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Puerto Rico Itinerary: Things To Do In Old San Juan


Modified: December 27, 2023

by Perry Towers



Welcome to Old San Juan, a charming and historic neighborhood nestled on the island of Puerto Rico. With its cobblestone streets, colorful buildings, and rich cultural heritage, Old San Juan is a must-visit destination for travelers seeking a unique experience. This enchanting district is located on the westernmost point of the islet of San Juan, surrounded by the sparkling waters of the Caribbean Sea.


As the second oldest European-founded city in the Americas, Old San Juan is steeped in history and boasts a wealth of architectural gems from colonial times. The neighborhood is known for its well-preserved forts, beautiful plazas, and stunning cathedrals. With its vibrant arts scene, mouth-watering cuisine, and warm hospitality, Old San Juan offers a delightful blend of past and present.


Whether you’re a history buff, a food enthusiast, an art lover, or simply in search of sun-drenched beaches, Old San Juan has something for everyone. This article will guide you through the highlights, hidden gems, and must-visit spots in this captivating neighborhood. Get ready to immerse yourself in the beauty, culture, and flavors of Old San Juan.


So grab your walking shoes, a sense of adventure, and let’s begin our journey through the vibrant streets of Old San Juan. From exploring the historic fortresses to indulging in delicious local cuisine, we’ll show you how to make the most of your time in this historic Caribbean gem. Let the adventure begin!


Exploring the Historic Streets of Old San Juan

Step back in time as you wander through the narrow and picturesque streets of Old San Juan. The neighborhood is a living testament to Puerto Rico’s colonial past, with its well-preserved architecture and historic landmarks. Start your exploration at the iconic San Juan Gate, a grand entrance that once served as the main access point to the city.


As you stroll along the colorful streets, you’ll be greeted by charming buildings adorned with ornate balconies, vibrant facades, and intricate ironwork. The pastel hues of the houses create a visually striking scene, perfect for capturing memorable photographs.


Be sure to visit Calle del Cristo, one of the most famous streets in Old San Juan. This bustling thoroughfare is lined with boutique shops, art galleries, and charming cafés. Take your time to browse through the shops and discover unique souvenirs, handmade crafts, and local artwork.


Another must-visit street is Calle San Sebastián, known for its lively atmosphere and vibrant nightlife. It comes alive during the weekends with street performers, live music, and cultural festivals. This is the perfect spot to immerse yourself in the local culture and experience the vibrant energy of Old San Juan.


Don’t miss the opportunity to explore the many plazas scattered throughout the neighborhood. Plaza de Armas is the main square, where you can relax on a park bench, admire the beautiful fountain, and soak in the surroundings. Nearby is Plaza Colón, named after Christopher Columbus, featuring a stunning monument in his honor.


While wandering the streets, keep an eye out for the iconic blue cobblestones, known as adoquines. Dating back to the 16th century, these hand-carved stones were used as ballast on Spanish ships and have since become a symbol of Old San Juan’s unique heritage.


As you explore the historic streets of Old San Juan, you’ll find numerous museums and historic sites worth visiting. From the Casa Blanca, the oldest continuously occupied residence in the Americas, to the Museo de las Américas, which showcases the history and cultures of the Americas, there’s no shortage of intriguing places to discover.


So lace up your walking shoes and get ready to immerse yourself in the captivating history, architecture, and culture of Old San Juan. The streets are yours to explore, and each corner holds a story waiting to be uncovered.


Discovering the Forts of Old San Juan

One of the most iconic features of Old San Juan is its impressive forts. These formidable structures were built by the Spanish empire to protect the city from invaders and have played a significant role in Puerto Rico’s history. Visiting these forts is like stepping back in time and exploring the military prowess of the past.


The first fort you should visit is El Morro, officially known as Castillo San Felipe del Morro. This historic fortress stands proudly on a peninsula overlooking the Atlantic Ocean. As you walk through its massive walls and towering watchtowers, you’ll gain a deep appreciation for the strategic importance of this imposing structure. Explore the labyrinth of tunnels, climb to the top for breathtaking panoramic views, and marvel at the cannons that once defended the island.


