Employee’s Vacation to Key West

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An Employee Experience: At VacationHomeRentals.com we spend every day ‘eating, breathing and sleeping vacations’, but we don’t do enough ‘taking vacations.’ In our industry, going on vacation should qualify as a field expedition, right? We’ll have to run that by HR.

In the meantime, we’ve decided to establish a new blog series that chronicles the vacationing experiences of VHR employees. Ideally, this series will provide the readers with a few chuckles and motivate our employees to spend a week trading in the keyboard for a Frisbee. This week we’ll see an employee’s vacation to Key West. You ready, Brendan?


I just returned from four days in Key West, and, man, do I love that city!

The trip began with a 6am flight from Logan International Airport; while the infamous Boston traffic didn’t present much of a hindrance at that hour, the sleet and freezing rain proved to be a worthy adversary. Typically a forty minute trip from my house to the airport, took closer to two hours and produced an undershirt dampened by the fear of missing my flight. Fortunately for me, the flight was slightly delayed and I didn’t have any problems boarding; unfortunately for the guy next to me, my undershirt was still damp, and I was likely exuding the stresses of a potentially missed flight and a failure to sufficiently deodorize. He had terrible morning breath, so I’ll call it even.

For me, the most crucial step to ensuring a successful vacation is to have the iPod fully equipped. Think about the Trainspotting soundtrack, or the Singles soundtrack or, better yet, Kill Bill – are you kidding me? RZA’s work on Kill Bill is really what made that film. Well, the music you choose to listen to while on your vacation is going to be your soundtrack, and, just like with movies, the soundtrack can make or break your vacationing experience. I used the 90 minutes of flight time from Boston to Fort Lauderdale to compile a playlist for the second leg of the trip, the drive from Fort Lauderdale airport to Key West. When constructing a playlist, the most important element is the setting in which you’ll be listening to said playlist. In my case, I was picturing sitting in the rental convertible with the sun shining and the warm breeze blowing through my beard. A sampling of the stellar compilation is below:

The Band – When I paint my masterpiece
Harry Belafonte – Day-o
Grateful Dead – Franklin’s Tower
Blind Melon – Change
Led Zeppelin – ½ of Zeppelin III, their only album I listen to.
Neil Young – Ambulance Blues
Phish – Runaway Jim
Sierra Leon Refugee Allstars – Living Like a Refugee
Bob Marley & Peter Tosh – Their complete works

Oh, and, of course, no road trip through the Keys would be complete without The Champs’, ‘Tequila’.

I arrived in Key West by 2pm, and had a pleasant sunburn by 5:30pm. Is it unhealthy to welcome a sunburn? Sure. Do I feel bad about it? Not even close. After the winter we had, I will gladly trade my wet boots and mittens for a painful-to-the-touch sunburn any day of the week.

The home we rented couldn’t have been better. There was a magical garden encompassing a beautiful terracotta stoned pool that provided the ideal venue for both morning coffees and after dinner nightcaps. key west vacationAnd the location of the home was ideal. It was far enough from Duval Street that we weren’t kept up all night from the overindulgers, but not too distant so that the bike ride home was manageable when we were the ones doing the overindulging.

I love bicycles and live music, and thus I love Key West. The bicycle is the most common form of transportation on the Island, and venues like the Green Parrot and Hog’s Breath host incredible bands both daily and nightly. But my favorite characteristic of Key West is the absence of social expectations. Sure, you have to be 21 to drink alcohol, 18 to smoke cigars and 16 to drive but conversations between 60 year olds key west bike vacationand 22 years olds, sharing nothing more than adjacent barstools, occurs more frequently in Key West than anywhere else I’ve been. No one cares how old you are, or how much money you make. Perhaps it’s the unmatched Happy Hour specials, but folks in Key West just seem so genuine and happy – it is both refreshing and reassuring to spend a couple of days amongst such a communal approach to life.

It had been almost five years since I last took a vacation. The rejuvenating this vacation produced can’t be ignored, and it surely won’t be another five years before my next vacation – especially since JetBlue gave me a $600 voucher due to delays! Thanks a bunch for reading, and I encourage you all plan your trip to Key West today!


Posted in Beach vacations, Employee Vacations, Family vacation spots, Florida vacations, Mancations

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