Best Caribbean Island You’ve Never Heard Of: Anguilla

Why you should go: Don’t you love its television ads? Never seen ’em? Exactly. Anguilla is a 35-square-mile island speck located in the British West Indies, a quick hop from St. Martin. It’s somehow managed to stay under the tourist radar for eons, which has made it a favourite of famous couples like Brad and Jen. Since the island offers 33 beaches, you’ll be able to find a quiet stretch to claim as your own.

Fits to a T: If you want to plant your butt on a beach chair, splash in turquoise waters and not worry about trying to see every museum and historical building, Anguilla is for you. Just enjoy the spectacular sun, good rum and nice locals who don’t try to sell you coconuts or hair-braiding services.

Ideal place for discreet canoodling: Take a short cruise to Scilly Cay, where the only thing you’ll hear is your own heavy breathing and the gentle lapping of waves.

Try it, you’ll like it: Grilled lobsters the size of puppies, swimming with dolphins at the new Dolphin Fantaseas, and the quintessential beach bar, Johnno’s, for late-night dance grooves.

For more info: go-anguilla.com or anguilla-vacation.com

Best Island for Natural (and Surgically Enhanced) Beauty:
Santorini, Greece

Why you should go: This Greek island is one of the best known because of the sunsets, which are so achingly beautiful that they bring tears to even the most cynical eyes, and the black sand beaches of Perissa and Kamari, which are teeming with perfect, bronzed bodies that appear to have been dipped in caramel.

Fits to a T: Santorini is a friendly, volcanic island with great beachfront discos. As an added bonus, no matter where you go, you’ll be far away from screaming kids. The island’s steep cliffs (some 1,000-feet high) make it a family-hostile destination.

Ideal spot for discreet canoodling: Head to the secluded beaches on the east side of the island, away from the hordes that infest towns like Thira and Oia. But before you roll around and get sand in unnatural places, put down a blanket: Black sand gets extremely hot and will sear your flesh faster than Las Vegas asphalt.

Try it, you’ll like it: After a few glasses of raki (a local drink that’s stronger than ouzo), all is right with the world.

For more info: santorini.net

Best Hot Destination with a Hot Name: Chile

Why you should go: In a country that resembles a long string bean (one that is 4,329 kilometres long), you can explore volancoes and glaciers, swim and snorkel in the ocean, climb up and ski down snowcapped mountains, bake on the beach, see Venetian-style architecture, feel the Latin heat, and get drunk on cheap local wine. Chile is a one-stop shop for good times—and one that is gathering steam as a vacation destination.

Fits to a T: You’d have to be a complete freak to not find something to do in Chile. It really does have it all. From December to March, Canadian beach-bunnies should hop to Viña del Mar, the trendy seaside resort town with bars, booze, babes and boys on prominent display. When ski season starts here, head south, way south, to Chilean ski resorts, which do booming business from June through August. Also, make sure to visit Chile’s Easter Island, off in the middle of the Pacific Ocean, where you can see over 600 moais (a.k.a. statues) constructed by ancient people.

Ideal place for discreet canoodling: The privacy of your hotel room works best for any of your sexcapades. Inhabitants of this country are 89 percent Catholic—kind of conservative yet friendly.

Try it, you’ll like it: In the capital city of Santiago, hobnob with the bohemian set in the Barrio Bellavista area, which is full of restaurants and bars. Try the beef (better than what you’re used to here) and the seafood (especially the crab and scallops) to fuel your fun and frolicking. Sip the pisco sours (grape brandy with lemon, egg white and sugar) carefully or you’ll find yourself chewing sand on the beach when you wake up in the morning.

For more info: visit-chile.org

Best Island Getaway on the Planet: Maui, Hawaii

Why you should go: Year after year, Maui finishes on top of those best-of lists published by the big travel magazines. It’s no wonder—this Hawaiian island has it all in a tidy, freakin’-gorgeous package, from whale watching to steamy volcanoes, and lots of “lei” jokes.

Fits to a T: With stunning sunsets, hidden waterfalls and bikini-populated beaches, Maui has a vibe that’s both romantic and sexy. So it should come as no surprise that it’s a much-drooled-over destination for honeymooners.

Ideal spot for discreet canoodling: For the ultimate blow-the-budget experience (starting from $613 a night), the Fairmont Kea Lani Maui has a Suite Romance package that virtually guarantees a life of bedded bliss with breakfast in bed, a candlelight dinner, and a spa package that finishes with an ocean-side couples’ massage. Keep the lava of love going with a plunge in your own private pool.

Try it, you’ll like it: A hike through the Haleakala Crater (it’s scenic and a good cardio workout), a killer brunch at the Maui Prince in Makena, some hula lessons (cheesy, yes, but also strangely erotic), and anything with macadamia nuts (pancakes, ice cream, etc.).

For more info: visitmaui.com

Best Rough-Around-the-Edges Vacation: Havana, Cuba

Why you should go: This city of 2.2 million is a wonderfully unpolished gem that’s full of historic cafes and steamy nightlife. Sure, there’s lots of peeling paint and rust, but that’s all part of the charm. If Havana was located in Italy, it would be called Venice for those reasons. Cool alert: With the renewed interest in rebel leader Che Guevara, due in part to The Motorcycle Diaries film (based on Guevara’s journals), Cuba and its capital have never been hipper. To see just how hip, take a stroll with attitude along the popular Malecón seawall and join the parade of chic Cubans.

Fits to a T: For anyone who doesn’t want a homogenized Cuban experience (i.e., seven days at an all-inclusive in Varadero), Havana offers the real deal, from fantastic music performed in city squares, to large grilled lobsters and all the trimmings for less than $25.

Ideal spot for discreet canoodling: The Tropicana may have been the It club of the 1950s, but it still grooves today with
a spectacular show featuring 200 stunningly gorgeous performers. And with all those writhing bodies fanning the flames of lust, soon you’ll be playing footsie (and more) under the table.

Try it, you’ll like it: Tour the city’s legendary watering holes like El Floridita and Dos Hermanos (both Hemingway favourites), and La Bodeguita del Medio (where Marlon Brando sucked back mojitos).
Note: There’s an ugly side to a country with a communist government. Many things you can enjoy—certain cafes, nightclubs, stores and even beaches—are off-limits to the Cubans.

For more info: gocuba.ca

Best Undiscovered Destination for Cheapskates and Adventure-
Seekers: Honduras

Why you should go: Let’s be frank. This country hasn’t exactly had a stellar reputation in the international scene, wedged between turbulent countries like Nicaragua and El Salvador as it is. In the last decade, though, Honduras got it together and is now poised to knock off the hip-but-offbeat crown worn by Costa Rica. Two other bragging points: The size of the coral reef surrounding the islands is second only to Australia’s Great Barrier Reef, placing Roatan in the Bay Islands among the very best diving spots in the world; and its Mayan ruins (like those in Copan) rival Mexico’s, minus the infestation of tourists.

Fits to a T: Honduras isn’t as slick as other countries. It’s rough around the edges and is suited to those with an adventurous spirit. If you’re a couple who likes good bang for the buck (60-cent beer, anyone?), Honduras is an excellent cheapie alternative to more pricey destinations.

Ideal spot for discreet canoodling: Try Roatan’s Palmetto Bay Plantation, where reality TV’s Temptation Island 3 was filmed. Couples cozy up in hammocks by the sea and gaze at one another lustily over sunset dinners.

Try it, you’ll like it: Honduran cigars, guaro (a licorice-tasting liqueur that you should sip, not chug) and sliced green mangoes sprinkled with salt and cumin from street vendors.

For more info: travel-to-honduras.com