Caribbean Travel: Exploring the Large Islands – Cuba, the Dominican Republic, Jamaica and Puerto Rico

For many people living in northern climates in places like Canada, the United States and northern Europe, winter is the season where we just want to get away from the cold and darkness. At this time of year we all start to long for warm weather, gorgeous sandy beaches and the crystal blue waters of the ocean.

One of the world’s most popular winter getaway regions is, of course, the Caribbean. A map of the Caribbean will reveal a large assortment of islands, some quite large and many really tiny. Among the most frequented tourist destinations are some of the large islands in the Caribbean: Cuba, the Dominican Republic, Jamaica and Puerto Rico.

Caribbean beach
Caribbean beach (image by breezy421)

The weather in the Caribbean is most favourable during the first half of the year, while June to November is officially hurricane season. March is usually the most popular month to travel to the Caribbean, which also coincides with the most expensive season.

These four large Caribbean islands are very popular because of their scenic beauty and their well-developed tourist infrastructure, their cuisine, culture and music.

  • Let’s start with Cuba, the largest Caribbean Island. While American citizens still face travel restrictions going to Cuba, Canadians consider it one of their favourite winter escapes. Its two large cities, the capital Havana, and Santiago de Cuba, the country’s second largest city, are popular tourist destinations due to their history, architecture and cultural offerings. Most leisure travellers congregate in resort areas such as Varadero, Cayo Coco or Holguin. Many independent travellers also like to explore other parts of Cuba and visit some of the nature areas in Pinar de Rio province or spend time in historic cities such as Santa Clara, site of Ernesto “Che” Guevara’s most successful battle during the Cuban Revoluation, or Trinidad, a picturesque colonial city and designated UNESCO World Heritage Site.
Colourful car in Havana
Street scene in Havana (image by César Marques)
  • The Dominican Republic is another perennial favourite for winter getaways. It shares the eastern two thirds of the island of Hispaniola while Haiti is located on the west side. Santo Domingo is the oldest European city in the Americas and was founded in 1496. The colonial centre of this city is a designated UNESCO World Heritage site. The Dominican Republic is an extremely popular destination for package vacations in resort areas such as Punta Cana, La Romana, Sosua and Cabarete. The country has many different national parks and nature reserves and has recently become a hot destination for eco-travel.
The Cathedral of Santo Domingo
The Cathedral of Santo Domingo (image by Fernando Rossi)
  • Jamaica is a lush tropical island with outstanding natural beauty. Its capital Kingston has not traditionally been a tourist destination and is primarily the country’s administrative and economic centre. Tourism mainly congregates in the resort towns of Montego Bay, Negril and Ocho Rios, which is also a popular cruise ship destination. Dunn’s River Falls, near Ocho Rios, with its terraced waterfalls, is one of the country’s most sought after destinations. Locals and tourists alike enjoy climbing up the waterfalls that are shaped like steps of a giant set of stairs.
Dunn's River Falls
Dunn’s River Falls (image by Corvair Owner)
  • Puerto Rico is an island rich with rainforests, lush green mountains, alluring beaches, and its own historical sightseeing bonanza.  With its brightly painted houses and historic colonial buildings, the capital San Juan is a popular magnet for tourists as well as an important cruise ship port. El Condado is the city’s popular beach-side neighbourhood. San Juan is one of the oldest cities in the Americas, as the first settlement was established here in 1508. Along the coastline are several important resort areas, including Dorado, Palmas del Mar and Luquillo. Eco-travellers will enjoy the El Yunque National Forest or the relatively tranquil islands of Culebra and Vieques.
Brightly coloured houses in San Juan
Brightly coloured houses in San Juan (image by Steve Rhode)

The large Caribbean islands offer so many facets to travellers: from impressive history and architecture to water sports , eco- travel, colourful cultures, music, cuisines and nightlife to pure relaxation and enjoyment, the Caribbean offers something to everyone.


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