Private & Custom Tours
Ciclismo Your Way — Pedal Your Passion
You don’t just travel together.
You share something that stays with you.
At Ciclismo Classico, we don’t simply design bike tours—we create experiences that become part of your life story. Moments that unfold on quiet roads, around long tables, and in the company of people who matter.
With Ciclismo Your Way, that experience becomes deeply personal—shaped by your group, your pace, and your vision.
For over 35 years, we’ve brought people together through the simple, powerful act of riding a bike. And somewhere along the way, something happens. A rhythm forms. Laughter comes easier. Strangers become friends. Friends become La Famiglia.
That’s the Ciclismo Magic.
Here’s a little insider secret: nearly 20% of our journeys are private or custom, often created to celebrate milestone birthdays, anniversaries, reunions, and once-in-a-lifetime moments.
Simply arrive, ride, connect, and let it unfold.
Peace of Mind Guaranteed.
Transform your life—one pedal stroke at a time.
Which Option is Right for You?
1. 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 →
2. 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 →
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. Reserve a Private Tour Departure
Make one of our journeys entirely your own.
Choose a favorite Ciclismo itinerary and experience it exclusively with your group in a reserved private departure—either by reserving an existing departure or selecting dates that work best for you. These are journeys refined over decades, where every turn in the road, every café stop, every moment has been thoughtfully considered.
But what makes it special is not just where you go—it’s who you share it with.
Ideal for:
- Friends who ride together and want to experience something deeper
- Cycling clubs and annual group trips
- Families celebrating meaningful moments
This is where the journey becomes yours. The group finds its rhythm. The days begin to flow. And before long, something shifts—you’re no longer just traveling. You’re sharing something real.
Private Group Tour Pricing & Benefits
For a private group of 10, the tour is priced at our standard advertised rate.
As your private group grows, so does the value. Private groups of 11–18 receive $400 per person savings,
Alumni, if you reserve early—before our Alumni savings period ends—you’ll enjoy an additional $200 per person savings*
Because these savings depend on the final private group size, they are deducted from your final balance is sent.
Smaller groups are always welcome to travel privately, with adjusted pricing to ensure the same high level of care and experience.
Our private departures are ideally designed for 10–16 guests—where the energy is right, the connections deepen, and the experience feels complete.
All the beauty of a perfected journey—shared only with your people.
* The max alumni early sign-up savings that can be combined with the group savings is $200
2. 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:
- 2–8 friends or couples
- 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
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 celebration in a vineyard at sunset. A journey that blends cycling, culture, and connection in a way that feels uniquely yours.
Our team brings decades of experience designing award-winning journeys across Italy and beyond. But more importantly, we know how to listen—and how to translate your ideas into something extraordinary.
A custom jersey for your group. A private dinner with a local chef. A surprise moment you didn’t see coming—but will never forget.
This is where the details matter. Where the unexpected becomes the highlight. Where your custom group becomes something more than a group.
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.
A fully bespoke experience—crafted with intention, care, and a touch of Ciclismo magic.
Ride, connect, and savor every moment—we’ll take care of the rest.
How It Works
Simple. 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.