Dream Island Escapes

Craving an island vacation? Get inspired by these exotic destinations.

Kicking Back in Key West

Follow our guide to the best food and fun in this quirky little town made famous by the likes of Buffett and Hemingway.

  • Print
  • |
  • Email
Key West Tour
Photographer Laura Davick

Road Trip

Catch a ride on the Conch Tour Train ($29 adults, $14 ages 4–12, discounts for online purchases; 800/868-7482 or conchtourtrain.com). Since it first starting giving tours in 1958, the train has offered insights―mostly true―into Key West’s past.

As you roll past blazing bougainvillea cloaking gracious clapboard houses, you’ll learn about the Overseas Railway (completed in 1912 at a cost of $30 million), the sponge trade (destroyed by a 1939 blight), and former Mayor Sonny McCoy’s 1978 feat (waterskiing all the way to Havana).

More Ways To Get Coastal Living



JavaScript must be enabled to use this Calendar module.

Dreamy Massachusetts Cottage

A colorful oceanfront cottage captivates a whole new generation of beachgoers in a dreamy Massachusetts resort town.

Cottage by the Sea