Guided Destination Ride
€995 – €1,695
The Great Quest. Hero’s Journey. An epic expedition of Odysseus.
Then there’s every cyclists' pursuit of the perfect ride. That search ends right here. Take your pick from the following three odysseys (or complete the trilogy for special prizes). Yet be warned: Preparation is your ally.
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 making the most of life.
Allow me to gladly fill that role.
| 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.
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.
For answers to your top questions and to contact me, click here.
Spend €750 on Guided Rides and request a complimentary Region & Ride Guide.
Peak season Guided Rides fill months in advance. Please check the availability of your desired dates before booking.
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.
She became my first cycling coach when I turned professional and has continued to guide, encourage, and challenge me throughout my career.
Before I met Alison, I knew of her accomplishments in professional cycling. When I met her, I was so excited that she was willing to ride with me and share her stories and experiences. She became my first cycling coach when I turned professional and has continued to guide, encourage, and challenge me throughout my career.
In 2021, I achieved one of my top goals of earning the title Olympian, which is an accomplishment attributed to my positive beginnings in the sport.
Surround yourself with amazing people, like Alison, and some of their greatness will rub off on you, too. I can't recommend riding with Alison highly enough.
ALISON JACKSON, OLYMPIAN
Abbotsford, Canada
Newbie
As a #newbie, it was an absolute privilege to take on cycling in the Italian country side with Alison.
As a #newbie, it was an absolute privilege to take on cycling in the Italian country side with Alison and Lucca Cycling Club.
Just think about it. A sleek Ferrari red road bike arrives at your apartment or hotel, and Alison is outside the next morning to take you on the Chianti Classico, Fiesole and Monte Morello or Consuma and Vallombrosa, depending on the time of year, weather, and what you are looking for.
But first, she will make sure you are dialed in your kit, which in my case included a trip to the local bike shop to switch out cleats. You will learn more from three days riding with Alison than you would from months or years riding on your own. From technique and positioning to routes, destinations, gear, and (critically) cycling fashion, Alison delivers at the highest level. If you are like me, you want to learn from the best, so what are you waiting for?
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!
Is Alison a guide or a coach? Hard to say — I honestly think we got 2 for 1!
I recently organized a trip there for my daughter and me, and my biggest issue was safety and would Emily be able to handle it. Hooking up with Alison was the best thing I could’ve done. Is Alison a guide or a coach? Hard to say — I honestly think we got 2 for 1! Every day, Alison showed up with safe and suitable rides for a 15-year-old girl who decided to join a local cycling team upon her return.
For me, born in Italy and brought to North America before I could see the beauty of Italy, riding with Alison was the best sightseeing tour ever. My biggest regret is that I only stayed a week, but a week spent with a wonderful person that shared her passion for cycling with us.
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!
My guided ride with Alison in the hills around Lucca was the most fun I've ever had on a bike!
The roads and views were amazing, and the whole experience was perfectly tailored for me. I loved learning about the area and hearing about some of the local cycling culture, and it was just the right balance of challenging climbs and easy cruising along the seaside.
In addition, I took advantage of Alison's DIY guide, which allowed me to do a couple of rides on my own on spectacular routes I would never have discovered on my own. Together, these things were the absolute highlight of my time in Tuscany.
JEREMIAH BENGE
Pittsburgh, USA
Training Partner
I practically got a training camp and a guided tour!
I practically got a training camp and a guided tour!
I strategically positioned to spend my family summer holiday around Lucca before my first ever Ironman 70.3 bringing a great chance to strengthen my climbing skills. Four days riding 1200-1800m of daily elevation were an excellent challenge for my body and mind. But I got one crucial thing: confidence that I'm able to make my most important climb this season.
I would also like to highlight how seriously Alison took my requirements. She asked to share my Ironman course, then crafted our training routes accordingly. I was very impressed on our first day to see the route which almost completely repeated the profile of my future race. Last but not least, Alison knows the best gelato shop in the region. I took a 15-minute detour to show that place to my friends and family. It was simply delicious!
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.
Alison’s love of cycling and Italy is truly inspiring for both the somewhat new to cycling and the lifetime aficionado.
This review is penned equally by the “somewhat new to cycling” and “aficionado.” We were staying in Florence, so Alison met us there — with bars, a smile and a sense of adventure. Alison planned a day filled with an amazing route, delicious pastry/sandwich shops (food always first), and every kilometer filled with history and breathtaking vistas. Those are the things that make riding with Alison so special. As far as riding goes, Alison is happy to ride at a conversational pace, at full tilt or anywhere in between, so whatever your riding ability, she is happy to oblige.
