Sitting by the pool at an all-inclusive in Riviera Maya, Mexico, I realized I had traveled all this way and spent all this money to just lay around and read. I had done this vacation before. This exact resort. The same restaurants. The same excursions. In fact, it was my fourth trip to an all-inclusive in Mexico. First in Cancun. Then Riviera Maya. Then Puerto Vallarta. Now back again.

I was bored—and worse, disappointed in myself for feeling that way. After all, this was the trip of a lifetime for some. But if I couldn’t get lost in new experiences, I decided I’d at least get lost in the pages of The Shining.

Some people seek the familiar in their travels, returning to favorite places to relax, just as they return to favorite authors. But during this trip, I realized I’m not one of those people. The next year, I decided on something completely new, an adventure to the Pacific Northwest.

I don’t remember why Portland, Oregon popped into my mind—I wasn’t a fan of Portlandia or anything—but it stuck there. So I ordered the Travel Portland visitor’s guide and started planning—imaging myself on suggested day trips, starring recommended restaurants, hikes and attractions.

Once there, I fell in love with Portland and with the simply joy of exploring a new place and learning about the locals.

• Driving the sun-speckled, winding roads along the Columbia River Gorge and discovering the Latourell Falls Loop, a moderate and peaceful hike located on the way to the famed Multnomah Falls.
  
• Feeling the thunder of Hale Pele tiki bar, the “House of the Volcano Goddess,” learning that the long line is a small price to pay for Salt & Straw ice cream, and trying bacon jam and sipping vinegars for the first time.
  
• Stopping to smell the roses—each sweeter than the last—at the International Rose Test Garden, which grows more than 600 varieties.
  
• Reveling in the vineyard views and sampling some of the finest pinot noirs of Willamette wine country. It’s pronounced “Will-AM-it,” thank you very much.
  
• Hiring a guide for a hiking trip, learning about the lichen and the banana slugs, taking a moments rest on cliff overlooking the Pacific Ocean all before heading to Cannon Beach. If you grew up wanting to be one of the Goonies, you’ll recognize it.

Portland was a nine-day dream. One adventure after the next. A feast for the senses. And a collection of memories. That was it—my wanderlust was ignited.

Growing up on the East Coast, I’d traveled up to Maine and down to Florida, all to visit family. But never west of the Mississippi. In a proverbial “light bulb” moment, I decided to embark on a quest to see all 50 states.

To check a state off my list, I set one rule: I had to stay overnight. Something about going to bed and waking up in a new place felt like I was doing right by it. I looked it up, it’s not a rule of the All 50 States Club—in fact, some people count airport stopovers—but it became my standard.

So, with my goal in place, I planned my first real road trip:

A flight to Vegas. Then a rental car to Kanab, UT, north to Lava Hot Springs, ID and Victor, ID, east to Cody, WY and Rapid City, SD, the the long drive to Lincoln, NE to visit friends before flying home.