Bermuda
When you visit Bermuda, you're likely to encounter men meandering around the capital city of Hamilton dressed in immaculate and prim work shirts tucked neatly into seemingly casual short pants. Their "Bermuda shorts" fit well in with the mystery that surrounds these isolated Atlantic islands — places that adhere to British conventions, elegance, and decorum while yet knowing how to have fun in the subtropical heat.
Typically, visitors to Bermuda are looking for a little extravagance. Spa treatments and afternoon tee times are popular diversions. Do you need a break from your golf clubs or a change of scenery after your facial? Try stretching out on the gorgeous pink sands of Elbow Beach or Horseshoe Bay Beach, wandering around Historic St. George, or brushing up on your naval history at the National Museum of Bermuda. These islands don't pretend to be "cool", but they do provide a delightful old-school elegance that's hard to discover elsewhere.