December to May is the best time to visit the Caribbean.
It’s a classic winter beach holiday destination, for both couples and families.
And it’s much more than that. This is not a destination where all the islands are similar. Far from it.
When planning a Maldives holiday you’re comparing different resorts, villas and activities.
For a Caribbean holiday there are many more variables. There’s far greater diversity between islands. Each has a distinct culture, style and sometimes a different language. Each creates a contrasting holiday.
We love the Caribbean because it offers great options for all types of traveller, whatever their style and interests.
But where in the Caribbean would be best for your winter holiday?
For Beach Lovers
Anguilla
While many Caribbean islands are blessed with great beaches, there’s a two-destination combination that makes the most sense for beach lovers.
Combine St. Martin and Anguilla, the most convenient islands when coming from Europe and islands with many of the region’s best beaches.
Anguilla is a small and sleepy island with over 30 stunning white-sand beaches. The vibe is a mix of barefoot relaxation and local, cultural exploration.
What’s so nice about Anguilla is its size. You can easily go anywhere on the island in less than an hour. There’s great dining, a distinct island culture, plus beaches for lounging, dancing, snorkelling and more.
You can easily just hang around the resort for a week and have an amazing beach holiday, as a couple or with kids. Then there’s so much you can explore in easy half-day or even two-hour trips.
First fly to the island Saint Martin. It’s the easiest entry point to the Caribbean, thanks to good two-leg flights with Air France and KLM.
Stay at La Samanna, A Belmond Hotel, which is located on a magnificent beach. Then take a very short flight or one-hour boat to Anguilla.
Cap Juluca, A Belmond Hotel
In Anguilla we recommend Cap Juluca, A Belmond Hotel, for two key reasons.
It’s located on probably the best beach in the entire Caribbean – Maundays Bay. And the secluded location makes it feel like a private beach, even though no beaches here are technically private.
Secondly, an amazing recent renovation has created a real sense of intimacy and space at the resort , as well as a signature Moroccan meets Mediterranean design.
Overall, this is one of few beach properties we happily recommend to both couples and families. There’s tranquillity and things to do for every guest.
But you should be a beach lover, because Anguilla is really among the ultimate global destinations for beaches.
For Island Hoppers
The Caribbean is different to the Maldives and the Seychelles when it comes to island hopping.
Hopping between islands takes more time and is more challenging, as you are travelling between countries and territories. The logistics aren’t as straightforward and you must allow some time for customs and immigration.
However, it’s not overly challenging, even with kids, and the rewards are many. On one two-week trip to the Caribbean you could easily explore four different countries, cultures, cuisines and landscapes.
There was a surge in interest for this type of holiday last winter. Our travel designers know the best options based on your interests.
This article about island hopping in the Caribbean summarises the best options for couples, families and adventurers.
For Nature Seekers
Dominica is a really undiscovered version of the Caribbean, an island of rainforest, hot springs and wild coastlines.
Although the occasional cruise ship spends a day in the small capital of Roseau, this island is not touristic. Note – don’t confuse Dominica with the Dominican Republic, they’re different islands and countries in different parts of the Caribbean.
Dominica is best for couples who seek an active holiday in nature.
It’s for people who want to kayak or yacht to deserted beaches, walk through the jungle to waterfalls, and spend long days on four-wheel drive and walking trails. Dominica is a truly unspoiled island on an impressive scale, with one remarkable place to stay.
Secret Bay
Secret Bay is a modern all-villa resort with just ten villas, located on the cliffs of a remote island bay, far from just about anywhere. It’s the only property we recommend in Dominica.
It’s like a private-island-like experience, with endless rainforest-to-ocean views and residential-style villas completely set apart from each other.
Each villa has a dedicated host and concierge, a private pool, lots of indoor and outdoor living spaces plus the stupendous views. Then there are guides who lead adventures into the nature Dominica is known for.
Secret Bay is also Relais & Chateaux property and we’re very impressed with how they’ve build the resort sustainably, with local and sustainably sourced tropical hardwoods.
