VÉLOSKI VINES & CLIMBS “UNPLUGGED” BICYCLE TOUR OF TUSCANY
May 30, 2025 to June 15, 2025
Tuscany elicits visions of rolling hills covered with vineyards, wheat, olive orchards and cypress trees, all dotted with villas and Etruscan
villages perched atop the highest hills. We envisioned a different approach to a cycle tour of Tuscany when we first started making plans to
return after many years of absence. The notion was to “unplug” from the tourist squirrel cage. To that end we created a blend of
characteristically old Tuscan villas and villages throughout the landscape as seen from roads less traveled. And we added a mixture of
lodging and dining experiences to the tour to better appreciate the rich variety of flavors and personalities that are quintessential Toscana!
May 30, 2025 to June 15, 2025
Day 1 Florence, Italy (Firenze)
Arrival day May 30, 2025
3 routes
5-40 miles : 460-3730 feet climbing
Welcome to Firenze, the birthplace of the Renaissance and one of our
favorite cities! Our lodging in Florence offers a unique experience to
reside in an Italian villa built in the Liberty style in 1917. Each room is
uniquely arranged within the family villa and in a central location from
which to explore Florence. A variety of restaurants are within an easy
walk. Our hostess, Angelina, is a wealth of knowledge and willing to share
her knowledge of local sites and roads.
BELOW IS A SAMPLE ITINERARY AND MAY VARY FROM OUR ACTUAL TRIP.
Day 2
Laterina, Italy
43 miles : 3300 feet climbing
Departing Florence, our route begins by heading toward Arezzo. Parked cars will line the road for the first few kilometers! Heading into the Florentine Hills, near the town of San Donato, a compelling wine and olive oil factory dominates the hilltop. Fattoria Torre A Cona is an 18th century villa whose cellars protected famous works of Michelangelo and Donatello during WWII, including statues of the Medici Chapels and the Duomo of Florence. The ride from Florence to Le Fornaci is the perfect introduction to Tuscany along curving undulating roads, amid vineyards and ancient olive groves. Enjoy the colorful tapestry of Tuscany. Le Fornaci will welcome you with a swimming pool, and an evening of extensive wine tasting, local cheese, and foods.
Day 3,4
Cortona, Italy
47 miles : 3200 feet climbing
Stay Over Day
2 route options
22-37 miles: 1760-4390 feet climbing
Our ride from Laterina to Cortona is rewarded with lodging within the walled city at the Hotel San Michele. Cortona is perhaps best known these days as the setting for the book and movie “Under the Tuscan Sun”.
Our stay over day will allow for resting and perusing the museums, art galleries or going for a ride through nearby villages. Gorgeous, hillside Cortona has a long history dating back even before its time as an important Etruscan center. Top attractions include the Duomo (Cathedral), the small Museo Diocesano across the piazza with its superb art collection, and the fascinating Museo dell’Accademia Etrusca with its assembly of Etruscan and Roman era items. Cortona is also bursting with splendid churches spanning many periods.
Day 5, 6
San Quirico d’Orcia, Italy
3 routes
39-44 miles : 2720-3700 feet climbing
Day 6
San Quirico d’Orcia
3 routes
26-48 miles : 2800-4250 feet climbing
San Quirico is a quiet contrast to Cortona. Approximately 2,500 inhabitants, San Quirico was once a main stop on the road connecting Northern Italy to Rome. Travelers continue stopping here to enjoy a walk thru town to admire ancient architecture, modern shops or sit at a sidewalk café to sip a café.
Horti Leonini, late Renaissance gardens were created in 1575 during the rebuilding of walls damaged in the war between Siena and Florence, the gardens today also include a modern rose garden and statues created in the 1990’s. Enjoy a gelato from one of several options and stroll through the gardens. Or perhaps a day by the picturesque pool reading and napping is the perfect activity. Our “stayover day” cycling options are many and varied along roads less traveled, including a few portions of the nearby Strada Bianca roads of l’Eroica-Gaiole or l’Eroica-Montalcino.
Day 7
Montalcino
2 routes
28-48 miles : 2800-4200 feet climbing
Montalcino is the city of Brunello red wines. The medieval town is dominated by the imposing Rocca or fortress built in 1361. And, for Strada Bianca enthusiasts we have created a route that includes portions of the l’Eroica-Montalcino. Legend has it that first kisses at sunset on top of the fortress walls seal relationships for life. Enjoy!
