wywh1 of 53
🇦🇮Anguilla
‘Flying’ to Anguilla Aboard Calypso Charters Fast Ferry
There's more than one way to fly to Anguilla, thanks to American and Tradewind Aviation. Calypso Charters, though, is still my favorite.
🇻🇮St. Croix
Pleasant Feather Leaf Path to Butler Bay, St Croix
Every great undersea adventure begins with a walk. Often, these walks are somewhat arduous. Not at the Feather Leaf Inn, however.
🇹🇨Middle Caicos
Sunrise Perch Atop Dragon Cay Overlook, Middle Caicos
Every sunrise is a gift. Some gifts, though, are more special than others. Sunrise at Dragon Cay Resort is one such extra-special gift.
🇹🇨Providenciales
Lunching Between Twin Palms at Omar’s Beach Hut
Pure, natural, and eminently intoxicating West Indian vibes served daily – yeah, there’s nothing not to like about Omar’s Beach Hut.
🇦🇮Anguilla
Wading Out Grey Skies in the Pool at Nevaeh Anguilla
Grey skies do nothing to dampen the mood at Nevaeh Anguilla. At least they didn't for me when I stayed here in September 2021.
🇻🇮St. Croix
Rainbow Beach Sunset – Still Sweet…Mostly
Wrapping up "Sunday Funday" in Saint Croix with a Rainbow Beach sunset isn't what it used to be, but that's not all bad.
🇧🇧Barbados
Sauntering Into Silver Seas in Barbados – Wish You Were Here?
Azure seas embody the ideal Caribbean beach aesthetic. Silver seas in southern Barbados, though, are uniquely special in their own right.
🇦🇮Anguilla
Malliouhana Stairway to the Sea – Wish You Were Here?
The Malliouhana stairway takes you to a rocky outcropping that juts out due west above the surf; a sublimely sweet sunset perch.
🇹🇨Providenciales
Hogging The Pool at The Somerset on Grace Bay, Turks and Caicos
I much prefer natural pools over the man-made variety. Still, there's no denying the joy of having a swanky resort pool all to oneself.