Another brutal winter is practically frost-nipping at my toes, and I’m yearning for a tropical island escape. Once the thermometer drops below 50, I start scrolling airfares more often than my social media feeds, ready to trade snow boots for flip-flops.

After exploring 15 sun-kissed Caribbean islands from historic Havana to surf-ready Rincon, I’ve got the inside scoop on the top tropical havens. Soft sand beaches that stretch for miles, lush jungles and volcanoes to explore, authentic music and cuisine, parties that sizzle into the night – the Caribbean has it all.

I still have fond memories of sipping rum cocktails on the beach in St. Lucia as locals played calypso and reggae into the night. According to the Caribbean Tourism Organization, over 28 million people sought out that island bliss in 2022. With over 7,000 islands scattered across the Caribbean like emeralds in a blue jewel box, where should you go?

To help you find that perfect mix of adventure, culture and relaxation, I’ve compiled my list of the top 10 Caribbean islands for an unforgettable tropical getaway this winter.

In this travel guide, I’ll share insider tips and hidden gems amassed from my two decades of visiting and writing about the Caribbean to help you plan an unforgettable sunny escape this winter.

Overview of the Caribbean’s Top Islands

From the ritzy glamour of St. Barts to the lush rainforests of Dominica, the Caribbean islands offer incredible diversity.

Each island has its own unique culture, cuisine and attractions waiting to be explored. The region enjoys warm weather year-round, with temperatures typically ranging from the mid-70s to high 80s.

And with so many islands to choose from, you’re sure to find the perfect spot for luxury, adventure, partying or pure relaxation. Let’s dive in and explore some of the best the Caribbean has to offer!

How I Chose the Top 10 Islands

Selecting just 10 Caribbean islands for this list was no easy task, with so many wonderful options across the region. I based my selections on a few key factors:

• Natural beauty – Stunning beaches, lush rainforests, majestic mountains and underwater wonders
• Activities & attractions – A diverse range of adventures, historic sites, party scenes and relaxation
• Accommodations – Quality and variety of hotels, resorts and villas
• Cuisine – Delicious local and international food options
• Culture – Vibrant arts, music, festivals and friendly locals
• Accessibility – Ease of air travel from the US and availability of flights

Balancing all of these elements, I curated this list of what I consider the 10 best Caribbean islands for an unforgettable tropical vacation. Let’s count them down!

#10 Grand Cayman

Kicking off our list is the sleek, sophisticated island of Grand Cayman, the largest of the Cayman Islands trio located south of Cuba. Famous for its world-class diving and snorkeling sites, Grand Cayman also offers plenty of topside beauty and luxury.

Highlights and Attractions

• Diving and snorkeling along the island’s coral reefs and dramatic ocean walls
• Epic Seven Mile Beach with powdery white sand and calm turquoise waters
• Unique attraction Stingray City, where you can swim with friendly stingrays
• High-end shops and restaurants in the capital Georgetown
• Boat trips for snorkeling, island hopping and sunset cruises
• Golfing on championship courses like The Links at Safehaven

Best Time to Visit

Grand Cayman enjoys warm weather and sunny skies throughout the year. High season runs from December to April, seeing the most visitors and highest hotel rates. May through mid-December brings fewer crowds and lower prices, making it a great time for deals.

Where to Stay

Grand Cayman offers a wide range of accommodation options to suit different budgets and styles.

On Seven Mile Beach, luxury resorts like the Ritz-Carlton and Westin provide lavish amenities alongside the island’s best beach. For mid-range comfort, the Holiday Inn Resort and Hampton by Hilton are solid picks. Budget travelers can enjoy smaller hotels and guesthouses around Georgetown.

Renting a condo or villa also brings spacious comfort with amenities like kitchens. With its high-end reputation, expect elevated prices, but deals can be found off-season.

Average Flight Cost from US

Expect to pay around $500 roundtrip for flights to Grand Cayman from most major US cities. Deals under $400 are possible during the rainy season from June to October.

#9 Barbados

Barbados exudes a lively spirit and rich culture rooted in West African and British influences. Nicknamed “Little England,” Barbados has sophisticated touches blended with gorgeous natural highlights.

Highlights and Attractions

• Relaxing on picturesque beaches along the island’s calm west and south coasts
• Touring century-old plantation houses like St. Nicholas Abbey and Sunbury Plantation House
• Enjoying fresh seafood and spicy Bajan cuisine with cooling rum drinks
• Experiencing sporting events like polo matches and cricket games
• Trying surfing and windsurfing on the island’s east coast
• Visiting Harrison’s Cave with its stalactites, underground lakes and waterfalls

Best Time to Visit

December to May sees peak visitation during the drier season when northeast trade winds bring lower humidity. June through November brings higher humidity and chances of rain, but fewer tourists and lower rates.

