Where to Stay in the Caribbean
A LOCAL’S GUIDE
Where to Stay in the Caribbean
A Local’s Guide to Choosing the Right Island
I’ve spent more than twenty years sailing the Caribbean, running yachts between many of the islands in this guide.
I’ve anchored off them, provisioned in them, hidden from squalls behind them, waited out weather in their harbors, and spent enough nights ashore to know that no two islands are alike.
People often ask me where they should go in the Caribbean.
My answer is always the same.
“It depends.”
Not because I’m trying to avoid the question, but because the Caribbean isn’t one destination.
A week in Anguilla feels nothing like a week in Dominica.
St. Barts and Tortola might only be a day’s sail apart, but they’re worlds apart as vacations.
So before we talk about hotels, we need to answer the more important question.
Which island is actually right for you?
Once you’ve figured that out, each island below links to a complete guide where I break down the different areas to stay, the hotels I’d recommend, and, just as importantly, the ones I wouldn’t.
You’ll notice something else.
I only recommend a handful of hotels on each island.
That’s intentional.
After two decades in the Caribbean, I’ve learned that recommending twenty hotels is the same as recommending none.
I’d rather tell you exactly where I’d send my own family.
If You Only Read One Section
| If you want… | Start Here |
|---|---|
| Your first Caribbean trip | St. Martin |
| Money isn’t the deciding factor | St. Barts |
| Sailing, chartering, a new anchorage every morning | Tortola or Virgin Gorda |
| To slow down and forget what day it is | Nevis |
| White sand and beach bars | Anguilla |
| Mountains, rainforest, waterfalls, hiking | St. Lucia or Dominica |
Which Caribbean Island Is Right for You?
Nobody plans a vacation by saying, “I think we’ll visit the Lesser Antilles.”
You picture the trip first.
Long lunches overlooking the water.
A beach you can walk to every morning.
A quiet villa.
A sailing charter.
Great restaurants.
A place where you don’t need much of a plan.
The island comes second.
That’s how I’ve organized this guide.
Choose Your Island
These aren’t places I researched for a weekend article.
They’re islands I’ve sailed to, anchored off, lived on, worked in, or returned to year after year.
Some I’ve visited dozens of times.
A few I’ve probably visited hundreds.
That’s the perspective you’ll find throughout Between Two Seas.
Not the highlights.
The judgment that only comes from spending enough time somewhere to know what really makes it special.
Best for First-Time Visitors
St. Martin
The island that does almost everything well, and puts Anguilla and St. Barts within easy reach.
If someone asked me to recommend one Caribbean island without knowing anything else about them, I’d probably say St. Martin.
Not because it’s the prettiest island. It isn’t.
Not because it’s the quietest. It isn’t.
And not because it’s the most luxurious. It isn’t that either.
It’s because it does almost everything well.
You can spend the morning at a French bakery in Grand Case, the afternoon on a beach, and finish the day with one of the best dinners you’ll have anywhere in the Caribbean.
Then tomorrow, if you feel like exploring somewhere different, Anguilla and St. Barts are both just a short ferry ride away.
That’s hard to beat.
One thing most first-time visitors don’t realize is that St. Martin isn’t one destination.
Grand Case feels completely different from Simpson Bay.
Orient Bay has a different personality than Anse Marcel.
Choosing where you stay matters almost as much as choosing the island itself.
Think St. Martin is your island? I’ll show you exactly where I’d stay, who each neighborhood is best for, and the handful of hotels I’d confidently recommend.
Best for Luxury
St. Barts
Expensive, polished, and still the island I’d pick for the best luxury trip in the Caribbean.
People who have never been to St. Barts usually think it’s all about luxury.
They’re not wrong.
But that’s not why people fall in love with it.
The island simply works.
The restaurants are consistently excellent.
The beaches are beautiful.
The towns are easy to explore.
Everything feels polished without feeling pretentious.
Yes, it’s expensive. Very expensive.
But if you’re looking for one of the best luxury destinations in the Caribbean, I don’t think anything else quite compares.
Most visitors arrive through St. Martin before taking a short ferry or flight.
Don’t think of that as an inconvenience. Think of it as part of getting there.
Some of the best places in the Caribbean ask you to make one extra step. They’re usually worth it.
Think St. Barts is your island? Here’s how I’d get there, where I’d stay, and which hotels are actually worth the money.
Best for Beaches
Anguilla
No big resorts, no long list of things to do. Just the best beaches in the Caribbean and nowhere else you need to be.
If your vacation revolves around beautiful beaches, Anguilla belongs near the top of your list.
I’ve spent plenty of time on islands with bigger resorts, busier towns, and longer lists of things to do.
That’s never been Anguilla’s appeal.
You come here to slow down.
Long beach walks. Lazy lunches. A swim before breakfast. Another before dinner.
Somewhere around the third day, you stop looking at your watch.
Most people arrive through St. Martin.
It sounds more complicated than it is.
A short ferry ride later, you’re on one of the finest beach islands in the Caribbean.
Think Anguilla is your island? I’ll show you where I’d stay, which beaches I’d return to every morning, and the hotels I’d actually book.
Best for Slowing Down
Nevis
Quiet without being empty. One of the few islands left that still feels genuinely unhurried.
The first thing most people notice about Nevis is how quiet it feels.
Not empty. Not sleepy. Just unhurried.
The island has managed to avoid becoming the kind of place that builds itself around tourism.
That’s part of its charm.
