There’s no better way to start your San Juan trip than stepping 465 years into the past. Old San Juan is a 7–10 block area with 16th and 17th century Spanish colonial buildings that have been carefully restored. See El Morro — the oldest Spanish fort in the Americas from 1539 with stunning views of the coast and the crashing waves beneath you. Don’t miss the Ballaja Barracks that acted as housing for regiments in the nineteenth century and now acts as the Museum of the Americas where you can wander through four permanent exhibits on Caribbean history, African heritage and Spanish colonialism. Then stop in Quincentennial Plaza where you can see the 40 foot El Tótem Telúrico tower built in 1992. 

Let a Princess guide take you to all of these sites and walk you through hundreds of years of history in the heart of San Juan.

Guarding the eastern entrance to San Juan, you’ll find Castillo San Cristóbal — a fort sprawling over 27 acres. This fortress is one of the biggest Spanish fortifications in the New World and was built in 1634 to protect San Juan from inland invaders. It successfully defended against Ralph Abercromby’s forces during the Battle of San Juan in 1797. Hike around the fortress walls for great views of the cliffs and hear the military and cultural stories about this unique fort from your Princess guide.

There’s no better way to start your San Juan trip than stepping 465 years into the past. Old San Juan is a 7–10 block area with 16th and 17th century Spanish colonial buildings that have been carefully restored. See El Morro — the oldest Spanish fort in the Americas from 1539 with stunning views of the coast and the crashing waves beneath you. Don’t miss the Ballaja Barracks that acted as housing for regiments in the nineteenth century and now acts as the Museum of the Americas where you can wander through four permanent exhibits on Caribbean history, African heritage and Spanish colonialism. Then stop in Quincentennial Plaza where you can see the 40 foot El Tótem Telúrico tower built in 1992. 

Let a Princess guide take you to all of these sites and walk you through hundreds of years of history in the heart of San Juan.

Nothing says vacation like sun-soaked beaches, deep blue oceans and swaying palm trees. Find that — and the R&R you’ve been craving — by kicking back and relaxing on Carolina Beach. Sprawl out on the pristine white sand or wade out into the water to cool down. Brought the whole family? There’s a kiddie waterpark where young kids can spend the day splashing. Don’t forget your sunscreen! 

Looking for an exclusive and quiet beach day? Visit VIVO Beach Club on Isla Verde where you can relax, swim and play using the exclusive resort’s amenities. It’s the perfect way to get the relaxation you need without any crowds.

Enter old town through the Puerta de Aguas or Puerta de San Juan, also known as the San Juan Gate. The entryway is bright red, the gate is 16 feet tall and 20 feet thick and leads you to the romantic Paseo La Princesa. As you walk through, note the inscription that says, “Benedictus Oui Venit In Nomine Domini” which translates to “Welcome those who come in the name of God” — a nod to the Catholic origins of San Juan. You’ll feel like you’re traveling in the sixteenth century when you hit this iconic landmark on your tour of San Juan.

If you’re an architecture buff, look no further than the Capitol of Puerto Rico, a Renaissance style, domed structure that houses the government. This white marble building was designed by Rafael Carmoega, the first state architect in Puerto Rico, and the Capitol was completed in 1929. Don’t forget your camera because you’re not going to want to miss this architectural gem! 

Stop at this photo op and a few other highlights of downtown San Juan with Princess to make sure you don’t miss the essentials.

El Yunque is the only tropical rainforest in the U.S. and sacred to the indigenous Taíno people of Puerto Rico. Hike the lush trails surrounded by colossal ferns, pine trees and hibiscus blossoms as big as your dinner plate! Don’t miss an excursion to La Coca Falls — a cascade of 85 feet of water over a mossy cliff. Climb up Observation Tower (1,575 feet above sea level) to see the best views of the sprawling jungle. 

Strut your stuff along the most iconic walkway in San Juan: Paseo de la Princesa. This promenade from 1853 sees millions of visitors a year and connects you to Old San Juan and the San Juan Gate. As you walk, you’ll see the ocean, the city walls, manicured gardens, a playground for your kids and the iconic Raices Fountain. This walk is the perfect addition to a day of sightseeing in San Juan or a way to wind down with your significant other after a romantic dinner.

Did you know that the oldest church on U.S. soil and the second oldest church in the Western Hemisphere is in San Juan? Catedral de San Juan Bautista was originally built in 1521, and was soon after completely destroyed by a hurricane. It was rebuilt in 1540, and it’s still standing in the same spot despite being pillaged and looted in 1598 and losing its roof to a 1615 hurricane. Admire this iconic church on a walk through the city.

San Juan’s oceanfront neighborhood Condado has everything you need for a great visit to the city: stunning beaches, delicious food and some of the best shopping on the island. When you’re in Condado, you can paddleboard through a lagoon or eat alongside the coast with sunset views. Plus this neighborhood has one of the best beaches in San Juan. Visit Condado Beach to enjoy the sunshine, crystal clear waters and beachside food shacks where you can get hot fritters and mashed plantains as you enjoy a perfect beach day.

Get ready to rumba… and cha-cha, merengue and tango at this San Juan nightlight hotspot. During the day, the placita is a market with local produce, colorful stalls and restaurants. When the sun goes down, that’s when the music turns on and the party starts. Salsa dance on the streets of San Juan — and grab a delicious empanada and cocktail for a quick break.

The perfect way to end a day in San Juan is to sail off into the sunset and soak in the stunning views of San Juan Bay. For the last 500 years, this bay has served as Puerto Rico’s main connection with the outside world — and it’s still one of the city’s busiest ports today. Hop on a sail boat to get the best views of the sun dipping beneath the waves and coloring San Juan in rich oranges, pinks and purples.

