Dominican Republic vs. Cuba
Battle of the bargains

Best beaches: It’s hard to beat Cuba’s nearly 6,000 kilometres of fine beaches, coral cays and secluded bays. The largest island in the Caribbean, Cuba also boasts the spectacular sugary sand of Varadero, a waterfront playground where naughty meets nice and everyone has fun. The coastline of the Dominican Republic is no slouch either, with almost 1,600 kilometres for seaside frolicking. The northern side of the island—think Puerto Plata—has café au lait-coloured sand, while the south—especially around Punta Cana—has the lighter, powdery variety. Check out Cabarete, a laid-back resort town that flies under the radar but boasts world-class windsurfing and plenty of bars and eateries for sipping Presidente brewskis.

Cuisine scene: No doubt the food at all-inclusive resorts here can be bland, but there are flavourful Cuban dishes to make up for it off property in the country’s bustling towns of Havana and Santiago de Cuba. Try fried plantains or lobsters the size of kittens, served with a side of rice and beans. Those looking for great food on vacation might have better luck in the Dominican Republic, which shows off its Spanish colonial roots with its national dish bandera (a mix of rice, beans, plantains and meat). Nosh on anything with salsa criolla, a spicy tomato-based sauce that could make even a piece of cardboard taste good.

The hearty party: No question about it: Varadero is the spot for mojito-fuelled nightlife, featuring discos with a constant thump-thump-thump. But if it’s the authentic Cuban scene you crave, visit the jazz bars in Havana. They may not look sleek, but they are oh so happening. The Dominican bar scene kicks into full gear after 11 p.m., as the hips of tourists and locals alike—well lubricated with rum punch—become ready to do the merengue, the national dance.

What it’ll cost ya: Cuba is still cheap, but may not stay that way post-Castro, when U.S.-style consumerism could hit. So go now. Where else can you get a B & B for about 20 bucks a night? Prices in the Dominican Republic seem to be slowly creeping upward, but it’s still relatively inexpensive compared to some other islands.

WINNER! Thanks to its cheap and cheerful spirit and pristine, lily-white sand beaches, Cuba triumphs.

Jamaica vs. Bahamas
Cultural clash

Best beaches: It’s easy to reach the beach in Jamaica. The island is rimmed with plenty of spots where any couple looks great swimming: he in his teeny-weeny Speedo, she in her bikini and ankle bracelet. Hedonism is the order of the day here, so unwinding on a lounger with a slushy frozen drink in hand is strongly encouraged along Jamaica’s beaches, such as Long Bay, Montego Bay, Ocho Rios and Negril. In the beautiful Bahamas, with its 700-plus islands, there’s always a slice of sand for those sun-seeking twosomes who want some privacy. On Nassau, the ritzy Cable Beach and other beaches by the picturesque South Ocean are the best places to bask in the rays.

Cuisine scene: Jamaica is the land of jerk, mon. Spices and hot peppers slowly seep into chicken, sausages, pork, goat and fish while they simmer. It will make you sweat just as much as a limbo contest at high noon. The West Indies influence adds spark to Bahamian dishes, such as stew fish and souse, the local soup. If you don’t like seafood, pack plenty of PowerBars. It’s all about the surf, not so much turf here. Conch (pronounced “konk”) is the local hero. It doesn’t taste like much on its own, but it’s decent with lime juice and spices or deep-fried.

The hearty party: This is hardly a fair match. Jamaica, the land of Rasta, reggae, ska, Bob Marley and rum has a well-earned reputation for being a place where you’ll have no worries and be happy. Your woman no cry either. The Bahamas can most certainly groove too, but up against Jamaica, it’s like Sunday school.

What it’ll cost ya: Jamaica and the Bahamas are somewhat on par when it comes to costs. Jamaica is a tourist-savvy island that has resorts and dining options spread over a wide range of price points. You’ll have no problem finding all-inclusive packages that won’t cripple your bank account this winter. The Bahamas is geographically closer to Canada, so you may reap some benefits from lower fuel costs for flights. It’s also a place that would do nicely as a long weekend getaway, just a bit further than Florida for us Canucks.

WINNER! This one has been declared a tie. While the beaches of the Bahamas are superstars, Jamaica does have an amazing party scene.

Antigua vs. Aruba
A-list showdown

Best beaches: Flying over Aruba, hills are pretty scarce in this relatively flat island dotted with aloe plants and the odd windmill. Fortunately, great ribbons of sand are plentiful, especially the peach-hued stretch running from Palm Beach to Eagle Beach. In pint-sized Antigua, waves of tourists hit spots like Jolly Beach for aqua fun, but the best kept secret is the picture-perfect secluded stretches of sand in Barbuda, Antigua’s nearby sister island. Just how lovely are they? Well, lingerie giant Victoria’s Secret shipped in a gaggle of leggy beauties to shoot one of its sexy catalogues there.

Cuisine scene: Aruba is thoroughly international, with influences ranging from Spanish to East Indian to Dutch (the official language), so a good meal isn’t hard to score. Creole-style seafood is a menu mainstay, along with pan bati, a kind of pancake made with cornmeal, handy for sponging up sauces. The pickled conch, calco tempera, is good, if you don’t mind chewing on something akin to rubber bands. Antigua edges ahead by a nose for its fiery side, which comes across in its cuisine and Susie’s Hot Sauce, a local condiment that feels as if it could melt your tongue in seconds if overused. Try yummy stuff like fungi and pepper pot stew (cornmeal and okra pudding—sounds grotesque, but tastes good). Here’s a tip you can road test: If you eat something too hot, kill the burn in your mouth with a pinch of sugar.

The hearty party: Arubians know how to get down and dirty alongside sunburned tourists. Oranjestad is the place where you can meet locals and jump-start the evening with power sipping during happy hour. Party buses and cruises are also abundant. As for Antiguan tourists, they do it with style: Many head to Shirley Heights (an old British fort near Falmouth Harbour) to dance on top of the hill while watching the sunset with a bottle of the local brew, Wadadli, in hand.

What it’ll cost ya: It’s a dead heat here. Both islands can be incredibly expensive and offer a plethora of luxury accommodations and eateries. But, thankfully, both can be more affordable if you hang out at local haunts. Avoid tourist traps by asking cab drivers for tips and watching where the islanders go. In other words, don’t follow the pasty guy from Jersey wearing a thick gold bracelet and white loafers with socks.

WINNER! It’s a close call, but Antigua wins for its lush, diverse terrain and clean beaches.