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Are you feeling down due to the frigid winter weather and eager to try something different? Are you in the process of booking a getaway to a warm, tropical location? If so, Puerto Rico is the ideal place to savor the sun and bask in the sand.

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With the limited resources and time available, you have to choose between different destinations. So, choosing the one that fits your needs and interests best is important.

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This complete guide will tell you everything you need to know about the different places, like the best things to see and do, the weather, how much it will cost to visit, and what festivals and events are happening each month.

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The “island of enchantment” is popular with tourists for many reasons, such as its closeness to the U.S., its lively native culture, and its beautiful beaches and natural landscapes.

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Keep reading to learn more about the best tropical vacations by month and the things to do.

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Best Tropical Vacations by Month

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Quick Overview

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Whether you are looking for a romantic honeymoon, an exciting adventure, or a peaceful cultural experience, this guide will help you decide which destination is best suited to your holiday.

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Depending on the types of activities you want to do, the climate, and any special events taking place, Puerto Rico is an ideal destination for a tropical getaway during every month of the year, except for June, July, August, and September.

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1. Best Tropical Vacation in January – Puerto Rico

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During the winter season, the mild climate of Puerto Rico tends to attract many travelers, which leads to an increase in the cost of airfare and hotel rooms and more people on the roads in the historic area of San Juan.

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Those who plan their best island vacations meticulously should start looking for discounted flights and hotel reservations as soon as they can before their journey begins.

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Events To Check Out:

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• Puerto Rico exuberantly celebrates New Year’s Day (Día de Año Nuevo), making it an excellent time to visit.
• The 6 of January is celebrated as Three Kings Day in recognition of the Three Wise Men.
• The Natalicio de Eugenio María de Hostos is celebrated as a public holiday a few days after his actual birthday, which is on the 8 of January, to commemorate the life and works of the renowned Puerto Rican writer and independence fighter.
• Annually, the third week of January is marked by the Festival de la Novilla in San Sebastian, a rural town that celebrates a heifer with an array of festivities.
• Every year in January, the city of Old San Juan in Puerto Rico hosts the San Sebastian Street Festival, which is the biggest event of its kind on the island. It typically lasts a few days.

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2. Best Tropical Vacation in February – Puerto Rico

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During the month of February, there are many fun things to do in Puerto Rico, such as the Coffee Harvest Festival. The Carnaval de Ponce (Ponce Carnival) is one of the most thrilling February events, featuring a grand procession on the streets.

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Athletes who enjoy running can take part in the San Blas Half Marathon, which welcomes all participants.

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At the tail end of February, the temperature begins to rise, and in some uncommon cases, it can even get as high as the mid-90s. In general, the standard temperature for February is 77 degrees, and the chances of precipitation are low.

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Events To Check Out:

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• Each year, the Maricao Coffee Festival (sometimes referred to as the Coffee Harvest Festival) marks the conclusion of the coffee harvest season with a huge celebration.
• The San Blas de Illescas Half Marathon is the number one running competition in Puerto Rico, with approximately 1,500 participants.
• In Puerto Rico, Valentine’s Day is a very popular holiday, so it’s a good idea to book reservations at restaurants early on and take advantage of any offers they may have.

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3. Best Tropical Vacation in March – Puerto Rico

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Puerto Rico is widely accepted as one of the optimal places to travel during the month of March due to its favorable climate.

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Temperatures range from the low 70s to the mid 80s, making it the perfect atmosphere for events such as Carnaval Brujo and the not-to-be-missed Taste of Rum for grownups.

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Even though March is the last full month of the busy winter season, it is still expensive for tourists to visit. However, it is also the month of the Ponce Carnival, which is one of Puerto Rico’s most famous events.

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Events To Check Out:

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• The Ponce Carnaval, which is also referred to as The Carnaval Ponceño, is celebrated in the town of Ponce in the days preceding Ash Wednesday.
• Every March 22 is commemorated as Emancipation Day, which celebrates the end of slavery in 1873.
• Taste of Rum.
• Puerto Rico Open.
• Festival Casals.

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4. Best Tropical Vacation in April – Puerto Rico

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In Puerto Rico, April marks the beginning of spring and is one of the busiest times for visitors. Like in the U.S., National Park Week is a highly anticipated event starting on April 16th.

