These Are the 10 Best Caribbean Islands to Visit in September, From Nassau to Aruba to Roatan

By: - August 31st, 2026
nassau beach
Cabbage Beach on Paradise Island.
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From Barbados and Nassau Paradise Island to Aruba, Grenada and Providenciales, these 10 Caribbean destinations combine September hotel deals, accessible flights and some of our favorite places to stay.

Barbados, Nassau Paradise Island and Aruba are three of our favorite Caribbean islands to visit in September, but they’re hardly the only ones. From Roatan and Curaçao to Grenada, St Kitts, Tobago, Saint Lucia and Providenciales, September opens up a surprisingly broad collection of island vacations.

And this is one of those months when the numbers can change the vacation calculus. Caribbean Journal found rooms at Barbados’ The Crane Resort for just $178 per night for Sept. 1-8, while Miami-Nassau airfare has been available for $293 roundtrip and a brand-new all-inclusive resort is opening in Curaçao on Sept. 1 with rates we found starting at $413 per night.

That is the real September story. Some of the Caribbean’s best hotels become considerably more approachable after the summer vacation rush, while nonstop flights keep much of the region within a few hours of major US gateways.

We’ve been traveling to these islands for years, staying at their hotels, eating in their restaurants and returning to the beaches and neighborhoods that make them different. These are the 10 islands we’d be looking at for a September Caribbean vacation.

all-inclusive resorts caribbean best
The beach at Colony.

Barbados

Barbados may be the most compelling pure hotel-value play on this list right now. CJ recently found a $178 nightly rate at The Crane for Sept. 1-8, an unusually low number for a resort that first opened in 1887.

The Crane is one of our picks, particularly if you want residential-style accommodations and a resort that can function as a destination of its own. We’d also look at Colony Club, a Luxury Collection Resort, the West Coast favorite we’ve stayed at repeatedly; recent Sept. 4 pricing was about $501 including taxes and fees.

Barbados has flights from all over the US right now, from JetBlue in Boston and New York to American from JFK and Miami.


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About the author

Caitlin Sullivan began her career with Caribbean Journal as Arts and Culture editor before shifting to travel full time. She writes frequently on the Caribbean cruise industry, flight networks and broader travel news. Her most frequent Caribbean destination? Nassau.
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