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Six Tropical Escapes Under $500


The Deal Detective is’s resident bargain hunter, Kate Hamman. She’s always on the lookout for new travel deals and invites you, dear reader, to submit your own questions.

When the temperatures drop, many of you start to daydream about basking on a beach in the hot sun. How do I know? Credit the influx of questions I’ve recently received about the Caribbean, Hawaii, and Mexico. Instead of answering each one individually, I’m going to instead present the best deals I’ve found in all three of these places.

Let’s begin with the Caribbean. It’s typically not hard to find a decent deal to one of its tropical islands, especially if you’re flying from the East Coast. However, the winter months are the Caribbean’s high season, which means you’re likely to pay more than you would in the summer. It also matters where you’d like to go, as you’re more likely to find specials to more popular destinations such as the Bahamas, Puerto Rico, and the Dominican Republic than you are to St. Thomas, Martinique, or Grenada.

I priced a five-night vacation to the Dominican Republic starting at $499 per person (without taxes and fees). The offer includes all-inclusive accommodations at the Coral Costa Caribe Resort, round-trip airfare from Miami (other departure cities are available at a higher price), Trip Mate weather insurance, and $100 coupon if it rains during your stay. Travel is valid through April 30, but you must book by January 18.

Though this isn’t the cheapest price I found to the Caribbean—I also saw deals to Puerto Rico starting at $399 (without taxes and fees) and the Bahamas starting at $439 (without taxes and fees)—I believe this deal offers the best value because the resort is all-inclusive, which translates to big savings on your food and drinks budget.

Next, let’s take a closer look at Mexico. The country’s high season is similar to the Caribbean’s, although Mexico is also a pretty hot spot during the summer as well. The more popular destinations such as Cancun, Los Cabos, and Puerto Vallarta tend to be less expensive than the more “exotic” locales like Zihuatanejo.

If you have to get away now, I priced a three-night package deal to Puerto Vallarta starting at $354 per person (without taxes and fees). The deal includes accommodations at Villa del Palmar Beach Resort and Spa and round-trip airfare from Los Angeles (other departure cities are available at a higher cost). Travel is valid between January 25 and March 8.

Once again, you can find cheaper prices to Mexico, including all-inclusive three-night hotel and air packages starting at $349 per person (with taxes and fees), but you may find it worth paying a little extra for a good place to stay. If you have any questions about the quality of a hotel, be sure to read other traveler’s reviews at our sister site, TripAdvisor.

Last, but certainly not least, are the ever tropical Hawaiian Islands. One reason to rejoice when planning a trip here is that the winter months are actually considered Hawaii’s low season, so you stand a better chance of finding a good deal now versus later. It will also more likely be a cheaper option than the Caribbean for my west coast readers. Plus, the more popular destinations such as Oahu, Maui, and the Big Island have a great selection of deals.

I priced a three-night package to Oahu starting at $459 per person (without taxes and fees). The deal includes one-bedroom condo accommodations at Aston Waikiki Sunset resort, round-trip airfare from San Francisco (other departure cities are available at a higher cost), a book of coupons, and two-for-one luau tickets. Plus, kids 12 and younger stay, play, and eat for free.

As with the other destinations, this wasn’t the cheapest deal I found, but your money is well spent on the extra space of a condo. However, I saw several deals to Oahu starting at $335 per person (without taxes and fees).

As you can see, there are deals aplenty to places that will warm your chilly bones. You just have to decide what deal fits your needs. A good rule of thumb is to look for places that are easy to reach by air from your departure city. From there, when you go can make or break your piggy bank. And finally, decide what you’re willing to sacrifice in the name of savings and what’s just not worth giving up. Stir all of these things together, add a pinch of flexibility, and you have the makings of a great vacation at the right price.

Where else would you recommend going during the cold days of winter? Have you seen a deal that is too good to be true? Please share your experiences in the comment field below.

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All prices, dates, and booking details listed here were valid at the time of publication. Some information may have changed since that time.

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