The 5 Best Caribbean Islands to Visit This Winter 2025

This top tier list offers insights on the best Caribbean islands to visit this winter with something for every traveler. It includes Caribbean Islands that have reliable winter weather, low hurricane risk, high-quality activities, and overall offer the best experience for travelers during the peak season December to March.

1. Tobago, Trinidad and Tobago

Best For: Cultural Immersion, Eco-Adventure, and Value Travelers.
The Vibe: The greener, less-commercialized sister island of Trinidad. Tobago offers an authentic Caribbean experience with a focus on local festivals, diving, and nature reserves.
Winter Highlight: The drier climate makes hiking the rainforest reserves (like Main Ridge) and exploring waterfalls ideal. It's a great spot to avoid the massive crowds of other islands.
Must-Do: Visit the stunning Nylon Pool and experience the authentic culture of the Holiday Season in Tobago.

Frequently Asked Questions About Tobago

Is Tobago safe for tourists? Yes, Tobago is generally safe, particularly in popular tourist areas like Crown Point and Store Bay. Standard travel precautions are advised.
What is the best way to get to Tobago? Travelers typically fly into Trinidad (POS) and take a short domestic flight or high-speed ferry to Tobago (TAB). There are also some direct international flights, especially from Germany, US, UK and Canada.
What is the currency in Tobago? The official currency is the Trinidad and Tobago Dollar (TTD), but US dollars are widely accepted at hotels and major tourist spots

2. St. Lucia

Best For: Honeymooners, Romance, and Breathtaking Scenery.
The Vibe: Dramatic, volcanic, and lush. St. Lucia is defined by the iconic Pitons (two volcanic spires) and is a top destination for luxury all-inclusive resorts and boutique villas focused on privacy.
Winter Highlight: The weather is superb—sunny and dry—perfect for boat tours, snorkeling, and enjoying those spectacular resort views.
Must-Do: Hike Gros Piton (or simply admire it from a distance) and take a therapeutic sulfur spring mud bath in Soufrière.

Frequently Asked Questions About St. Lucia

Do you need a passport to go to St. Lucia? Yes, US, Canadian, and European citizens generally require a valid passport for entry and a return ticket.
Is St. Lucia expensive? It can be. While it has budget options, St. Lucia is generally known for its high-end, all-inclusive resorts, making it mid-to-high on the price spectrum.
What side of St. Lucia is best for hotels? The north (Rodney Bay) is best for nightlife and activity, while the south (Soufrière area near the Pitons) is best for romance, dramatic views, and luxury villas.

3. Barbados

Best For: Foodies, Friendly Locals, and High-End Luxury.
The Vibe: Sophisticated and proudly Bajan, Barbados mixes British tradition with vibrant Caribbean spirit. It's famous for its spectacular West Coast beaches and dynamic culinary scene.
Winter Highlight: The dry season begins in December, offering perfect beach weather. This is also the season for sailing regattas and polo matches.
Must-Do: Attend the Oistins Fish Fry on a Friday night for authentic local food and dancing, and visit a historic rum distillery.

Frequently Asked Questions About Barbados

What is the best month to visit Barbados? January through April offers the driest, sunniest weather, making it the peak time for visitors.
Is Barbados walkable? The capital, Bridgetown, is walkable, and many smaller towns are, but you will need transport (bus or taxi) to travel between major regions like the West and South Coasts.
What is the capital of Barbados? The capital is Bridgetown, a UNESCO World Heritage site known for its colonial architecture.

4. Puerto Rico

Best For: Short Getaways, History Buffs, and Ease of Travel (US Citizens).
The Vibe: A vibrant US territory offering a blend of old-world charm (Old San Juan) and modern convenience (San Juan). It is accessible with short, direct flights from many US cities.
Winter Highlight: Ideal temperatures for exploring the city's cobblestone streets and visiting the island's unique bioluminescent bays (the darker winter nights enhance the glow).
Must-Do: Walk the historic walls of El Morro Fortress in Old San Juan and dine on authentic Mofongo.

