How To Spend Three Days In San Juan, Puerto Rico
San Juan boasts with some of the most beautiful beaches in Puerto Rico.
I had the opportunity to visit Puerto Rico for two weeks in February for a work trip, and my mind is still dreaming of the gorgeous weather, stunning water, and all the incredibly friendly people I met.
This island ticks all of the boxes when it comes to what makes a destination great, especially the capital city of San Juan. It’s one of the oldest cities in the United States that dates all the way back to the conquistadors!
The ocean around San Juan is great for snorkeling.
For quick context, Juan Ponce de León and his Spanish sailors colonized the island in 1508, and it remained a colony until 1898. In these decades, vast complexes, fortifications, and churches were built, which is why many still line the streets today.
While I highly recommend you explore more of the island if you have a chance, my time was spent mostly in San Juan. From fascinating historical sites, architecture, and a UNESCO World Heritage Site to pristine beaches and delicious fusion food incorporating the flavors of Spain, Cuba, Mexico, and Africa, there is so much to do and see. Plan on staying two or three days here to fully experience all that San Juan has to offer. Here’s an itinerary to help you get started!
Day 1: Hit The Beach Then Lote 23
After your flight and you’ve settled into your accommodation, pack some beach supplies and head off to relax on one of the picture-perfect stretches of beach. Even though San Juan is the capital city, it still has some of the best beaches in Puerto Rico.
If you want to go swimming, you can’t beat Escambron Beach. Here you’re able to snorkel and you may even spot some sea turtles!
If you’re traveling with kids, La Playita del Condado is a great beach to visit because the tides aren’t too strong. Rent a couple of chairs and an umbrella and spend an afternoon relaxing and cooling off in the ocean.
Then for lunch, visit Lote 23 in Santurce for the ultimate food truck experience. Hop from kiosk to kiosk to sample the flavors of Puerto Rico. Get one of Puerto Rico’s most well-loved dishes, mofongos, made with fried green plantains mashed with crispy pork skin and garlic at El Cuchifrito. There are also burgers, vegan options, tacos, and refreshing cocktails.
Calle de la Fortaleza is known as one of the most colorful streets in the city.
Day 2: Take To The Streets On A Walking Tour
One of the best ways to explore the colorful buildings and charming streets of Old San Juan is through a walking tour.
The Paseo de la Princesa boardwalk is lined with fountains, lamp posts, and trees and makes for a beautiful stroll. Plus, you’ll also find street vendors, art exhibits and shops, restaurants, bars, and even live music.
The views from Castillo San Felipe del Morro are not to be missed!
Castillo San Felipe del Morro is a protection fortification (complete with canon) built at the tip of the San Juan Bay dating back to the 1700s. This is one of the most famous landmarks in the city, and features multiple floors with barracks, kitchens, storages, courtyard, and exceptional views of the city walls. Purchasing a ticket here ($10) will also give you entrance to the next site I recommend, Castillo de San Cristóbal.
Avoid the crowds at San Juan’s castle by going in the morning.
The city’s historical defenses are a UNESCO World Heritage Site – this includes Castillo San Cristóbal. This castle is the largest Spanish fort in America and dates all the way back to the 1600s. The fort here is still miraculously preserved, and you can climb to the top for amazing views of the city. I recommend visiting in the morning before it gets too hot and there are more crowds.
The Plaza de Armas is one of the main squares in San Juan. Located on San José Street, it was designed to serve as the original main square for the city. You’ll know you’re in the right spot when you see the fountain in the square representing the four seasons. This is a perfect spot to find a cafe, enjoy a coffee, and rest.
Umbrella Street is probably one of the most photographed places on the whole island! While I was there they had swapped out the umbrellas for string lights and paper doves but this street is named after the colorful umbrellas that float overhead. The whole road is Fortaleza Street, and only a small portion has the umbrellas (or that season’s featured decor). To get there, head down Fortaleza Street towards the residence of the Governor of Puerto Rico – here is where you’ll find umbrella street. I love that this section of the road is closed to traffic, so you don’t have to worry about cars blocking your perfect Instagram shot.
Exploring the colorful streets in Old Town San Juan.
There are so many incredible restaurants to consider when dinner time rolls around, but my favorite was The Canon Club. Connected to the old Gallery Inn, The Canon Club is a sophisticated restaurant that will take you back to an old San Juan from the mid 1700s. The old crumbling brick, glass chandeliers, and authentic canons will transport you to another era while you dine on rich cuisine and listen to the live music from the grand piano. The environment here is enchanting, and the outdoor patios are full of lush greenery and blue pools. It’s truly gorgeous and you’d never know it all existed from the street outside.
If you can’t get a reservation at The Canon Club, then you can also try the Princesa. Located in Old San Juan, this restaurant is surrounded by trees and vegetation, bringing the theme of tropical paradise to your dining experience. The menu is inspired by Puerto Rican cookbooks published between 1859 and 1950, so this is an ideal place to gain an authentic taste of Puerto Rican cuisine.
Views from the the Castillo de San Cristobal.
Day 3: Go On A San Juan Bay Cruise Then Create Your Own Artwork
You may be feeling a bit tender after your day of walking… But that doesn’t mean you can’t carry on sightseeing and experiencing the liveliness of San Juan! A San Juan Bay cruise is a perfect addition to a walking tour, as you’re able to see the seaside sights from a whole different perspective. Boat cruises aren’t all historical, though – many of them play music and offer delicious food onboard.
Looking for something a bit different? A fun experience to book is San Juan Sip and Paint. With a Puerto Rico-inspired cocktail in hand and the expertise of local artists, you’ll be guided through a painting lesson. Even if you’ve never wielded a paintbrush before, don’t worry! Beginners are welcome.
If you want a bit of an after-party, head to Placita de Santurce. A market during the day, at 6 pm this space erupts with music and dancing. Salsa the night away and when you need a snack, take your pick of empanadillas and fried fritters from the vendors that line the street.
From fascinating historical sites to colorful streets and beachy paradises, San Juan is a destination that ticks all the boxes for the perfect tropical vacation.
When To Go To San Juan
December to March is the high season. During these months you’ll experience sunny days and very little rain. However, you’ll have to deal with crowds and higher prices.
You can save some money if you travel during April to June. A lot of the hustle will have died down, but the rainy season hasn’t hit yet.
To really save money and avoid tons of fellow travelers, you can visit between July and November – many hotels offer off-season prices perfect for budget travelers because this is hurricane season and tropical storms are more frequent.
Hi, I'm Ashley!
I’m a travel creator, marketing strategist, and girl who’s always got her passport in hand. My goal is to inspire you to book that bucket list trip, say yes to adventure, and use your weekends to build the life you dream about. Follow along for travel tips, flight hacks, and lots of tropical vibes!