Island guides
Choose the coastline that feels like you.
These are not one-size-fits-all suggestions. Browse by mood, trip style, or region, then use each guide to match an island, a hotel rhythm, and the right way to get there from the Midwest.
Showing 13 of 13 island guides
Greater Antilles
Puerto Rico
Old San Juan color, rainforest air, beach time, and an easy first island escape with plenty of texture.Western Caribbean
Grand Cayman
Clear water, excellent beaches, and an effortless rhythm for travelers who want the details to feel easy.Greater Antilles
Jamaica
Music, mountain views, generous hospitality, and a beach escape with real texture.Atlantic islands
The Bahamas
Fast-feeling escapes, bright water, and enough variety for a long weekend, family break, or cruise add-on.Southern Caribbean
Aruba
Reliable sun, trade winds, and beaches built for doing very little very well.Southern Caribbean
Curaçao
Colorful Willemstad, small coves, and a more textured Dutch Caribbean escape.Eastern Caribbean
Barbados
Atlantic energy on one coast, calm Caribbean water on the other, and an easygoing food-forward spirit.Atlantic islands
Bermuda
Pink sand, pastel architecture, and an Atlantic escape that feels distinct from the Caribbean.Eastern Caribbean
U.S. Virgin Islands
Easygoing U.S.-based island time with bright water, distinct personalities, and room to move between St. Thomas, St. John, and St. Croix.Atlantic islands
Turks & Caicos
Wide beaches, clear shallows, and an understated island week built around water, space, and a good home base.Eastern Caribbean
St. Lucia
Volcanic peaks, lush interiors, and a more cinematic island rhythm for travelers who want the scenery to do some work.Eastern Caribbean
Antigua
A harbor-and-beach island with an easy social energy, coves to explore, and an itinerary that can stay light.Southern Caribbean
Bonaire
A quieter Dutch Caribbean counterpoint: brilliant water, rugged shoreline, and a trip that rewards curiosity over spectacle.Not sure where to begin?