San Juan, Puerto Rico, is a vibrant city where the tropical charm of the Caribbean meets rich history, colorful culture, and stunning coastlines. Wintering here is becoming an increasingly popular option for those looking to escape colder climates, offering a perfect blend of relaxation and adventure. However, as with any destination, there are ups and downs to consider before making the leap. Here’s a look at the good, the bad, and the beautiful aspects of spending winter in this warm, welcoming city. >> Jump to the bottom for our “Best Of” list.
The Good
As a U.S. territory, traveling to Puerto Rico is a breeze for U.S. citizens. There is no need for a passport, and flights from the mainland are relatively affordable and frequent. Additionally, the island offers modern amenities, including great healthcare, reliable transportation, and an overall welcoming atmosphere for visitors and long-term residents alike.
Warm Weather Year-Round
One of the biggest draws to San Juan in the winter months is, of course, the warm weather. While the rest of the northern hemisphere is shivering through snowstorms, temperatures in San Juan hover around 70-80°F (21-27°C) year-round. The island’s pleasant tropical climate offers sunshine and the opportunity to wear shorts and flip-flops even in December or January.
Rich History and Culture
San Juan is steeped in history, with its cobblestone streets, centuries-old forts, and colorful Spanish colonial architecture. Old San Juan, a UNESCO World Heritage Site, is a must-visit, where you can explore landmarks like El Morro and San Cristóbal Forts, as well as vibrant plazas and charming buildings. Museums, art galleries, and local festivals keep you engaged in the island’s heritage throughout the season.
Outdoor Activities and Beaches
Whether you’re into surfing, hiking, or simply relaxing on a beach, San Juan offers plenty of outdoor activities. From the city’s beautiful beaches like Condado Beach and Ocean Park to nearby nature reserves, there is no shortage of places to enjoy the sun, sea, and sand. You can spend your winter days surfing, snorkeling, or exploring the lush trails of El Yunque National Forest just outside the city.
Delicious Cuisine
Puerto Rican food is a flavorful fusion of Spanish, African, and Taino influences. From mofongo (fried plantains) to lechón (roast pork) and tostones (fried green plantains), the culinary delights are sure to satisfy your taste buds. Many excellent restaurants line the streets of San Juan, and street food vendors serve delicious local treats, making it easy to indulge in authentic Puerto Rican flavors.
Convenient Travel
As a U.S. territory, traveling to Puerto Rico is a breeze for U.S. citizens. There is no need for a passport, and flights from the mainland are relatively affordable and frequent. Additionally, the island offers modern amenities, including great healthcare, reliable transportation, and an overall welcoming atmosphere for visitors and long-term residents alike.
The Bad
Still Paying the High Price
While San Juan can be a paradise, it doesn’t come cheap. The cost of living here can be significantly higher than in other parts of Puerto Rico or mainland U.S. This includes higher prices for dining out, groceries, and accommodation. The demand for vacation rentals and long-term stays often pushes up prices in popular areas like Condado and Old San Juan, making it a bit more difficult to find budget-friendly options.
I was able to split a 2-bed room apartment with my friend (another digital nomad) for $3,200 for the month. So all in, boarding costs (utilities, parking etc.) was $1,600 per person for the month.
Tourist Crowds (psssst Cruise Ships)
San Juan attracts tourists from around the world, especially during the winter months when people are fleeing colder temperatures. As a result, popular attractions can become crowded, and some areas can feel tourist-heavy. If you’re looking for peace and quiet, you might find some of the more popular spots a bit overwhelming.
Limited Public Transportation
While San Juan has some public transportation options, including buses and a metro system, they may not be the most reliable or convenient. For easy access to many areas, you’ll likely need to rent a car or rely on taxis and rideshare services, which can add to your transportation costs.
Sunchaser Tip: A lot of blog posts and Airbnb reviews say Ubering around is very cheap in Puerto Rico. Maybe compared to New York? But the cost from the airport to old town was a normal seeming fee of $60-75 during the Christmas season. And rides around town are between $5-$30—normal.
From Ocean Park to Old Town, we preferred the local bus. When my Uber dropped me off in Old Town, I still had to walk 3 blocks with my luggage to our place on the 60th block of Fortaleza.
Hurricane Season
Although the winter months are generally pleasant in terms of weather, Puerto Rico’s hurricane season runs from June to November. While the likelihood of a hurricane hitting during winter is low, it’s always a consideration when living in a tropical climate. It’s important to stay informed about weather patterns and be prepared for any storms.
