How to Find Caribbean Vacation Deals, Sales, Bargains and Specials

How to Find Tropical Travel Sales, Packages and Specials

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It's hard to put a price on paradise, but nobody wants to spend more than they have to on their Caribbean vacation. Here's my easy guide to how to getting great Caribbean getaway deals, sales, bargains, and specials, so you can spend more time on the beach and less worrying about the bill at the end of your trip!

  1. Travel in the off-season. The best deals in the Caribbean are available from May to mid-December, with discounts of up to 40 percent off high-season rates at hotels and resorts. May and September-December are generally considered the shoulder season; the lowest prices are available June-August.
  2. Go where the airlines go. Airfare prices in the Caribbean follow the basic laws of competition: they're cheaper to destinations served by multiple carriers. Puerto Rico, Nassau (Bahamas), the Dominican Republic and Jamaica are examples of islands where you'll find many airlines flying at competitive prices. That helps keep overall trip costs down, particularly when you're booking hotel/air package deals (see below).
  3. Check the travel deals online. Sign up for hotel and resort e-mail newsletters for info on Internet specials. Follow resorts on Twitter and Facebook. Some hotel chains promise that the best rates can be found on their own websites. Check Rates and Read Reviews on TripAdvisor.
  4. Take advantage of hotel loyalty programs. Major resort chains like Marriott and Hilton continue to increase their presence in the Caribbean, meaning those loyalty points you earned on that weeklong business trip to Cleveland can be redeemed for some Caribbean R&R. You'll earn more points while you vacation, too!
  5. Don't overlook small villas, inns, B&Bs, and paradores. Not only is it often cheaper to stay at small, locally run inns, you'll have the chance to meet real residents of your island destination and get more immersed in island culture than you can at a mega-resort.
  6. Stay at all-inclusive resorts. I have two words for you: "cost certainty." All-inclusives in the Caribbean run the gamut from modest to luxury, but this is a great way to avoid sticker shock when you check out at the end of your stay. Most Caribbean all-inclusives include activities and basic water sports; some even include local tours and alcoholic drinks for one upfront price.
  7. Seek out the 'bargain' islands. The Dominican Republic has the reputation of delivering the best bang for your buck in the Caribbean. Puerto Rico, especially San Juan, is also attractive for bargain-hunters.
  8. Book package deals. Caribbean air-hotel packages designed by resorts, airlines, tour companies, and travel agents can often deliver better value than booking separately, especially in the high season.


  1. Book efficiency rooms and cook your own meals. The cost of food is the one thing that surprises most visitors to the Caribbean. To save money, shop at local markets and prepare some of your own meals. Another great way to get a real 'taste' of island culture!
  2. Eat where the locals eat. Hotel restaurants are almost universally overpriced. Instead, check out independent local restaurants near tourist areas – they're usually cheaper even when you include the cab ride! Reputable roadside food stands are another option.
  3. Use public transportation. Taxis and limos are expensive in the Caribbean, like everywhere else. Local buses can be a cheap, colorful, and (usually) reliable alternative. Santo Domingo, capital of the Dominican Republic, has a subway, and in San Juan, there's a commuter railroad (although it doesn't yet serve the tourist areas).
  4. Use ferries as cheap 'tours.' Narrated harbor tours are grand but local and commuter ferries often provide the same views (minus the commentary) for a fraction of the price.
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