The legendary Hamptons, a cluster of wealthy enclaves on Long Island's South Fork, remains a celebrity summer playground, with splashy restaurants and nightclubs galore. But lovely beaches, fishing and kayaking attract off-the-A-list visitors, as well. Old money oozes throughout Southampton, while new wealth reigns in East Hampton. Montauk is a hit with fishermen and surfers. The Long Island Railroad travels the Hamptons in an hour. The Sag Harbor Whaling Museum and Montauk lighthouse are popular stops.

Westchester County, a collection of towns that serve as a popular suburb for the bordering New York City, is also the gateway to the Hudson River Valley, an area that promises a plethora of outdoor activities, from sailing to bird-watching to cross country skiing. The County also contains Rye Playland, a popular children's amusement park, historic sites from the American Revolution, the African American Heritage Trail and several famous houses, including Lyndhurst, a Gothic Revival mansion.

The first time you go to New York, go ahead and be a sight-seer—everyone should visit the Statue of Liberty, the Met, Times Square, etc. But on a return trip, pick a neighbourhood and go deep. You’ll find hole-in-the-wall bars, great delis, quirky shops… exploring the non-touristy side of New York is an incredibly rewarding experience for a traveller.

If you’re looking for a budget-friendly island holiday, consider the Bay Islands. Each one appeals to different travellers—Roatan’s the most developed (but still not as built-up as, say, St. Thomas), Guanaia’s rustic and Utila’s in between. All three have great dive spots and beaches.

The sapphire waters of Cephalonia are steeped with history. The large Greek island was home to Odysseus, the legendary king hailed in Homer’s The Odyssey. Fortunately, it won’t take you ten years to get there. Explore the enchanting caverns of the Drogarati caves, sail to Ithaca on a glass-bottomed boat or marvel at the ancient artifacts inside the Archaeological Museum of Argostoli, Cephalonia’s main town. Or just hide from it all at one of the island’s many private beach coves.