STARTING AT
$4299
per person
Italy's Quintessential Cycling Tour: The Tuscany Region
Tuscany is beautiful in a way that only makes sense from a bike saddle — at the speed where you can smell the wild rosemary, hear the gravel of the strade bianche beneath your wheels, and actually stop when a hilltop village demands it.
This is a week spent moving through one of the world's most storied landscapes: sun-drenched valleys, cypress-lined roads, vineyards that have been producing wine since before anyone was keeping records. By day you ride. By evening you eat very well, drink better, and sit with people who are quickly becoming your favorite travel companions.
No museums required. No tour buses. Just the roads the locals use, the places they eat, and eight days that will recalibrate your definition of a good trip.
DAY 1
Day One: Arrival in Florence
ARRIVAL You land in Florence and shuttle to San Gimignano.
EVENING After checking in to the La Collegiata Hotel, join the group for an authentic Florentine dinner.
MEALS Dinner
ACCOMMODATIONS La Collegiata Hotel
DAY 2
Day Two: San Gimignano to Siena | 45KM
Ride out of San Gimignano on quiet country roads through rolling hills, vineyards, and olive groves.
At midday, stop at Fattoria Castello di Monteriggioni for a picnic lunch in the vineyard, followed by a tasting of the estate's wines.
In the afternoon, pass the walled village of Monteriggioni and continue on to Siena. Spend the evening exploring the Piazza del Campo and the city's historic center.
ACTIVITIES Vineyard picnic · Wine tasting
MEALS Breakfast | Lunch | Dinner
ACCOMMODATIONS Hotel Athena
DAY 3
Day Three: Siena Loop through the Crete Senesi | 55KM
Head south from Siena into the Crete Senesi, a landscape of soft clay hills, open farmland, and cypress-lined roads that looks unlike anywhere else in Tuscany.
Ride to the small medieval town of Asciano for a break before continuing on to Tenuta La Campana. Here, join a local truffle hunter and their dogs to search for truffles in the surrounding countryside.
Return to Siena in the afternoon, with the evening free to relax or explore.
ACTIVITIES: Riding through Crete Senesi landscape · Truffle hunting
MEALS Breakfast | Lunch | Dinner
ACCOMMODATIONS Hotel Athena
DAY 4
Day Four: Siena to Radda in Chianti | 40KM
Today we leave Siena and ride north into the Chianti Classico region, where the roads wind past vineyards, olive groves, and stone farmhouses.
Stop at Castello di Brolio, the historic home of the Ricasoli family, where the original Chianti wine recipe was created. Tour the grounds and enjoy a tasting of the estate's wines.
Continue on to Radda in Chianti, a small medieval village set high in the hills, and spend the evening in the heart of wine country.
ACTIVITIES: Wine Tasting
MEALS Breakfast | Lunch | Dinner
ACCOMMODATIONS Reais & Spa Vignale
DAY 5
Day Five: Radda in Chianti Loop | 30KM
Enjoy a shorter ride today through the heart of Chianti. Follow quiet roads past vineyards and forests to Castellina in Chianti, a hilltop village with views across the valley.
Stop at Castelvecchi for a wine tasting, then return to Radda with the afternoon free to relax, explore the village, or linger over a long Tuscan dinner.
ACTIVITIES: Wine Tasting
MEALS Breakfast | Lunch | Dinner
ACCOMMODATIONS Relais & Spa Vignale
DAY 6
Day Six: Radda in Chianti to Florence | 50KM
Say goodbye to Chianti as you ride north through vineyards and rolling hills, with the final stretch bringing you into Florence.
After arriving, enjoy lunch on your own before a guided walking tour of the city, with stops at Florence's most famous sights and the stories behind them.
In the evening, join a real Florentine Nonna in her kitchen for a hands-on pasta making class, then sit down together to enjoy the dinner you've made.
ACTIVITIES: City Tour Florence | Pasta Making with Nonna
MEALS Breakfast | Dinner
ACCOMMODATIONS Hotel Cavour
DAY 7
Day Seven: Florence Departure
Today marks the end of our journey in Tuscany, and we must prepare to depart from the tour. As we reflect on the memories we've made, we feel a sense of bittersweet emotion. While we're sad to leave this beautiful place behind, we're also excited for the adventures that await us in the future.
We'll always cherish the moments we spent here, and the people we met along the way. As we say our final goodbyes, we'll carry the spirit of Tuscany with us wherever we go.
MEALS Breakfast
DATES & PRICING
October 18-24, 2027
7 DAYS / 6 NIGHTS starting at $4299 per person double occupancy
Limited Spaces
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La Collegiata Hotel
La Collegiata Hotel
La Collegiata, now a charming hotel, was originally built in 1587 as a Capuchin friars’ convent thanks to the will of the local community. The first historical traces date back to the cistern engraving of 1589 and the convent’s consecration in 1599.
San Gimignano, famous for its medieval towers, still preserves its authentic charm. The convent and the adjoining church, from which the hotel takes its name, feature an architectural style predating the late Renaissance. During the Napoleonic era, the convent was occupied and abandoned, but today La Collegiata is a unique place where history and hospitality meet.
Hotel Athena Siena
Hotel Athena Siena
4-star, family-run hotel located inside the historic walls of Siena, Italy, offering classic Tuscan rooms and a panoramic rooftop terrace.
The undisputed highlight of the property is the San Marco Terrazza, the hotel's panoramic rooftop bar. It offers a breathtaking 180-degree view that perfectly balances two worlds: to one side, you look out over the ancient tile roofs and stone walls of medieval Siena; to the other, the rolling green hills of the Tuscan countryside. It is widely considered one of the best golden hour spots in the city to sip a Chianti or enjoy a sunset aperitif.
Even though it feels tucked away and peaceful on the edge of the walls, you are incredibly close to the action. It is only about an 8-to-10-minute stroll up charming, historic streets to the jaw-dropping (Duomo) and the iconic Piazza del Campo (where the famous Palio horse race takes place). You get the quiet nights of the edge of town, but zero transit stress.
Relais & Spa Vignale
Relais & Spa Vignale
What makes the Relais exceptional is its blend of right in the middle of a medieval Tuscan village. Instead of being an isolated countryside resort, it sits directly on the edge of the town of Radda, meaning you can walk right out into cobblestone alleyways for dinner, yet open your bedroom shutters to panoramic views of rolling vineyards.
The estate holds massive historical significance for wine lovers. It is one of the historic homes where the Chianti Classico Gallo Nero (Black Rooster) Consortium was originally conceived. The villa dates back to 1750 and still retains its original family crest on a massive stone fireplace, ancient water wells, period frescoes, and its own private 18th-century chapel.
Hotel Cavour
Hotel Cavour
Hotel Cavour offers a mix of rich history, such as being housed in a 13th-century Florentine mansion where Dante Alighieri famously met Beatrice... and trendy modern amenities like rooftop terrace bars with stunning cathedral views.
The location is unbeatable. You are a 3-minute walk from the Piazza del Duomo and less than 10 minutes from the Uffizi Gallery and Ponte Vecchio
Perfect for our last night together!
