Christmas in Flip-Flops? Now’s the Time to Plan Your Holiday Island Escape

Categories

 

It might be July, but here’s a little reality check — Thanksgiving is only four months away, and Christmas is just five. While that might sound far off, in the travel world, now is exactly when you should be locking in your holiday plans — especially if you’re dreaming of skipping the snow and spending the holidays somewhere warm.

The best island resorts and flights fill up fast this time of year. If you wait until the leaves start to turn, you’ll likely find fewer options and higher prices. So if you’ve ever thought, “Maybe this year we do something different…” — this is your sign to start planning.

 

Here are seven islands that make the perfect escape for Thanksgiving, Christmas, or New Year’s. Whether you want to travel with family or just sneak away for some peace and sunshine, there’s something here for everyone.

 

1. St. Lucia – A Little Luxury, A Lot of Relaxation
   Towering Pitons, waterfall hikes, and romantic resorts? Yes, please. Many resorts go all out for the holidays with festive meals, live music, and island-inspired decor — but without the chaos.

 

1. Kaua’i or Maui, Hawai’i – No Passport, No Problem
   Want a tropical getaway without international travel headaches? Hawai’i is your answer. Kaua’i offers quiet, nature-focused escapes, while Maui blends beaches, great food, and holiday fun.

 

 

1. Madeira, Portugal – Europe’s Best-Kept New Year’s Secret
   This beautiful Atlantic island throws one of the most spectacular New Year’s Eve fireworks shows in the world. Combine that with ocean-view dining and old-world charm, and it’s a holiday trip to remember.

 

1. Aruba – Festive, Easy, and Sunny
   Aruba is a go-to for travelers wanting consistent weather, white-sand beaches, and a festive vibe. Expect holiday dinners by the sea and fireworks lighting up the Caribbean sky.

 

 

1. Canary Islands, Spain – Where It’s Always Spring
   If you’re looking for something a little different, the Canary Islands are a warm-weather gem with scenic landscapes and a laid-back European feel — perfect for a holiday that’s both sunny and cultural.

 

1. Grenada – Spice Things Up This Season
   Nicknamed the Spice Island, Grenada is full of charm, flavor, and calm. You’ll find cocoa farms, quiet beaches, and boutique hotels that make for a cozy, off-the-beaten-path holiday.

 

 

1. Virgin Gorda, BVI – Unplug and Unwind
   No malls. No crowds. Just you, the ocean, and maybe a glass of champagne on the beach. Virgin Gorda is perfect if your ideal holiday includes total peace and space to reconnect.

 

What to Pack for Your Island Holiday

 

Packing smart makes your island getaway smoother, especially during the busy holiday season. Here are a few traveler-approved items I recommend for clients heading to warm-weather destinations:

 

• Dejaroo Mesh Beach Bag – Lightweight, roomy, and sand shakes right out. Ideal for beach days, boat tours, or poolside lounging.
  https://amzn.to/4oaPp4L

 

• Compression Packing Cubes – A game-changer if you’re trying to fit multiple outfits into a carry-on. Keeps everything organized and flat.
  https://amzn.to/40AKVKp

 

 

• Pelican Waterproof Phone Pouches – 2 Pack – Perfect for protecting your phone while snorkeling, kayaking, or lounging by the water.
  https://amzn.to/3UtsSCk

 

• 18-Pack TSA-Approved Travel Bottles Set – Leak-proof and airport-friendly. Great for your sunscreen, shampoo, and skincare favorites.
  https://amzn.to/4m8UbOg