This is definitely a place for the adventurous who like to be among the first to discover a new island and resort.
For the Super Stylish
St Barts has always been the most stylish island destination in the Caribbean. The A-listers have been holidaying here for almost 50 years.
Culturally it feels like a slice of the French Riviera in the Caribbean. The language is French, the harbour is dominated by yachts of the super variety, and villas sprawl across the hillsides. It’s an island deserving of its reputation as a playground for the rich and famous.
The beaches are prettier than in France though, plus the season is longer, from December to May. Christmas and New Year are incredibly busy (like August in St Tropez), the rest of the year is really nice.
Downtown Gustavia is the ultra-glitzy main street dominated by designer boutiques and top restaurants, the Caribbean’s most stylish place to be.
This is a small island with an atmosphere almost like Courchevel. It’s really a place to see and be seen, to shop, to indulge at restaurants and party at beach clubs
While mountain backdrops and beautiful beaches can be discovered all across the island, Saint Barths is more for those who prefer dresses and heels over hiking boots and outdoor adventures.
Cheval Blanc St-Barth Isle de France
Pure French elegance is the vibe at this glamorous resort on Anse des Flamands. It’s indulgent and opulent, a place where you dress up for the breakfast restaurant.
On an island to be seen, Cheval Blanc is the hotel to be seen, where the service is near theatrical and the LVMH links are clear to see. There are Dior pop-ups during winter and a Guerlain spa among the extras.
We particularly like the hillside villas overlooking the beach, or the villas right on the sand with a private pool.
That said, it’s not the most private of resorts on the island. Rosewood Le Guanahani is more secluded, away from the island’s glitzy streets, and definitely a better choice for families.
Saint Barths also has a fantastic variety of private serviced villas for rent. A key advantage of these villas is you get a wider choice of location around the island, including overlooking Gustavia.
For Privacy Seekers
The Caribbean also offers private island-type experiences, similar in style to those you already know in the Indian Ocean, but not always on a private island per se.
These are usually at small islands off a main island, rather than an archipelago of private island resorts like you see in the Maldives. Or they’re set on remote beaches, naturally cut off from any other people or other developments.
Necker Island
Necker Island is the most exclusive and is only bookable as an exclusive-use island for most of the year. It’s located in the British Virgin Islands.
This is Sir Richard Branson’s private island, where the Virgin Limited founder hosts annual gatherings for global entrepreneurs to holiday together.
For select weeks each year, Necker Island is open for celebration weeks, when it can be booked on a villa by villa basis. As availability is limited, Necker Island is typically the island you base a Caribbean island hopping itinerary around.
Jumby Bay Island & Hermitage Bay in Antigua
The island of Antigua presents two very compelling options for an all-inclusive Caribbean beach holiday. It’s where Leo Messi, among many others, goes for this holidays.
Hermitage Bay is the choice for couples, where we recommend the hillside suites. It’s a resort on a wild and otherwise undeveloped peninsula, with only 30 accommodations. Not a true private island but with the vibe and privacy of one.
Jumby Bay Island is also very discreet and exclusive, a good choice for families with its excellent beach and activities for all ages.
Amanyara, Turks and Caicos
On the shores of an 18,000 nature reserve in Turks and Caicos, Amanyara overlook almost a kilometre of white sand beaches.
All Aman properties have a premium on privacy. In general, they are not properties where none hotel guests can use any facilities, or even take a coffee in the bar.
The villas have stunning black infinity pools and genuine privacy, with the facilities and experiences making Amanyara a retreat for all ages – the wellness is fantastic.
It’s best for beach stays of one week or more and the easiest flight access is via Miami. COMO Parrot Cay is another good option to consider in Turks and Caicos.
Your Winter Caribbean Holiday?
What type of winter traveller are you? Which Caribbean island and resort seems most suited to your style?
We’re here to provide personal recommendations and to tailor a winter beach holiday that meets all your preferences.
Do you like Caribbean – Which Island is Best for You??
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