Where to Stay

On Barbados, luxury seekers can enjoy renowned resorts like Sandy Lane and the Fairmont Royal Pavilion, set along the island’s placid west coast.

There’s also a wide range of mid-range hotels, smaller inns and self-catering apartments available, especially in St. Lawrence Gap. Many affordable guesthouses and Airbnbs can be found around Bathsheba on the rural east coast.

For larger groups, renting a villa offers space, privacy and amenities like pools. As Barbados caters to upscale travelers, expect elevated prices, but shop around for off-season deals under $200 per night.

Average Flight Cost from US

Flights to Barbados from the eastern US average around $500 roundtrip. West Coast travelers can find specials under $600 roundtrip if booking ahead.

#8 Turks and Caicos

With over 40 small islands and cays, Turks and Caicos boasts some of the Caribbean’s dreamiest beaches and aquatic adventures. Though less developed than neighbors like the Bahamas, it offers plenty of upscale options.

Highlights and Attractions

• Grace Bay Beach on Providenciales – a 12 mile (The stretch from Leeward to Northwest Point) of powdery white sand
• Snorkeling and diving the astounding coral reefs and walls
• Visiting secluded cays and islands for a castaway vibe
• Trying watersports like kiteboarding, advanced fishing and sailing
• Enjoying fresh seafood like conch and lobster any day of the week
• Shopping and dining in Provo’s Grace Bay or the Saltmills plaza

Best Time to Visit

December through April brings ideal sunny, dry weather but also peak crowds and prices. May to July offers stunning beaches with fewer tourists, while late August to November sees potential storms but discounted hotel rates.

Where to Stay

On Providenciales, Turks and Caicos’ main island, the Grace Bay area offers luxurious resorts like the Grace Bay Club, West Bay Club and Seven Stars Resort, right on Grace Bay Beach.

Mid-range options like the Sands at Grace Bay and Ocean Club Resorts offer great locations at lower prices.

For budget stays, guesthouses and Airbnbs can be found outside Grace Bay in other Provo areas or on smaller islands. Villas are also popular, providing amenities with ample space.

As an upscale destination, Turks and Caicos commands higher prices, but deals can be found, especially May-December.

Average Flight Cost from US

Nonstop flights to Turks and Caicos average around $500 roundtrip from the eastern US, while west coast travelers can find deals around $650 roundtrip.

#7 Aruba

Aruba captivates with blond beaches, gentle surf and a mix of Dutch heritage and Caribbean flair. Located just north of Venezuela, this sunny island offers splendid weather and outdoor adventures.

Highlights and Attractions

• Spending days relaxing on sugar-soft Eagle Beach
• Trying windsurfing, kitesurfing and stand-up paddleboarding
• 4×4 off-road adventures around the island’s rocky northern region
• Sampling Dutch specialties like bitterballen alongside Caribbean cuisine
• Enjoying diverse nightlife and casinos in Palm Beach and Oranjestad
• Snorkeling amid shipwrecks and coral gardens
• Visiting the historic Spanish fort Zoutman and the giant gold mill ruins

Best Time to Visit

Aruba sees pleasant weather year-round outside the Caribbean hurricane belt. High season for tourists runs from mid-December to mid-April. Low season from mid-April to mid-December brings fewer crowds and lower hotel prices.

Where to Stay

Along Aruba’s famed Palm Beach, luxury resorts like the Ritz-Carlton Aruba, Hyatt Regency, and Marriott offer top-notch amenities and easy beach access.

Mid-range options like the Holiday Inn and Boardwalk Hotel provide nice stays for less. Budget hotels, Airbnbs and guesthouses abound away from the main tourist strip. Timeshares like the Marriott Surf Club also attract families.

For groups, apartment rentals and private villas bring extra space and privacy. While not cheap, Aruba’s ample options allow finding nice stays at moderate prices, especially in the off-season.

Average Flight Cost from US

Nonstop flights to Aruba average around $400 roundtrip from the eastern US and under $600 from the West Coast when booking ahead.

#6 Jamaica

Jamaica bursts with vibrant culture amid gorgeous scenery ranging from lush rainforests to golden sand beaches. The birthplace of reggae and home to Bob Marley, Jamaica infuses its welcoming spirit into every visit.

Highlights and Attractions

• Lounging on Seven Mile Beach stretching along Negril’s west coast
• Hiking through the misty Blue Mountains for incredible views
• Ziplining over forest canopies near Ocho Rios
• Sampling jerk chicken, fresh seafood and tropical fruit from roadside stalls
• Partying till dawn at Kingston nightclubs pumping reggae and dancehall
• Visiting Bob Marley’s former home, now a museum, in the village of Nine Mile
• Touring historic plantations like Rose Hall Great House

Best Time to Visit

December to April tend to be drier with moderate humidity, while June to November brings higher chances of rain. Most key events and festivals happen in springtime before the rainy season kicks in.

