This triangle-shaped island — sitting about 8 miles off the coast of Cape Cod, Massachusetts — has been a secret summer hideaway of the rich and famous for more than a century. Today, the "Hollywood East" reputation is going strong — thanks to frequent visitors like President Barack Obama, David Letterman and Bill Murray, among many others. But despite the all-star summer lineup, a laid-back lifestyle rules the island. The main draw rushing Vineyard visitors off the ferry is the chance to let their hair down for a long weekend. Sure, you'll find insanely expensive summer cottages, and a pricey dining atmosphere to match, in some corners of the town of Chilmark. But low-key towns like Vineyard Haven and Menemsha are still predominantly focused on their marine industries and offer a more casual experience. Even the island's must-have souvenir — a Black Dog sweatshirt — is informal. So swap the stilettos for your scrappiest flat sandals, and do play it cool when you spy some film stars in Edgartown; everyone deserves a slice of a Vineyard vacation.
In Hawaii, the Big Island is like the sometimes awkward older sibling. Forgotten in favor of adorable little brothers and sisters, her attributes are often glossed over. Maui is for fun and families. Oahu attracts surfers, partiers and outdoor adventurers. Kauai is for romance and luxury. And the Big Island is just … big.
Majestic is more accurate. Geographically unique, the Big Island boasts everything from black sand beaches to snow-covered peaks, from hardened lava deserts to steamy and lush rainforests. And it's still growing. The Big Island's trump card – the active, fire-spitting Kilauea volcano – has been increasing the island's land mass since 1983. During the most recent eruption in May 2018, volcanic activity caused eruptions, earthquakes and the collapse of the Halemaumau crater. It's true that if you arrived here hoping for a stereotypical Hawaiian getaway that's full of luaus and a honeymoon-esque atmosphere, you've probably missed the mark. But the hiking trails and state parks that are here hold sights that no other Hawaiian island can boast of. And the beaches are colors you've probably never seen.
Cancún is nothing if not resilient. Consider the debilitating effects Hurricane Wilma had on the region in 2005 – drowned shores, destroyed storefronts and capsized boats. But now, this skinny "7"-shaped barrier island in southeastern Mexico is once again a go-to spot for beaches, golfing and nightlife. Cancún also remains one of the most affordable vacation destinations in the Western Hemisphere, even during the self-indulgent spring break season.
So what's there to do here? Cancún's beaches are spectacular spots to try some jet skiing and parasailing. And there's also a host of after-hours activities; be sure to check out the acrobatic dance performances at the Coco Bongo Cancún. This area is also close to one of the most recognizable sites of Mexico – don't miss out on the chance to behold Chichén Itzá, a large Mayan archaeological site that is one of the new Seven Wonders of the World.