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Trips + Giggles Top 5 Family Travel Tips with Matt Villano

How this traveling dad makes family travel not just fun but creative, too!


Welcome to the third installment of Trips + Giggles Top 5, where we ask parents for their best tips for the Top 5 family travel situations--Packing, Flying, Road-Tripping, Hotel Living and Finding Fun. After all, the best advice always comes from parents who have been there, done that, and cleaned up that.

Hi! I'm Matt Villano. I am a travel writer who covered adventure travel exclusively for seven years before I became a dad in 2009. Since then, I’ve transitioned into writing mostly family travel, with some soft adventure every now and again. Today my older daughter is 6 and my younger one turns 4 in September. I write about a bunch of other stuff, too: business, technology, science, and gambling. I also write corporate content. There aren’t many dull moments around these parts.

PACKING: Packing when traveling with our kids always is a struggle. It’s not the clothes—those are small and easy to put just about anywhere (seriously, I’ve packed an entire weekend’s worth of clothes for our younger girl in my computer bag). It’s the whole process of figuring out who’s taking what, where. Right now we’ve got two girls so my wife and I split ‘em up. I pick one girl and pack for the two of us; my wife picks the other girl and packs for the two of them. We’re due to have another daughter in November, and I’m sure her arrival will prompt us to rethink the entire strategy yet again. (Beside, when you’re packing diapers and wipes, all bets are off.)

In addition to the clothes distribution, we allow each girl to bring a small backpack (something each will be comfortable wearing) stuffed with her own things. We allow no more than three stuffed animals (we call them “friends”) per trip. We also tell the kids to bring their own markers and crayons in these bags (though I usually bring backups just in case). Finally, I take a carry-on bag that I fill with plane toys and plane snacks. (True story: The bag I use for this actually used to be my bag for overnight trips to Vegas.) Plane toys comprise everything from word searches and books for the older girl to window clings and drawing pads for the younger one.

We never leave home without Dum-Dum lollypops, which the kids love for minimizing discomfort on take-offs and landings. We also always bring Perler beads to do in the mornings when we stay at hotel rooms. They’re easy to pack and the kids love ‘em. Beside, every hotel room has an iron.

FLYING: I touched upon this a bit above with my mention of the Perlers. We’re big on art projects. We’ll usually bring construction paper and glue sticks or tape to make stuff on the plane. When we fly around the holidays we usually make paper chains and give them to the flight attendants, who always love it. We’re really not big into technology, but we allow each girl one movie or three programs per flight. This means we have 90 minutes of complete silence. For the rest of the time, we play word games, tell stories, draw, and read books.

In recent months, my kids have been really into what we call “Progressive Storytelling.” One of us starts a story, then we all take turns telling the story and winding it in another direction. We grew this pastime out of Rory’s Story Cubes, a game with nine dice that depict pictures designed to lead a story. (We discovered THAT game on a trip to Ireland back in 2013.)

ROAD-TRIPPING: Progressive Storytelling is also great for the car. We also play a game we call “Last Letter,” where we pick a category and we come up with words that start with the last letter of the word before. (For example, if you say, “Seattle,” I’d say, “Edgartown,” and you could then say, “New York.”) We really try to avoid technology in the car at all costs. The most high-tech we get is allowing the girls to pick which music we play. They almost always choose Ellie Goulding or Taylor Swift. In terms of strategy on a road trip, we try to stop at least every 90 minutes. I bring a beach ball and let the kids bop it around at every stop. This helps them get the wiggles out. It also helps me move my legs, which I appreciate.

HOTEL LIVING: I was lucky enough to get to write for Four Seasons when we lived in London (fall and winter of 2013), so we’ve stayed at some pretty incredible spots. In terms of urban accommodations, the Four Seasons Canary Wharf was pretty spectacular; we had a suite overlooking the Thames and the girls showed up to find their beds covered in flower petals and Minnie Mouse comforters. The Four Seasons in Hampshire was equally exquisite, but for completely different reasons. The place sits on 500 acres of open space. Staying there is like having your own manor, all to yourself.

Truth be told, however, we actually prefer vacation rentals. Every year we take a trip of three weeks or more, and we usually rent a house for the duration. This year we did this on San Juan Island, in Washington State (I’m actually completing this questionnaire from the house). You can read more about why we chose this place here. The house is in the middle of nowhere, with wide open fields for the girls to run on. That’s exactly what we wanted. We really like to embed.

In terms of tips for surviving being in a room…we’re big into making ordinary things fun. We let the kids build pillow forts and jump from bed to bed and turn ice buckets into doll/stuffed animal carriers. At bedtime, the girls share a bed and we give each of them separate covers (so they don’t fight over who’s being a cover hog). We have White Noise apps on all of our mobile devices and we crank those suckers up at night so my wife and I can carry on conversations at normal volume levels once the kids have gone to sleep. I’ve become so addicted to those sound machines, I can’t sleep without them.

FINDING FUN: For our family, fun usually involves some sort of outdoor activity. Beaches are high on the list, largely because my kids can have fun doing just about anything on a beach. So long as we have balls to toss, we can hang in any park or field, too. Pool time is always popular, but both of our girls get cold really fast, so we’ve learned that small doses of pool time can go a long way. The kids prefer outdoor activities that keep them moving (as opposed to, say, riding in boats).

Also, they are TEN times easier to deal with before lunch—we actually take a 90-minute break every day for them to have “down time” back in our hotel room (or another quiet spot). Beyond this, we like to think we can be flexible. The one area we’ve found we can’t really roll the dice is bedtime. Our kids are VERY routine-oriented. If we keep them up past 8 p.m. on any given night, we usually pay the price with unusual behavior the following day.


Trips + Giggles Top 5 Family Travel Tips with Zach Everson

Trips + Giggles Top 5 Family Travel Tips with Adrienne Evatt

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