Why you’ll love it: São Miguel, the largest of nine islands that make up the Azores, is a naturalist’s dreamscape that combines dramatic, fog-crowned lakes, and relaxing hot springs along with slender waterfalls and even colorful, Hydrangea-lined highways. By late September, airfare dips to around $500. For both, expect to shell out approximately $800 for a round-trip ticket during peak summer travel. Delta has a seasonal summertime connection from JFK that touches down in Ponta Delgada in under six hours. Travel time: Bostonians, rejoice! The quickest way to this lush island in the middle of the Atlantic is a less than five-hour red-eye with Azores Airlines from Logan International (depending on the wind, don’t be surprised if you find yourself in Portugal 30 minutes ahead of schedule). Kastalia Medrano Hike along Lagoa das Sete Cidades in São Miguel, Azores. It’s ubiquitous, but East Ender’s is a cut above. And definitely don’t go back home without sampling the world-class jerk chicken. If you can make it during the first week of May, you can catch the annual Carnival festivities, known here as Batabano.

Keep walking, if you must, on the renowned Mastic Trail, which cuts through a rad a nature preserve. It’s free, though it’s worth paying a small fee (meaning a gratuity) for a guide to give you a more thorough experience. Not really an ocean person? That’s cool-you can go to Hell, a surreal landscape of black limestone. Maybe feed a stingray while you’re there. For a smoke show beach, which we're going to assume is one of your higher priorities, head a few minutes south to Seven Mile Beach. Visit the Cayman Turtle Centre to swim with sea turtles (and learn about local marine life). On a short trip, you’ll get the most out of your time on Grand Cayman, the largest. Why you’ll love it: The Caymans are three islands, each with a different vibe. Aim for March or April, the sweet spot when hotel rates drop but the rainy season hasn’t quite yet kicked in. A round trip will run probably $300 to $550. From Chicago or New York, it’s still under four hours. Travel time: You’re in Miami? Great! A direct flight for you is just an hour and a half.

Weekend trips