Old San Juan 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.

Enjoy a new perspective on Old San Juan—and soak up Caribbean breezes and sunset views—aboard this evening boat tour. Following pickup at select local hotels, hop aboard the boat and find a comfortable seat on the deck. Then, spy highlights like Paseo De La Princesa, La Fortaleza, the San Juan City Walls, and more, all while the sun goes down. Light refreshments and alcoholic drinks are available on board.

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.

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. 

Stroll the cobblestone streets of Old San Juan with a small group (10 people or fewer) on this 2-hour cocktail and history tour. Visit three bars to learn about why Puerto Rico is considered the 'Rum Capital of the World' and sip rum-infused cocktails at each location. Minimum age is 18 years old.

Explore the waters around San Juan on a miniboat, which holds a small group of up to four people. You'll get great, photo-worthy views of the shoreline and listen to guided commentary as you travel. A small group means personalized attention from your guide and an intimate atmosphere.

Explore Old San Juan at the most magical time of day during a sunset walking tour around the historic centre of Old San Juan. Exploring on foot means you’ll notice architectural details that you might otherwise miss if you were traveling in a traditional tour vehicle, while guide commentary brings the town to life with stories you’re unlikely to find in the guidebook.

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'.

Experience one of the Americas’ oldest cities, San Juan, on a sightseeing tour. After a convenient hotel pickup, travel by private luxury vehicle with a personal guide to Old San Juan, Isla Verde, Santurce, and other important districts in Puerto Rico’s beautiful capital. Learn about the city’s culture while visiting historic landmarks, trendy neighborhoods, art galleries and museums, and beautiful beaches—all on one fun and hassle-free outing.

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.

This experience is a roadtrip to all the best & most desired spots of Puerto Rico in one tour. The instagram trip focuses on visiting the most insta-worthy sights for pictures, history, culture and adventure by visiting Old San Juan, the rainforest, a clear water beach and a local restaurant thats serves authentic puertorrican food. This is a true local experiences that visits the world famous east side of Yunque rainforest. We also visit the top spots of Old San Juan with short commentary on the history. Later we visit a local's favorite beach that has lovely clear warm waters for the perfect island getaway. We end the tour having lunch at a local family chinchorro so that you can live the experience of eating in an authentic and real puertorrican family. This trip includes transportation and usually last from 8-10 hours duration. This is the tour of the best sites and most scenic pictures of the island all in one. A true local experience, with a local, as a local.

Visit the Caribbean Island of Puerto Rico, and explore its capital city, San Juan, on this 2.5-hour tour. Stroll down cobblestone streets, and see the brightly colored buildings that line the area. Encounter famous sights like Cathedral of San Juan Bautista, Casa Blanca, and San Jose Church. Get a feel for what it was like during the Spanish colonial era as you walk through the Puerta De San Juan, one of the only gates left that served one of the oldest cities in the world.

Discover one of San Juan’s hidden waterfalls on this full-day adventure. Hike through the mountains and countryside of Puerto Rico until you reach this beautiful waterfall. Swim at the base in deep, natural pools to refresh before heading to a local establishment for a delicious Puerto Rican meal—at your own expense.

Stroll the cobblestone streets of Old San Juan and taste some of the local cuisine during this 3-hour food and walking tour. With your local guide, hear about the history of this 16th-century colonial city, pausing to duck into coffee shops and cafes. Sip a rum cocktail and taste traditional Puerto Rican food at 4 stops during the walk. With your small group of fellow food and history lovers, explore an old convent and get stunning views of the city's impressive forts and other landmarks.

Discover the rich history of Puerto Rico on a historic walking tour through Old San Juan. This small-group excursion stops at key landmarks including the Fortress, the Gate of San Juan, the oldest cathedral in the United States, and the Bastion. At each stop, your guide sheds light on the over 500-year history of the island from the indigenous settlers, to Spanish conquistadors, to its modern-day history as a territory.

Discover the capital of Puerto Rico during this half-day walking tour of Old San Juan. Journey back in time with your tour guide and learn about the rich history and culture of the island. Visit key landmarks including the historic San Juan Gate, the basilica, the governor’s residence, and the old naval arsenal as you explore. Conclude your tour at a restaurant dubbed as the birthplace of the piña colada.

This private sailboat charter from San Juan allows you (maximum 6 passengers) to choose your own adventure. Sail around the bay and harbor of Old San Juan with an experienced captain and crew at the helm; you can choose to help sail or just relax and enjoy the ride. Bring whatever you prefer to sip on, as you watch the scenery. Ask any questions you may have about boating or about owning a boat; your crew is there to educate you on potential future boat sailing and ownership. Our prices already include all taxes and fees.

Get unrivalled views of Puerto Rico’s natural and historical landscapes during a helicopter tour that lets you see the island from a fresh perspective. Designed with time-pressed travelers in mind, this private tour ensures you have the helicopter all to yourself, so you can guarantee a window seat. Plus, you can choose a start time that suits you.

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.

We will drive you to the heart of Old San Juan where you are able to walk the beautiful cobblestone streets, shop for various local artisan products, eat tasty borinquen food, and absorb the history. Get a taste of the flavor and culture Puerto Rico is proud of! We will provide you a detailed driving tour with commentary on the important San Juan Landmarks. We will travel past the famous Castillo San Cristóbal and over to the ship docks and everything in between. We know where the gems are, so do not be afraid to ask. Make sure you see everything you want to see in the remarkable Viejo San Juan. This driving tour includes Old San Juan, Condado, Isla Verde, Pinones, ect and surrounding areas with amazing information about the local history.

Clue Murder Mystery is far from your average history tour. Have you ever played the game clue? What about an escape room? Well, imagine each of these combined into a self-guided investigation that leads you around Old San Juan! During your investigation, you will be walking to 8-10 spots that are tourist favorites, local hotspots, history, scenery, or just somewhere we think boasts the uniqueness of Old San Juan. Guess what else?! You have the freedom to grab a drink, stop and shop, or do whatever your heart desires along the way. We want you to explore the downtown area near the cruise port as you please! Clue Murder Mystery is also a great team-building activity because of the way it requires multiple mindsets to solve the clues. You must work together if you want to be the fastest team to solve the murder mystery. Check our Google and TripAdvisor reviews to see what everyone has to say about our Murder Mystery in 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.

Founded in 1509, San Juan has over 500 years of history. Get to know the highlights without the hassles of research when you join a professional historian in their Audi SUV for this private door-to-door tour. See the Caparra Ruins and Historical Park, where the first settlement was created; take a walking tour of the Old San Juan walled city; after lunch (own expense) discover Santurce, a more modern district.

Explore the historic area of Old San Juan on a small-group walking tour. Step back in time, over 500 years, and learn about the island of Puerto Rico from your guide. As you walk, pass by important landmarks while your guide regales you with history and tidbits about the local culture.