The Most Affordable Winter Island Getaways


The winter weather is officially here for most of us across the country, and the dark post-holiday time is just around the corner. That means that you may be ready to pack for your favorite La Blanca swimsuit and not much else and head for the tropics.

Unfortunately, while the idea of an island vacation seems amazing during the winter, you may end up paying a premium for it. For most islands in the Caribbean, the winter is the high season, meaning it’s the most expensive time. 

Some islands are less expensive than others, however, and the following is a roundup of some of the more affordable island destinations to think about visiting this winter or perhaps next. 

Dominican Republic

The Dominican Republic tends to be one of the cheapest destinations in the Caribbean regardless of the time of year, including winter. 

The Dominican Republic has beautiful beaches and fantastic weather, as well as golf and one of the biggest perks, is the many all-inclusive resorts you can choose from. While an all-inclusive resort may not give you the full cultural experience, it can save you money on food and drinks. 

You’ll find sunshine year-round in the Dominican Republic, and Punta Cana is one of the top tourist destinations on the island. 

Puerto Rico

Puerto Rico has so many benefits, in addition to being an affordable Caribbean destination. It offers 270 miles of coastline, and it’s fairly easy to travel to Puerto Rico. Since it’s a U.S. territory, you don’t need a passport, and they use the U.S. dollar. 

In Puerto Rico, you can visit El Yunque, which is the only tropical rainforest included in the U.S. National Forest system. You can hike the trails to see La Mina waterfalls, or you can enjoy the history of San Juan. There are even two forts dating back to the 16th and 17th centuries. 


Jamaica is the quintessential island destination in the Caribbean and for the most part, it’s also an affordable option. You can escape the winter weather and get some jerk chicken while listening to Bob Marley tunes. 

If you love to party, you might want to head to Negril. Negril has clubs and a festival atmosphere. Montego Bay is family-friendly, and Ocho Rios is a popular destination in Jamaica as well.


Curacao is one of the ABC islands. These are Dutch Caribbean islands that also include Aruba and Bonaire. 

Curacao has around 40 beaches, and the capital city of Willemstad offers colonial architecture, cafes, and shopping. The island’s west side is less inhabited and features fishing villages and hills while the south side of the island is known for offering some of the world’s best diving.

The rainy season isn’t a big issue in Curacao, and it’s outside of the hurricane belt. You can get warm, beautiful weather anytime you visit. 

Much like Aruba, Curacao has a unique cultural heritage as well. It’s close to South America, so that’s a big part of the culture, and at one point in history, Curacao was ruled by Spain. In the 1600s many Jewish refugees came to the island and then following that time, island control was shuffled between the Dutch and British empires. 

Now, Curacao is an independent state, but citizens have Dutch passports. 


Barbados has turquoise weather and powder sand, and its capital is a UNESCO World Heritage site. 

All the beaches are public in Barbados, and there’s a British vibe to the island.

Barbados isn’t generally one of the cheapest places in the Caribbean to visit, but you can make it affordable by choosing one of the smaller hotels and eating and drinking at the less expensive and touristy places on the island. 

The west coast of the island is the Caribbean side, and one of the top beaches there is Paradise Beach. 

Paynes Bay is a beach where you might want to try your hand at watersports, and there’s also Pebbles Beach, which is very quiet. 

U.S. Virgin Islands

Finally, the U.S. Virgin Islands includes St. John, St. Croix, and St. Thomas.

There are a lot of non-stop flight options to the U.S. Virgin Islands, and you don’t need a passport if you’re a U.S. citizen. 

St. Thomas is likely to be the easiest island to reach as far as direct flights from the U.S., but it’s also where many cruise ships land for the day, so keep that in mind. St. Croix is the quieter of the islands and it’s well-known for its growing culinary scene.