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The month of April marks the start of the wet season, lasting until November and the amount of rain varies depending on which part of the island you are in.

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Events To Check Out:

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• The day of Jose de Diego commemorates the “Father of Puerto Rico,” a lawyer and politician of high standing that fought for the island’s freedom.
• All across the island, people gather to celebrate Good Friday and Easter Sunday.
• National Park Week.
• A recreation of the conflict that occurred in 1791.

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5. Best Tropical Vacation in May – Puerto Rico

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When you are in Puerto Rico, be sure to visit the Festival del Chapín to savor some of the most delicious seafood around.

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Furthermore, anyone can enjoy the Festival of Orchids, which showcases the exquisite beauty of the orchids that are native to the island.

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The temperature can reach and even exceed 90 degrees Fahrenheit in the month of May, so if you plan to attend Mojito Fest, make sure to drink plenty of fluids.

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During the month of May, expenses for trips are reduced, and it is also the month for one of the greatest jazz festivals in the Caribbean.

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Events To Check Out:

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• Every spring, Puerto Rico plays host to one of the most renowned jazz festivals in the Caribbean region, the Heineken Ventana al Jazz Festival.
• Every year, La Campechada commemorates a distinguished Puerto Rican artist and showcases their art and cultural heritage. To fully experience the celebration, visitors should plan ahead as the city chosen changes annually.
• Festival Del Chapín.
• Festival of Orchids.
• Mojito Fest.
• Festival Tierra Adentro.

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6. Best Tropical Vacation in June – Antigua

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After a hectic springtime, the atmosphere in Antigua becomes tranquil in June. At this time of year, the average daytime temperature is 87° F.

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This Caribbean island is one of the best tropical vacations spots to relax. You also get to enjoy its 95 miles of beautiful soft white sand beaches.

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Events To Check Out:

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• Have a meal, go shopping, and explore the maritime history of Nelson’s Dockyard.
• One can behold the beautiful scenery of the ocean from the Devil’s Bridge National Park.
• It is possible to go swimming and snorkeling with the amicable stingrays in a place called Stingray City.

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7. Best Tropical Vacation in July – Florida Keys

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Every year, the people of the Florida Keys commemorate Ernest Hemingway’s legacy with Hemingway Days, a week-long event that includes readings, book signings, and a short-story contest directed by his granddaughter and writer, Lorian Hemingway.

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This is a way for them to honor the renowned author. One of the major attractions at the event is a competition where people dress up as Ernest Hemingway, complete with white beards.

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These people also engage in a simulated version of “running with the bulls,” paying tribute to Hemingway’s work, “The Sun Also Rises.”

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During Hemingway Days, the Key West Marlin Tournament is held in celebration of the late author’s passion for the sport.

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Starting on July 18 and ending on July 21, Hemingway Days will take place, with the marlin tournament running from July 17 to July 20. This makes the Florida Keys one of the best holiday destinations in the month of July.

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Events To Check Out:

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• It is possible to spend some time on a distant isle at Dry Tortugas National Park by camping.
• Explore the underwater world by snorkeling near a living coral reef.
• Go on a sightseeing excursion focused on the darker moments of history.
• Look for the top-quality Key lime pie.
• Paddle a kayak to the abandoned settlement known as Indian Key.

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>> Discover the best hotels and resorts in Florida Keys

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8. Best Tropical Vacation in August – Cuba

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Early August is an ideal period to tour Cuba. This is right before September and October, when the eastern part of the country usually experiences hurricanes and storms.

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Even though it sometimes rains in the afternoons in August, most days in Cuba during this month are usually very sunny.

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A trip to Cuba in August is a great time to see the Carnival of Havana, a traditional Cuban celebration that you must see. Participants flock to the streets and dance the night away.

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In August, the International Festival of Cuban Rumba takes place, and those who are intrigued by Cuban music, culture, and dance should not miss it.

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In the evening, be sure to check out the salsa bars in Havana to show off the steps you have learned.

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Cuba has a lot of different places to stay, but tourists are advised to rent a Casa Particular.

