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Windward Ways & Tobago Cays

Dec 4, 2026 — Dec 12, 2026

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8 Nights on Star Legend

Dive, snorkel and swim with fish and sea turtles in Tobago Cays Marine Park, Bonaire National Marine Park and the proposed Speyside Marine Protected Area. Swim in a picture-perfect waterfall pool surrounded by the oldest protected rainforest in the Western Hemisphere, the Main Ridge Forest Reserve. Take in the volcanic beauty of the Pitons on St. Lucia, where rainforest meets some of the healthiest coral reefs in the Caribbean. And discover Bonaire, with its stunning desert-palette motifs like pink flamingos on white salt pans. Those who are looking for the classic Caribbean will find it in Mayreau — fewer than 300 inhabitants, and just 1.5 square miles, making it a port exclusive to yachts. And those who love colonial harbors will enjoy British Bridgetown as well as the triple Dutch treat of Kralendijk, Willemstad and Oranjestad.

Popular Highlights

Four magical colonial towns (including two that are UNESCO-listed) contrast with out-of-the-way ports and bays.

Snorkel the impressive coral reefs of Tobago Cays at the confluence of the Atlantic Ocean and Caribbean Sea.

Have your binoculars ready for birdwatching on Bonaire, home of flamingos, Amazon parrots and native parakeets.

Visit Mayreau, the smallest island of the Grenadines, and enjoy the exclusive Signature Beach Party.

Willemstad is a UNESCO site known for its brightly colored architecture.

Additional Information

Insider Tips

* You’ll find some of the best beaches in the Caribbean on Aruba. Aside from the beach resorts, every stretch of sand on the island is open to all, and easily accessible by public transportation.
* Mayreau is about as uncrowded as you can get. But if even that’s too much for you, head to Mopian. Surrounded by reef, the tiny dollop of sand has room for just one thatch umbrella.
* Bonaire’s arid climate contributes to its exceptionally clear waters, a quality that has helped make it the #1-rated dive destination in the Caribbean.
* If you plan to snorkel or dive, bring an underwater camera. Colorful fish like blue tangs and damsel fish are everywhere. And with luck, you may spot a hawksbill, a green turtle, or even a seahorse.
* For a taste of authentic Curaçao cuisine, cross Willemstad’s Queen Emma Bridge (the “Swinging Old Lady”) to Plasa Bieu. The pitched-roof food court offers many island favorites, plus the chance to mingle with hungry locals.