After a big surge in interest for Caribbean holidays, we’ve put together three different itineraries to get you dreaming of turquoise waters.
With good flight connections through Amsterdam or Paris, these three itineraries have similar overall logistics to a beach holiday in the Maldives. A two-leg flight followed by a choice of islands, from 15 to 90 minutes away.
Each Caribbean island is very different to the next, even if they all share the same beautiful sea. Most of them are their own country. These three itineraries combine diverse islands with short scheduled flights, so it’s easy to explore two or more destinations on a single holiday.
The Caribbean was the headline destination of Explorer IV magazine and we’ve previously shared our favourite Caribbean beach resorts, and winter 2023 – 2024 recommendations.
After all the interest from our clients, we’re sharing these classic itineraries. Don’t follow them exactly though. They’re just a starting point. We’ll personalise your holiday to you.
First-Time Caribbean for Couples
Two very different islands and resort experiences come together on this itinerary for couples.
After a 6am departure from Prague you’ll land in Saint Martin around mid afternoon. You can fly onward the same day, but La Samanna, a Belmond Hotel, is definitely worth a couple of nights first on Saint Martin. The beach here is simply divine and can be instant justification for choosing the Caribbean over the Indian Ocean.
It’s a one-hour flight from Saint Martin to Antigua where we recommend staying in a hillside suite with private pool at Hermitage Bay. Hidden on a wild and undeveloped part of the island, this is an all-inclusive property with only 30 suites.
Hermitage Bay is very private, very exclusive, very carefree, yet with a real Caribbean heart and soul. You feel you’re in a new, exotic destination, even without meeting anybody else.
Antigua is the tranquil, lazy beach leg of your holiday, for spending more your time around the resort. Next, fly directly to St Barths, an island with a completely different vibe. Here it’s French glamour, designer restaurants and opulence all around.
Cheval Blanc St Barth is our choice for couples, especially in combination with Hermitage Bay. The location is very central, so you can really explore the town and rest of the island.
Now it’s time for a morning in the Guerlain spa. An afternoon on a yacht, exploring the island’s beaches. Shopping, snorkelling, some seriously good restaurants, plus also the resort’s barefoot vibe.
This combo will offer you three islands with very different characters, and three resorts with very different styles. Flights back to Europe leave in the late afternoon, so take a private yacht or short 15-minute flight back to St Martin to start your homebound journey.
Caribbean For Families
This Caribbean beach holiday for families combines the same three islands, but with a different choice of resorts. Saint Martin, Antigua and St Barths.
The large car-free Jumby Bay Island is the more family focused Antigua all-inclusive property. It’s where celebrities like Lionel Messi holiday with their kids.
Villas at Jumby Bay are scattered around the island and the breadth of inclusions is ideal for family members with different interests.
Think spa, water sports, cocktails and Champagne, kids club, doing nothing or doing it all. Like Hermitage Bay, Jumby Bay Island is very spacious, but the atmosphere is a lot more towards families than couples.
For families going to St Barths we recommend Rosewood Le Guanahani. Firstly it has two different beaches and the peninsula location is the most private of all the island’s top hotels.
Stay in a multi-bedroom villa with a pool and make use of both the spa and kids club. St Barths isn’t a big island, so you’ll have plenty of opportunities to go out exploring too.
If a three-stop holiday feels too much for your family, then there are some great single resort holidays to consider instead. COMO Parrot Cay in Turks & Caicos is the truest private island resort in the Caribbean. Its size, privacy and multi-bedroom villas are ideal for large families.
Or fly to Saint Martin and hop across the water to Anguilla. Here we prefer the freshly renovated Cap Juluca, A Belmond Hotel, for the service, suites and stupendously beautiful beach. The larger Four Seasons Resort & Residences Anguilla is also a good choice, maybe a better choice in terms of the kids clubs.
Exclusive Island Hopping Adventure
First time explorer to the Caribbean? Designing a Caribbean itinerary has similar opportunities and challenges to a multi-resort holiday in the Maldives. Some islands are easy and efficient to combine, others are not.
Of course air charters are available, as are private yachts between islands. With scheduled flights, the best island hopping order will be:
1. Saint Martin. This is simply the most comfortable and fastest way into the Caribbean. It’s not just a layover destination like Malé. Saint Martin has spectacular beaches, great shopping and a true Caribbean holiday vibe.
2. British Virgin Islands (BVI). A 40-minute flight brings you to a private-island-resort-style holiday on these forested volcanic islands. If you can, build a holiday around a celebration week on Necker Island. Rosewood Little Dix Bay is excellent too, especially the suites with private pools on the western side of the resort.
3. Antigua. While BVI has a distinctively American feel, Antigua brings that soulful, vibrant and colourful atmosphere many associate with the Caribbean. It’s a one hour flight to get here and we can highly recommend either Hermitage Bay or Jumby Bay Island.
4. St Barths. After all inclusive beach bumming in Antigua there’s the change in vibe after a 40-minute flight to St Barths, where it really does feel like a slice of the French Riviera. This is the island where you’ll spend the least time in and around your resort, with the island’s shopping and restaurants key to its appeal.
5. Anguilla is a quite fabulous large island, with a few low-rise houses and sublime beaches accessed by unmarked roads. You get a sense of exploration, a sense of an undeveloped Caribbean island. St Barths to Anguilla is only a 15-minute flight and both Cap Juluca and the Four Seasons are barely a 15-minute transfer from the airport.
6. Returning to Saint Martin is a short boat ride or 10-minute flight.
We love this ambitious island hopping combination because you’re not merely experiencing different resorts, you’re experiencing different countries. It’s all the same Caribbean sea yet each feels so distinct.
Your Caribbean Holiday
Which islands most attract you to the Caribbean? Which resorts get you most excited?
Now is the time to explore this spectacular archipelago. The infrastructure is well established, top five-star resorts await, yet it’s not an overdone beach destination.
