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

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.

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.

Nassau Paradise Island

Few Caribbean destinations make a spontaneous September trip easier than Nassau Paradise Island. You have beaches, a deep restaurant scene, historic Nassau, Paradise Island and an enormous range of hotels barely an hour from Miami.

CJ recently found Miami-Nassau airfare for $293 roundtrip for Sept. 10-14, and similar $293 fares were still appearing across multiple September dates when we checked Aug. 31.

Our hotel trio starts with Graycliff Hotel and Restaurant, still one of the Caribbean’s most distinctive small hotels and home to one of its great wine cellars. Sept. 1 rates were starting around $507 including taxes and fees when we checked.

We also like Goldwynn Resort & Residences on Cable Beach, where Sept. 13 rates were recently around $552 including taxes and fees. If you want the full Paradise Island experience, Atlantis Paradise Island remains in a category of its own, particularly when the water park, restaurants and sheer volume of things to do are part of the appeal.

Aruba

September is an especially interesting time to consider Aruba, whose location in the far southern Caribbean gives it a different weather profile from many islands farther north. It’s one of the reasons we’ve long liked Aruba for late-summer and early-fall trips.

Our focus here is Embassy Suites by Hilton Aruba Resort, a resort we’ve stayed at and one that makes a particularly strong case for a September vacation. You get the extra space of an all-suite hotel, a large pool complex and a location across from the water between Palm Beach and Eagle Beach.

The suite setup is a big part of the appeal, particularly for families or longer stays, and breakfast is included. There’s also the evening reception that has long been one of the signatures of the Embassy Suites brand.

Miami-Aruba roundtrip fares were starting around $501 for September when we checked Aug. 31. The nonstop trip is roughly three hours, making Aruba an easy long-weekend option from South Florida and an even better proposition if you can stretch the trip for a few more nights.

If you want an Aruba vacation with more room, useful inclusions and easy access to two of the island’s most popular beach areas, Embassy Suites by Hilton Aruba Resort is the hotel we’d be looking at for September.

Roatan

This island off the coast of Honduras gives you something very different: a Caribbean island built around diving, snorkeling and direct access to the Mesoamerican Reef. West Bay Beach remains the center of the island’s resort experience, with clear water, easy snorkeling and a long sweep of sand.

Our hotel pick here is Kimpton Grand Roatan Resort and Spa, the island’s standout luxury resort and the place we’d choose for a September stay. We found September nightly pricing dropping as low as $308 late in the month, with several other dates in the mid-$300s.

The resort sits directly on West Bay Beach, giving you one of Roatan’s best combinations of beach access, diving and a full-service luxury hotel. If Roatan is the choice, we’d keep it simple: stay at the Kimpton and build the trip around the reef.

Miami-Roatan airfare was starting around $834 roundtrip for September when we checked, although fares varied considerably by date. This is one destination where changing the travel dates by even a few days can make a meaningful difference in airfare.

Curaçao

There may not be a more interesting September hotel story in the Caribbean than Curaçao. The island’s hotel boom continues on Sept. 1 with the debut of TUI BLUE Curaçao, and CJ found opening rates starting at $413 per night.

But our first hotel choice remains Baoase Luxury Resort, one of our favorite hotels in the Caribbean, with private-villa accommodations and a small-scale luxury experience that bears little resemblance to the island’s larger resorts. Kura Botanica Hotel is another CJ favorite after our stay there, particularly if you want to base yourself amid the historic architecture and restaurants of Willemstad.

Miami-Curaçao nonstop flights take roughly three hours. American’s September fares were starting around $840 roundtrip when we checked, although connecting options can sometimes undercut the nonstop price substantially.

Curaçao also gives September travelers the same southern-Caribbean geographic advantage as Aruba, while adding one of the region’s best urban experiences in Willemstad.

Grenada

If the September trip is supposed to revolve around the hotel as much as the destination, Grenada belongs near the top of the list. The island has quietly assembled one of the Caribbean’s deepest collections of high-end independent resorts.

Spice Island Beach Resort is the classic, an all-inclusive luxury hotel directly on Grand Anse Beach. The resort is currently promoting 40 percent savings on its best available rates for September stays, which makes this an unusually good month to consider it.

We’d also look at Calabash Luxury Boutique Hotel, one of the region’s enduring family-owned luxury hotels, and Silversands Grand Anse, the modern counterpoint with its striking beachfront pool and contemporary rooms and suites.

Miami-Grenada roundtrip airfare was starting around $600 for September when we checked. Grenada also rewards leaving the resort: this is an island for rum distilleries, waterfalls, chocolate, mountain drives and afternoons along Grand Anse.