Where to Stay

In Jamaica, all-inclusive resorts dominate in Montego Bay and Negril, like the family-friendly Beaches and adults-only Sandals.

Ocho Rios and Kingston offer affordable smaller hotels, guesthouses, and Airbnbs for those wanting local immersion. Upscale boutique hotels provide luxury in lush romantic settings like Strawberry Hill in the Blue Mountains.

Villas also work for larger groups seeking space, kitchens, and amenities. While all-inclusives carry premium rates, traveling in the off-season brings lower prices. Overall, Jamaica offers diverse options across different budgets.

Average Flight Cost from US

Nonstop flights to Jamaica from the US East Coast average around $350 roundtrip, while the West Coast sees deals around $500 roundtrip.

Booking.com

#5 Dominican Republic

The Dominican Republic shares the eastern half of Hispaniola island with Haiti, blending jaw-dropping scenery with a vibrant culture. Music, dancing, delicious cuisine and incredible beaches define the DR experience.

Highlights and Attractions

• Lounging on palm-lined beaches surrounding Punta Cana
• Surfing at Cabarete on the north coast, with its perfect wind and waves
• Dancing the night away at the bars and clubs of Santo Domingo
• Going cave tubing through underground caverns and jungle rivers
• Trying merengue and salsa dancing lessons
• Sampling local dishes like mofongo mashed plantains and fresh seafood
• Admiring stilt houses at Lago Enriquillo, home to American crocodiles

Best Time to Visit

December through April offer the most reliably sunny skies, though temperatures remain high year-round. June to November brings more rain, but fewer tourists and often discounted hotel rates.

Where to Stay

The Dominican Republic boasts incredible all-inclusive resorts, especially in Punta Cana and Puerto Plata, ranging from family favorites to adults-only.

In Punta Cana and Puerto Plata, luxury all-inclusive resorts like Excellence Punta Cana, Majestic Elegance, and Viva Wyndham Dominicus Beach offer lavish amenities directly on prime beaches.

In Santo Domingo’s colonial zone, boutique hotels like the Sheraton Santo Domingo and Hodelpa Nicolás de Ovando provide historic charm. Surf havens like Cabarete have excellent surf camps and smaller inns like Natura Cabaña Boutique Hotel for immersive stays.

Villas like Casa Bonita Tropical Lodge and Vacation Rentals Santo Domingo allow for spacious stays with kitchens.

With diverse options, travelers can find quality Dominican stays across budgets.

Average Flight Cost from US

Flights to Punta Cana from the eastern US average just $350 roundtrip, while the west coast runs around $600 roundtrip.

#4 Bahamas

This archipelago of 700 islands lies just 50 miles southeast of Florida, luring travelers with spectacular beaches and diverse adventures. Nassau on New Providence island serves as the Bahamian capital and transportation hub.

Highlights and Attractions

• Snorkeling with dolphins at Blue Lagoon Island
• Kayaking through a glowing bioluminescent bay at Grand Bahama
• Playing with pigs at Pig Beach on the secluded Exuma Cays
• Diving to shipwrecks and underwater caves filled with sharks and rays
• Strolling the pink sand beaches of Harbour Island
• Exploring the sprawling Atlantis mega resort and waterpark on Paradise Island
• Partying at Fish Fry on Potter’s Cay in Nassau

Best Time to Visit

December to May offers warm and sunny weather across the islands before the rainy season hits. June through November see higher humidity and chances of storms, along with discounted hotel rates.

Where to Stay

In Nassau and Paradise Island, iconic luxury resorts include Atlantis, the Ocean Club, One&Only, and Sandals Royal Bahamian. More affordable hotels dot the downtown and Cable Beach areas.

On Out Islands like the Exumas, Abacos and Eleuthera, boutique resorts, rental cottages, and villas prevail. Options range from basic guesthouses to lavish beachfront villas like Kamalame Cay.

Avoiding peak season offers discounted rates. The Bahamas offers varied options, though expect elevated prices in New Providence.

Average Flight Cost from US

Flights to Nassau from the eastern US average just $200-$300 roundtrip. From the West Coast, look for deals around $500 roundtrip.

#3 US Virgin Islands

Though ravaged by the hurricanes of 2017, the US Virgin Islands have largely rebuilt to showcase their laidback vibes and pristine beaches. Three main islands – St. Thomas, St. John and St. Croix – offer diversity amid natural splendor.

