"Whenever I find myself growing grim about the mouth; whenever it is a damp, drizzly November in my soul; whenever I find myself involuntarily pausing before coffin warehouses, and bringing up the rear of every funeral I meet; and especially whenever my hypos get such an upper hand of me, that it requires a strong moral principle to prevent me from deliberately stepping into the street, and methodically knocking people’s hats off – then, I account it high time to get to sea as soon as I can." 

-Moby Dick


This is the winter of us malcontents.  The obnoxious wild blows as if that last gust were meant to be personal.  This time of year, many of us cannot be bothered to leave the house, unless it is someone’s birthday or our own anniversary.  There is nothing to be done.  I have written extensively how to dress for cold weather, but today I want to talk about how to skip town.

First, a formula.  How much money do you make in one week before taxes?  That is how much you are going to spend on this adventure.  Keep in mind that the difference between Miami and Fort Lauderdale doesn’t matter when your goal is to fly far away from here, to any port in a storm.  You will reserve a third of your weekly earnings for each of the triplets: transportation, lodging, and food.  If need be, put the first two on your credit card, and let your warmer self work it off in the spring.

The joy of the getaway is not in what you will bring, but in what you will not need.  To help you limit what you bring, it’s best to pack in something light, such as the classic doctor’s bag.

If at any point you think you need to add a shoulder strap, you’ve packed too much.

There is no space for a laptop, no room for dress shoes, barely enough space for a spare pair of trousers.  You have enough room for a swimsuit (but no towel), a toothbrush, your phone charger, a comfortable shirt for the evenings, and little else.  

The decision to skip town is best made on the day of.  That is to say, if you’re on your way to the gym after work, but you "accidentally" book your tickets at lunch, you should be able to pack in your gym bag everything you will need that night.  This is probably the 300th reason not to carry a cheap gym bag.


As for travel, I cannot recommend the red-eye enough.  If you take a midnight flight on Thursday night, you might be on the beach before you can technically check in to your hotel.  Round trip flights are always cheaper for vacation travelers who can stay longer than a Saturday night.  How you handle work on Friday is your business.

Try to book the latest flight home you can.  Last month, I flew home from the Caribbean on a 10:00 PM flight, and I spent the entire day at the beach and watched the sun set before heading to the airport.  I was glad that I packed a quick-drying Vilebrequin swim suit. 

Do not pack a book.
 This is an escape from everything, including yourself.  Get one of those airport bookshop titles with the short chapters and the obese typeface.  Learn how the other half wastes their time.  Find out what color is your parachutte, or how far John Edwards fell from grace.

Do not pack sunscreen.  However, choose your sunscreen when you arrive, and keep in mind what story you left behind and what evidence you might wear home.

Do not feel guilty.  Taking the red-eye will reset your clock and keep you rested, but prevent you from the temptation of sleeping in.  Drag yourself to the beach in the morning, lotion up, don’t think about work, drink plenty of water, and just try to be as happy as possible.