Ideas for Merry Holiday Family Travel

holiday family travelSomehow it’s the middle of November already–the weather is colder and the holidays are creeping up! If you’ll be making some holiday family travel plans for this winter, it’s time to get started!

Travel budgets tend to take a back seat to holiday wish lists, but according to TD, over 80 per cent of Canadians are members of at least one travel rewards program. It’s time to use those points to put towards a present for yourself–a vacation! When using points, booking early is key to securing the flights and accommodations you want. And here are five ideal (and very different) holiday vacation ideas that are festive and fun, and most importantly, baby friendly!

playa ancon, trinidad, cuba beach, holiday family travel

Playa Ancon – Trinidad, Cuba


A tried and true (and incredibly affordable) favourite, Cuba is an easy holiday family travel getaway with multiple destinations, lots of departures, and plenty of direct flights from most Canadian gateways. The weather can be breezy at this time of year, but a green Christmas is most definitely assured and Cuba’s warmth comes mostly from the people anyway.

frenchman's cove, jamaica, holiday family travel

Frenchman’s Cove, Jamaica (courtesy Jamaica Tourist Board)


When I think of a Reggae Christmas, I (sadly) think of a painfully cheesy Bryan Adams holiday song from the ’80s–complete with an appearance by Pee Wee Herman in the video. In order to cleanse that image from my brain, I recommend a trip to Jamaica, STAT. Even if the weather outside is frightful, the weather in Jamaica won’t be, and there are just so many amazing and baby-welcoming resorts to choose from. Why not gift yourself a week at a resort with a Vacation Nanny?

holiday family travel

Walt Disney Parks & Resorts/Matt Stroshane

Walt Disney World

Just imagine the most magical place on Earth at the most magical time of year… Yes, it’s crazy busy, but it’s also truly magical. Walt Disney World is a family favourite of ours, and the last time we visited it was between Christmas and New Year’s Eve. The parks were quite crowded but if you go with a plan it’s easy to manage and you won’t be disappointed. Cinderella’s Castle lit with icicle lights is something to behold, and with super fun events like Mickey’s Very Merry Christmas Party you’re bound to have a holiday you’ll never forget.

holiday family travel

Christmas in Midtown, NYC (courtesy NYC & Company/Joe Buglewicz)

New York

We just returned from a long weekend in NYC, and there is nothing quite like Manhattan decorated for the holidays. New York is surprisingly baby- and family-friendly, with plenty of places to roam and explore. The holiday season is certainly the busiest and priciest time to visit New York, but the festive spirit is alive and well, and the twinkly lights and all the trimmings should make a trip here top every Christmas wish list.

Vieux Quebec, courtesy Tourisme Quebec

Vieux Quebec, courtesy Tourisme Quebec

Quebec City

There is no place prettier than Quebec City during the holidays. There are few places colder, mind you, so you and baby will have to bundle up! Last year their famed Ice Hotel had a Frozen-theme, and there’s really no doubt that Bonhomme and Olaf would become fast friends. While the cobblestones and steep streets of Vieux Quebec aren’t exactly stroller-friendly, the Quebecois culture could not be more welcoming of families. The fanciest and chicest of restaurants will greet you and baby with open arms, even if they don’t have a high chair 😉

Now while I can offer up some great holiday family travel suggestions, TD has a few more tips for making the most of those credit card reward points:

  • Take advantage of additional benefits that your travel rewards credit card may offer, such as travel insurance coverage, concierge services and airline perks.
  • Consider giving the gift of travel this holiday season by using points to book a flight for a family member or close friend to visit.
  • Beyond flights, consider using points to book a hotel stay or activities while on vacation.

Many thanks to TD for supporting this post.

Main image courtesy Walt Disney World Parks & Resorts/Todd Anderson

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11 Responses to Ideas for Merry Holiday Family Travel

  1. Inspiring ideas!!

  2. OK, you’ve convinced me. I must go to Quebec during the holidays sometime!

  3. Allison at #

    I wish that Cuba was a place that U.S. citizens could visit more easily. It looks lovely, and tropical beaches are always welcome this time of year.

  4. Dabare at #

    I love to visit Walt Disney. Last year I got chance to visit during the Christmas season. Planning to go in June again.

  5. Anderson at #

    Merry Christmas all.

  6. Elaine at #

    Better get to Cuba now before our American friends flood in to see what they have been missing all these years!

  7. Katy at #

    This is a great list! My hubby and I are expecting our first in April 2015 and have a few trips planned (brothers wedding in NYC when baby is 8 weeks, CA & AZ to see family/friends when baby is 4-ish months) but we really, REALLY want to take a trip to Germany for Christmas 2015. Has anyone been to Germany at Christmas, or traveled to Germany with a very little one? I’d love some pointers!

  8. Anita at #

    Disney world is magical during christmas time!

  9. shoba at #

    great post !
    thanks for posting …

  10. Anna at #

    Awesome article to read and Great tips.I Love it….Thank you so much…

  11. Great…thanks for providing best ideas for merry holiday family travel, it will helpful for families who want to know about this travel with own family. Keep it up!

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