luxury yacht or a catamaran. Let's sail with Sail San Juan Bay!

Designed with kids in mind, the Old San Juan Sightseeing Educational tour offers a 2-in-1 experience in history and science, providing family fun designed to keep all ages engaged and learning! Kids will participate in a variety of exciting, handpicked on-the-go science experiments to learn about Puerto Rico's history, geology, geography, flora, and fauna.

After meeting at the entrance to the Compañía del Turismo at La Princesa promenade, kids and adults will enjoy a guided, narrated tour of the five centuries of history in Old San Juan and Puerto Rico led by a certified guide, Ed.D. - Professor Nat. Yummy frozen traditional Puerto Rican natural treats await the kids, and coffee for the adults, throughout the adventure!

We will walk along the monuments, fortifications, and rare sights, learning about Puerto Rican and Old San Juan history and planning. The kids' experience is the main focus, and we move at their pace. ❤️

(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.

We will meet in Old San Juan and start our shoot walking through hidden alleys and its historic landmarks for 1 hour. I will Use differently lenses on my DSL camera including specialty, telephoto, macro and wide-angle lenses to produce high quality photos of unique shots. You can either pose as you want, have me direct you, or just simply walk as I take candid photos while you enjoy the sights.
My photography style leans towards the creative/artistic style, but I also do other styles as documentary and lifestyle styles. After the shoot, I will process and edit the photos and deliver to you.

We will tour you through the waters of San Juan Bay and on a confortable Yamaha Wave Runner with cruiser seats. Our jet ski are equipped with a ladder for easy boarding from the water.

In our tour you will have the opportunity of observe multiple historic places like Castillo San Felipe from the water and have fun at the same time. You can take a relaxing bath in the water, feel the breeze and clear your mind.

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.

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.

A kaleidoscope of tropically-colored colonial houses mix with the blue-green glow of the Atlantic Ocean in one the best-preserved colonial cities of the Americas. You could easily fall under San Juan’s spell with its labyrinth of blue cobblestone streets, dramatic walls, imposing fortresses, historic churches and sleepy plazas.

Perfectly suited for discovery on foot, our self-guided audio tour allows you to set the pace and explore at your leisure as you uncover the stories of this amazing city.

To discover this fascinating city in your own time and at your own pace just download this self-guided audio tour, pop in your headphones, open the map that comes with your download and start walking.

The tour will take approximately two hours, but you can pause the audio guide when needed. Grab a bite to eat or do some shopping along the way.

Please note that this tour is only available in English.

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.