Private & Custom Tours
Ciclismo Your Way — Pedal Your Passion
At Ciclismo Classico, we create experiences that become part of your life story—moments unfolding on quiet roads, around long tables, and in the company of people who matter. For over 35 years, we’ve brought people together through the simple act of riding a bike, where laughter comes easier, connections deepen, and strangers become friends… and friends become La Famiglia. With Ciclismo Your Way, each journey is shaped by your group, your pace, and your vision—that’s the Ciclismo Magic.
Nearly 20% of our journeys are private or custom, often designed to celebrate milestone birthdays, anniversaries, reunions, and once-in-a-lifetime moments.
Ready to talk to a Group specialist? Call 1-800-866-7314
Which Option is Right for You?
1. Join an Existing Tour Departure
Have a smaller group? Join a scheduled journey and become part of something bigger—connecting with fellow travelers while sharing the experience with your own circle.
Learn more below →
2. Reserve a Private Tour Departure
Our most popular way to travel. Share one of our beautifully crafted journeys exclusively with your group with a reserved private departure—your people, your rhythm, your experience from start to finish.
Learn more below →
3. Create a Custom Tour
Looking for something entirely your own? We design it with you—every detail shaped around your passions, your pace, and what matters most.
Learn more below →
1. Join an Existing Tour Departure
Sometimes the best way to begin is to simply join the journey. If you’re traveling with a smaller group, this is a wonderful way to experience Ciclismo—sharing the road with fellow travelers while still creating your own story together.
Perfect for:
- 6-10 people
- Travelers who enjoy meeting like-minded people
- Those looking for a seamless, ready-to-go experience
What it feels like:
You arrive as a small group—and before long, you’re part of La Famiglia. There’s something special that happens when groups come together on the road. Conversations linger. Laughter carries. Connections form naturally.
Group Benefits:
Joining an existing departure is often the most accessible way to travel together, with preferred pricing and the added richness of a shared experience. See our Ways to Save Page.
2. Reserve a Private Tour Departure
The Joy of Sharing an Extraordinary Journey. Some experiences are simply better when shared with the people who matter most. Whether you’re celebrating a milestone, organizing your annual cycling club adventure, planning a family reunion, or traveling with lifelong friends, a private Ciclismo departure transforms an exceptional vacation into a truly unforgettable shared experience. Choose one of our award-winning itineraries and enjoy it exclusively with your group.
Two ways to travel privately:
Option A – Reserve an existing departure (Best Value)
Reserve one of our published departures exclusively for your group. Because these departures have already been carefully designed and scheduled, they offer the best value while rewarding larger groups with preferred pricing and exclusive Group Organizer benefits. The finest boutique hotels are often the smallest. To enjoy the widest choice of departure dates and our favorite family-owned inns, we recommend reserving your private departure 9–12 months in advance. Many of our preferred hotels book well before the season begins.
Option B – Request your preferred dates
Need to travel on dates outside our published schedule? We’ll be happy to explore creating a private departure around your preferred schedule. Because opening a new departure requires additional planning, guide scheduling, hotel coordination, and pricing, a Private Departure Planning Deposit may be required before we begin developing your proposal. This deposit is applied to your trip balance once your departure is confirmed.
Ideal for:
- Friends who ride together
- Cycling clubs and annual group adventures
- Families celebrating milestone birthdays, anniversaries, and reunions
- Affinity groups and special-interest organizations
Private Group Tour Pricing and Benefits:
Our private departures are ideally designed for 10–16 guests, where the experience is at its most dynamic and the value is at its best.
- 10 guests: Standard advertised tour price.
- 11–16 guests: Enjoy preferred group pricing, with savings that increase as your group grows.
- Ciclismo Alumni: Alumni may combine their Group Savings with up to $200 in Alumni Early Sign-Up Savings.*
- Group Organizers: Enjoy exclusive organizer benefits as our way of thanking you for bringing your group together.
Private group pricing and savings are based on the final confirmed group size and are applied to your final balance. Groups of fewer than 10 are always welcome. Because many of the costs of operating a private departure remain the same regardless of group size, pricing is adjusted to maintain the exceptional guides, support, accommodations, and personalized service that define every Ciclismo journey.
* The maximum Alumni Early Sign-Up Savings that may be combined with Group Savings is $200. No other promotions, discounts, or offers may be combined.
3. Create a Custom Tour
You dream it. We design it. This is Ciclismo Your Way at its most personal.
Tell us what you imagine—not just where you want to go, but how you want to feel—and we’ll bring it to life. A ride through hidden villages, a vineyard celebration at sunset, a journey where cycling, culture, and connection come together in a way that feels entirely your own. With decades of experience designing award-winning journeys across Italy and beyond, we know how to listen—and how to turn your ideas into something truly special. From a custom jersey for your group to a private dinner with a local chef, to a surprise moment you didn’t see coming—but will never forget—this is where the details matter, and the unexpected becomes the highlight.
Perfect for:
- Milestone celebrations and once-in-a-lifetime moments
- Affinity groups and shared passions
- Travelers seeking something deeply personal
Pricing:
Each custom journey is designed individually based on your group, destination, and level of experience. A one-time design fee applies.
How It Works
How It WorksSimple. Thoughtful. Guided every step of the way.
Start the Conversation by Calling 1-800-866-7314
Tell us about your group and what you’re dreaming of- whether private or customer, we can do it all!
Find the Right Fit
We guide you toward the best path—private, custom, or join
Refine & Confirm
We shape the details and bring your journey into focus
Travel with Confidence
We handle everything—so you can simply ride, connect, and enjoy
Peace of Mind Guaranteed
What Our Private and Custom Groups Feel
“This wasn’t just a trip—it was something we’ll talk about for years.”
“We showed up, and everything just flowed. It felt effortless—and deeply personal.”
“We didn’t just visit places—we experienced something real.”
Make It an Experience Before the Trip Begins
Why not start the journey together?
Schedule a Zoom Info Session with Ciclismo Founder Lauren Hefferon. Add a glass of wine, gather your friends, and turn it into a relaxed, inspiring “Zoom Party.”
Because the experience begins long before the first pedal stroke.
Sign up for a Zoom Info Session
Travel with your people.
Pedal your passion.
Transform your life—one pedal stroke at a time.