Team Tuscany - Touring the wine country

Custom planning

Team Tuscany, a group of 5 Canadian friends; Amy, Courtney, Gwen, Mike and Tom from the coast of Halifax, Nova Scotia with varying experience in recreational road cycling, approached Bicissimo with the prospect of touring Tuscany and over the border to Umbria on two wheels early in May. Their focus, naturally, would be experiencing the stunning scenery that riding through the regions offers, blended with the typical local wine and food as a reward for their efforts! After a brief exchange of route preferences during the initial custom planning stage, the Team confirmed their point-2-point schedule; starting in Florence, travelling south east to Arezzo, still in Tuscany, then crossing the border to medieval Gubbio, Umbria followed by a shorter ride day west to Cortona, before slightly detouring via Lago di Trasimeno en route to the Vini Nobile producing region of Montepulciano and working back towards Florence, stopping in Siena after traversing the Val d’Orcia and Crete Senesi.

6 transfer days between cities, would be spread over 10 days in total. The Team’s focus, was not only to see the amazing historic centres with a couple of days in each, but to really enjoy the best cycle tourism in the regions. It became obvious that carrying their own luggage on bikes would soon detract from that enjoyment as the team were happy to be self-guided throughout. This added a logistical challenge, on top of planning the most ideal bike friendly route between stops.

Tour Stats

Point-to-point self-guided riding 10 days – 6 cities/towns.

Start Florence: – Arezzo – Gubbio – Cortona – Montepulciano – Siena – Finish in Florence.

Total: 478 km, 8,300 m climbing.

Full route planning for 6 ride days.

Road bike hires and luggage transfers arranged. (accommodation/flights not included).

Optional in-ride and on-line support available when needed.

The first hurdle was securing five road bike rentals from a trusted provider for the Teams arrival in Florence, and the second was to organise luggage transfers between booked accommodation, a series of Airbnbs located in the historic centres of each destination. Planning a self-guided tour is no easy challenge, checking and verifying local cycle friendly low traffic roads, double checking turns and distances, locating reliable options for well timed stops and sites of interest. So it was a pleasure to offer a luggage transfer service and the chance to experience some of the incredible route Bicissimo had planned for Team Tuscany, and that everyone was looking forward to.

After a final pre-trip video call with the whole Team, the first time I would meet them offline in Florence was on their departure, Day 1 to Arezzo.

Luggage Transfer

Incisa

Loro Cuiffenna

Incisa

Strada del Vino

Montevarchi Plain

Monte Amiata

Val d’Orcia

Firenze – Arezzo – Gubbio

As planned, once in Italy Team Tuscany were ready to meet me with luggage outside the bike rental and were looking forward to setting off. They had already checked over their rental bikes the day before and ridden up to Piazza Michelangelo. On the tight streets of Florence there was only room to say ‘Ciao’ and do a quick on-road pick-up, before the queue of scooters became too irrate. A more formal welcome came half way up the first climb out of Florence on the road to Incisa. After a brief pause on the lovely view point in the full spring warmth and sun, the Team tackled the rest of the stiff climb befoe the sweeping decent to the valley plain of Montevarchi.

Loro Ciuffena was the planned lunch stop town perched on the side of the hills with panoramic views overlooking the vineyards on the lower slopes. The ridge road, Strada del Vino was clearly popular with local cyclists, as I only saw a couple of cars pass while I took some pics of the area. The Team were soon onto Arezzo with steep narrow cobbled lanes, and the main piazza where the route finished for the day was crammed with historic buildings and monuments as a lovely backdrop to celebrate arrival with a few Spritz Aperols.

Ride Schedule

Day 1: Firenze to Arezzo – 84.7 km, 1,380 m

Day 3: Arezzo to Gubbio – 101 km, 1,859 m

Day 3 was Arezzo to Gubbio, and the longest day on the bike for the tour. Although the Team was enjoying the depths of the Appenines with stunning views, there was much climbing and descending to be done. I found myself in the vicinity of the Team following the luggage pick up from Arezzo, so I jumped ahead and prepared the Taverna del Verziere in Montone, Umbria for their arrival. Exquisite rabbit or truffle pasta was pranzo on the terrace overlooking the hills lining the Toscana/Umbrian border, with a cheeky bottle of rose shared between the Team. Buonissima!

Arezzo Piazza

Cortona View

Cortona Descent

Bicissimo Self-Guided

A quick tyre pressure check and and some sunscreen application followed coffee and a brief visit to the highest viewpoint in town and then Team were on their way again. The route took them deeper into the hills through Pietralunga and towards Cantiano before dropping down into the medieval town of Gubbio, with their luggage already available at the destination accommodation after I had worked around some tricky logistics getting ten rucksacks to their Aibnb tucked away at the back of the old town.