This iconic landmark literally means “The Fortress,” but you’ll quickly find it’s not like the stone forts in the city: it’s a bright blue palace! The original structure was built almost 500 years ago, but it was taken over by the Dutch before being remodeled in 1846 as the governor’s palace. Over 170 governors of Puerto Rico have lived and worked here! Because the current governor uses La Fortaleza, there are limited tour times, so be sure to head out in the morning if you want a look inside and at the manicured gardens. 

No trip to La Fortaleza is complete without walking the nearby street, Calle Fortaleza. It’s one of the most photogenic streets in the city with brightly colored buildings on both sides and umbrellas suspended overhead.

The world’s largest rum distillery? Say no more! Casa BACARDÍ is Puerto Rico’s home of rum since 1962 when the company started making rum outside of Cuba for the very first time. Take a tour of the distillery where you can learn about the origins of the world’s most awarded rum — or do a guided tasting where you can sample the beverages as you go.

Hit the shops at the largest shopping center in the Caribbean when you visit the Plaza Las Américas. The Plaza is home to over 250 stores, 15 movie theaters and 50 restaurants, so you’ll never run out of things to do. Looking for something truly Puerto Rican? Head to the third level of the Central Atrium where you can admire and buy Puerto Rican crafts year-round and delicious produce on the weekends.

Sculptures, paintings and photographs, oh my! The Museo de Arte houses over 1,000 works of art by Puerto Rican artists, and the collection dates back to the 1600s. The museum is split into two wings — one in a 1920s Neoclassical building and the other in a modern construction designed by Puerto Rican architects. With only 24 galleries, you can see the museum in a day and learn more about the island’s history and culture. Don’t miss the stained-glass piece by Eric Tabales called Taíno Sun Rising in the east wing.

Every city has its artsy district, but San Juan’s is truly special because the buildings are decorated with murals done by some of the best muralists in the world. Walking through the area is like walking through a museum, with a little more fresh air. This area was once a rundown district, but the city reclaimed it with an art-based beautification project that now draws visitors from all over the world. Feeling hungry? Head to Lote 23 where you can find a wide variety of hot street food options, including a traditional Puerto Rican chinchorro called La Sobrina.

Travel to the past by visiting San Juan’s oldest residency and modern-day museum. The Casa Blanca Museum was built as the home for the first San Juan governor, legendary explorer Juan Ponce de León, and now it houses sixteenth and seventeenth century artifacts that show you what life was like back then. Walk through a kitchen from the 1500s and the lush tropical gardens outside. Make sure to check out the views of San Juan Bay!

Escape the hustle and bustle of the city and enjoy an almost 7 mile boardwalk along the coast and through the mangrove forests. Rent bikes or walk the whole way, while stopping at beautiful beaches that pique your interest. If you’re looking to get up-close-and-personal with the mangrove trees, rent kayaks and head out into the lagoons. 

Piñones is also famous for its miles of food stalls where you can sample the best of Puerto Rican cuisine. Good rule of thumb: if the food stall has a long line, it’s worth trying. Make sure to pick up some alcapurrias, fried fritters, and frituras, deep fried seafood balls.

Golden sand, rows of palm trees and colorful underwater coral reefs make Escambrón Beach a Caribbean paradise. The waters here are clear and calm, which make them a great spot for experts and beginners alike. When you snorkel here, you will likely see blue tangs, sergeant majors, fairy basslets and yellow snappers. And if you’re lucky, people sometimes spot squids, seahorses, rays and manatees!

Put yourself right at the beating heart of San Juan culture — its performing arts center from 1981. Here, you can catch international theater performances (like the famous run of Hamilton) and performances by the Puerto Rico symphony and philharmonic orchestras. There’s usually more than one event happening here, so you’ll almost certainly be able to find a show. Don’t miss the 40-foot aluminum sculpture by artist Luis Torruella that towers outside!

Calling all plant lovers! The University of Puerto Rico's Botanical Garden in San Juan has more than 30,000 native plant species — including endangered ones. When you visit, you can wander the paths through the gardens and see all the unique flora and fauna of Puerto Rico, plus lakes, waterfalls, and sculptures. Don’t miss the bamboo tunnel, and keep your eyes peeled for local birds like the Puerto Rican parrot.

If you’re bringing the whole family to San Juan, you’ll love the children’s museum. It has over 100 hands-on and interactive exhibits for everyone from your grade school kids to teenagers. Explore a real plane donated by American Airlines, take a ferry through the “jungle” to Lake Blasina, explore the mini zoo and see who’s the fastest on the go-kart track.

Musicians are going to love this niche museum dedicated to a legendary Spanish cellist. Pablo Casals lived the last 17 years of his life in San Juan and composed his masterpiece “El Pessebre” here. At the museum, you can look through his library and tape recordings — as well as one of his cellos and his piano. If you’re looking to learn more about an influential musician or get off the beaten path during your time in the city, this museum is the perfect hidden gem.

Did somebody say party? If your Caribbean cruise is in January, you’ll want to make sure you’re in town for the San Sebastián Street Festival or SanSe as locals call it, which is held the third weekend of the year. This is Puerto Rico’s largest and most vibrant festival of the year and marks the end of the long Christmas season. 

For several days, the streets of Old San Juan are full of live music from local musicians, impromptu dancing everywhere you look and circus performances. The whole festival kicks off with Comparsa de los Cabezudos, a pageant that brings Puerto Rican folklore characters like Doña Fela and Diplo to life.