Which Caribbean Island Is Right for You? 18 Islands Compared

The question I’m asked most in winter is “which Caribbean island should we go to?” I don’t need to ask you three questions back. I need to ask one.

the only question i ask

What type of experience are you looking for? Based on that answer alone, I will intuitively match the perfect island, and the right place to stay on it, to your needs: whether you’re motivated by the best beaches, the culinary scene, nightlife, value for money, child-friendly experiences, secluded romance, adventure, or something else entirely.

The only other thing I’ll ask is your preferred (or maximum) budget. Not every island can cater for every budget. But every island can cater for every traveller type, whether that’s a family, a solo traveller, a couple or a group trip. That is the Caribbean’s quiet superpower, and it’s why the list below is organised by what each island does best, not by who it’s for.

the caribbean, island by island

I only recommend islands I have experienced and visited personally, which is why this list is 18 long and not 30. These are the ones I know, how I sell them, and what I send people there for.

the leeward islands

Anguilla

For the best beaches in the world. I said what I said. Belmond Cap Juluca is what dreams are made of, truly. But a big misconception is that Anguilla is only for the ultra-rich: there are plenty of comfortable places to stay set on stunning beaches. Speak to me and I’ll get you there.

Antigua & Barbuda

For 365 beaches: one for every day of the year. Carnival is a fantastic experience here and well worth building the trip around.

St Martin / Sint Maarten

For those who like a mix of nightlife with beaches, and two countries on one island: the French side, St Martin, is quieter and known for its food, while the Dutch side, Sint Maarten, brings the beach bars and nightlife. Anguilla and St Barths are both an easy hop.

St Kitts

For authentic Caribbean charm and a twin-island experience: St Kitts and Nevis are a ten-minute water taxi apart, so you can do both in one trip.

Nevis

The gentler half of the twin-island pair: one road, one mountain, old plantation inns, and ten minutes by water taxi from St Kitts.

the windward islands

St Lucia

For dramatic landscapes and volcanic beaches: the Pitons, the rainforest, and sunsets that stop conversation.

Dominica

The nature island, and truly one of my favourites. The free-diving capital of the world, resident whales, known as the edible island; the Indian River, Champagne Reef, the Boiling Lake, the hiking. Just incredible. I will be back.

Mustique, St Vincent & the Grenadines

Mustique, for an exclusive hideaway in the Grenadines: total privacy and shoulder-rubbing with the world’s wealthiest. Bequia and Canouan for a more relaxed version of the same water.

Grenada

For all the best bits of the Caribbean in one place. A personal favourite of mine, four visits in, this tri-island state is known as the Spice Island, and it is as beautiful as that sounds: green, quiet, authentic, and with a direct flight from the UK.

Barbados

For the culinary scene. The fish cutters at Caboose are an absolute must, and the restaurant scene on the west and south coasts is the best in the region.

the greater antilles

Jamaica

For the vibes and the culture. There are plenty of all-inclusive resorts for those who prefer to fly and flop, but we have also tailored 14-day honeymoons spanning the entire island, and they have proved a big hit.

The Dominican Republic

For all-inclusive resorts at any budget, done brilliantly. For those seeking more adventure, head up to Samaná during whale season.

Puerto Rico

For old-town charm and dancing in the streets. Old San Juan is colour, cobbles and salsa spilling out of doorways, and El Yunque rainforest and the bioluminescent bays are an hour away.

The Cayman Islands

For the bioluminescence, horse riding on the beach, and a culinary scene that competes with Barbados, all paired with stunning beaches.

the virgin islands

The British Virgin Islands

For island-hopping at your own leisure. A fantastic network of ferries connects the larger islands, so it is a great way to explore as a family, a couple or solo, and there are plenty of wellness options too, Aerial BVI among them. It is known as the billionaires’ playground, and it is also where I once called home.

the bahamas and turks & caicos

The Bahamas

I’d suggest skipping Nassau and venturing further afield. Harbour Island and Eleuthera are incredible: the Potlatch Club and The Farm are both wow, frequented by a long list of celebrities, and it is where Lenny Kravitz calls home.

Turks & Caicos

For ultra-luxe. South Caicos is a must for anyone wanting more water-based adventure; Starfish Alley was incredible, and the level of service and food here is extremely high.

the abc islands

Aruba

For Eagle Beach. Bucuti & Tara is a favourite, and it is a really fun island; I’d say five nights is enough, and it pairs well with the other ABC islands.

when to go

December to April is peak: dry, breezy, busiest and priciest. Book a year ahead for Christmas and February half term.
May and June are my favourite months: still dry, hotels at shoulder rates, the sea at its warmest.
July to October is hurricane season, and I will not send you in September. Many resorts close for the peak, and honestly, no price saving is worth the risk of being caught in a hurricane. Having seen first-hand, two years after Irma, what it did to very dear friends in the BVI, no price saving is worth it. Early summer and late autumn can work on the southern islands, which sit mostly outside the belt; ask me, and whatever we decide, travel insurance that covers hurricanes is non-negotiable.

the mistakes i see most

Choosing the hotel before the island. A great resort on the wrong island is still the wrong trip.
Underestimating transfer times. On Jamaica and the Dominican Republic the airport can be two hours from the hotel. We route around this.
Assuming all-inclusive means lower quality. The best Caribbean all-inclusives are excellent; the trick is knowing which.
Not pairing islands. A week on Antigua and a few nights on Barbuda, Grenada with Carriacou, or St Lucia with Dominica, often beats ten nights in one place.

Good to know

cultural etiquette in the caribbean

Eighteen islands in and the thing I most want clients to know is that these are countries, not resorts. A few habits that will make every trip warmer:

Say good morning first. Before you order, ask or buy anything: good morning, good afternoon, good evening. It is the single most important rule in the Caribbean, and skipping it reads as rude in a way visitors do not realise.
Dress for where you are. Swimwear is for the beach and the pool; cover up in town, in shops and in restaurants. Camouflage clothing is illegal for civilians on several islands, including Barbados, Antigua, St Lucia, Grenada and Jamaica, so leave it at home.
Remember whose beach it is. Legally, most Caribbean beaches are public, but in practice resort development has quietly cut locals off from stretches of coastline their families have used for generations, and on some islands that is a sore point. Be mindful of it: don’t treat a beach as the hotel’s private property just because the loungers are, share the sand graciously with islanders enjoying their own country, and support the local vendors, fishermen and beach bars you find there.
Sundays are quiet. Church matters, shops close, and the pace drops further still. Plan a beach day, not an errand day.
Island time is real, and it is not slow service. Things happen when they happen. Lean into it; it is half of what you came for.
Ask before you photograph people. Market traders, fishermen, children: a smile and a question first, every time.
Each island is its own nation. Grenadians are not Jamaicans, Bajans are not Antiguans, and the accents, food and music are proudly different. Learn the name of the island you are on and use it.
Tip as you would at home. Ten to fifteen per cent in restaurants unless a service charge is included, and a few dollars for drivers, porters and the people who look after you all week.
Respect the laws, which are stricter than you might expect. Drug laws are severe across the region, and attitudes and laws towards LGBTQ+ travellers vary island to island. I will always tell you honestly which islands I would recommend for whom, so do ask.
Buy local. Rum from the distillery, spices from the market, art from the maker. The islands feel the difference, and so will you.

not sure where to start?

Answer the two questions I'd ask you on a call and I'll point you to an island. Then let's talk it through.

Find your island

which caribbean island is right for you?

Two questions, the only two I'd ask you on a call. Tell me what you're looking for and roughly what you'd like to spend, and I'll point you to the island, the place to stay and when to go.