St Kitts

September makes St Kitts intriguing because some of its best hotels can fall into dramatically different price territory from winter. The island also gives you an easy two-island vacation, with Nevis sitting just across the Narrows.

Our luxury choice is Park Hyatt St. Kitts Christophe Harbour, with 77 rooms, 44 suites and three villas on Banana Bay. We recently looked at six of our favorite places to stay in St Kitts, and the Park Hyatt remains one of the island’s signature resorts.

But September opens other possibilities. Belle Mont Sanctuary Resort has promotional rates starting at $245 before tax, while Sunset Reef St Kitts has been offering rates starting around $500 before taxes and service charges.

Miami-St Kitts roundtrip airfare was starting around $641 for September when we checked Aug. 31.

Tobago

Tobago is the outlier here, and that is precisely why we like it. This is the choice when the vacation is less about a conventional resort strip and more about rainforest, diving, small beaches and exploring an island that still feels remarkably uncrowded.

Blue Waters Inn in Speyside is the hotel we’d choose for a dive-centered Tobago vacation, tucked beside Batteaux Bay with easy access to some of the island’s best underwater sites. Late-September pricing was recently starting around $114 before taxes, with totals around $126.

Magdalena Grand Beach & Golf Resort gives you a larger resort experience, with September rates recently around $247 before taxes. We’d also consider Coco Reef Resort & Spa for its location near Store Bay and Pigeon Point.

Getting here usually requires more planning than the other islands on this list, typically connecting through Trinidad or another Caribbean gateway from the United States. That extra step is part of the tradeoff for reaching an island that remains very different from the region’s busiest destinations.

Saint Lucia is one of the Caribbean’s strongest September choices if you want an all-inclusive resort stay with easy access to the island’s dramatic scenery. Our focus here is Secrets St. Lucia Resort & Spa, the adults-only all-inclusive that gives Saint Lucia a newer option in a category that continues to grow across the region.

Secrets is the choice if the priority is a resort-first vacation: multiple dining options, pools, beachfront time and the convenience of an all-inclusive stay without having to plan every meal or activity separately. It also gives couples another reason to consider Saint Lucia beyond the island’s long-established collection of boutique and ultra-luxury hotels.

That makes September especially interesting. Hotel pricing tends to soften after the summer travel period, while Saint Lucia still gives you the combination of beaches, rainforest, the Pitons and resort amenities that has made it one of the Caribbean’s signature couples destinations.

Providenciales

September can change the economics of Providenciales more than almost anywhere else in the Caribbean. Grace Bay is one of the region’s most expensive winter destinations, which makes a September stay particularly appealing when hotel rates ease.

Our pick here is Windsong on the Reef, one of our favorite resorts in Turks and Caicos because it puts you directly on a snorkeling reef without giving up the Grace Bay setting. That combination is the real draw: you can walk out from the resort and be in the water over coral within minutes.

Windsong also gives you a more intimate alternative to some of Providenciales’ larger luxury resorts, with suites and residential-style accommodations that make it especially useful for couples and families who want more space. September rates are often meaningfully softer than peak winter pricing, making this one of the better times to look at the resort.

Miami-Providenciales roundtrip airfare was recently showing around $615 for Sept. 14-28. The nonstop flight is under two hours, which keeps Providenciales among the easiest luxury Caribbean escapes from South Florida.

If your September trip is built around the beach, snorkeling and a quieter resort experience, Windsong is the Provo hotel we’d be looking at first.

We also like The Sands at Grace Bay, especially for families who value larger accommodations, and Rock House, the cliffside resort that provides a completely different Turks and Caicos experience from the long beachfront resorts of Grace Bay.

Which September Island Is Right for You?

If price is driving the decision, start with Barbados: a $178 room at The Crane is the kind of September number that can remake an entire vacation budget. Nassau Paradise Island is the easiest quick getaway, particularly with Miami airfare around $293 roundtrip.

Choose Aruba or Curaçao if weather geography is high on the list, Grenada or Saint Lucia if the hotel and the landscape are equally important, and St Kitts if you want a luxury resort vacation with the option of adding Nevis. Roatan and Tobago are our picks when diving and underwater experiences are central to the trip.

Providenciales is different again. September is an opportunity to experience one of the Caribbean’s most coveted beach destinations when some hotel rates retreat from their winter highs.

That variety is why we like the Caribbean in September. The month can put a historic Barbados resort below $200, get you from Miami to Nassau for under $300 roundtrip, open the door to a brand-new resort in Curaçao and make some of the region’s most expensive islands considerably more accessible.

And with 10 very different islands on the table, the best September Caribbean vacation may simply come down to what kind of island you want when you land.

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