Carribbean Holidays: A Guide for the Cheap Bastard

Caribbean all-inclusive

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So you want to escape the doldrums of winter with a trip to the sunny Caribbean, but you’d also like to avoid subsequent months of abject poverty?

Don’t worry, be happy. You can afford to laze on a white sand beach, sip rum beverages at a swim-up bar, grow weary of steel drum music, stuff yourself stupid at the buffet and return home with a bronze glow that will make your friends hate you.

Follow a few simple cost-cutting guidelines to get the most bang for your buck out of a sun-drenched getaway.

A little incentive: a lot of beaches down there are “clothing optional.” And, sprinkled among the herd of portly German topless grandmothers with eczema, there are always a few pretty young ladies too.

1. Pick a Holiday That Suits You

All-inclusive resorts are everywhere down south, and they’re a great option if you want an easygoing, no-hassle holiday full of food, drink and sloth. Package deals typically include airfare, three meals a day (more if you’re feeling gluttonous) and all the drinks your liver can filter.

Cruises are like giant floating hotels that magically appear in a new place every morning. Each cruise line offers a distinct experience for a different target demographic, so choose wisely. (If you hate kids, perhaps avoid Disney. Don’t like seniors? Avoid Holland America.) Cruises are generally more expensive than resorts, especially if you like to imbibe, since booze is not included in the price. But there are lots of ways to keep costs low and fun high. Stay tuned.

Renting a villa in some sunny locale is a viable option for vacationers who like to be more adventurous and self-sufficient. But we’ll largely ignore this option here, because that kind of holiday is really as cheap or expensive as you choose to make it.

2. Narrow it Down

Not all Caribbean destinations are created equally. The Western Caribbean — an area that encompasses places like Jamaica, the Dominican Republic and Puerto Rico — is closest to home for North American travelers, and generally cheaper as a result. The Eastern Caribbean (Turks & Caicos, St. Lucia, Trinidad and Tobago) and the Southern Caribbean (Aruba, Bonaire, Curacao) tend to be correspondingly pricier.

Determine just how luxurious you want your holiday to be. A five-star resort will cost more — but usually not prohibitively more — than a one-star cockroach sanctuary. Sometimes those couple hundred extra bucks are worth it. Be frugal, not miserly.

3. Book Smart

Caribbean couples

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If you want to pay less than the average schmo, don’t travel at the same time as all the average schmoes. If you book your trip outside of peak times, you won’t have to pay peak prices. Keep in mind that the rainy season is generally from June through December. An ideal time to head south could therefore be April or May — a nice way to bid farewell to your winter blahs and return home to spring weather. There are loads of websites offering last-minute deals, including Expedia, Travelocity, Hotwire,, Orbitz and others.

As a rule of thumb, you can usually snag a great deal if you wait until the last minute. Resorts and cruise ships would rather fill a room at a reduced rate than have it sit empty, and they’ll drop their prices as bait for johnny-come-latelys.  Keep in mind, though, that you might find yourself with slim pickings if you wait too long.

But if you decide on a cruise, don’t gamble too much on a last-minute deal. You might get a decent price but end up feeling like a scurvy-scabbed stowaway in steerage if all the best cabins have already been snagged. The ideal time to book a cruise, both for pricing and peace of mind, is 90 to 120 days before departure, according to Cruise Secrets Exposed.

4. Choose Wisely

The secret to finding an awesome, affordable holiday is doing your research. Read customer reviews! A resort’s official website will promise an unparalleled paradise where your wildest dreams will come true, but actual customer reviews might tell a more nightmarish tale of bedbugs and Montezuma’s Revenge. To repeat: read customer reviews! A site like offers insights from the critics who matter most — people who traveled before you. They’ll also be able to tip you off to hidden costs and money-saving techniques specific to your destination.

5. Never, Ever, Ever Pay the “Official” Price.

There’s the official price of a cruise or resort stay, and then there’s the price you should actually pay, which is always significantly less. Loads of sites offer discounted rates on all-inclusive packages and cruises, and the savings can sometimes be hundreds of dollars. Sites like and Vacations2Go tend to offer deeply discounted rates.

6. Try to Travel for Free!

Cruise free

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Some resorts and cruise lines are willing to put you up for free if you’ve got a special skill and are willing to share it with your fellow vacationers. Are you a dance instructor? Computer whiz? Arts and crafts guru? Expert shutterbug?  Offer to share your expertise through occasional on-board lessons for fellow passengers, and the cruise line might just put you up for free, or at a significantly reduced rate.

7. Pack Smart

Be sure to take all the important staple items with you — toothpaste, sunscreen, shades, pills and the like — or else you can expect to pay preposterously jacked-up prices to buy them at your destination.

Pack some dollar bills for tipping. A buck or two for the cleaning staff and bartenders early on will likely get you some preferential treatment. Too cheap to give money? Giving things like pencils, notebooks, buttons and other token trinkets might be appreciated too. But keep this in mind: as poor as you think you are, you’re certainly no poorer than the resort/cruise employees. So cough up a little dough, Ebenezer.

Travel mug all inclusive

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For the boozer: take a big, insulated travel mug to your all-inclusive resort, and ask the bartender to fill ‘er up. It won’t save you any money, since drinks are included in the price, but you’ll save yourself endless trips to the bar for drinks in thimble-sized cups.

Smuggle booze onto the cruise. Cruise lines want you to buy their overpriced drinks, but you can save a bundle if you BYOB. Clear booze disguised in water bottles (or shampoo bottles, if you’re paranoid) will spare you the pain of a hefty bar tab to settle when you disembark.

8.  Get the VIP Treatment (and Discount)

Resorts and cruise lines desperately want to make the customer happy — especially if that happy customer might be good for business in the future. Try telling the desk clerk you’re a notable travel writer, or you’re scouting a location for an upcoming wedding or corporate retreat. They might deem you worthy of a room upgrade, free services or shipboard credit. A little white lie never hurt anyone, right?

 9. Choose Your Own Adventure

No matter where you go, you’ll surely meet an agent who tries to sell you on “once-in-a-lifetime” adventure — swimming with dolphins, say, or zip-lining over the forest canopy. Listen to their sales pitch, figure out what sounds fun, say thank you, then hail a cab and go do it yourself. By cutting out the middle man, you’ll save loads of money and avoid the crowded busloads of fellow tourists. You can probably haggle with the cabbie and tour operator on price, if you’re feeling extra cheap.

10. Fake Your Own Death and Live Off the Land on an Island Paradise

This one’s self-explanatory.

Desert Island

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