Leeward Islands

Visit any one of the Leeward Islands for a memorable vacation in the Caribbean. St. Maarten, Anguilla, St. Barths, Saba, St. Eustatius, St. Kitts, Nevis, Antigua and Barbuda, Guadeloupe, The Saints, and Dominica make up these group of islands in the West Indies.

No visit to St. Maarten would be complete without checking out the Sunset Bar and Grill, where guests can sip on cocktails while enjoying front row seats to planes taking off and landing right overhead!

If you’re keen on celebrity spotting (or you happen to be one), drop by St. Barths, beach playground of the world’s rich and famous, on Christmas Day. Here, you’ll be surrounded by yachts and mega-yachts up to 530 feet long. You can catch the impressive midnight fireworks show as the New Year is celebrated, and then mosey into a locals bar in town…where you just might find Jimmy Buffet borrowing a band’s guitar for an impromptu performance!

Dotted by palm trees, kissed by cresting waves…Anguilla is a postcard come to life. This idyllic isle is delightfully depicted in the well-known book, A Trip to the Beach, which recounts the adventures of the Blanchard couple from Vermont who decide to move to the Caribbean. Visitors can even eat at the Blanchard’s Beach Shack, a now-established local staple for beach dining.