Another must-see fort is Castillo de San Cristóbal, the largest fortification built by the Spanish in the Americas. This impressive fortress protected the land entrance to Old San Juan and features a network of tunnels, dungeons, and ramps. Take a guided tour to learn about the fort’s fascinating history and hear tales of battles and sieges that took place centuries ago.


Both El Morro and San Cristóbal are UNESCO World Heritage Sites and offer guided tours, exhibits, and stunning views of the city and ocean. These forts are not only historically significant but also provide a captivating experience for visitors of all ages.


If you want to delve deeper into the history of Old San Juan’s forts, make sure to visit Fortín San Juan de la Cruz, also known as El Cañuelo. Located at the entrance of the San Juan Bay, this small fortification guarded the city from enemy ships, and its strategic location offers fantastic views of the coastline.


Exploring the forts of Old San Juan is not just a journey through history but also an opportunity to appreciate the architectural brilliance of these monumental structures. The strategic placement, intricate designs, and engineering marvels of these forts are a testament to the ingenuity of the builders.


So take a step back in time and discover the forts that have stood the test of time in Old San Juan. Whether you’re a history enthusiast or simply seeking awe-inspiring views, these forts will leave an indelible impression on your visit to this enchanting neighborhood.


Admiring the Stunning Architecture of Old San Juan

Old San Juan is a treasure trove of architectural wonders, boasting a blend of Spanish colonial, Gothic, and neoclassical styles. From the moment you set foot in this historic neighborhood, you’ll be captivated by the beauty and grandeur of its buildings.


One of the most iconic architectural landmarks in Old San Juan is the Cathedral of San Juan Bautista, also known as San Juan Cathedral. This magnificent structure dates back to the early 16th century and features intricate stained glass windows, ornate decorations, and a stunning facade adorned with sculptures and carvings. Step inside to marvel at the heavenly beauty of this sacred place and take a moment for quiet reflection.


As you wander through the streets of Old San Juan, you’ll encounter numerous buildings with impressive balconies. These beautiful ironwork balconies, known as rejas, are an integral part of the neighborhood’s charm. Adorned with delicate designs and often overflowing with lush greenery, these balconies add a touch of romance and elegance to the architecture.


Another architectural gem is La Fortaleza, the official residence of the Governor of Puerto Rico. This majestic mansion, built in the 16th century, is a UNESCO World Heritage Site and showcases a captivating blend of Moorish, Gothic, and neoclassical styles.


For a glimpse into the opulence of the past, visit Casa de España, a striking example of Spanish Renaissance architecture. This stunning building, adorned with intricate details and frescoes, is now home to the Puerto Rico Tourism Company and occasionally hosts cultural events.


One cannot miss Paseo de la Princesa, a majestic promenade that features beautiful arches, grand fountains, and lush gardens. This charming walkway provides a picturesque setting for a leisurely stroll, showcasing the harmonious fusion of nature and architectural beauty.


As you explore the streets, be sure to look out for the unique blue paint adorning many of the buildings. This tradition started centuries ago when it was believed that the color blue would ward off evil spirits. Today, the vibrant blue hues continue to add to the whimsical charm of Old San Juan.


The stunning architecture of Old San Juan not only reflects the neighborhood’s rich history but also serves as a testament to the craftsmanship and artistic flair of the architects and builders. As you admire the intricate details and the majestic facades, you’ll feel transported to a bygone era.


So take your time to appreciate the architectural marvels of Old San Juan. Discover the hidden details, snap photos of breathtaking facades, and let yourself be swept away by the allure of this historic neighborhood.


Enjoying Local Cuisine and Drinks in Old San Juan

No visit to Old San Juan would be complete without indulging in the mouthwatering local cuisine and sipping on refreshing tropical drinks. The neighborhood is a food lover’s paradise, offering a diverse array of traditional Puerto Rican dishes and flavors.


Start your culinary adventure with a visit to one of the many local bakeries, known as panaderías, where you can savor freshly baked pastries and breads. Try a traditional Mallorca, a sweet and fluffy pastry topped with powdered sugar, or indulge in a quesito, a cream cheese-filled danish.


For a taste of Puerto Rican street food, head to La Placita de Santurce, a vibrant square located just outside Old San Juan. Here, you’ll find an array of food stalls offering favorites such as alcapurrias (deep-fried fritters), mofongo (mashed plantains with meat or seafood), and bacalaitos (salted codfish fritters).


