Best. Vacation. EVER. (Part 2)


Clockwise, from top-left: View from the villa in St. John, game night in Toronto, the lone sunny day in Northern Michigan, fancy sunglasses shopping in Montreal

Last week, I encouraged you to talk to your travel buddy to see if you both really are on the same page when it comes to the five things you each look for in a good vacation. Caitlyn and I completed this exercise and then moved on to part two: Listing our five favorite overnight (or longer) trips we’ve taken together. We only named our favorite trips (the “cream of the crop” denoted by an * and four others, in no order). I have to say, I was a bit surprised by how this all shook out. Here’s what we said:

Caitlyn’s 5 favorite vacations:

  1. Toronto*
  2. Boston
  3. St. John
  4. Montreal
  5. Caribbean cruise

Kris’ 5 favorite vacations:

  1. Chicago*
  2. Toronto
  3. Boston
  4. St. John
  5. Washington, D.C.

I would consider that a win for ‘true love.’

Things I learned that surprised me: My wife picked Toronto as her favorite destination. First off, I didn’t even think this would make the list, let alone be her favorite and NOT my favorite (I’m a huge Maple Leafs fan, which is why you should all be gasping right now). I suppose the day spa, intertwined with shopping for fancy yarn on West Queen Street and delicious vegetarian fare made this a lock. Also, she did NOT list Chicago on her list. Maybe it’s because we’ve been there a thousand times and because she spent the first few years of her life living there, but I was a bit surprised by the omission. Last, but not least, I was surprised not to see Northern Michigan on the list. Perhaps, Caitlyn doesn’t associate visiting family (her grandparents live there) with vacation? Or, perhaps, this summer’s damp weather at an arts and crafts show she was presenting at soured the experience? Who knows.

Things that were reassuring: We both had three of our top five picks match. Hooray! I would consider that a win for “true love.” Also, even though she prefers “warmer climates,” that doesn’t automatically rule out northern cities. Thankfully, we visited Boston, Toronto and Montreal all in late spring, so the weather wasn’t bad at all.

Now it’s your turn! Do you and your loved one see eye-to-eye on best vacations?


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