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#TravelTuesday Q&A: Oregon or Puerto Rico for a First Big Kid Adventure

puerto rico family travel
Q: Hi Playground! I’m planning a big first airplane trip with my 9-year-old son, departing from the Philadelphia area. Trying to decide between a summer adventure to Portland, Oregon, or an early winter getaway to Puerto Rico. What do you think? ~ Thanks! LK Berry

A: Hi LK, These are two fabulous options, and I’ll start off by saying your son will love both and is super lucky!

I’m a big fan of Portland, OR, especially in late summer when it feels like everyone in the city is outside enjoying their short summer season. You’ll see families everywhere biking, boating in the Willamette River, and playing in the parks. Plus the Multnomah Waterfall just outside the city is easy to reach and a fabulous day trip. And everyone in Portland loves ice cream (okay, this last one is a little bit of projection since I ate ice cream the whole time I was there and always had to wait to  in line while spying lots of happy kids with cones).

Now, that all said, if I have to choose between Portland and Puerto Rico, I’m going with Puerto Rico. Here’s why: Puerto Rico is one of my favorite family destinations, I’ve brought my son there multiple times over the years and we’ve explored a lot of the island and always had a fabulous time. It’s the most “bang for your buck” in terms of easy travel from where you live: 3 hours and you’ll be in a tropical paradise with an entirely new culture and language, but, and here’s the great part, since Puerto Rico is a commonwealth of the US, you won’t need a passport or to exchange money.

Puerto Rico | family travel

Old San Juan is a great place for a 9-year-old to explore. Cobblestone streets lined with candy-colored houses lead to massive Spanish forts and fortifications looking out over the sea, a spot it’s impossible for kids not to imagine themselves having big adventures (like fighting off pirates or defending the city) in. Fly a kite on the massive lawns at El Morro and then have a dinner of kid friendly small-bite tapas . When you’re done with the city part of your explorations, head to the beach in Condado where you can catch a wave and some rays while the folks at home are bundling up in hats and scarves. It’s truly a win-win.

Have a great trip!

Have a family travel question?
Email Melissa at


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