Playa Sucia, Cabo Rojo, Puerto Rico. Photo by Benjamin Lizardo, Unsplash

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Winter has arrived, which means that with each drop in temperature, we begin to fantasize about a tropical paradise, palm trees, and sipping a piña colada. Those who enjoy the winter season are fortunate; however, I am not one of them.

Fortunately, there are places where summer is year-round, with average temperatures in the mid-80s and 90s. So, to avoid the cold winter months, you only need to perform one magical trick: find your passport and visit Puerto Rico.

Best Tips & Tools to Plan Your Trip

But where exactly is this tropical paradise? Right in the Caribbean Sea, east of the Dominican Republic, and west of the Virgin Islands.

While you will usually communicate in Spanish and English, some things are universally understood, such as salsa rhythms, a good mood, and a summer vibe. Of course, they will also understand the language of the official currency, the US dollar (USA theritory).

But you should be very careful because this is a place where your perfect vacation can quickly turn into a terrible nightmare.

Don’t worry; this travel guide will teach you everything you need to know about Puerto Rico’s weather before you book your flight. So, are you ready for some travel tips? I don’t want to put you under too much pressure, but winter has arrived, so we need to act quickly.

Rojo Cabo, Puerto Rico. Photo by Jonathan Lampel, Unsplash
Rojo Cabo, Puerto Rico. Photo by Jonathan Lampel, Unsplash

The Best Weather Conditions

High Season: From mid-December to April

“Hmm, we could go to tropical places during the winter,” thought every resident of every country where winters are long and cold. I don’t need to explain why, do I? Generally speaking, the best weather occurs from mid-December to April.

It’s a dry season (February is the driest month), so rain, every traveler’s worst nightmare, has the least chance of ruining your vacation. While you’re dancing to salsa rhytm and sipping your piña colada, the good weather will reward you with average temperatures between 71° and 83° Fahrenheit (22°C and 28°C). Magic, I told you.

So, what can you do while others in your country are freezing and building snowmen?

You can enjoy the best beaches, such as Culebra’s Flamenco Beach, as well as the colorful streets and cruise ships in Old San Juan. Visit Tamarindo Beach for snorkeling or scuba diving, El Yunque National Forest for beautiful nature, Rincón for surfing, and Mosquito Bay in Vieques for the most magical kayaking experience with the microorganisms that light up the water.

I promise you that your grandchildren will hear about this experience. If that isn’t enough, you can also go whale watching, zip line, or learn about Puerto Rican cuisine, which is a unique blend of Spanish, American, and Taino influences.

I recommend trying mofongo, tostones, and seafood specialties in every way. Also, if you want to spend the holiday season or the new year here, bring something sparkly because the winter months are full of festivals, festive vibes, and delicious Christmas food. Of course, the high season will bring high prices.

Warm weather is something that we all desire, so keep in mind that you will not be the only one who has the brilliant idea of traveling to tropical areas during the winter.

This means that hotel prices and crowds on the island will peak, particularly in March, the busiest month. If you’re now disappointed because you want to enjoy Puerto Rico’s charms at slightly lower prices and with fewer crowds, don’t worry; I have something for you as well. Keep reading.

San Juan Puerto Rico. Photo by Wei Zeng, Unsplash
San Juan Puerto Rico. Photo by Wei Zeng, Unsplash
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More Affordable But Still Perfect

Shoulder Season: From mid-April to June

Perhaps you dislike crowds or your budget requires that you look for less expensive options, so consider the shoulder season, which runs from mid-April to June. That way, you can avoid peak season as well as winter and spring breaks. Remember that June is the hottest month, but May is the best month.

Why? Well, the peak tourist season has just ended, and hurricane season hasn’t yet begun, so you’ll have nice weather with average temperatures ranging from 73 degrees Fahrenheit (23°C) to 85 degrees Fahrenheit (29°C).

This means you can take your time exploring El Yunque Forest, hiking to La Mina Falls, surfing, attending one of the many festivals, or taking stunning bioluminescent bay tours.