Ride Schedule

Day 5: Gubbio to Cortona – 77.7 km, 1,505 m

Day 6: Cortona to Montepulciano – 63.6 km, 916 m

Gubbio – Cortona – Montepulciano

Day 5 luggage pick up was delayed by restricted access due to the Sunday festival prelude to the iconic Festa dei Ceri. The team were well on their way to Cortona for their third ride day since leaving Florence, with a prolonged vino fuelled lunch stop in Umbertide, and not in any rush to miss out on the scenery along the valley road. The long drag up to the switch back climb into the historic centre of the walled city had tremendous views as far as Lago di Trasimeno and Monte Amiata.

Refuelled on Umbrian cuisine the evening before, the shorter Day 6 ride from Cortona to Montepulciano was also flatter, and blessed with warm weather and sun. The planned lunch stop was a lovely little Osteria in Castiglione with panoramic views of Lago di Trasimeno which were soaked up by the Team, along with much fabulous vino to fuel them to Montepulciano. As Day 6 accommodation was out of town, the Team rewarded themselves later in the day with a stop for aperativo in Montepulciano after the long steady climb up to the town wall.

Santa Maria Alla Rassinata

Montone

Monte Nerone

Cortona

Quercegrossa

Dario Panini Truck

Strade Bianche

Montepulciano – Siena – Firenze

Unfortunately on fifth ride of the tour, Day 8, some wet weather had caught up with the Team and meant that only Amy and Mike would ride to Siena that day, with the rest of the Team travelling by train. Although greyer than they were used to the days prior, a misty Val d’Orcia still has an incredible majestic feel, with vibrant greens of the hills outlined by the Cipressi. With the sun struggling to break through, riding togther, Amy and Mike had made great progress on an undulating route, as I caught up with them at a cafe in San Giovanni d’Asso purely by chance as the GPS tracking link stuggled to give me an updated location due to the poor weather. After a few pastries and coffees, the daring duo headed eagerly towards Asciano and Siena in damp conditions.

My own challenge was not just to get ahead of them, but to beat the others arriving into Siena by train. Unable to unload luggage directly at the accommodation due to Zona di Traffico Limitata (ZTL) restriction on non-authorised access, this meant laborious trips from the central car park to Piazza del Campo, or ‘ il Campo ‘ in the rain! The entire Team managed to re-group within the city for a late lunch and avoid the showers, with dry clothes waiting at their Airbnb. The next days forecast, Day 9 which was scheduled as a rest day in Siena, was much better. Those who missed out the day before managed to experience the magic of the Crete Senesi and rode the route to Asciano in reverse and back from Siena with some sun.

Ride Schedule

Day 8: Montepulciano to Siena – 73.1 km, 1,235 m

Day 10: Siena to Firenze – 77.7 km, 1,414 m

Day 10 was the final ride 6 back to Florence to complete the six city grand two-wheeled tour of Tuscany and Umbria. The Team kindly assisted me with luggage collection, even though this may have put them at a disadvantage due to an unstable weather forecast. However it remained dry as they set off north of Siena all dressed in matching Chianti Classico kit, remembering not to ride on the Piazza del Campo (which may incur a fine for cyclists). The first stop of the day was Castellina-in-Chianti, via Quercegrossa for a small bite and a sip of….Chianti obviously. As the weather became more inclement, the Team pushed on and arrived in Panzano-in-Chianti just beating a heavy hail downpour while I munched on a very tasty Panino Pastramino from the Dario Cecchini (a local Tuscan butcher and chef) Panini Truck. The Team were quickly ushered into a local gelateria by the owner to dry off and wait for the black clouds to pass, counted by the numbers of cappucinos and espressos consumed! The ridge road fom Panzano to Florence is particulaly quiet out of season, and offers fab views over the Chianti hills, while it weaves through wine estates before the fast final approach from Impruneta to Arceti and Piazza Michelangelo where the team found themselves about 480km previously. The sun had also made an appearance and their central finish in the Florentine capital was as glorious as the start, with much celebration of their achievement awaiting Team Tuscany that evening. Bravissimo!

Panino Pastramino

Panzano

Firenze

Italian bike tours with style!

Location
Kingston-Upon-Thames, Surrey, UK
Phone
UK : 0044 (0)7729 729628
IT : 0039 347 356 8789
Email
team@bicissimo.com
Office Hours : Monday to Friday (excluding National Holidays)
10:00 – 18:00 CET
Registered UK Company
08081886

What People Say About Us

We had a fantastic few days riding in Chianti, a mix of great support and self-guided rides

Rowland GroupRadda-in-Chianti

Simon designed us the perfect route from Florence to Rome over 4 days, lakes, hills, strade bianche, wine and no traffic!

The BunnellsSelf-guided point-2-point

The Val d’Orcia is a stunning area for cycling, it was well worth having expert support and guidance for our trip.

Mike JVal d’Orcia and Monte Amiata

The Bicissimo self-guided trip planning exceeded our expectations. The team provided excellent routes between our choice of destinations on a loop throughout parts of Tuscany and Umbria. If we do another trip in the future, Simon will be our first call.

Team TuscanyTouring Tuscany - Self Guided & Luggage transfers