Last Minute Vacation Planning Tips for Procrastinators and Everyone Else

Him:         Hey Babes.Keisha's roadside spot

Me:           Yeah Babes?

(Yeah, we call each other Babes with an ‘s.’)

Him:         I think we should get outta town for New Year, maybe something tropical.

Me:           Babes, do you know it’s December 18?

Him:         Yeah.

Me:           Do you know people usually book New Year’s eve vacays a year ahead?

Him:         You can do it.

Planet-tails!Him was right. I can and I did. I’m an odd combination of fly-by-the-seat-of-my-pants and anal-retentive-nosey AF-planner-extraordinaire. So although I found this task to be daunting, I was up for the challenge.

As I spent every waking moment between December 18 and the day we booked our accommodations searching and planning, I couldn’t help but learn a few things:

1) Bring sand to the beach. Or nah. I prefer to know the person I’m going to kiss at midnight. I don’t want to share my hope and plans for the new year with a random. I enjoy the excited usies and bottomless champagne on the flights. I love basking in the shared afterglow on the flight home. But hell, if you like strange, you know I won’t judge you.

2) Don’t get stuck on a certain location. If you only have two weeks tops to make a New Year vacation come true, you can’t afford to be rigid. Expand your horizons. Watch Anthony Bourdain. To be perfectly clear, read on for #3.

3) Think outside the Caribbean. Like I said, don’t get stuck on a location. Americans often act as if the world just drops off after the Caribbean islands. It doesn’t. I know the islands are close and that you won’t have to use as much vacation time from work to travel there. When I began my hunt for vacancies, I started in the Caribbean for that very reason. I got lucky and found a lovely ocean front condo in Jamaica. However, it was the ONLY accommodation I could find that was up to my standards on the entire island. Repeat. The ONLY. I just got lucky. Don’t rely on luck though. I was open to Colombia, Argentina, and I’m always open to Thailand, but like I said… I. Just. Got. Lucky.

4) No room at ANY of the inns? Go rogue. An alternative to the resort is the vacation rental market. Websites like homeaway.com allow you to rent beach houses, condos or whatever you require all over the world. The site has photos, reviews, maps and more – everything you need for due diligence. My accommodations were in theory part of a resort with its own private beach. In reality, it was just an upscale condo that we rented from the owner. I used the site for the first time for this trip and it was a lifesaver.Michelle!

5) When you snooze, you sometimes lose. So you are successful with lodging, but what about the rest? Anybody who’s ever waited until the last minute to try to make NYE party or dinner reservations, even in your own town, knows it can be close to not happening never. Try booking a local chef. I employed the services of a true gem of a lady, Michelle. She cooked a couple of meals per day while I gallivanted on the beach. I’d come home to authentic Jamaican food and a clean condo. I couldn’t ask for anything more.

6) Lounge. Thank me later. Holiday travel is too unbelievably exhausting and the entire airline industry hates you. Seek comforts wherever you can even if you have to just throw money at it. If you aren’t already a member of some airline’s lounge club thing, entry is usually extended with the purchase of a business or first class ticket. You can also buy one-day passes. Do whatever you can. Did I mention the “free” drinks?

Since you’re reading this, I know you’re in a hurry and have no time to waste. Let me know if any of this helped. Also, do you have any tips? I’m sure this last minute trip won’t be my last.

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