Highlights and Attractions

• Snorkeling amid coral gardens at Trunk Bay on St. John
• Hiking to the cliffs and sugar mill ruins on St. Thomas
• Enjoying pampering at the beachfront spas and resorts
• Exploring forts and historic buildings from the Danish colonial era
• Shopping and dining in the colorful towns of Charlotte Amalie and Christiansted
• Visiting Buck Island and its 19th-century lighthouse

Best Time to Visit

The dry season from December to April brings lower humidity and fewer storms. May to early July see lower hotel rates before rates climb again in late summer high season. The islands can see storms from August to November.

Where to Stay

In the USVI, St. Thomas offers large resorts like Marriott Frenchman’s Cove along with boutique hotels like Crystal Cove. St. John favors eco resorts like Caneel Bay and intimate villas.

On St. Croix, beachfront condos and hotels like The Buccaneer provide options. Smaller guesthouses and Airbnbs exist across the islands for budget stays. Expect high season rates, but off-season sees deals at nice properties.

With rebuilding post-hurricanes, it’s wise to check current conditions at hotels before booking.

Average Flight Cost from US

From the US East Coast, flights to the USVI average around $350 roundtrip. West Coast travelers can find deals from $550 roundtrip.

#2 Puerto Rico

Puerto Rico offers an intoxicating blend of Spanish colonial heritage, natural beauty and vibrant culture. Festivals happen year-round, highlighting music, food and dance.

Highlights and Attractions

• Surfing excellent breaks at Rincón on the west coast
• Marveling at the Arecibo Observatory, one of the world’s largest radio telescopes
• Trying exhilarating zip-lining across forest canopies
• Sampling authentic mofongo, empanadas and pinchos street food
• Dancing the night away at oceanfront bars and clubs in San Juan
• Exploring the massive stone fortresses El Morro and San Cristóbal
• Lounging on golden beaches along the east coast like Luquillo

Best Time to Visit

December to April offer the most ideal weather across the island. May to late November bring higher chances of rain and storms, along with lower hotel prices outside of San Juan.

Where to Stay

In San Juan, boutique hotels like O:live and Hotel El Convento blend historic charm and modern comforts. Iconic resorts like Dorado Beach, a Ritz-Carlton Reserve offer indulgent escapes along the coasts.

Smaller inns like Hacienda Tamarindo and Casa Sol Bed & Breakfast provide local immersion, while rental villas like Villa Iris suit groups.

Surf destinations like Rincón offer excellent surf camps and laidback stays at spots like Rincón Beach Resort.

Average Flight Cost from US

Nonstop flights to San Juan average around $250-$350 roundtrip from the continental US year-round.

#1 St. Lucia

And topping off our list of the Caribbean’s best islands is the simply stunning St. Lucia. Dramatic Pitons rising from the sea, volcanic beaches, verdant rainforest – St. Lucia stands out for its jaw-dropping natural splendor and friendly local culture.

Highlights and Attractions

• Sailing and snorkeling around the iconic Pitons near Soufrière
• Hiking to tumbling Toraille Waterfall surrounded by lush foliage
• Ziplining over forest canopies near Castries in the island’s north
• Diving amid shipwrecks and colorful coral reefs
• Sampling Creole cuisine infused with spices and local produce
• Enjoying street food and nightlife around Rodney Bay and Gros Islet
• Basking on pretty palm-fringed beaches like Anse Chastanet

Best Time to Visit

December to April offer warm temperatures and drier weather. May to early July see lower hotel rates in the lusher rainy season. Late summer brings higher humidity before drier weather returns in fall.

Where to Stay

St. Lucia boasts exceptional luxury resorts like Jade Mountain and Ladera Resort known for their dramatic Pitons views and amenities. Mid-range picks like East Winds Inn and Royalton Saint Lucia provide comfortable stays for less.

Smaller boutique hotels, guesthouses, and Airbnbs can also be found, especially in Rodney Bay and Castries. Large villas work well for families and groups seeking extra space.

Traveling in the off-season enables finding deals across St. Lucia’s high-end resorts and intimate accommodations.

Average Flight Cost from US

Flights to St. Lucia from the US tend to average between $500-$800 roundtrip. The lowest fares are often found departing from major eastern airports like New York, Boston, and Miami, averaging around $500-$600 in the off-season. From the West Coast, flights run slightly higher, averaging $600-$800 for a roundtrip.

The peak winter travel season between mid-December and April sees the highest prices, while September through early December offers the best deals under $500 roundtrip.

Booking Your Next Caribbean Island Vacation

From luxurious resorts and pristine beaches to exciting adventures and unique cultures, the Caribbean Islands have so much to offer for your next tropical getaway.

Each island provides its own flavor and attractions to discover. I hope my list of the top 10 islands helps you choose the perfect destination to escape the cold and escape to paradise!

Let me know if you have any other questions – I’m always happy to help further narrow down the options based on your travel style and preferences.

 Here’s to an unforgettable vacation in the Caribbean! 

 

Booking.com