Guided Destination Ride
€995 – €1,695
The Great Quest. Hero’s Journey. An epic expedition of Odysseus.
Then there’s every cyclist’s pursuit of the perfect ride. That search ends right here. Take your pick from the three odysseys below (or complete the trilogy for special prizes). Yet be warned: Preparation is your ally.
Oh, the Places You'll Go
You've received the call to adventure. You could go it alone, but you need a firm grasp of reason, a sure path back home, and an indispensable enabler to make the most of life. Allow me to gladly fill that role.
- Tuscany Immersion: Lucca to Siena (150 km, 2400 m)
- Renaissance Journey: Lucca to Florence (125 km, 2200 m)
- Apennine Escape: Lucca to Bologna (185 km, 4200 m)
Click the links above to find out what kind of meraviglia comes along with each ride.
Hit the Ground Riding
Step One: Register Interest
Contact me here with your destination of choice, desired dates and, if required, your bike rental sizes.
step two: guarantee your ride/s
Guarantee availability by purchasing rides and bike rentals once your plans are confirmed.
step three: anticipate sms details
You'll receive a message via iMessage, WhatsApp, or email with all ride details two to three days before.
step four: ride high
Let's get out there and after it! 😅
Nice is Good and Excellent is Better
The clock is ticking and each day we only get older and we simply don't have time for average. My rides aren't cheap, but they're more than worth it. So much so I train year-round for them.
| Ride | Group Size | Price |
|---|---|---|
| Lucca to Siena | 1 - 5 | Starting at €995 |
| Lucca to Bologna | 1 - 5 | Starting at €1295 |
| Lucca to Florence | 1 - 5 | Starting at €995 |
Prices exclude travel insurance and bike rentals. We provide bars, gels and a private Mercedes shuttle back to Lucca.
Book with Confidence
If you need to cancel, we refund 50% of the booking value up to 14 days before the ride date. Should you cancel within 14 days of the ride date, the entire booking will be non-refundable.
Please take a few minutes to review our cancellation policies and strong recommendation for travel insurance by clicking here.
Biking with Benefits
Fitness Points Gauranteed
Endorphin Booster
Memories Promised
Slow Travel Approved
I take my job as Top Guide to heart, and my clients agree it's well worth it.
Cycling Tips
She became my first cycling coach when I turned professional and has continued to guide, encourage, and challenge me throughout my career.
alison jackson, oly
Vermilion, Canada
Newbie
As a #newbie, it was an absolute privilege to take on cycling in the Italian countryside with Alison.
josh goldstein
Los Angeles, USA
Guided Tour
Is Alison a guide or a coach? Hard to say — I honestly think we got 2 for 1!
alex pagnotta
Montreal, Canada
Guided Tour
My guided ride with Alison in the hills around Lucca was the most fun I've ever had on a bike!
jeremiah benge
Pittsburgh, USA
Training Partner
I practically got a training camp and a guided tour!
andriy derevyanko
Kyiv, Ukraine
Florence
Alison's love of cycling and Italy is truly inspiring for both the somewhat new to cycling and the lifetime aficionado.
annie & matt
Texas, USA
Cycling Tips
I had an amazing ride!
bonnie leung
Vancouver, Canada
Training Partner
It was a perfect day.
jared spier
Winnipeg, Canada
Tour Guide
Riding with Alison is a gift.
chet scott
Ohio, USA
Newbie
I had never ridden on a road bike before, but Alison was an incredible coach providing me with the best tips and tricks and within the first few kilometers, I felt very comfortable and confident on the road.
jess liu
New York, USA
Guided Tour
She immediately put my fears to rest and led me through parts of the landscape that I would have surely missed left to my own resources.
steve chase
Carbondale, USA
Lucca to Siena
At the risk of hyperbole, riding from Lucca to Siena is a transcendent experience.
chris bail
Chapel Hill, USA
Guided Tour
It was worth every penny.
victoria stokes
United Kingdom
Guided Tour
After our last trip, I was so inspired by her that I took up cycling and have been training every day since.
emily
Montreal, Quebec
Guided Tour
I didn't expect to find an ex-national champion to ride with who'd tow me along at 40km/h one minute and the next ride side by side talking about Lucchese lifestyle, setting up a business, sports psychology and life as a pro-rider.
simon hunt
London, United Kingdom
Training Partner
It was my first time in Tuscany, and I wanted to see all the beautiful scenery around as well as having some good training days.
patrick
Oslo, Norway
Florence
After getting home, I found myself shopping for — and buying — a new road bike.
jon
Pittsburgh, USA
Guided Tour
Humbled, appreciative, and unforgettable cycling in Lucca/Tuscany.
bob levin
Los Angeles, USA
Guided Tour
The decision to ride your bike through the hills of Tuscany is easy, but it can go downhill quickly if you're not with the right guide. Alison is that right guide!
lorenzo grigio
Boulder, Colorado
Cycling Tips
After riding with Alison, I learned the technique to descend in control, take my time on the corners, and ride with confidence.
karen paterson
Uxbridge, Canada
Guided Tour
Alison designed rides that were perfect for our ability — I'm 71 and my wife is 70.
bob & lisa
Mill Valley, California
Guided Tour
With gratitude for the uncommon experience of cycling Lucca.
dan & friends
Minneapolis, Minnesota
Guided Tour
I could never have had "this experience" on my own without an amazing guide.
brady wilson
Guelph, Ontario
Lucca to Siena
Alison's Destination Ride from Lucca to Siena should be on every cyclist's bucket list.
david vernon
Kigali, Rwanda
Guided Tour
We will always remember this trip and be grateful to the kind souls we met along the way.
joanna
Alabama, USA
Guided Tour
It's been a dream come true to ride here.
gord & cindy
Langley, British Columbia
