San Juan, Puerto Rico Weekend Trip Guide | Beyond Florida with Sarah
Real Floridians know the Sunshine State has seasons. And when it gets chilly by our standards, we start looking for warmer air and a change of scenery. That’s where San Juan comes in!
It’s been one of my favorite winter getaways for the past six years, and it’s incredibly easy to reach from Florida. With direct flights from Tampa, Orlando, and now Lakeland, you can be there in just 2.5 to 3 hours, and step straight into warm weather, beautiful beaches, rich history, and even a tropical rainforest.
Here’s my guide to five must-visit spots for a quick and easy escape from Florida to San Juan.
1. Stay & Explore in Old San Juan
For a short trip, my favorite place to stay is Old San Juan itself. This historic district dates back more than 500 years, and you can truly feel that history as you wander the cobblestone streets past pastel-colored buildings, historic churches, and massive forts like El Morro and Castillo San Cristóbal.
There are plenty of Airbnb options in historic buildings, or for a unique stay, I recommend Hotel El Convento, a former convent turned luxury hotel right in the heart of the old city.
Because Old San Juan is so walkable and compact, you won’t need a car to enjoy the restaurants, shopping, attractions, and nightlife nearby.
Some of my favorite places to eat include:
Coffee & breakfast: Delicadas, Puchy’s Café, CaféLab, St. Germain Bistro Bar
Traditional Puerto Rican food: Deaverdura, Restaurante Raíces
Other great eats: Pirilo Pizza Rústica, La Madre
2. Take a Day Trip to El Yunque
If you’re up for a day trip, book a tour or rent a car to explore El Yunque, the only tropical rainforest in the U.S. National Forest System, and a place that holds deep cultural significance in Puerto Rico.
One of my favorite hikes is Mount Britton Trail, which leads to a circular, castle-like stone tower with incredible views. On a clear day, you can see the forest canopy, the Atlantic Ocean, the Caribbean Sea, and Puerto Rico’s eastern coast.
To get there, you’ll drive a winding park road, find parking (which can be tricky during peak times), and then tackle a steep climb. The trailhead starts at about 2,493 feet in elevation, and the 0.8-mile hike gains roughly 600 feet. It’s a workout, especially if the trail is slick, sturdy tennis shoes or hiking boots are a must.
3. Eat, Drink & Wander at the Luquillo Kiosks
An easy stop before or after El Yunque is the Luquillo Kiosks. This stretch features around 60 family-owned kiosks serving everything from Puerto Rican classics to cocktails and souvenirs, all right next to the beach.
Most spots are open-air, some with views of that stunning blue water. If you want to get out on the ocean, you’ll also find jet ski rentals and other water activities right on the beach.
4. Experience Nightlife at La Placita de Santurce
While Old San Juan has great nightlife, especially along Calle de San Sebastián, La Placita de Santurce is a must if you’re looking for a more local vibe.
By day, it’s a traditional marketplace. By night, it turns into a lively gathering place with live music, dancing, street performances, bold public art, and excellent people-watching.
5. Unwind on the Beaches of Isla Verde
One of the best things about San Juan is that you don’t have to leave the city to find a beautiful tropical beach. Isla Verde is under ten minutes from the airport and offers golden sand and turquoise water.
There’s a public beach, but I love booking a ResortPass for an easy beach day. My go-to is Courtyard by Marriott Isla Verde Beach Resort, where I’ve stayed twice and also used day passes.
With a large pool and a fantastic stretch of beachfront, it’s the perfect way to wrap up a quick San Juan escape before heading back to Florida.
