Destinations / Caribbean
Caribbean Travel Guide
Every island is a different trip: all-inclusive ease in Punta Cana, the best beach in the region in Turks and Caicos, no passport needed for Puerto Rico, the Pitons in St. Lucia. I'd pick the island for the beach and the season, then the resort. Here's how they compare.
Caribbean
Where I'm sending people now
Sargassum seaweed usually washes in from about April to October and was heavier than normal in 2026. November to March is the cleanest stretch. Aruba rarely gets it.
December to April for dry weather and calm seas. May and June are good value. Hurricane season runs June to November, peaking August to October.
Luxury resorts run about $500 to $2,500+ a night depending on the island, with Turks and Caicos at the top. Taxes and fees add 12% to 21% on most islands.
Never pack ammunition, even a single stray bullet: it's a serious crime in Turks and Caicos and the Bahamas. Book refundable rates or travel insurance for trips from August to October.
Places in the Caribbean
Which one is right for you?
Punta Cana
Great for
All-inclusive trips, families, groups, easy beach weeks
Skip it if
You want to explore towns and restaurants off the resort, or you're going in peak seaweed season
Turks and Caicos
Great for
Honeymoons, beach lovers, snorkelers, families who want calm water
Skip it if
You want culture, nightlife or a budget trip; it's one of the priciest islands
Puerto Rico
Great for
First Caribbean trips, food lovers, long weekends, families
Skip it if
You want a quiet, remote island feel the whole time
Saint Lucia
Great for
Honeymoons, hikers, couples who want views over beach time
Skip it if
Long, winding transfers bother you, or you want wide white-sand beaches
The Bahamas
Great for
Quick getaways, families, boat days, out-island escapes
Skip it if
You want a local, cultural feel on Nassau; that's in the out islands
Aruba
Great for
Reliable weather, families, couples, travel in hurricane season
Skip it if
You want lush rainforest or mountains; Aruba is dry and flat
Know before you go
Getting there
Most islands have nonstops from big US hubs like Miami, Atlanta, Charlotte, New York and Dallas, plus seasonal flights from Toronto and London. If you're coming from farther away, Miami is the easiest connection for most of the region, and London has direct service to Saint Lucia, the Bahamas and Turks and Caicos.
Getting around
It varies a lot by island: Aruba and Puerto Rico are easy self-drive places, while Saint Lucia's mountain roads make a driver the smarter call. Uber is not a given in the Caribbean, so I pre-book airport transfers almost everywhere.
Money and tipping
US dollars are accepted on nearly every island I recommend, but check your bill: many resorts and restaurants add a 10-15% service charge plus government tax, so you're not tipping twice. Bring small bills for drivers, porters and boat crews.
How I'd spend 7 days
Pick one base for a 7-night trip:
Days 1-7 Turks and Caicos for calm, clear water and an easy flight
Days 1-7 Saint Lucia for the Pitons, rainforest and a romantic vibe
Days 1-7 Aruba for dry, reliable weather and a lively food scene
Days 1-4 + 5-7 Puerto Rico, Old San Juan then the rainforest coast or Vieques
Hotels I'd book in the Caribbean
Things to do in the Caribbean
Where to eat in the Caribbean
La Yola
Playa Blanca
Coco Bistro
Grace's Cottage
Marmalade
Santaella
Dasheene at Ladera
Boucan by Hotel Chocolat
Dune
Graycliff
Flying Fishbone
Zeerovers
Where I'm sending people now
Hawaii
Maui, Kauai, Oahu and the Big Island, and how to pick between them.
Italy
Rome and the Amalfi Coast, with the hotels and tours worth booking ahead.
Caribbean
Punta Cana, Turks and Caicos and Puerto Rico, all-inclusive and not.
Caribbean FAQ
Which island is best for a first Caribbean trip?
Punta Cana for an easy all-inclusive, Puerto Rico if you want food and culture with no passport, Turks and Caicos for the best beach, Aruba for reliable weather, St. Lucia for a honeymoon with views, and the Bahamas for the shortest flight.
When is sargassum seaweed season?
Usually about April to October, peaking in summer. 2026 was one of the heaviest years on record. November to March is the cleanest time, and Aruba rarely gets it.
When is hurricane season?
June 1 to November 30, peaking from August to October. Aruba is south of the main hurricane belt. For those months, book refundable rates or get travel insurance.
Do I need a passport?
Yes for every island here except Puerto Rico, which is a US territory. The Bahamas wants six months of validity left on your passport.
Can I pack ammunition by mistake?
Don't. In Turks and Caicos and the Bahamas even one stray bullet is a serious crime and travelers have been jailed. Empty every bag before you pack.
All-inclusive or not?
All-inclusive makes sense in Punta Cana, where you'll mostly stay on the resort. In Puerto Rico, Turks and Caicos and Aruba, the restaurants are part of the trip, so I'd book room-only or breakfast.
Which island has the shortest flight from New York?
The Bahamas, at about 3 to 3.5 hours. Turks and Caicos, Puerto Rico and Punta Cana are about 4 hours, and Aruba and St. Lucia about 5.