Ciclismo Your Way

"You Dream It, We Design It"

The grand buffet of adventures on this website is just the primo piatto (appetizer) for many of our imaginative guests. In fact, one in five Ciclismo tours is custom designed for special events, milestone moments, personal challenges… whatever occasion you want to celebrate. Call us and we’ll tailor an imaginative itinerary combining everything you want in a tour, and nothing you don’t.

Want to “shop til you drop” with your galpals touring Italy’s best ceramics and... shoes (we’ll carry your parcels so you can bike to the next bargain)? Do a fundraiser challenge that will excite you to ride it, and inspire your pledgers to support it? Ride with the family in a mini carnival with loops tailored for the entire cycling clan, from figlio to nonno? Indulge in a unique stargazing tour, spending each night looking moonward atop medieval hilltowns? We began this custom service in Europe, and now we’re delighted to offer it closer to home as well.

Here are some of our favorite Ciclismo Your Way adventures:

In Europe

Stargazing Like Galileo

Love gazing at the stars? Astronomy buffs, planet watchers and stargazers will thrill at our celestial cycle across Tuscany tracing the path of “the father of astronomy”. Pedal under the Tuscan sun by day, peer into Galileo’s modern day telescopes by night as we visit the many observatories around Florence, Pisa and Siena, with commentary provided by a renowned academic who will travel with the group.

Bike and Betrothal

David Andinolfi and his fiancé Marisa wanted to tie the knot and ride into a Tuscan sunset together. We planned a wedding for 30 of their close friends and family at a tiny Renaissance chapel in Reggello. The intimate feast and festa overlooked vineyards, vistas, and a golden sunset at the historic, four-star Fattoria degli Usignoli. Guests gently walked and cycled off the feast with four lazy days of bike ‘n’ hike.

Funride and Fundraise

Steve Rosenberg, a dedicated MS fundraiser, wanted a fresh, challenging, new route for his favorite annual cause. None of his teammates had ever been to Italy, so we designed a route for them in Umbria. They opened it up to other fundraisers and so not only raised funds for MS and had a blast of a vacation, they made brand new cycling friends.

In North America

Like the Mother Country without Jetlag – The Berkshires

A favorite for Europhiles wanting to stay stateside, active families or your first bike ride in New England, our route in Massachusetts’ lush Berkshire mountains is sure to satisfy. You can potter around Hancock Shaker Village with its wonderfully preserved shops, savor the purest air on the Ashuwilticook Rail Trail, and the mile-hungry will hallucinate they’re cycling the Italian or French Alps by conquering the climb and thrilling descent over Mount Greylock.

Just for the Hill Of It

Upon getting a long awaited promotion, a long time alum and dedicated climber wanted to celebrate by scaling the highest peaks without going across the pond. We whipped up a hilly holiday in undulating southern Quebec. Picture ancient mountain ranges, beautiful back roads dotted with colorful villages, delicious coffee, duck pate, charming auberge (inns) and a World War I airplane all rolled up in a warm baguette - the top brass couldn’t have a finer ride to the top.

History Buff’s Heaven Down South in Colonial Virginia

History seekers swoon at this week-long ramble along of Virginia’s Tidewater and Hampton Roads. These colonial byways are filled with scenic peninsulas, wetlands, uplands, sandy beaches, and some of the best and easiest road cycling in the state. Highlights include the Dismal Swamp National Wildlife Refuge and historic Richmond, the capital of the confederacy.