Winter Break Do-Over: Your Silver Lining Playbook 

Winter Break Do-Over: Your Silver Lining Playbook 


More often than not, there are two versions of Winter break.  There is the postcard perfect, Hallmark made for tv movie, Disney dreamland version of Christmas and New Year’s Eve (and everything in between) and there is the “this didn’t go at all as planned” version.  Maybe it was the weather that stranded family members as 1/2 the place settings for Christmas dinner sat sad and empty.  Maybe it was the dreaded bug that had you and 1/3 of your family bed-ridden throughout vacation.  Maybe it was the lost luggage that was just the straw that broke the camel’s back as you (the proverbial camel) worked to calm everyone down as you pull into your in-laws’ place.  Whatever it was, life in general doesn’t go as planned and when you throw in kids, family, and a little winter the odds are against you.

Sitting fireside to enjoy a hot toddy , a sweet treat or a good book is pretty sweet!

My solution to life in general is to allow for do-overs, be flexible, and create your own happiness.  These can be done on a small scale such as taking the kids out of their routine for 30 minutes to grab a treat and 30 minutes of uninterrupted chit chat time together at a local café, or grabbing a coffee alone for 30 minutes before you run an errand. These can also be done on a larger scale.  One night away in a hotel is often a great way to capture a winter break do-over without completely breaking the bank.

How to get away without breaking the bank.  Only go for one night.  One night away can turn into a two day extravaganza.  You might not be able to check in until afternoon, but if you are going somewhere nearby  travel  time is minimal and often you can take advantage of the pool or nearby attractions before checking in to make the most of the day.  Take advantage of specials.  Rue La La, Groupon, Hotel Tonight, all offer deals on hotels and you can search by location and date especially if you do it last minute.  Be sure to read the small print so ther are no surprises and if you have questions don’t hesitate to chat with the help desk.  Cross check prices by going to the hotel sites themselves and that will let you see what amenities the hotel has as well. Lastly, check the hotels twitter feed and Facebook page to see if there are any specials there.


A hotel pool is always a treat, some hotels offer special amenities for children including video games (we have no gaming systems at home so for us a hotel gaming system is a huge treat), being away from the piles of laundry and dishes and the “to do” lists of home allows everyone to just slow down a bit and focus on spending time together. Bring along a simple craft project to do together.  Pack a deck of cards and teach the kids a few games you used to play with your family or put a few of those board games at the back of the toy chest into a bag and bring it along too.    Take a trip to the library and stock up on graphic novels, favourite picture books from when the kids were little, and bring that along too.

Before you leave or perhaps on the drive over to your holiday do-over destination, talk to the family about the hotel amenities and what activities are nearby and let everyone choose one thing they want to do.  The only rule is that no one can reply to any other person’s request. Nothing is allowed to be judged a good or bad idea (within reason) and don’t plan on trying to do everything. It is okay that you packed a box of games that no one ends of playing.

Here are a few recommendations for your family holiday do-over.

Royal Sonesta Boston: Great location if you want to pop into the Museum of Science. Skip the crowds and just go in for a quick 4D movie experience, a show at the planetarium, or an IMAX movie. You can also just stay in the hotel and take advantage of the large pool, Art Bar is very family-friendly for all your meals or you can head out to some nearby spots such a Tahaza, Commonwealth Cambridge, and Tatte.

Burlington Marriott:  The pool is pretty big, we even got a good family game of Marco Polo in when we had the pool to ourselves. Get lost in books at the nearby Barnes and Nobles or catch a movie nestled into the very comfy lounge seats at the AMC Burlington, have a healthy, tasty family snack time together at Clover, and/or indulge in gelato at Tuscan Kitchen.

If you live near Toronto or you want to splurge and get out of town Germaine and Porter Air (perfect for a first time family flight too).  (Details coming soon)

The Hyatt Regency has a wonderful saline pool, two little mascot pups (perfect for mean parents like us who will not let our dog-lover son have a puppy of his own)  and is ideally located if you want to catch a show with your musical loving family.  It is also steps from some fun shoppping at Primark and a tasty adventure in Boston’s tiny little Chinatown.  Skating on Frog Pond is just steps away as well and you can warm up with a French hot chocolate at the Thinking Cup on your way back to the hotel.

Taj Boston:  Nestled on the corner of Newbury street and across from the Boston Gardens, the Taj is a perfect holiday do-over location.  Pretend to be a tourist in your own city.  Warm your toes by the fire in one of the fireside suites or in the lounge/bar by the fire. Have Tea at the Taj or spend the night.  Any way to indulge in a little of this luxury will definitely count towards a holiday “do-over”

Charles Hotel is at the heart of Harvard Square, steps from the Charles River, Harvard University and the mix of independent and familiar chain stores that make up Harvard Square. If you’ve done Boston or you just want something a little less urban than the Charles Hotel is a great option.

Hotel Veritas is a swanky little boutique hotel perfect for a no-kids escape. Right in Harvard Square, you can catch a show at the ART visit Harvard’s art museums or hop on the red line and head into Boston for dinner, a show, a stroll?

New and Notable: Godfrey Hotel

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