Seafood lovers will delight in the variety of fresh seafood options available in Old San Juan. From succulent shrimp to tender octopus, you’ll find an abundance of flavors from the sea. Don’t miss the opportunity to try a classic Puerto Rican dish, like arroz con camarones (rice with shrimp) or pescado en escabeche (pickled fish).


To quench your thirst and cool off from the tropical heat, sip on some refreshing local drinks. Order a piña colada, Puerto Rico’s national drink, made with coconut cream and pineapple juice, or try a rum cocktail featuring the famous Puerto Rican rum. For a non-alcoholic option, opt for a jugo de parcha (passion fruit juice) or a cold and creamy limber, a Puerto Rican version of a popsicle made with fruit juice and sweetened milk.


When it comes to dining experiences, Old San Juan offers a range of options to suit every palate. From cozy family-run restaurants serving home-style meals to upscale establishments offering innovative fusion cuisine, there’s something to please every food lover.


After a satisfying meal, take a leisurely stroll along Calle San Sebastián, where you’ll find a vibrant nightlife scene with bars and clubs. Enjoy live music, dance to salsa rhythms, and sip on creative cocktails as you immerse yourself in the energy and excitement of Old San Juan after dark.


So come hungry and thirsty to Old San Juan, and let the flavors of Puerto Rico tantalize your taste buds. From traditional dishes to tropical drinks, the culinary delights of this neighborhood are sure to leave your palate satisfied and your heart content.


Shopping for Unique Souvenirs in Old San Juan

When it comes to shopping for unique and memorable souvenirs, Old San Juan is a haven for treasure seekers. The neighborhood offers a wide range of shops and boutiques, each offering its own distinctive selection of items that reflect the local culture and craftsmanship.


One of the must-visit spots for souvenir shopping is Calle del Cristo, a charming street lined with boutique shops and art galleries. Here, you’ll find an assortment of handmade crafts, including vibrant paintings, intricately designed ceramics, and beautifully crafted jewelry. Take your time to explore the art galleries, where you can discover unique works by local artists that capture the essence of Puerto Rico.


For those passionate about fashion, a visit to Old San Juan is an opportunity to find one-of-a-kind clothing pieces and accessories. Browse through the independent boutiques on Calle San Francisco or Calle San José, where you’ll discover stylish garments made by local designers. From trendy clothing to handmade accessories, you’ll find fashion-forward items that showcase Puerto Rican creativity and style.


If you’re looking to bring a taste of Puerto Rico back home, be sure to visit one of the neighborhood’s specialty food stores. These stores offer a wide variety of local products, from coffee and spices to traditional sweets and sauces. Pick up a bag of freshly roasted Puerto Rican coffee or a jar of delectable artisanal salsa to savor the flavors of the island long after your trip has ended.


No visit to Old San Juan is complete without exploring the vibrant souvenir shops that line the streets. Here, you’ll find an array of trinkets, postcards, and traditional Puerto Rican souvenirs to commemorate your trip. Look for the iconic vejigantes masks, hand-painted with bright colors and intricate designs, or pick up a bottle of locally produced rum to enjoy a taste of Puerto Rico back home.


For a truly unique and meaningful souvenir, consider visiting a local artisan market or fair. These often showcase the talent and craftsmanship of Puerto Rican artisans, offering handmade products that reflect the island’s rich cultural heritage. From intricately woven baskets made from palm leaves to handmade musical instruments, these markets are a treasure trove of authentic and unforgettable souvenirs.


Shopping in Old San Juan is not just about finding souvenirs; it’s about supporting local businesses and celebrating the creativity and talent of Puerto Ricans. So take the time to explore the shops, chat with the store owners, and find that special item that will forever remind you of your time in this enchanting neighborhood.


Exploring the Art and Culture of Old San Juan

Old San Juan is not only a visual feast for the eyes with its colorful architecture and stunning landscapes, but it is also a hub of artistic and cultural expression. Immerse yourself in the vibrant art scene and discover the rich cultural heritage that adds depth and soul to this historic neighborhood.


