For travelers in search of a warm-weather escape, there’s nothing better than a winter getaway to the Caribbean. While the season is traditionally the region’s busiest—and most expensive—there are still pockets of value for those willing to be strategic about where they go. According to Kayak travel trends expert Sarah Kennedy, “The Dominican Republic is having a moment this winter, with three destinations making our list, thanks in part to new and expanded flight routes.” She also adds that Jamaica’s recent reopening makes it “a great moment to show affordable spots like Kingston and Montego Bay some love and support the island’s recovery while soaking up their sun, culture, and hospitality.”
To identify the most affordable destinations, we enlisted the team at Kayak to analyze flight searches to the Caribbean made between Sept. 1 and Dec. 4, 2025, for travel during peak winter dates from Dec. 21, 2025, through Feb. 28, 2026. The below rankings are based on average round-trip economy airfare and nightly hotel rates for standard double-occupancy rooms, highlighting where winter travelers can still find relative value despite peak-season demand.
Nassau, The Bahamas
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Average combined flight and hotel cost: $635
Nassau is among the easiest Caribbean capitals to reach from the U.S., with lodging ranging from large all-inclusive resorts to smaller hotels and guesthouses. Plus, public beaches such as Junkanoo Beach, Cabbage Beach, and Cable Beach remain free to access. When hunger calls, low-cost meals and tropical drinks like “Sky Juice”—a local delicacy—are easy to find at Arawak Cay, which is home to a slew of mom-and-pop bars and restaurants, while free tours at John Watling’s Distillery offer a practical way to spend an afternoon. For culture beyond the beach, the National Art Gallery of The Bahamas provides context on the country’s artistic past and present, and nearby landmarks such as the Queen’s Staircase add an extra dose of history.
Santo Domingo, Dominican Republic
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Average combined flight and hotel cost: $635
Most visitors head straight to Punta Cana, but Santo Domingo is also worth a visit. Compared to the former, the latter is more compact and less crowded, offering a more in-depth look at the country’s history, particularly in the UNESCO-listed Zona Colonial, where picturesque plazas and walkable streets make it easy to explore on foot. Winter also brings a steady run of cultural events, including Grupo Bonyé’s free Sunday concerts and traditional celebrations such as the Guloyas Festival (nearby in San Pedro de Macorís) and Duarte Day, providing a culturally rich alternative to the country’s resort-driven beach destinations.
Montego Bay, Jamaica
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Average combined flight and hotel cost: $742
Montego Bay is reopening gradually after the devastation of Hurricane Melissa last fall. While some resorts remain on phased reopening timelines, some everyday attractions—including public beaches and sections of the Hip Strip’s restaurants and bars—are ready to welcome back visitors. For example, properties like S Hotel Montego Bay and nearby Excellence Oyster Bay are currently open, while others remain on staggered timelines. Of course, given the gradual pace of recovery, travelers should check the current status of hotels and resorts ahead of booking.
Kingston, Jamaica
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Average combined flight and hotel cost: $759
Also in the wake of Hurricane Melissa, sections of Kingston are beginning to reopen for tourists. And while recovery efforts are still ongoing, key institutions and public spaces like the National Gallery of Jamaica and the Bob Marley Museum are welcoming back visitors. There are also historically significant areas like Trench Town, commercial centers like Coronation Market, and public sites including National Heroes Park and Hope Botanical Gardens. Not only does visiting Kingston this winter provide insight into Jamaica’s cultural life, but it also supports local businesses as recovery efforts continue.
Oranjestad, Aruba
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Average combined flight and hotel cost: $764
Nicknamed “One Happy Island,” Aruba stands out for its beautiful beaches and friendly locals, and its capital, Oranjestad, offers a practical base for exploring. The city is known for its colorful Dutch colonial architecture and concentration of small, locally run restaurants and bars that help keep costs in check. Many of the island’s most popular beaches, including Eagle, Baby, and Palm Beach, sit a short drive away, along with breezy oceanfront spots like Bugaloe, Pelican Nest, and MooMba, where drinks and meals are typically less expensive than at larger resorts.
San Juan, Puerto Rico
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Average combined flight and hotel cost: $830
San Juan strikes a rare balance between accessibility and affordability, especially during the winter high season in the Caribbean. That’s because no passports are required for U.S. travelers, and frequent flights help keep airfares competitive. With its colorful buildings and cobblestone streets, Old San Juan provides walkable access to historic sites such as El Morro and Castillo San Cristóbal, while public beaches in Condado, Ocean Park, and Isla Verde are easy to reach. Nature and outdoor lovers need not miss El Yunque National Forest for scenic hikes among tropical flora and cascading waterfalls.
Puerto Plata, Dominican Republic
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Average combined flight and hotel cost: $933
Although it’s a popular cruise port, Puerto Plata is often overlooked by travelers planning longer stays. Set between the coast and the mountains, it offers striking scenery and ample opportunities for both beach time and inland excursions. A cable car carries visitors partway up Mount Isabel de Torres, within Isabel de Torres National Park, where lush forest, botanical gardens, and a statue of Christ the Redeemer overlook the city. Along the coast, travelers can take their pick of beaches—from the buzz of resort-lined Playa Dorada to calmer nearby beach towns like Sosúa and Cabarete.
St. Thomas, U.S. Virgin Islands
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Average combined flight and hotel cost: $1,115
St. Thomas offers a balanced mix of beaches, culture, and history, which means it has something for every type of traveler. The capital, Charlotte Amalie, founded by the Danish in the 1600s, remains an active port, and it’s also home to historic sites such as Fort Christian, Blackbeard’s Castle, and the 99 Steps. Beyond the harbor, beautiful beaches like Magens Bay and Coki Point are easy to reach, while ferries to nearby St. John make it easy to island-hop.
Simpson Bay, St. Maarten
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Average combined flight and hotel cost: $1,134
Set on the Dutch side of the island, Simpson Bay is known for its long stretch of sugar-sand beach (nearly two miles) and its dense mix of restaurants, bars, and small hotels. Its location next to Princess Juliana International Airport means the beach is only minutes from arrival, and it also places Maho Beach, where planes pass dramatically low over the sand, within easy reach. The capital, Philipsburg, is a short drive away, and the French side of the island makes for an easy day trip, too.
Punta Cana, Dominican Republic
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Average combined flight and hotel cost: $1,169
As one of the Caribbean’s most visited destinations, Punta Cana continues to draw travelers in search of fun in the sun. The coastline stretches for about 30 miles, offering a range of settings for your vacation. Much of the area’s appeal lies in its concentration of all-inclusive resorts—from family-oriented options like Club Med Punta Cana to adult-only properties such as Secrets Cap Cana—where bundled rates covering accommodations, dining, and activities simplify logistics.
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