One of the highlights was meeting The Butcher of Panzano (as in “Butcher Shop” — not Sweeney Todd). Such a character and beware of his endless bottle of Chianti… Aficionado deeply appreciated the Gino Bartali plaque that Alison shared in the Panzano town square. There is not enough word count here to talk about all the other experiences except that we can’t wait to return.
Our two-day booking turned into a three-day booking and a 2023 trip planned with Alison. On the next trip, we will get to sample some post-ride gelato from the “best gelato ever” as it was closed when we went this time — that and some amazing, fun and beautiful riding. 🙂
ANNIE & MATT
Texas, USA
Cycling Tips
I had an amazing ride!
I had an amazing ride with Alison!
I made a spur of the moment decision to go cycling alone while on a trip with girlfriends. I have not ridden outside of Canada, so I wanted some guidance and along came Alison. She was very responsive to my questions before signing up. I didn't have any expectations in terms of where to cycle other than some mountains with a view. I met up with her in Lucca and we went on a 125km ride around the local mountains, stopping for some coffee and amazing pizza on the way. She showed me some amazing views of the region and provided some history about where we were. She even gave me some cycling tips to improve on my techniques. I couldn't have asked for a better guide. I would definitely ride with her again.
BONNIE LEUNG
Vancouver, Canada
Training Partner
It was a perfect day.
It was a perfect day.
I tasked Alison with designing a ride to Siena, coming into the piazza using the finish from the Eroica Pro race. It was an experience that was important to me, as it represented a really precious memory with someone I loved and lost.
Alison designed a route for us that started and finished in Volterra, featured a bit of strade bianche on the way and took us through beautiful countryside and climbs... but it was the route into town that was the highlight. Not only did she find a quiet way to get right onto the final roads, but as we rode those last WVA-killing, 15-20% pitches, she had the strength to pull out her phone and capture images and video of the ride - and we weren't going slow.
Even beyond the route, and the gelato (also very good), the most impressive part of the day was riding with someone who gave me the time to take it all in and had the empathy to understand when I needed an extra moment to reflect on things.
That ride couldn't have achieved all it did without a guide as special as Alison.
JARED SPIER
Winnipeg, Canada
Tour Guide
Riding with Alison is a gift.
Riding with Alison is a gift.
She is a pro who can ride you into the pavement if you prefer. She is a friend who is comfortable to ride tempo beside you and talk about Joseph Campbell and the meaning of it all. We rode together for only two days. I know Lucca like a good friend - Alison too.
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.
Riding with Alison through Lucca Cycling Club is an absolute must if you want to see the most beautiful parts of Tuscany and learn the thrill of road cycling.
Though I had taken indoor cycling classes prior to the trip, 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.
Though I had only planned on one solo ride at first, after our first session, I was totally hooked and signed up for another ride as well as a group ride with my whole family. Alison not only showed me the breathtakingly picturesque backroads of Tuscany, but also how exhilarating a challenging ride of 50+ km with tough climbs can be. Alison couldn’t have been a better, more encouraging coach, challenging me in the best way possible and coaching me through any issues I was having.
I had visited Italy a few times before, but this was undoubtedly the most memorable experience I’ve had and a trip I will remember for a lifetime. As a newly converted cyclist, I hope to visit again and ride with Alison, but next time as an even more advanced rider!
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.
Both Lucca and Alison are gems that I will look forward to revisiting in the future.
Over our years of visiting many parts of Italy, often by bicycle, we were overwhelmed by our time in Lucca. The city is often overshadowed by the "big names" — Rome, Florence and Venice, but after our week enjoying this unique city and the nearby attractions of Pisa, Cinque Terre and the wonderful villages in the mountains and forests of the Garfagnana to the north, we will not be distracted again. We will return!
The icing on the cake for me was my guided ride through the countryside surrounding Lucca by Alison Testroete, the former Canadian National Champion and the principal of the Lucca Cycling Club. At my age, I was a bit intimidated by signing on with Alison for a ride, but 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.
At the risk of hyperbole, riding from Lucca to Siena is a transcendent experience.
Cycling through the ancient walls of Lucca and the surrounding farmland to climb into the misty hills of Tuscany is simply awe-inspiring. Soon your heart will be pumping on the climb to Volterra before you fly through descents, gravel, and flats into the final climb… this ride has it all.
CHRIS BAIL
Chapel Hill, USA
Guided Tour
It was worth every penny.
Cycling with Ali was one of the best experiences we had during our holiday in Tuscany.
She was just so helpful from beginning to end, from booking the hire bikes to finding the best route for my husband and me. Our capabilities are very different, but Ali managed to find a ride that was perfect for both of us with amazing cafe and restaurant stops along the way. The whole day was so relaxed, and I would thoroughly recommend it to anyone of any ability. I had booked this in for my husband's birthday as a surprise and it was worth every penny - we still talk about it now because we enjoyed it so much! Thank you so much once again, Ali!
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.