Amazing Beach Getaways You’ll Actually be Able to Afford this Winter

Sun and sand await, and these beach destinations offer the best winter vacation value.

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While northerners may sing “Let It Snow” in December, by the middle of winter the frigid weather is not such a welcome sight. If you’re dreaming of a winter getaway with sun and sand, however, it can cost you dearly. Beach resort areas tend to be much more expensive during the winter, and flights fill up fast.

There are some beach destinations that are a consistently good deal, however, thanks to lower demand, higher supply or favorable exchange rates on the U.S. dollar. We looked at one-week departures leaving on a Friday or Saturday from several northern U.S. cities, including Boston, New York, Newark, Chicago, Minneapolis, Denver and Seattle, to find the best flight deals and vacation package bargains this winter.

Here are some of the best and most affordable options for a warm and sunny vacation in 2020.

Fort Myers and Sanibel Island, Florida

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The clear flight price winner in our research was Fort Myers, on the warm Gulf of Mexico in the southern quarter of Florida. Multiple airlines are flying here now, some nonstop, with roundtrip prices less than $100 from Newark and Chicago. The only city on our list not offering a flight here for less than $300 roundtrip was far-flung Seattle.

There are a wide array of places to stay on Ft. Myers Beach, Sanibel Island and Captiva Island, including many vacation rental homes. Unfortunately, the somewhat limited selection of hotels and condos here get booked up fast in high season, so plan ahead and snatch a good deal when you find it.

It’s not unusual to see 3-star hotel prices topping $300 in February, and the high-end places can be double that. Families and groups can often do better renting a large house.

Tempting Deal: Chicago to Ft. Myers on United for $97 — Roundtrip, Nonstop, Regular Economy

Key West, Florida

You can get that warm and tropical Caribbean feeling without leaving the U.S. by flying all the way down to Key West, Florida. One of the country’s oldest and most interesting settlements, the city has fairly reasonable flight prices from the eastern half of the U.S.

Roundtrip flights were available for $400 or less from every market we checked, often dipping below $300. There are even nonstop flights from Newark and Chicago. You can also take a ferry from Ft. Myers.

Rates at most waterfront or historic area hotels come in between $300 and $400 per night in high season, however, so it may make sense to rent a car and explore some of the other islands between there and Miami if you’re staying a week. Prices can drop by half for equivalent properties in less popular areas.

Tempting Deal: Three-night getaway package from New York City for less than $1,000 per person at The Perry Hotel, The Gates, or Doubletree (Including Airfare)

Cancun and Riviera Maya, Mexico

The most popular beach resort zone in North America keeps building new hotels in a market that already looks saturated, so prices haven’t really gone up for years. For an all-inclusive package where you pay one price and you’re done, this whole region (including Costa Mujeres and the Riviera Maya) offers a great value.

Economy flight prices range from $250 to $500 from most eastern and Midwestern cities, plus charter companies offer package deals with flights and hotel that are some of the best beach vacation bargains you’ll find.

Read the resort customer reviews carefully though, and know what you’re getting. You can’t expect gourmet cuisine, top-shelf liquor and tricked-out rooms at the very lowest rates.

Tempting Deal: One-week all-inclusive vacation at Bahia Principe Grand Tulum for $1,320 per person with roundtrip flight package from Minneapolis on Southwest

Montego Bay and Negril, Jamaica

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The first time I traveled to the Caribbean from New York City back in the 1990s, I snagged one of the best flight deals I could find and we ended up in Jamaica. Montego Bay airport is still one of the best-priced destinations from the eastern half of the U.S.

Roundtrip flights are consistently between $290 and $500, and there are three resort zones to choose from: Montego Bay itself, Ochos Rios and Negril.

The latter has the prettiest Caribbean beaches and a nice range of places to stay, from cliff-side villas to sprawling resorts. Plus, it’s easy to rent a car or motorbike here to explore other parts of the island.

Tempting Deal: One-week all-inclusive stay at the Royalton Negril Resort & Spa in a luxury junior suite for $1,760 per person with a non-stop flight from Chicago

Punta Cana, Dominican Republic

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Like Jamaica, the Dominican Republic has long been a price leader when it comes to good flight deals and packages for a sun and fun getaway. Punta Cana is a popular destination wedding choice for its good resort values. Additionally, direct flights from New York or Chicago sometimes drop below $400 roundtrip.

There are more than 200 hotels on or near the beach in this region, stretching from Juanillo to Bavaro, so there’s plenty to choose from in a variety of price ranges. Off-beach hotels start as low as $30 per night, while 5-star all-inclusive ones start as low as $200 in the height of winter.

Tempting Deal: Family room for two adults and two kids, seven nights for $2,076 all-inclusive at Be Live Collection Punta Cana

Guanacaste, Costa Rica

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While most flights into Costa Rica go to the interior capital of San Jose, some airlines fly to Liberia, which is an hour or less from some of the best coastal beach resorts. There are chain hotels and independent options stretching from the Papagayo Peninsula down through the Nicoya Peninsula.

You can find everything from villa resorts and yoga retreats to basic surf shacks. And you can often fly there roundtrip for less than $500 from JFK, Newark or Minneapolis.

There are a few all-inclusive resorts in this area, but you probably don’t want to be stuck in one place in a country that offers so many nature and adventure options away from the pool. Plan to do some exploring.

Tempting Deal: Costa Rica Dream Adventures offers one-week packages for $1,400 or less per person with hotels, transfers, guided activities and some meals.

Or rent an SUV with a roof rack and make your own path down the Pacific from Liberia. In Nosara alone, there are eight hotels with a pool going for $100 or less per night.

Other Spots to Consider

Distance and longitude have some impact on warm getaway flight deals. While eastern U.S. cities have good airline prices to the Caribbean, Florida and Cancun, western cities have good prices for Puerto Vallarta, Los Cabos and Hawaii. The presence of a budget carrier or Southwest in your market can make a big difference.

You can sometimes find good flight deals to Cartagena, Colombia if you want to fly to another continent for less than $500, especially if you’re willing to fly on Spirit Airlines.

Flights to Roatan in Honduras are seldom cheap, but once there you’ll find some of the best dive resort prices in this hemisphere. And finally, if you stretch your flight budget to around $800, you can get to Southeast Asia from western cities like Seattle.


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Tim Leffel

Tim Leffel is an award-winning travel writer and editor who runs the Cheapest Destinations Blog and Perceptive Travel. He is the author of five books, including The World's Cheapest Destinations--now in its 5th edition--and A Better Life for Half the Price. He has also contributed to a wide variety of publications such as USA Today, Lonely Planet, American Way, Global Traveler, and Outside Online.

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