Lonely Planet has partnered with San Juan-based travel community Platea to provide comprehensive guides, curated lists and insider tips for your next trip to Puerto Rico.

A visit to San Juan is an excellent idea any time of the year. The vibrant capital city of Puerto Rico possesses a litany of lures. Year-round balmy weather, a thriving culinary and bar culture, varied accommodations and abundant historical opportunities make for an excellent destination for all types of travelers.

Opportunities to explore history present themselves all over the island. This year, Puerto Rico celebrates the 500th anniversary of the founding of Old San Juan, the oldest city in the U.S.

Part of the celebrations (which are a year late due to COVID-19) includes two special exhibits at the Museo de San Juan that trace Puerto Rico’s history and art, as well as a two-hour walking tour of Old San Juan. Castillo San Felipe del Morro (El Morro), Castillo de San Cristóbal, La Fortaleza and other historic sites await visitors to Old San Juan. 

The island also ranks as one of the most affordable Caribbean islands to visit. You can save even more money, depending on what time of the year you visit. San Juan plays host to several festivals and events throughout the year, but there’s always something happening. 

Here’s our guide to exploring San Juan’s most popular hot spots any time of the year.

Silhouette's of people canoeing during sunset at Condado Lagoon in San Juan.
December to March provides some of the best weather in San Juan © Dennis van de Water / Shutterstock

Enjoy beautiful weather during high season: December to March

Avoid a lot of the rain and humidity from December to March. The average temperatures are in the low 80s. Winter months bring North Americans to the island to escape cold weather, driving higher prices for flights and hotel stays in the Metro area. 

Additionally, San Juan is one of the Caribbean’s busiest cruise ports, receiving throngs of cruise ship visitors regularly. Sunny days and milder temperatures make relaxing beach days and outdoor excursions even more enjoyable. If you’re planning a Christmas visit, book well in advance. Hotels fill up quickly months in advance.

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Save a few dollars during shoulder season: mid-April to June

Perhaps the optimal time for visiting Puerto Rico is the shoulder season. Winter crowds have left, cooler, dry temperatures remain, and discounted hotel rooms and cheaper flights are in relatively good supply. Tours and restaurants are typically easier to secure during shoulder season, which can make for a more relaxing experience. 

A foodies guide to San Juan

Less crowds during the offseason: July to November

June and July are high-season months for Puerto Ricans, but generally offseason for international travelers. Fewer crowds provide a better opportunity to experience the island’s food, culture and local customs at a more relaxed pace. 

Because it’s the preferred beach season by Puerto Ricans, you’ll likely share the sand with more locals. It’s a perfect chance to meet new people and create meaningful connections. Your new friends can share off-the-grid places to eat and explore that you might not have learned about otherwise.

When is hurricane season in Puerto Rico? 

Although hurricane season officially runs from June 1 to November 30, hurricanes rarely disrupt travel plans and reliable forecasts allow for effective planning. Historically, the most damaging storms have occurred during the months of August and December.

San Juan’s hottest bars for cool cocktails and tropical nights 

Participants on the street during Saint Sebastian street festival.
San Juan's San Sebastián Street Festival is the unofficial closing of the world’s longest holiday season © J Erick Brazzan/Shutterstock

January is for closing out the holiday season 

January is one of Puerto Rico’s coldest months. In San Juan, average daytime temperatures hover around 84 degrees Fahrenheit and night-time temperatures can dip to the low 60s. 
Key events: Three Kings Day occurs on January 6 to commemorate the Wise Men; San Sebastián Street Festival is the unofficial closing of the world’s longest holiday season.

February draws the crowds 

This is one of the busiest months for tourism in Puerto Rico. The weather during February is almost ideal, but prices tend to be higher. Restaurants and hotels offer special deals near Valentine’s Day, so be on the lookout for discounted packages when you’re booking your accommodations.

Rum tasting
In March, San Juan celebrates the Taste of Rum Festival © Getty Images/Lonely Planet Images

March is when the American spring breakers descend 

March is popular for American spring breakers and travelers escaping colder climates. It will also be more crowded at major tourist attractions in San Juan, so it’s wise to plan ahead.
Key event: Taste of Rum Festival

April is the perfect time to hit the beach 

April is prime beach time thanks to warmer daytime temperatures. 
Key events: Good Friday and Easter Sunday celebrations occur islandwide

May is ideal for families 

Enjoy a slower pace and sunny weather during the month of May.
Key events: Saborea Puerto Rico and  Puerto Rican Danza Week

June is best for outdoor activities 

Make the most of your time in San Juan in June. During this month, the days are usually the longest between dawn and sunset.
Key event: Noche de San Juan 

July is for budget travelers

A visit during July awards travelers with offseason hotel rates and fewer crowds around the pool. 

August is rainy season 

This month brings the island’s hottest and wettest weather of the year. 
Key events: San Juan International Billfish Tournament and SOFO Culinary Fest

Coffee and chocolate cake at cafe in National Gardens
September activities in San Juan include a Coffee and Chocolate Expo © Anders Blomqvist / Lonely Planet

September offers beachy solitude 

You’ll likely have the beach all to yourself after Labor Day. Generally, Puerto Ricans don’t go to the beach after that because it’s too cold for them.
Key event: Coffee and Chocolate Expo

October is crowd free 

Fall is an ideal time to visit San Juan. Typically crowded Metro area beaches like Atlantic, Condado and Isla Verde see fewer visitors.

November is filling your belly 

Thanksgiving isn’t a recognized holiday on the island. However, many restaurants – especially those located within resorts – offer a special Thanksgiving menu. We recommend you book ahead to secure your special dining experience.

December is filled with holiday celebrations  

Christmastime is an exciting time to visit Puerto Rico. Locals here celebrate one of the world’s longest holiday seasons. Festivities begin the day after Thanksgiving and generally end three weeks after New Year’s Day. 
Key events: Old San Juan's White Christmas Festival and Lighting of the Town of Bethlehem

You might also like: 

Best classes and workshops in San Juan
Top 5 day trips from San Juan 
Best hikes in El Yunque National Forest  

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