Frequently Asked Questions About Puerto Rico

Do US citizens need a passport for Puerto Rico? No, US citizens do not need a passport to travel to Puerto Rico, as it is a US territory. A valid government-issued ID is sufficient.
What part of Puerto Rico has the best beaches? The eastern coast (like Fajardo and Luquillo) is popular, but the islands of Vieques and Culebra (especially Flamenco Beach) are globally famous for their pristine sand.
Is Puerto Rico safe to travel to? Yes, Puerto Rico is considered safe for tourists. As with any large city, exercise caution in less populated areas and at night, especially in San Juan.

5. Curaçao

Best For: Divers, Snorkelers, and European Architecture.
The Vibe: A Dutch Caribbean gem known for its UNESCO World Heritage capital, Willemstad, with brightly colored colonial buildings and excellent coral reefs just offshore.
Winter Highlight: The island is outside the hurricane belt and experiences minimal rainfall, providing superb visibility for diving and snorkeling year-round.
Must-Do: Take a photo in front of the floating Queen Emma Bridge and spend a day exploring the many hidden knip (coves/beaches) along the west side.

Frequently Asked Questions About Curaçao

Is Curaçao known for good snorkeling? Yes, Curaçao is renowned for its excellent, accessible snorkeling and shore diving, with healthy coral reefs often starting right off the beaches.
What currency does Curaçao use? The official currency is the Netherlands Antillean Guilder (ANG), but the US dollar is widely accepted everywhere on the island.
Is Curaçao very touristy? While popular, it retains a less commercial, more authentic feel than some of its Caribbean counterparts, focusing on local culture alongside tourism.

Plan Your Trip Today!

Book your stay now through February 1st — to take advantage of our winter special. Spend $US 70/night for 1 guest or $US 99/night for 2 guests double occupancy. Rate includes daily breakfast with your own souvenir towel to take home. Beach chairs, bicycles and arranged transportation available. Use promo code HELLOSUN25 to secure your rooms today. Follow @RestorationsTobago for more updates.

One of the most popular things to do in Tobago is spend time with the ocean. There are many ways to do that whether it's a trip to the beach or a water sport. One such sport involves trips below the water's surface. Whether it's scuba diving or snorkeling, there's a lot of amazing sights sitting just below the surface. Experience what a Tobago diving adventure can add to your vacation by checking out these great dive spots.

Buccoo Reef

Buccoo Reef, Tobago is home to the largest coral reef on the island. The waters are more shallow in the coral gardens and the entire area averages about 10 meters in depth. The deepest point is 15 meters and visibility runs from 10-30 meters. This dive is perfect for beginners and offers views of some amazing reef life. This is also a great place for snorkeling. You can access Buccoo Reef from Pigeon Point or Store Bay.

Flying Reef

Flying Reef is in Canoe Bay, Tobago on the south end of Crown Point. Flying Reef is a great dive for beginners as the waters are shallow, running 5-14 meters. This is a drift dive, meaning the current will play a factor in your dive. Flying Reef is home to rays, turtles, sharks, snappers and other fish. You can also see a sunken ship's anchor. The anchor is a gathering place for Porkfish and Bermudan Chub.

Kariwak Reef

Kariwak Reef is a great beginner's option and perfect for kids who are learning. This reef runs an average depth of 11 meters with it maxing out at 14 meters. Visibility is good and the reef is home to rays, eels, barracudas and a whole host of fish. This is also a great spot for night diving. You can access the reef from Store Bay either from the beach or by boat.

Tobago diving is one of the best experiences you can have on your visit to the island. There are many more locations to explore but these diving spots are a great way to venture into diving. To get started on your next adventure, be sure to book a stay at Restorations Tobago.

STORE BAY

BEST PHOTOGRAPHY SPOTS