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These are homes that have opened up to travelers and can be found all over the country. By lodging with a local during your visit to Cuba, you can understand the Cuban way of life in-depth. It’s the ideal way to submerge yourself in the country’s incredible culture!

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Events To Check Out:

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• Take a walk through the roads of Trinidad.
• Consume a mojito at some point in Havana.
• Take a tour of Havana in a vintage vehicle.
• Attend a performance of a musical stage show.

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9. Best Tropical Vacation in September – Yucatan Peninsula, Mexico

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The Yucatan Peninsula in Mexico is a part of the Caribbean region, situated on the nation’s eastern coast.

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Cancun, Playa del Carmen, and Cozumel are all in the Yucatan region of Mexico, which is a great place to visit in September if you don’t mind the warm weather and the occasional rain.

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Although Mexico is located in a hurricane-prone region, hurricanes are not common. September is one of the rainiest months, with short-lived storms that usually happen in the afternoon.

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This can be a nice reprieve from the sweltering temperatures. Also, Mexico doesn’t get a lot of tourists in the fall, which could be good for you.

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That said, if you’re planning on traveling with your dog, it might be a good idea to visit Puerto Rico this time of the year.

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Events To Check Out:

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• Scuba diving.
• Appreciate the lovely view from Tulum.
• Take a leisurely walk through the city streets of Playa Del Carmen.
• Take a dip in the Hallowed Cenote.

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10. Best Tropical Vacation in October – Puerto Rico

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In Puerto Rico, October is a good time to avoid the crowds and do things that are popular there. If you want to experience music, food, and art from the area, you should go to the Festival Nacional del Platano.

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During the month of October, Puerto Rico experiences rain quite often, yet temperatures remain at a balmy 75 degrees or higher.

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Even though hurricanes are more likely to happen at this time of year, smart travelers can take advantage of the lower prices on the best hotels in Puerto Rico and plane tickets.

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Events To Check Out:

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• Festival of the Peasant is a celebration that takes place every year to honor and recognize the efforts of agricultural workers.
• Attend the Le Lo Lai Festival each Tuesday at 6 pm at Fort San Cristobal to experience classic Puerto Rican music and dancing.
• An event that celebrates the banana as a national commodity.

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11. Best Tropical Vacation in November – Puerto Rico

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In the month of November, the temperatures start to become slightly chillier, even though hurricane season is still ongoing. An added bonus is that the Puerto Rican baseball season starts at this time and goes on until the end of January.

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During this important month in Puerto Rico, there are parades, fairs, and other celebrations held across the island. Those interested can learn more about Puerto Rico’s history or participate in local activities such as fishing at the Festival del Ceti.

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During November, the climate stays in a cozy range between 72 and 86 degrees Fahrenheit.

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Events To Check Out:

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• Puerto Rico cocktail week is a festive occasion to honor the unique alcoholic beverages that are found on the island. It is recommended that you sample some of the rum that is offered.
• Bobbin Lace festival.
• Discovery day.
• Festival del Ceti.
• On November 19, Puerto Rico celebrates the day that Christopher Columbus arrived in 1493 with Discovery Day, which is a public holiday.
• At the conclusion of November, the Festival Nacional Indígena honors the Taino culture and Puerto Rico’s aboriginal roots.

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12. Best Tropical Vacation in December – Puerto Rico

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From December to March, Puerto Rico has the best weather of the year. This is a time with low humidity and little rain.

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Going on vacation in December offers many celebratory activities, yet there is a cost associated with it. Nevertheless, people who prepare for their next trip well in advance can save money.

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Besides Christmas, December is a great time to learn about and enjoy the traditional crafts of Puerto Rico. Puerto Rico puts on a lot of events to honor its local artists, like the Festival del Pelate.

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In Puerto Rico, the air becomes less moist in December, and temperatures range between 70 and 84 degrees Fahrenheit.

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Events To Check Out:

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• Puerto Rico has numerous festivities for the Christmas season, including the Hatillo Masks Festival, the Lighting of the Town of Bethlehem, and the Old San Juans White Christmas Festival.
• December 24, referred to as Nochebuena in Puerto Rico, is an excellent occasion for tourists to witness the festivities and book in advance for a special Christmas meal at any of the eateries on the island.
• Festival del Pelate.

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