Leeward Islands

The lush storybook shores of the Leeward Islands have long been a natural playground for pirates, explorers, and sailors seeking rum, sun, and silver crescents of sand. This stunning string of islands captures some firm favorite destinations in its arms — from honeymoon Antigua to sublime St. Kitts, you can spend weeks chartering around these super chic islands. Caught between the rolling surf of the Atlantic and the blue hues of the Caribbean, you can take your pick between hammock-swaying harmony, historic expeditions, or glorious adventures in the great outdoors.

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Once the winds of hurricane season have passed, Antigua is quintessential Caribbean. The former British colony still has a slice of stiff upper lip mostly linked to its love of cricket and its UNESCO-recognized Nelson's Dockyard. When you aren't wandering the historic sugar mills of Betty's Hope or gazing at the fortifications of Shirley Heights, life is truly a beach for yacht charters cruising the baby blue waters of Antigua. There are no less than 365 beaches providing a silver, white, and peach hue to Antigua's outline, from gin-colored snorkeling shores to kite surfing or glamming it up with a cocktail in hand.


Antigua's baby sister can be a show stealer thanks to her flamingo pink sands, flocks of frigate birds, and collection of caves. Barbuda may be a quick hop, skip and sail from Antigua, but it tends to be visited less frequently ensuring ample of space for AvYachtsTM members who choose to drop anchor on these postcard-pretty shores. At just 17 miles long, this sliver of Caribbean bliss boasts the Frigate Bird Sanctuary, home to one of the largest colonies of these seabirds outside of the Galapagos, along with 150 other feathered species. The powdered, crushed-seashell shore that makes up Pink Sand Beach is another draw to this exotic little island.


This off-the-beaten-track Caribbean destination is not for the faint of heart but is recovering from the catastrophic volcano eruption that wiped out two-thirds of its island back in 1995. However, in the 21st century, Montserrat is certainly on the upswing and is being rediscovered for its allure as The Emerald Isle of the Caribbean.

Only 10 miles long, this smoldering jewel of an island offers a different flavor to the Caribbean you are used to — Think dreamy black sand beaches, volcano observation spots, ashen landscapes to the south, and verdant velvet green hills and forests to the north. Bikers and hikers can take to the shady hills after stashing the yacht, and divers and snorkelers are sure to be smitten by the otherworldly underwater rock formations caused by volcanic spitfire.


Two destinations packaged into one; St. Kitts is rarely mentioned without including her partner in crime — Nevis. Despite being separated by only a narrow strait, these two spots couldn't be more different. St. Kitts is big, bright and bustling, with plenty of tourist development and a raucous slice of nightlife. Nevis is pegged together with beautiful quiet beaches and the pinprick-sized capital of Charlestown.

Active AvYachtsTM members can tackle the 3,200-meter climb to the sweeping vista summit of Nevis Peak or push through the jungle, where sweet-pea flowers, waterfalls, and oversized butterflies congregate. Over on St. Kitts you can ride the sugar train, go wreck diving, and perfect your handicap at one of the award-winning golf courses.


Surrounded by tantalizing atolls, the little island of Anguilla is all heady rum punch, reggae beats, and a Caribbean authenticity that keeps her on the map. Despite being just 15 miles long, Anguilla is home to 33 beaches — many with soft white sands and mirror-like waters offering crystal clear visions of the coral reef that lies beneath. Be sure to take the tender over to Sandy Island, where local crayfish is served on this tiny slip of powder perched in the middle of the turquoise blue sea.