caribbean
Why should I plan your trip? Because 'the Caribbean' isn't one island, it's thirty, and no two are alike.
RECOMMENDED STAY
Ideal Duration
STARTING PRICE
Per Person Per Day
IDEAL MONTHS
Best Time to Visit
$1,200+
7+ days
nov-jun
Twenty-Eight Nations, No Two AlikeTHE CARIBBEAN, PROPERLY MATCHED
People say "the Caribbean" like it's a single destination, and it's closer to thirty different countries and territories, each with its own terrain, history, and pace. Some islands rise into volcanic peaks. Others barely clear sea level and are made almost entirely of reef and sand. Some run on French, some on Dutch, some on a Creole all their own. The real work isn't picking a beach off a map, it's matching the actual character of an island to what someone is really looking for, and knowing which ones still feel like themselves rather than a resort chain's version of paradise.
Where to go in
the caribbean
St. Lucia
Twin volcanic peaks, the Pitons, rise directly out of the sea near Soufrière, giving this island a skyline most of its flatter Caribbean neighbors simply don't have.
Bahamas
Over 700 islands ranging from Nassau's energy to the Exumas' remote, swimming-pig-adjacent seclusion, close enough to the US for an easy long weekend that doesn't feel like one.
Turks & Caicos
Some of the whitest sand and clearest water in the region, low-rise development by design, and a pace built entirely around barefoot simplicity.
Antigua
365 beaches, one for every day of the year according to local lore, English colonial harbor towns, and a sailing culture serious enough to host its own major regatta.
ready to Travel to the caribbean?
DON’T TAKE MY WORD FOR IT
TRAVEL + LEISURE
"Casewit spoke to the impact and importance of exploring the world outside your comfort zone."
AUSTIN Based Traveler
"Excellence is the word that comes to mind when I think of Sarah Casewit and my recent trip.”
BOSTON Based Traveler
"So many nights, my last thought before falling asleep was what a lovely day we'd had together. We can't wait to plan our next trip with her."
PICK MY BRAIN
