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Puerto Rico Entices as Winter’s Cheapest Tropical Getaway

It seems I write about Puerto Rico every winter. But how could I pass up an opportunity to tell you about a great, consistent bargain destination, with downright cheap airfare from many cities and a sizable hotel promotion? Plus, when it’s below zero, what could be more attractive than warm sand and sunshine? Short flights, no passport required, and overall affordability also contribute to making Puerto Rico an ideal last-minute getaway, all for under $500.

Finding airfare to Puerto Rico

When I searched for airfare to San Juan from a handful of departure cities, I was a bit stunned—in a good way—at how the same basic low price was offered all-around for round-trips in January and February.

  • New York to San Juan: $240
  • Boston to San Juan: $243
  • Chicago to San Juan: $243
  • Washington, D.C., to San Juan: $243
  • Atlanta to San Juan: $245

From past experience, these prices are representative of what you’ll find throughout most of the year. They also include all taxes and fees, too. Who knew it could be so easy?

Finding a hotel in Puerto Rico

Often, finding a hotel deal for the same dates as the airfare isn’t so easy. However, for Puerto Rico this winter, the stars have aligned and both types of deals have converged, thanks primarily to the Puerto Rico Tourism Company’s Puerto Rico Now promotion. If you book a four-night stay for travel though April 30, you’ll receive up to a $250 food-and-beverage credit at participating hotels, most of which are upscale properties. You just have to book by January 21 through either, Expedia, Orbitz, or GoGo Worldwide Vacations. The only drawback is you’ll get the $250 as cash back after checkout, and you’ll only get back however much you spend on food and drinks at the hotel.

To make sure this offer would fit into a $500 budget, I checked prices at some of the hotels included in the offer. The lowest available rate I could find was $181.05 per night (on Expedia) at the swank, Art Deco style Normandie Hotel in San Juan. When shared with another person, the cost for four nights comes to $362.10 per person. Subtract your $125 portion of the $250 you would presumably spend on food and drinks, and you’d pay only $237.10 for hotel. Of course, you’re still paying for the food and drinks.

Since this hotel is located right in San Juan, you won’t need to spend money on a rental car, bringing your grand total—including airfare ($245) and hotel—to about $482. Not bad. Of course, this price depends on your departure city, cab fare, and any extra fees tacked on by the hotel.

If you don’t want to stay for four days or don’t think you’ll make use of the food-and-beverage credit, consider staying outside of San Juan at one of the island’s paradores. These family-owned inns are usually a good value, as many charge rates of around $100 or less per night.

A couple of years ago, I visited Hacienda Juanita, a former coffee plantation in the center of the island, and still find it to be a good bargain. The property is secluded in the mountains and surrounded by lush green rainforest. Rooms are simple, but some feature poster-style beds and antiques. When sharing a room with another person, you pay $65.48 each, including taxes, breakfast, and dinner. It doesn’t get much cheaper than that.

Here, a three-night stay, for instance, would come to $196.44. When adding airfare of $245, the total comes to $441.44, leaving room for the car rental you’ll need to get there. On Hotwire, I found car rental rates from $68.95, including taxes and fees, for economy and compact cars. If traveling with another person, divide the rate in half and pay only $34.48. Your grand total for the trip—including airfare, hotel, food, and car—now comes to $475.92.

With both of these scenarios, you’d have a little headroom in your $500 budget for extra activities, souvenirs, or whatever.

Depending on your travel style, there are many ways to enjoy a Puerto Rico vacation for very little money. Just let the deals lead the way, and you’ll be sipping a perfect piña colada (invented in Puerto Rico) in the warm sun in no time.

Email me your favorite money-saving tips for Puerto Rico, and I might publish them in a future article. Or, feel free to comment or suggest a new Escapes Under $500 destination.

(Editor’s Note: BookingBuddy and are members of the TripAdvisor Media Network, an operating company of Expedia, Inc. Expedia, Inc. also owns

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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