If your perfect vacation is reading by the pool, taking long walks, and enjoying dinners that stretch well into the evening, Nevis does that better than almost anywhere I know.
Fly into St. Kitts. Take the water taxi across.
It’s quick, straightforward, and arriving by sea feels like the proper introduction to the island.
Think Nevis is your island? I’ll show you where I’d stay and why it’s one of the few Caribbean islands that still feels wonderfully timeless.
Best Paired with Nevis
St. Kitts
Rainforests, old sugar plantations, and volcanic hikes, usually experienced as half of a two-island trip.
St. Kitts often lives in Nevis’s shadow.
I think that’s a mistake.
It has rainforests, old sugar plantations, volcanic hikes, historic forts, and some of the most interesting history in the eastern Caribbean.
It also pairs beautifully with Nevis.
I rarely think of them as separate vacations.
Spend a few days on each and you’ll experience two islands with completely different personalities.
Think St. Kitts is your island? I’ll show you how I’d divide my time between both.
Best for Sailing Charters
Tortola
Where some of the best sailing vacations in the world begin, a different anchorage every night.
Tortola is where some of the best sailing vacations in the world begin.
You certainly can spend your whole trip here.
But I don’t think that’s the best way to experience the British Virgin Islands.
The magic starts once you leave the dock.
A different anchorage every night. Lunch at one island. Dinner at another.
That’s what makes this part of the Caribbean so special.
Think Tortola is your island? Here’s where I’d stay before or after a charter, and how I’d spend every extra day.
Best for a Few Extra Days
Virgin Gorda
Relaxed without feeling sleepy, upscale without feeling exclusive. Stay past The Baths and you’ll understand why.
Virgin Gorda strikes a balance that very few Caribbean islands manage.
It’s relaxed without feeling sleepy.
Upscale without feeling exclusive.
Beautiful without trying too hard.
Most visitors come for The Baths.
They should.
But don’t make the mistake of leaving that afternoon.
Stay a few days.
That’s when you’ll understand why so many sailors keep coming back.
Think Virgin Gorda is your island? I’ll show you where I’d stay and how I’d spend the extra days.
Best for a Day, or Longer
Jost Van Dyke
White Bay, a Painkiller, and Foxy’s after sunset. Nobody comes here for the sightseeing.
Nobody comes to Jost Van Dyke looking for museums or sightseeing.
They come because it’s fun.
A lazy afternoon at White Bay.
A Painkiller with your feet in the sand.
Music drifting out of Foxy’s after sunset.
Some islands ask you to keep moving.
Jost asks you to stay awhile.
Think Jost Van Dyke is your island? I’ll show you where to anchor, where to stay ashore, and where I’d start the night.
Best for Getting Away From It All
Anegada
Flat, quiet, and remote, with beaches that seem to go on forever and lobster worth the trip alone.
Anegada surprises almost everyone.
It’s flatter than the rest of the British Virgin Islands.
Far quieter.
And wonderfully remote.
The beaches seem to go on forever, the lobster is famous for good reason, and the whole island feels like it exists at its own pace.
If you’re looking for nightlife, this isn’t your island.
If you’re looking for space, it might be exactly what you’re after.
Think Anegada is your island? I’ll show you where I’d stay and where I’d send you for the best lobster on the island.
Best for Sailors at Heart
Antigua
Sailing isn’t an add-on here. It’s woven into the island’s history, and you’ll feel it even ashore.
I’ve always thought Antigua makes more sense once you see it from the water.
Sailing isn’t something that was added for tourists.
It’s woven into the island’s history.
Spend time around English Harbour, watch the boats come and go, and it’s easy to understand why generations of sailors have kept returning.
Even if you’ve never stepped aboard a sailboat, you’ll feel it.
Think Antigua is your island? I’ll show you where I’d stay and where I’d spend an afternoon around English Harbour.
Best for Dramatic Scenery
St. Lucia
The Pitons, rainforest roads, and viewpoints that make you stop the car. Built for hikers as much as beach-goers.
Some islands make you relax.
St. Lucia makes you look up.
The Pitons dominate the coastline, the roads wind through rainforest, and almost every viewpoint makes you stop for a minute.
It’s one of the most dramatic landscapes anywhere in the Caribbean.
If you like hiking as much as beaches, you’ll never run out of places to explore.
Think St. Lucia is your island? I’ll show you where I’d stay, and near which Piton.
Best for Hiking & Nature
Dominica
Waterfalls, rivers, and volcanic peaks. The wildest island in this guide, and I mean that as a compliment.
Dominica isn’t the Caribbean most people imagine.
That’s exactly why I like it.
You’re not coming here for beach clubs or luxury resorts.
You’re coming for waterfalls, rivers, volcanic peaks, rainforest, and some of the best hiking in the region.
It feels wilder than almost anywhere else I’ve sailed.
If your idea of paradise involves boots instead of flip-flops, this is your island.
Think Dominica is your island? I’ll show you where I’d stay and which trails are worth the mud.
One Last Thing
There’s no single best island in the Caribbean.
There’s only the one that’s best for the trip you’re actually trying to take.
If you take one thing from this guide, take this. Don’t choose an island because it looked good in a photo. Choose it because of the kind of days you want to have.
Once you’ve picked one, the island guides above will walk you through where to stay, area by area, and which hotels I’d actually recommend.
I’ll keep adding to this list as time allows. Sailing has taken me to far more corners of the Caribbean than I’ve had time to write about yet.
Written from Palma, Mallorca.
39° 33.35′ N, 2° 37.57′ E
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