Winter Holidays in the Caribbean

With winter chills starting to drive folks in the northern United States stir-crazy, there's no better time than January to escape to the warm tropical paradises found in the Caribbean sea. As far as events go, the month starts with huge New Year's Eve celebrations all across the region and ends just as Carnival season is getting into full swing, making it great for travelers looking for a party.

However, winter is also the high season in the Caribbean, so you can expect to pay more for your flights and accommodations, even though January is considered the weakest month of the season for tourism. You'll want to book far in advance and keep an eye out for special deals, which may still be available due to January's lower-than-average tourism rate, and be sure to check Caribbean rates and reviews before you go.

Caribbean Weather in January

Generally speaking, you can expect January temperatures in the Caribbean to average a low of about 72 F and a high of about 82 F, but beach weather is not guaranteed since rain is likely on 11 days of the month and temperatures can be a bit on the cool side. Ultimately, it's more reasonable to expect sunshine and warm weather than sweltering days where you'll need to dip in the ocean to cool off, especially on islands like Bermuda that are in the Atlantic Ocean instead of in the Caribbean Sea.

Geography of the Caribbean

It's important to note that there are many destinations in the Caribbean to choose from, including several remote islands in the nearby Atlantic Ocean. As a result, these destinations are often classified for travel by the island groups you're visiting, including the Lucayan Archipelago, Greater Antilles, Lesser Antilles, the Winward Islands, and the Leeward Antilles.

The Lucayan Archipelago consists of the Bahamas and Turks and Caicos Islands while the Greater Antilles contains the Cayman Islands, Cuba, Haiti, Dominican Republic, Jamaica, Puerto Rico, and the Spanish Virgin Islands. Meanwhile, the U.S. Virgin Islands, British Virgin Islands, Anguilla, Antigua, Barbuda, Redonda, Saint Martin, Saba, Sint Eustatius, Saint Barthélemy, Saint Kitts, Nevis, Montserrat, and Guadeloupe all belong to the Lesser Antilles. The Winward Islands are Dominica, Martinique, Saint Lucia, Saint Vincent, The Grenadines, Grenada, Barbados, and Trinidad and Tobago, and the Leeward Antilles consist of Aruba, Caraçao, and Bonaire.

What to Pack

When it comes time to leave the winter cold behind, you won't need to pack your warm coat for this trip. Instead, what to pack for your Caribbean vacation really comes down to what you feel best in at the beach or what you'll be most comfortable wearing while partying, relaxing, or enjoying an outdoor event. Bring bathing suits and summer-weight clothing for the days and maybe a light sweater for nighttime chills. You'll also want to bring a light raincoat no matter where you go since January is a rainy month, especially if you're heading for the Bahamas or Bermuda.

January Events in the Caribbean

You can start the year with a bang at New Year's events or finish out your mid-winter holiday at an early Carnival celebration in Aruba and St. Kitts if you visit the Caribbean in January—you just have to know where to go and when to be there to catch all the action. Fortunately, there are plenty of January events in the Caribbean, many of which are public and free to attend.

New Year's Day

Parades are the order of the day in the Key West and St. Kitts, where the streets are full of revelers long into the evening, even after a full 24 hours of partying for New Year's Eve, but you're likely to find a big celebration to start of the new year in style no matter where you go.

Junakoo Festival

From Grand Baham to Abaco, this celebration of the new year is complete with parades, traditional Junkanoo music and dance, and several cultural demonstrations and events across the Bahamas.

Three King's Day

This Puerto Rican holiday takes place on January 6 in 2019 and is celebrated with a feast honoring the revelation of God incarnate as Jesus Christ. You can attend special services at local churches on the island or even sample some local cuisine at events across Puerto Rico.

Barbados Jazz Festival

Performers take over venues across Barbados including plantation homes, rum factories, and the Farley Hill National Park for a week of celebrating this musical tradition.


While many events, including the famous Trinidad and Tobago Carnival, take place in February and March, Aruba, Curacao, and St. Kitts all celebrate the annual tradition throughout January.

Spice Island Billfish Tournament

The 50th annual fishing tournament will take place off the coast of Grenada from January 21 to 26, 2019, attracting professional and amateur fishers from around the world for the competition as well as a boat parade and dinner.

January Travel Tips

  • Attractions and many restaurants are closed for New Year's Day, which is also true for Three King's Day in Puerto Rico and other Christian and Catholic-dominant islands.
  • Traveling around the first of the month is more expensive than the middle of January, and flying mid-week could save you money compared to weekend tickets.
  • Hotels aren't as likely to fill up in January as they are later in the winter season, but you should still start looking for a room well in advance to see if you can catch any early bird deals.
  • Avoiding major destinations like Key West for New Year's or Aruba during Carnival can also help you cut costs on your travel plans. If you don't care about attending a big-ticket event, make sure you check to see what's happening before you book your travel dates to avoid airlines jacking up prices for these annual celebrations.
  • Even though the weather's cooler, you still need to apply plenty of sunscreen if you plan to be outside a lot while in the Caribbean, especially if the winter cold has kept you indoors at home.
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