The Best Caribbean Islands to Visit This Winter
đ´ The Best Caribbean Islands to Visit This Winter: Warm Escapes Youâll Love
Dreaming of sunshine? These Caribbean islands offer perfect winter weather, swimmable beaches, and cozy resorts, making December travel easy and unforgettable.
đ Why I Love Caribbean Winters
Every winter, when the mornings cool down, I find myself craving sunshine and turquoise water. Weâve taken several quick winter getaways over the years â some last-minute, others planned months ahead â and every time, Iâm reminded why the Caribbean never disappoints.
The air feels softer, the ocean warmer, and thereâs something magical about stepping off the plane into bright sun while everyone back home is bundled up.
From December through March, the Caribbean offers the perfect weather. With daily highs in the 80s°F and sea temperatures around 79°F, you can swim, snorkel, and relax in comfort.
The best part: early December and late January often come with lower prices and lighter crowds.
đď¸ Top Warm-Weather Picks
| Island | Why Go | Best For |
|---|---|---|
| Aruba | Dry, sunny, and dependable weather â even in December. | Couples, sun-seekers. |
| Turks & Caicos | Soft white sand, calm water, upscale resorts. | Families and relaxed travelers. |
| Puerto Rico | U.S. territory â no passport needed. Culture + beaches in one trip. | Weekend escapes. |
| Jamaica | Friendly vibe, great all-inclusives, lush scenery. | Music lovers and first-timers. |
| Curaçao | Colorful Dutch architecture, diving, and fewer crowds. | Explorers. |
Top Things to Do
- Aruba: Snorkel at Boca Catalina, visit the Butterfly Farm, and unwind under the iconic Divi-Divi trees on Eagle Beach.
- Turks & Caicos: Take a half-day boat tour to Iguana Island or kayak through the mangroves.
- Puerto Rico: Walk the blue cobblestone streets of Old San Juan, then join a bioluminescent bay tour at Fajardo.
- Jamaica: Climb Dunnâs River Falls or float down the Martha Brae River for a calm, scenic ride.
- Curaçao: Explore Willemstadâs colorful waterfront and snorkel at Playa Kenepa Grandi.
Looking for more ideas? Check out curated GetYourGuide tours across these islands â from sailing adventures to culinary walking tours.
Dining Highlights
One of my favorite parts of Caribbean travel is the food â itâs fresh, flavorful, and full of local character. We love starting the day with tropical fruit and fresh pastries, then finding a seaside spot for lunch or dinner.
- Aruba: Try Zeerovers in Savaneta for fresh-caught fish served over the water.
- Puerto Rico: In Old San Juan, CafĂŠ ManolĂn is a local favorite for traditional dishes like mofongo.
- Turks & Caicos: Da Conch Shack is a must â casual, beachside, and famous for conch fritters.
- Jamaica: Scotchies in Montego Bay serves up authentic jerk chicken with spicy sauce.
âď¸ When to Go
Travel between early December and mid-month â right before holiday rates skyrocket if you can. Flights are smoother, beaches are quieter, and you can often snag resort discounts up to 30% off.
We once flew to San Juan in the first week of December and enjoyed three days of sunshine before the crowds arrived â it felt like our own private season.
đď¸ Where to Stay
- Aruba: Eagle Beach for peaceful mornings, Palm Beach for nightlife.
- Turks & Caicos: Grace Bay â calm water, walkable resorts, and upscale restaurants nearby.
- Puerto Rico: Condado for a mix of city and beach, or Rincon for surfing and sunsets.
3-Day Sample Itinerary
- Day 1: Arrive midday and check in to your beachfront stay. Take a walk at sunset and enjoy an early dinner with ocean views.
- Day 2: Spend the morning snorkeling or exploring a nearby island tour, then unwind at the pool or spa. Evening: local dinner with live music.
- Day 3: Enjoy a slow breakfast, a final swim, and some souvenir shopping before heading home â sun-kissed and recharged.
Cruise Options to These Islands
If you prefer to see multiple islands in one trip, a Caribbean cruise can be a relaxing way to go. Choose from short getaways or longer voyages depending on your schedule.
- 3â5 Day Cruises: Departing from Miami or Fort Lauderdale, these often visit Nassau, Grand Turk, or Bimini â ideal for quick escapes.
- 7-Day Cruises: From San Juan or Tampa, itineraries typically include Aruba, Curaçao, and St. Thomas, offering a richer island mix.
- Family-Friendly Lines: Royal Caribbean and Disney Cruise Line both feature top-notch kidsâ programs and private island stops.
- Luxury Cruises: Celebrity and Princess Cruises offer quieter, upscale experiences with exceptional dining and smaller ports.
Find current Caribbean cruise deals directly on Expedia.
đśď¸ What I Packed
Iâve learned to keep things light. A packable sun hat, a reef-safe sunscreen, and one of my favorite finds â a waterproof phone pouch from Amazon â always travel with me.
We also spend hours in the water, so it’s a small luxury to be able to take photos without worrying about my phone getting splashed.
𧳠Quick Tips Before You Book
- Watch for Expedia and Hotels.com flash deals in late November.
- Set flight price alerts from your home airport to multiple islands.
- Carry-on only during peak holiday weeks to avoid baggage delays.
- Bring a lightweight cover-up and UPF shirt â Caribbean sun feels strong even in winter.
Plan Your Trip
Before you go, compare flights and stays directly below â I use Expedia to check bundle deals and seasonal offers before booking.
â FAQ
Q: Is December hurricane season?
A: Nope! The season ends November 30, and early winter brings calm seas and consistent sun.
Q: Which island is the warmest in December?
A: Southern islands like Aruba and Curaçao stay driest and warmest (upper 80s °F).
