In October 2006, Deb and I hopped on a series of flights from Kalamazoo, Michigan to Florence, Italy. Deb was a seasoned world traveler but this was to be my first international trip. It was our first Trek Travel trip to ride the roads of Tuscany, but it ended up being so much more. That trip became the first of what, to date, are ten Trek Travel trips with many more planned for the future. We have been lucky enough to cycle through Italy, France, Vermont, the Pacific Northwest and various parts of California with Trek Travel.

Words by Adam Dingwall, Trek Travel Guest

Trek Travel Guests Adam and Deb reflect on their 10 trek travel bike tours

When I got the email from Jenny at Trek Travel asking if we could contribute to the blog by picking our three favorite trips, my first thought was, “How could I choose?” Each trip has been beyond compare in certain ways. The Tour de France trip was amazing in getting to stand on the road side and watch the cyclists go by so close you can feel their motion. The descent off Mount Bachelor into Bend on the Crater Lake and Oregon Cascades trip is 20 miles of perfectly smooth pavement where you hardly have to touch a pedal. The former California Coast trip provided the bucket list experience of cycling over the Golden Gate Bridge. Choosing our three favorite Trek Travel trips would be a little like picking our three favorite kids. But seeing that we don’t have kids, we’ll give it a shot in no particular order.

Trek Travel Guests Adam and Deb on a Tuscany Bike Tour


We’ve done the Tuscany trip twice, first in 2006 and again in 2014. Tuscany is the one place in the world I’ve been where, for me, the reality transcends the hype. The food, the wine, the people, the coffee, and the cycling are all sublime. Every moment of those trips seems to fuse into this memory of the best of my travels, it’s like one big Tuscan fresco. It’s also the trip that, in 2014, provided my all time favorite Trek Travel moment. The second day’s ride traverses the Val d’Orcia, riding up and down the beautiful Tuscan landscape and eventually rolling into Montalcino for lunch. When we arrived in town, we discovered our friends Tom and Andrea Meadows had already grabbed an outdoor table at Le Potazzine. The waiter came to take our order, starting with drinks. Tom, Andrea and Deb all ordered a glass of Brunello d’Montalcino while I ordered a coke; after all, it had been a long hot ride already and I was thirsty. The waiter sternly said, “No. Brunello” and walked away. Lunch proceeded through various courses and many glasses, or maybe bottles, of Brunello and me taking constant good natured gruff about ordering a coke. When it came time for the check, it was delivered to me along with a small, ice cold bottle of Coca Cola. Tom asked for the check to be split, but the waiter simply stated, “No. He ordered coke, he pays.” I loved it, happily paid the check, and then sought out the waiter to get our picture together, which I regularly use as my Facebook profile.

Trek Travel Tuscany Cycling Vacation

Trek Travel California Wine Country Bike Tour

California Wine Country

This is another trip that we’ve done twice, in 2012 and 2013. Deb is a big wine lover so riding amongst the vineyards of Napa and Sonoma is special for her. To be able to cycle past a winery that you are familiar with, or to discover a one that becomes a new favorite, is part of this trip. Plus, these places have wine clubs that ship straight to your house, which Deb thinks is perhaps the greatest example of commerce around. Like any Trek Travel trip, the cycling is wonderful–on lightly travelled roads and amongst traffic that is very respectable towards riders. But there are two things that set this trip apart for us. First, our favorite hotel in the world–Hotel Healdsburg–is part of the luxury trip. Second, on the 2013 trip we met three other couples that were to become our Trek Travel companions. We’ve now done Wine Country, Tuscany and Santa Barbara with Tom and Andrea Meadows, Rick and Gail Venner, and Darryl and Susan Forintos. We couldn’t ask for more fun than we get travelling with these folks. If we hadn’t signed up for Wine Country in 2013, we never would’ve met them.

Trek Travel San Juan Islands Bike Tour

San Juan Islands and Santa Barbara

I have to put these two together. These were our latest trips in 2015, so they are fresh in my memory. But the main reason is because these trips contained the two biggest climbs I’ve done: Mount Constitution and Gibraltar Road. If you ever meet me, you’ll quickly notice that I’m built a bit more like a linebacker than a cyclist. Climbing has never come easy and here in southwest Michigan the terrain on which to train for climbing doesn’t really exist. Standing at the top of Mount Constitution on Orcas Island looking across the water to Mount Baker on the mainland is an accomplishment I’ll forever hold dear. And the climb up Gibraltar taxed me in ways I never had anticipated.

It’s been an amazing ten years and ten trips with Trek Travel. We’ve made life-long friendships with fellow guests and guides. We’ve seen the world from the seat of a bike, a perspective that can’t be matched in any other way. A few years ago the president of Trek Travel, Tania Burke, along with her husband John, were in Battle Creek for Team Active Cycling and Fitness’ End of Winter Party. Deb and I were fortunate enough to have dinner with them. Tania asked us how our experiences with Trek Travel had been. “Tania,” I answered, “I still can’t think about our first trip to Tuscany in 2006 without getting goose bumps. If you told me that we could repeat any of our trips but we would have to pay twice as much, I’d write the check in a heart beat.”

There is nothing quite like Trek Travel for us.

Trek Travel Guests Adam and Deb on their 10th Bike Tour in Santa Barbara