Limited Nightlife for Some
While San Juan offers a great nightlife scene, with bars, clubs, and music venues, it’s not quite as bustling as some larger cities in the U.S. or abroad. If you’re looking for a constant party atmosphere or a diverse range of entertainment options, you might find the scene a bit quieter than expected during the winter months.
The Beautiful
Scenic Beaches & Hot Temps
San Juan’s coastline is undeniably stunning. Whether you’re strolling along the shores of Isla Verde or relaxing at the scenic Escambrón Beach, there are plenty of beautiful spots to catch a sunset. The warm golden hues that light up the sky as the sun sets over the ocean make for perfect photo ops and serene moments of relaxation.
Vibrant Culture and Festivals
San Juan has a lively cultural scene that shines especially during the winter months. Various festivals and events take place throughout the season, including the San Sebastián Street Festival in January (super crowded at night so fun to see once 😉 which celebrates Puerto Rican music, dance, and art. You can also enjoy traditional music and performances, and even take part in the island’s vibrant carnival celebrations.
Colorful Architecture (pssst feels like Spain)
The picturesque streets of Old San Juan are one of the island’s greatest treasures. The vibrant facades of historic buildings, with their pastel colors and intricate details, create an enchanting atmosphere that feels both timeless and inviting. The views from San Juan’s famous forts are equally breathtaking, offering panoramic vistas of the ocean and the city below.
Lush Natural Beauty
While San Juan is a bustling urban center, just a short drive away, you’ll find some of Puerto Rico’s most beautiful natural wonders. El Yunque National Forest is a must-see for nature lovers, with its tropical rainforests, waterfalls, and hiking trails. The island’s flora and fauna provide a stark contrast to the city’s vibrant urban environment, offering peaceful retreats in nature.
A Welcoming Community
One of the most beautiful aspects of wintering in San Juan is the warm, friendly people. Puerto Ricans are known for their hospitality and sense of community. Whether you’re staying for a few months or longer, you’ll likely find yourself embraced by the local culture and forming connections with both locals and fellow travelers.
Sunchaser Tip: If you’re looking for something a bit less “Cruise Ship,” check out the neighborhood’s of Parque or Ocean Park. There is a community beach bon fire and local Puerto Rican singing/drumming every Full Moon. Open to everyone. Cafe Regina (see below) is a good place to meet some friendly Expats.
Conclusion: Wintering in San Juan, Puerto Rico
Wintering in San Juan offers a unique mix of tropical relaxation, vibrant culture, and a rich history that is hard to match. While there are some challenges—like the cost of living and the occasional tourist crowds—the city’s beauty and warm climate make it an appealing destination for anyone looking to escape the chill of winter. Whether you’re soaking up the sun on a beach, exploring the colorful streets, or enjoying the local cuisine, there’s no doubt that San Juan provides a memorable and fulfilling winter experience. Just make sure to plan ahead and consider both the perks and potential drawbacks to make the most of your stay!
Our San Juan Bests (including some best evers!)
Best Beachside Brunch: Numero Uno. Hip but chill spot on the beach. You can watch the Kite Surfers in Dec/Jan. There is a $30 minimum per person. Complete with sand in your toes, vibey music, bean bags and umbrella loungers. People feel like they’re seen here, but in a chill Puerto Rico kind of way. Leave the Miami scene to the upper 48 😉
Best Gelato: Anita Gelato. Actually, the best gelato we’ve ever had. Be sure to enjoy the samples before you make your choice. The lines are crazy at night. So we opted for an 11am indulgence.
Best Cookies: Drunken Cookies. Seems like we’re starting a special feature of cookies on this blog. See our post What Trip Advisor Got Wrong About Sewanee, Tennessee.
Best Lunch Vibe: Cafe Caleta. For the love of Kale Salad. A heaping kale salad next to the historic basillica in old town. Only have 2-3 tables on the sidewalk, but it’s worth the wait!
Best Coffee Shop: Regina’s. Also a bit of a scene, but happy atmosphere, delicious breakfast food and they take their coffee pretty seriously. Still doesn’t touch espresso in Italy though.
Best Local Dinner: El Viejo Almacan. Get the sausage plate and empanadas. We met the bartender’s husband who was usually a server and covering for his wife. We were charming, he was charming, the food incredbile. Many moved from Argentina to PR for more opportunity. Live music, nice patio, and several authentic chandeliers.
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