The Great Escape: Why Summer’s the Best Time to Plan a Winter Getaway

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Playa Flamenco in Culebra, Puerto Rico

If there is one thing we know in Chicago, it’s that winter is always lurking around the corner. It’s the cool breeze on the beach that makes you shiver or the ice cream brain freeze that reminds you that in a few months, this is how your whole body will feel. So what do we do? We play hard for the two sunny months of the year – and we plan our winter escapes.

Plan it now.

It doesn’t matter if you have no specific place in mind or no one who wants to go with you. Block off your schedule, ask for time off, and build from there. Start monitoring airfare to destinations that look interesting to you. Rally the troops – you have a few months to generate enthusiasm among your circle of friends and plenty of time to give advance notice to people with kids and pets. You also have time to save some money for your trip or drop hints that the perfect holiday gifts are sunscreen and a giant hat to protect your poor pasty skin. Do it now, or risk finding yourself in February in a Netflix marathon-induced delirium, mumbling incoherently about vitamin D deficiency and crystal blue waters.

Start small.

It is July. I already have tickets to the January world premiere of Bel Canto, the Lyric Opera’s adaptation of Ann Pachett’s beautiful novel, for some much needed cultural stimulation. I have also booked a trip to sunny Los Angeles for Oscar weekend thanks to a Virgin Airlines flash sale and a group of ladies who are up for anything, even something as crazy as planning a simple weekend getaway seven months in advance. My winter sanity list grows daily, even as I’m biking through the summer streets and laying by the pool because I know I’ll be in no mood to plan once the first snow falls.

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Check out those sexy metatarsals!

Look for opportunities.

A few years ago, my job needed someone to go to São Paulo, Brazil in February. I jumped at the chance, and sweated my booty off in a box-like booth in a non-air conditioned convention center while struggling to communicate in my baby Portuguese. It was not fun. But those 30 minutes in the sun at the end of the day – and even the fact that I knew warm weather was immediately accessible – made it all worthwhile.

I also have friends who frequent Puerto Rico for business, and have conveniently latched on to them and their free accommodations. They’re too busy to hang out by the pool, but I am happy to do so on their behalf and meet them for dinner.

If your schedule is flexible – and you’ve not heeded my warnings to plan in advance – last minute deals are also a way to go. I used to consider myself above all-inclusive resorts, but find them to be a budget friendly, relaxing and sanity-saving winter option. If I must sacrifice a little adventure for predictability and men in tiny shorts bringing me daiquiris, then I am up for the challenge.

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Puerto Rico: beautiful beaches and retro footwear!

Have something to look forward to.

Sometimes you need to trick yourself and your battered psyche. Merely the idea of something fun on the horizon can get you through the stressful holiday season and the debilitating winter days when darkness falls all too soon. Plan something, anything. Mark it on your calendar in red pen. Slap some pictures of the beach or ski resort or anyplace other than your icicle prison in your office or at home. Having an end goal in mind as you trudge through the snow and question your life choices might not make sub-zero temps more bearable (that’s what furry hats are for), but provides a warm glimmer of hope deep within your frozen core.

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Happiness is Puerto Rico in the middle of February.

– KATHY

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