Itinerary
- Day 1
Pisa
You'll arrive in Pisa and get settled into your accommodation. The city's main draw is Piazza dei Miracoli, where you'll find that famous leaning tower (it's a UNESCO World Heritage Site from 1987). Spend the rest of the day wandering around at your own pace and getting a feel for the university town atmosphere.
Optional Activities
- Visit Piazza dei Miracoli square
- See the Leaning Tower of Pisa
- Explore the bell tower of the city cathedral
- Discover the university city atmosphere
Landmarks Leaning Tower of Pisa Piazza dei Miracoli Cathedral Bell Tower 
- Day 2
Pisa to Casciana Terme
Your cycling journey starts along the Arno river heading toward Pontedera. You'll stop at Castellani winery and the Amedei chocolate factory, then pedal through olive groves and vineyards. By afternoon you'll reach Casciana Terme, a spa town with Etruscan history and thermal baths that were discovered way back in the 11th century. It's about 50 km total with 290m of climbing and 180m descent.
- Meals
- Breakfast
Included Activities
- Cycling tour from Pisa to Casciana Terme
- Visit Castellani winery
- Visit Amedei chocolate factory
Optional Activities
- Explore thermal baths at Casciana Terme
- Learn about Etruscan history
Landmarks Castellani winery Amedei chocolate factory Casciana Terme - Day 3
Casciana Terme to San Gimignano
Cycle along the Via Francigena through vineyards and rolling terrain to San Gimignano, a medieval walled village with towers perched on a hilltop and listed by UNESCO. Plan on dinner with local food later. The route covers roughly 50 km with 755m ascent and 545m descent. If you'd rather overnight elsewhere, there's the option to go to Colle Val d'Elsa instead at 70 km with more climbing involved (1000m up, 980m down).
- Meals
- Breakfast
Included Activities
- Cycling tour from Casciana Terme to San Gimignano
Optional Activities
- Explore San Gimignano's medieval towers
- Dine at local restaurants in San Gimignano
- Alternative overnight location: Colle Val d'Elsa
Landmarks San Gimignano 
- Day 4
San Gimignano to Siena
Continue on the Via Francigena with views of Montemaggio and Monteriggioni (the fortress Dante mentioned in his writing) along the way. You'll arrive in Siena by day's end, where the medieval brick buildings and Torre del Mangia tower are hard to miss. This stage runs about 45 km with 740m of climbing and 675m descent. If you're coming from Colle Val d'Elsa, it's a shorter 25 km day with 445m up and 242m down.
- Meals
- Breakfast
Included Activities
- Cycling tour to Siena
Optional Activities
- Visit Monteriggioni fortress
- Explore Siena's medieval architecture
- Climb Torre del Mangia tower
Landmarks Monteriggioni Torre del Mangia Siena 
- Day 5
Siena to Greve in Chianti
Cycle to Castagnolli and visit Brolio Castle, a historic wine estate owned by the Ricasoli family. From there you'll head through Radda in Chianti, a classic wine village with Etruscan roots, then on to Panzano before finishing in Greve in Chianti (they host a Chianti Classico wine festival each September). Around 55 km for the day with 935m elevation gain and 1045m descent.
- Meals
- Breakfast
Included Activities
- Cycling tour through Chianti region
- Visit Brolio Castle and wine cellar
Optional Activities
- Wine tasting at Ricasoli family wine cellar
- Explore Radda in Chianti
- Visit Panzano
- Attend Chianti Classico wine festival (September)
Landmarks Brolio Castle Radda in Chianti Panzano Greve in Chianti - Day 6
Greve in Chianti to Florence
On your final cycling day, head to Mercatale to check out local wine cellars, then continue to Impruneta, which is known for its terracotta work. You'll finish in Florence, the Tuscan capital and birthplace of the Renaissance, filled with palaces, churches, monuments, and art throughout the city. It's roughly 35 km with 660m ascent and 840m descent.
- Meals
- Breakfast
Included Activities
- Cycling tour to Florence
Optional Activities
- Visit wine cellars at Mercatale
- Explore Impruneta's terracotta art
- Discover Florence's Renaissance architecture and art
Landmarks Mercatale Impruneta Florence 
- Day 7
Florence
After breakfast, you'll depart.
- Meals
- Breakfast