Start your exploration of the art and culture of Old San Juan with a visit to the Museo de Arte de Puerto Rico. This renowned museum showcases a diverse collection of Puerto Rican art, spanning from the 17th century to contemporary works. Admire paintings, sculptures, and installations that reflect the island’s history, identity, and artistic evolution.


Continue your artistic journey by wandering through the numerous art galleries dotted around Old San Juan. These galleries feature a wide range of artistic styles and mediums, from traditional oil paintings to avant-garde installations. Explore the local talent and perhaps even take home a piece of art that captures the essence of Puerto Rico.


As you wander the streets, keep an eye out for colorful murals and street art that adorns the walls of Old San Juan. These vibrant and thought-provoking displays of creativity add to the neighborhood’s vibrant atmosphere and provide a platform for local artists to showcase their talent.


To dive deeper into the cultural heritage of Puerto Rico, visit the Instituto de Cultura Puertorriqueña. This cultural institution hosts exhibitions, performances, and workshops that celebrate the island’s traditions, folklore, and artistic expressions. Immerse yourself in the music, dance, and storytelling that form the tapestry of Puerto Rican culture.


Take a moment to explore the numerous plazas scattered throughout Old San Juan. These open spaces often host cultural events, live music, and performances that showcase the island’s music, dance, and traditional arts. Enjoy the lively atmosphere and perhaps even join in the festivities.


Don’t forget to visit La Casa del Libro, a charming bookstore that specializes in Puerto Rican literature. Browse through the shelves and discover literary works that reflect the island’s history, identity, and literature. This is the perfect opportunity to take home a piece of Puerto Rican culture in the form of a captivating book.


As you delve into the art and culture of Old San Juan, remember to engage with the local community. Strike up conversations with artists, attend cultural events, and support local artisans and performers. By doing so, you’ll not only enhance your own experience but also contribute to the preservation and promotion of Puerto Rican art and culture.


In Old San Juan, art and culture pervade every corner, inviting you to participate and immerse yourself in the creative tapestry that shapes the identity of the neighborhood. So allow yourself to be captivated by the artistic expressions and cultural traditions that await you in this enchanting destination.


Relaxing and Sunbathing at the Beautiful Beaches near Old San Juan

When you need a break from exploring the historic streets and immersing yourself in the cultural delights of Old San Juan, the pristine beaches beckon just a short distance away. Bask in the warm Caribbean sun, feel the soft sand between your toes, and let the tranquil waters wash away your worries.


One of the closest and most accessible sandy retreats is Escambrón Beach. Located just outside Old San Juan, this picturesque beach offers a perfect blend of relaxation and natural beauty. With its calm turquoise waters and lush surroundings, Escambrón Beach is a popular spot for swimming, snorkeling, and sunbathing.


A bit further away, you’ll find the stunning Isla Verde Beach. With its wide sandy shores and crystal-clear waters, this beach is an ideal destination for beach lovers. Enjoy a leisurely swim, rent a kayak or paddleboard, or simply relax under the shade of a palm tree and take in the breathtaking views of the coastline.


If you’re seeking a more serene and secluded beach experience, head to Playa Peña in Santurce. This hidden gem offers a tranquil escape from the crowds, with calm waters and a serene atmosphere. Take a leisurely stroll along the shoreline, enjoy a picnic on the soft sand, or simply unwind as you listen to the soothing sounds of the waves.


For those who crave a bit of adventure, make your way to Piñones, a coastal area known for its vibrant atmosphere and diverse ecosystem. Here, you’ll find miles of sandy beaches, perfect for long walks and relaxation. Explore the nearby boardwalk, indulge in delicious local street food, and soak up the lively ambiance that makes Piñones a favorite spot among locals.


No matter which beach you choose, make sure to pack sunscreen, a beach towel, and plenty of water for hydration. And don’t forget to take a refreshing dip in the inviting waters to cool off from the tropical heat.


When visiting the beaches near Old San Juan, be mindful of your surroundings and follow any safety guidelines provided. Respect the natural environment and leave only footprints behind, ensuring that these stunning beaches remain pristine for future visitors to enjoy.


So, escape to the beautiful beaches near Old San Juan and let the sun warm your skin, the gentle waves lull you into a state of relaxation, and the stunning views inspire a sense of serenity. It’s the perfect way to recharge and unwind amidst the natural splendor of Puerto Rico.


