Caribbean islands in winter: where to go for festive sun, celebration and easy digital travel

The festive Caribbean: sun, parties and the reality behind the postcards

Visit in December and you’ll hit the sweet spot—temperatures hover around 28°C, with cool breezes keeping the humidity at bay. Christmas itself is a colourful, communal affair. In Barbados, the Bridgetown Christmas Market draws everyone from cruise passengers to local families picking up hand-painted baubles or sipping sorrel under the fairy lights. Puerto Rico’s Old San Juan hosts street festivals that start in early December and last well into January. New Year’s Eve in Jamaica? Find yourself in Negril as midnight fireworks explode over Seven Mile Beach, with reggae pulsing into the small hours. But here’s a practical note: the Caribbean’s festive calendar makes winter both magical and busy. Flights fill up and hotel prices rise quickly after mid-November. Cruise ships crowd ports in St. Thomas and Antigua; even once-sleepy Grenada has seen a rise in winter sunseekers. For a quieter spot, try St. Vincent or Dominica—less polished, perhaps, but with rainforests and waterfalls almost to yourself (and better last-minute deals).

Staying online: the truth about mobile data in the Caribbean

Here’s something I learnt the hard way: public Wi-Fi in the Caribbean is a patchwork at best. Resorts and big hotels often promise fast internet, but once you venture out—to market stalls, beaches or local guesthouses—coverage drops, speeds crawl, and secure connections are rare. Last December in Saint Kitts, I lost half a morning trying to download a boarding pass via a café hotspot that fizzled out every few minutes. Locals often run two phones or swap SIMs to chase the strongest signal. Digicel and Flow, the main networks, dominate much of the region, but their plans can be expensive for visitors and roaming racks up quickly—£6/$8/€7 per day is not unusual on a UK or US contract. If you’re island-hopping (say, flying from St. Maarten to Anguilla, then on to Antigua), you’ll hit different network footprints, sometimes even in the same day.

That’s why digital SIMs—eSIMs—are a game changer here. With a single QR code, you can drop onto local data at each stop, track usage in real time, and avoid the standing-in-line-for-a-SIM shuffle at tiny airport kiosks. Graba SIM’s Data Pulse dashboard and lock screen widgets helped me keep tabs on my data last Boxing Day, wandering between Saint Lucia markets (where network congestion peaked each evening) and quieter, rural stretches.

How to set up an eSIM for Caribbean winter travel

Here’s a step-by-step, based on what worked best for me:

Insider tips: making the most of Christmas and New Year in the Caribbean

Food-wise, don’t miss Bajan black cake or Jamaican sorrel punch (the ginger kick is serious). For New Year’s, locals in the Bahamas often head to Junkanoo parades—bright costumes, brass bands, and dancing until sunrise. Every island has its quirks: in Saint Lucia, early-morning church bells ring out on Christmas Day, while Antigua hosts Christmas morning beach parties—a tradition I stumbled into by accident, and now wouldn’t miss.

eSIM vs physical SIM vs roaming: the winter Caribbean in numbers

Frequently Asked Questions