Days 8, 9
Massa Marritima, Italy
2 routes
50-60 miles : 3800-5200 feet climbing
Massa Marittima loop riding options
4 routes
13-35 miles : 1200-3500 feet climbing
Today descend from Montalcino toward the sea through vineyards, farms and olive groves. The roads are well paved with very little traffic and grand vistas of distant hilltop towns. Paganico marks the culmination of our major descent from Montalcino. Stairstep climbs are generally brief as we follow ridgelines upward toward Massa Marittima. The routes traverse sparsely populated countryside with a few small town cafes and restaurants.
For the rest day, Loops to the sea, quiet roads to nearby hilltop villages or perusal of shops and museums.
Day 10 & 11
Volterra, Italy
2 routes
43-60 miles : 3600-6500 feet climbing
Day 11
Volterra loops
2 routes
26 or 28 miles : 2680 or 2750 feet climbing
Different initial descents from Volterra; same returning climbs
Volterra’s rich Roman and Etruscan history are waiting for you to explore and enjoy! Our two night stay will provide time to explore Volterra. Plenty of shopping opportunities here for alabaster stone keepsakes, jewelry, leather or bronze goods. You can rent an AudioGuide at the Tourist Information Office (Ufficio Turistico) in Piazza dei Priori 20 to learn more about the Roman amphitheater and other Etruscan history
Day 12
San Gimignano
2 routes
26-36 miles : 2000-3100 feet climbing
No tour of Tuscany is complete without a visit to the famous towers of San Gimignano, so we will arrive in time for lunch within the old walls of iconic San Gimignano. Enjoy this famous Tuscan town, photographed for its many towers. Towers were added fortification to wealthy homeowners houses during the medieval times. Enjoy!! We have organized a wine tasting at Poderi Arcangelo to sip some of their wines as well as olive oil. Then we will enjoy a countryside dinner on the terrace overlooking vineyards and olive groves. Evening light bathes San Gimignano
Days 13, 14, 15
Castellina in Chianti
3 routes
28-36 miles : 3000-3800 feet climbing
Days 14 & 15 – Castellina in Chianti activities to enjoy
3 routes
15-35 miles : 1250-3280 feet climbing
Three nights in this charming town will allow for a day trip into Siena, wine tasting at the Mazzei Winery and dinner in Osteria di Fonterutoli, or leisurely rides in the Chianti region. Another beautiful hillside location, with pool, and lovely views from the decks of the hotel.
Days 14 & 15 – Castellina in Chianti activities to enjoy
Chianti – wine, territory, lifestyle blend the fertile hills with a life all it’s own.
Siena – about an hour by bus to experience the central piazza, Duomo, tower and arcades
NOTE: check bus schedule with Reception the day before you plan to go to Siena (9:00 & 12:00 departs)
Radda in Chianti — notable vinoteka (wine tasting shops), beautiful country ride
Gaiole in Chianti – notably the start of the l’Eroica-Gaiole with numerous sections of Strada Bianca (White Roads). For you enjoyment we have created a few routes that include the fabled Strada Bianca roads too.
Poggibonsi – super fun curvy road gently sloping down to town from Castellina in Chianti
Monteriggioni — built between 1213 and 1219, roughly circular walls with 14 towers…nice lunch stop
Fonterutoli Castel – we met Francesco Mazzei at Trattoria Sbandati in Bend during a special wine pairing dinner a few Winters ago.. He loves cycling and making exceptional wines.
Day 16
Florence, Italy
32 miles : 2000 feet climbing
Our final day of riding returns to Firenze, climbs and descends gentle grades along ridges overlooking vineyards and olive groves to Greve in Chianti; . The piazza or town square offers a variety of shops, gelato, coffee, or lunch options. The Museo del Vino is open from 11:00AM – 4:30PM. Continuing from Greve we continue downstream on beautifully paved roads, where we climb a ridge to Impruneta for a final café lunch. The final 15km to Firenze is a ridge surfers delight, culminating in a sweeping traverse to Piazza Michelangelo and down to our hotel. Farewell dinner with one of our favorite local restaurants is always a great time of sharing stories of memorable experiences of Tuscany Unplugged.
DAY 17 — DEPARTURES
June 15, 2025
We will transfer you to Florence, Italy Florence Airport (FLR) (Amerigo Vespucci Aerporto) June 15, 2025.
We bid you a fond arrivederci! Until next time!!!
ARRIVAL PLANNING
May 30, 2025 – latest date to arrive into Florence, Italy. Florence Airport (FLR)
Extra Nights can be arranged for guests who arrive prior to 30 May or depart post 15 June, Airport Transfers will be on your own if you arrive early or depart after the trip ends.
DEPARTURE PLANNING
June 15, 2025 – We will transfer you Florence Airport (FLR), Italy and bid you a found farewell until next time!