Taking a Day Trip to the Nearby Islands from Old San Juan

While Old San Juan offers a captivating array of attractions, it’s worth venturing beyond its historic borders to explore the nearby islands that are just a short distance away. These beautiful and idyllic islands offer a chance to escape the hustle and bustle of the city and immerse yourself in pristine natural beauty.


One of the most popular day trip destinations from Old San Juan is the enchanting island of Culebra. Known for its powdery white sand beaches and crystal-clear turquoise waters, Culebra is a paradise for beach lovers and snorkeling enthusiasts. Flamenco Beach, consistently ranked among the top beaches in the world, will leave you in awe with its expanse of soft sand, gentle waves, and vibrant marine life. Spend the day swimming, sunbathing, and snorkeling to explore the colorful coral reefs and encounter tropical fish.


Another nearby island worth visiting is Vieques, known for its bioluminescent bay, captivating beaches, and tranquil atmosphere. Take a boat tour through Mosquito Bay to witness the magical phenomenon of bioluminescence, where the water glows blue-green at night due to the presence of microscopic organisms. Vieques also offers stunning beaches such as Playa Caracas (Red Beach) and Playa La Chiva (Blue Beach), where you can relax, swim, and soak up the sun.


If you’re up for an adventure, consider a trip to the uninhabited island of Icacos. This small island, part of the Cordillera Keys Nature Reserve, boasts pristine beaches, crystal-clear waters, and abundant marine life. Take a snorkeling excursion to explore the vibrant coral reefs and swim alongside tropical fish. Feel the sense of tranquility as you escape from the crowds and immerse yourself in the unspoiled beauty of nature.


When planning a day trip to the nearby islands, ensure to check ferry schedules and make necessary reservations in advance, as availability can vary. Pack essentials such as sunscreen, towels, snacks, and plenty of water to stay hydrated throughout the day. Additionally, be mindful of the environmental regulations and guidelines to help preserve the natural splendor of these islands for generations to come.


So, escape the mainland and embark on a day trip to the nearby islands from Old San Juan. Discover pristine beaches, vibrant marine life, and the wonders of nature. It’s an opportunity to create unforgettable memories and experience the true essence of Puerto Rico’s coastal beauty.



Old San Juan is a remarkable destination that offers a myriad of experiences for travelers seeking history, culture, art, and natural beauty. From the historic streets lined with colorful buildings to the impressive fortresses that guard the city, Old San Juan transports visitors to a bygone era while still embracing the vibrancy and energy of the present.


Exploring the cobblestone streets of Old San Juan allows you to immerse yourself in its rich history. Marvel at the architectural wonders that have stood the test of time and learn about the fascinating stories behind each building and plaza. The forts of El Morro and San Cristóbal provide a glimpse into the strategic importance of the island and the resilience of its people.


Beyond its historical significance, Old San Juan is a hub of art and culture. Visit museums, galleries, and cultural institutions to discover the artistic expressions that reflect the spirit of Puerto Rico. From traditional paintings to street art murals, there’s no shortage of creativity on display.


Indulge in the delectable local cuisine of Old San Juan, where traditional flavors and innovative fusion dishes come together in perfect harmony. Sip on tropical drinks, sample street food, and savor the fresh seafood that the island has to offer. And don’t forget to shop for unique souvenirs that showcase the craftsmanship and heritage of Puerto Rico.


When you need a break from the city, the pristine beaches near Old San Juan beckon with their soft sands and crystal-clear waters. Take a day trip to nearby islands such as Culebra, Vieques, or Icacos, where you can relax, swim, and witness the natural wonders of the Caribbean.


As your journey through Old San Juan comes to an end, take a moment to reflect on the memories and experiences you’ve gathered. The charm, beauty, and cultural richness of this neighborhood will leave an indelible mark on your heart. Old San Juan is a captivating destination that seamlessly blends the old and the new, ensuring an unforgettable travel experience for all who visit.


So bid farewell to Old San Juan, but carry its spirit with you as you venture forth. The memories, stories, and connections formed in this historic neighborhood will forever remind you of the beauty, resilience, and cultural diversity that Puerto Rico has to offer.