Dominican Republic and Aruba lead the way: the Top 4 best Caribbean destinations
The Caribbean continues to solidify its position as one of the preferred regions for Chilean travelers, with crystal-clear beaches, air connectivity, and offerings focused on relaxation and enjoyment
February is historically the busiest month for Chilean travelers. In the heart of the Southern Hemisphere summer, the Caribbean is one of the most popular destinations for escaping the heat, drawn by its white sand beaches, turquoise waters, and well-developed tourist infrastructure designed for relaxation.
According to Assist Card, a leading travel assistance company with more than five decades of experience, four Caribbean destinations are the most popular among Chileans during the summer season.
Dominican Republic
It tops the ranking, with Punta Cana as its main gateway. The destination combines direct air connectivity, a wide range of hotels, and a distinctly international profile. As an alternative, Bayahibe offers a quieter option, ideal for family trips. According to figures from the Civil Aeronautics Board, a total of 41,676 Chileans traveled to the Dominican Republic in 2025.
Aruba
Known as "The Happy Island," Aruba is renowned for its year-round sunny weather, white-sand beaches, and exotic landscapes. Part of the Kingdom of the Netherlands, it boasts an international airport in Oranjestad, located just minutes from tourist destinations like Palm Beach, one of the island's most famous resorts.
Puerto Rico
The Caribbean archipelago, an unincorporated territory of the United States, is known as "The Island of Enchantment." Puerto Rico boasts a diverse coastline, with iconic beaches such as Flamenco Beach, Condado Beach, and Luquillo Beach. The main point of entry by air is San Juan, from where internal connectivity is established.
Jamaica
The birthplace of reggae completes the Top 4. Jamaica is characterized by its relaxed atmosphere and cultural identity. The main air gateways are Montego Bay and Ocho Rios, two of the country's most developed tourist areas, without needing to go through the capital.
Travel protected
Assist Card emphasizes the importance of having travel assistance when planning a trip to the Caribbean. “Traveling to this region, like any international destination, can involve unforeseen events, from lost luggage to health emergencies,” stated Renzo Caldarella, Direct Sales Manager for Assist Card Chile.
In that context, the company launched a special promotion for the season offering up to 35% off and free children's benefits, applicable to the Privileged Multiple Trips 30-day product, which includes up to four children under 21 years of age at no additional cost.
With options that combine connectivity, tourist infrastructure and iconic landscapes, the Dominican Republic, Aruba, Puerto Rico and Jamaica are consolidating themselves as the preferred Caribbean destinations for Chilean travelers in the summer of 2026.