Ahh, resort life. Not a care in the world... once you're actually there. But in the planning stages, there are plenty of sleep-depriving questions hovering around your head, like: Which island is the right island? What does "all-inclusive" really mean? How much is that in-room Champagne service going to cost me?
If you’re not careful, resorts can pile on the charges and you'll end up stuck with a hellish bill in tropical paradise. You can still luxuriate on a budget -- in fact, doing things cheaply often means having a more authentic island experience. You just have to have a little savvy and know where to dig up the savings. Here's how to score discounts and take full advantage of those tasty, tasty freebies.
Choose your island wisely
Pretty much every Caribbean resort comes standard with a jaw-droppingly beautiful beach, so your first step is to pick an island that truly feels special. Do some basic research on island life (this is a good place to start). Does it serve as a popular port of call for cruise ships? Then you might want to think again -- islands that get heavy boat traffic are usually overpriced, crowded, and less authentic. Instead, go for a resort on one of the lesser-known islands. Underrated almost always means under budget.
Check the island's tourism board for special promos
When you're resort shopping, a good place to start is the country's tourism board website, or (gasp!) give its office a call directly. These friendly folks can recommend value-driven times to visit and hook you up with discounted promotions at hotels. In some cases, they'll even offer incentives -- right now the US Virgin Islands is celebrating its centennial anniversary, and the tourism board will pay you a bonus of 300 clams just for visiting.
Get discounts with your Costco membership
As if you needed another reason to love Costco. Besides 36-packs of toilet paper, a membership card at many buy-in-bulk warehouses comes with travel perks, including vacation packages to premium resort locations and deals on cruises and rental cars. Oftentimes they’re cheaper than what you’ll find on a discount travel site.
Don't assume "all-inclusive" means everything is free
You've probably skipped over the terms & conditions for literally everything ever, but this is one instance where ignoring the fine print is extremely ill-advised. Many resorts will limit your freebies to specific meals or bar service, and "all-inclusive" may not cover that hot stone couples massage you scheduled in the private seaside cabana. When in doubt, call the resort directly and ask about its policies. And definitely double-check to make sure gratuities are included in the fee.
Look out for the all-important pre-arrival email
Before you depart, your resort should send you a pre-arrival email. To repeat, this is a very important email. If your spam folder absconds with it, call and ask for another one, because it's filled with tons of valuable resort info and freebies you can get during your stay -- plush luxuries like extra pillows and towels, newspaper delivery, welcome drinks, and nightly tuck-in service.
Leave the resort for better, cheaper dining
Unless you're paying upwards of two grand a night for a menu that's curated by a James Beard Award-winning chef with an infinity pool in the dining room, the food at your resort may very well suck. Sometimes rubbery fish tacos aren't worth the all-inclusive price tag, so if you're a discerning diner, consider a resort that has promising local spots and authentic cuisine nearby. Your Instagram followers won't know the difference, you'll be better exposed to the island culture, and you’ll probably save a few bucks on dining. After all, tostones and beer always taste better by the beach.
Avoid Carnival season at all costs... unless you specifically want to party at Carnival
Carnival is a raucous, calypso-induced celebration, and one of the coolest things you can do in the Caribbean besides just napping on the beach. Countries like Barbados and Trinidad & Tobago go all out for these multiple-day benders. As you probably guessed, flights and hotel rates skyrocket. If you're on a budget, avoid the first week of March as a general rule, when most celebrations are held. No two parties are alike, and some celebrations are held in summer, so make sure you look up your country's Carnival calendar.
Buddy up with the bellman, not the concierge
Ask a concierge for food recommendations and he might point you to the hotel's "award-winning" restaurant for a prompt dinner at 6pm. You didn't come here for the early-bird special -- you want authenticity, dammit! Buddy up with your bellman -- he's the guy that's not paid well enough to hock lies about the resort, and he can tell you about the late-night food truck serving some of the best carnitas on the island. Thank him and remember to tip.
Renting a car? Stay on US soil.
If exploring your tropical paradise requires a set of wheels, know that foreign car rental comes with its own set of hassles and fees. Budget adventurers should try to stay within the United States: The Virgin Islands and Puerto Rico offer some of the best rates on rental cars because you avoid costly up-charges associated with renting a car abroad.
Score massive savings by playing resort roulette
Maybe you have your heart set on Montego Bay, but you don't really give a hoot which resort you stay in, so long as the daiquiris floweth aplenty. If that's the case, look into CheapCaribbean's "Deal of Fortune," a site that lets you book a luxury resort for up to 75% off the sticker price. Funny catch is, you don't know the name of the resort you're staying in until seven days before your trip.
Arrange for a complimentary airport pickup
Before you blow money on a taxi right out of the gate, most resorts offer a complimentary shuttle to and from the airport, so long as you remember to schedule the service beforehand. A speedy airport pickup will put you on the right path to a relaxing vacation as soon as you land. Plus, you get to walk out of the terminal and see your last name written on a placard. That's how you know you've really arrived.
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