Although temperatures rise as summer approaches, keep in mind that this is the start of the rainy season, which signals the start of the Atlantic hurricane season. But don’t worry; the chances of a hurricane during this time period are very low, and the rain usually doesn’t last long, so it won’t ruin your vacation.

However, the good news is that hotel prices are lower during the shoulder season in order to attract as many visitors as possible. So I believe we have the best investment-to-receipt ratio. However, if you require something even cheaper, continue reading (and be prepared to take some risks).

Castillo San Felipe del Morro, Calle Norzagaray, San Juan, Puerto Rico. Photo by Zetong Li, Unsplash
Castillo San Felipe del Morro, San Juan, Puerto Rico. Photo by Zetong Li, Unsplash

The Cheapest Option

Off-Season (Hurricane Season): From September to October

Off-season is the cheapest option, and it will give you quite an adrenaline rush, but not in a good way. Why? Well, this low season is, as in the other Caribbean islands, hurricane season. It actually lasts from June to November, but the most dangerous months are September and October.

Of course, this natural disaster does not happen every year, and it is up to you to determine if you are unlucky enough to have it happen when you book your vacation. In this scenario, pay special attention to the NOAA hurricane center. It’s worth noting that the most recent hurricane to strike this region was Hurricane Maria in 2017, from which Puerto Rico is still recovering.

In any case, if you decide to travel during this time, avoid the intense heat by visiting the best beaches, exploring the El Yunque National Forest, taking in the caves and waterfalls, attending the Fiestas de Santiago, and traveling to Ponce (the western side of the island receives less precipitation).

Also, while this is the off-season for tourists, it is also that time of the year when most locals are on the beaches and children are not in school, so the crowds are quite large. However, there will undoubtedly be fewer tourists at restaurants and resorts.

And what are the typical temperatures going to be like? Between 73°F (23°C) and 87°F (31°C). Although it appears to be ideal, keep in mind that this is a time of year with frequent rains (August is the rainiest month) and tropical storms, which can seriously disrupt your plans.

So, consider whether it is worthwhile to travel as cheaply as possible or whether it is preferable to invest more money in better-weather options. If you ask me, I would go with the higher-paying option, but you are free to make your own choice. Perhaps you’re luckier than I am. But, of course, get travel insurance. Just in case.

Rincon, Puerto Rico. Photo by Forrest Moreland, Unsplash
Rincon, Puerto Rico. Photo by Forrest Moreland, Unsplash

Family Vacations

Perhaps you intend to visit Puerto Rico with your family. In that case, you’ll most likely require more than just the best beaches. Fortunately, Puerto Rico is another name for fun, and there are plenty of festivals between December and February, especially in February, when Puerto Rico, particularly Ponce, becomes home to numerous carnivals.

This is also the driest season, so it is ideal for outdoor activities. Isn’t that perfect for family vacations with kids?

The Best Time for Surfing

Surfers, pick a date that is between November and March. Since Puerto Rico has some of the best beaches for this kind of activity, the waves on the west and north coasts will not let you down, and some of the most well-liked locations are Rincón, Cabo Rojo, Playa Domes, and Tres Palmas.

This is an excellent opportunity to meet people with similar interests because you will find surfers from all over the world here, especially if you happen to be in Playa Domes during the Rincón Surfing Fest in November. However, if you’re a beginner, consider going during the winter months, when the waves are smaller. Safety first.

Sunset in Puerto Rico. Photo by Javier Amador, Unsplash
Sunset in Puerto Rico. Photo by Javier Amador, Unsplash

Nightlife And Festivals

Hey there, lovers of festivals and nightlife, please put January and February on your calendar. Don’t miss the San Sebastian Street Festival in Old San Juan in January, where you can enjoy an abundance of colors, live music, entertainment, and food.

If you enjoy jazz, go to Jazz Fest; if you enjoy masking, choose February, pack your favorite costume, and head to one of the island’s carnivals. If you just prefer a classic night out, check out the nightlife in Old San Juan, Condado, or La Placita—or all of them. I’m not passing any judgment.

So, summer lovers, pack your swimsuits and flip-flops, get your dance moves ready, and vamos a la playa. I mean, who deserves it more than we do?

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