The Wrap-Around Holiday: The Easiest Way to Enjoy a Two-Week Vacation

It would be a shame for the kids not to see grandma and grandpa at Christmas; The other holidays during the year? Sacrifice them to extend your holiday.

One week vacations are nice, no doubt about it, but the opportunity to disconnect for two entire weeks comes with benefits.

First, this is not for families with infants or kids under the age of four. Anyone who has taken a one-week vacation with their family in tow… with diapers, pacifiers and 200 other infant-related items… will be certifiably insane by day six. Relaxing during a one-week vacation with a 13-month old represents a contradiction.

Going back to work and being settled in your home after seven days away is refreshing at this stage. The comforts, space and lack of movement are reassuring for everyone in the family – especially the parents!

When your child enters Kindergarten, you are now confined to the schedule dictated by the school. Taking a week off in October when school is in session doesn’t send the right message to your child. I don’t care how smart he/she is, parents have to espouse a message of dedication when it comes to schooling.

Now I’m nagging, forgive me, but I’m working up to something that will provide you with longer holidays. If you look at the calendar, there is one and possibly two other holiday timeframes during the year where you can break away for more than a single week.

This is called the wrap-around holiday, when you take time on week one, extend into the weekend and then take off the following work week / weekend.

I’ll assume you are like me and ditching the broader family during Christmas represents a cardinal sin. Imagine the anguish when you tell your parents you plan to travel to Bora Bora during the Christmas break. You mother will provide you with another trip – a guilt trip until her last dying breathe!

Thanksgiving is the first holiday I recommend to sacrifice in order to provide your immediate family the chance to enjoy two weeks away. This year, it falls on the 28th of November. If you go to work on Monday the 18th, catch an evening flight, and return to work on Tuesday, December 3rd, that equates to 13 days away from the office (but only 6 ½ vacation days).

Galway, Ireland: The day before Thanksgiving, 2018.

Oh the things you can do and the places you can go! My family took a jaunt to Ireland the week prior to Thanksgiving last year, and let’s be honest, those two and a half days on the week of Thanksgiving are a crock! Nothing gets done. Will you miss the joys of freshly cooked turkey, stuffing and cranberry sauce? Yes, but screw it! I was throwing back pints of Guinness and ate a dish of sheperd’s pie on Thanksgiving. You can always enjoy that holiday with the family the following year.

The trip we took also included my mother-in-law, whom I invited to join us. You read that correctly, I invited her to come with us. You may define that decision as clinically insane but she’s a saint. The other benefit – when we drove all around the southern part of Ireland, my son had a permanent distraction in the backseat. The result was he did not ask, ‘are we there yet’ a million times.

And my mother-in-law had the chance to see the Island where her ancestors roamed. This also made it a broader family vacation.

The other holidays? Check them out:

Christmas: If you’re family doesn’t adhere to the Christian faith, what’s stopping you? The 25th in December and New Year’s Day fall on Wednesday’s this year. Fly out the night of the 18th and you can take 15 days off in total, but it will likely equate to six or seven paid vacation days. That’s unless you work in retail, I can’t help you in that situation.

July 4th, 2020: School’s out, and therefore, your family should be out and about, trotting the globe. This holiday, unfortunately, falls on a Saturday, so a two-week vacation may equate to 8 days out of the office. Still, it’s better than asking your boss to be out of the office for 10-days total.

Labor Day, 2020: This holiday falls on September 7th next year and that extra week (per se), that will be classified as ‘Summer,’ will be a do-nothing week in the office. This represents another solid time to break away for two weeks. The other benefit: the majority of Europeans head back home at the end of August from the beaches of the Mediterranean. That represents an opportunity to possibly save money and avoid the brutal crush of the Euro crowd.

Think ahead and enjoy the fruits of your labor when your kids are old enough to travel on a more independent basis. A two-week holiday, to enjoy the sights of our national parks or the beaches of Hawaii, Florida or Mexico, will cement lifetime memories for your family.

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