Meet your guide and bikes at 5:30 pm at the hotel in the city center of Lucca. We will all get to know one another by embarking on our first excursion together into the old town with a local guide and a food crawl! Enjoy Lucca!

Guide: Included for the day

Meals: Lunch, Dinner

From Lucca to San Miniato: 46 kilometers on mostly flat roads with sections of wide trails and paths through wooded sections. Depart on a bike from Lucca after having ridden around the famous ancient city walls and visiting the historical city center. Following the pilgrimage route, we ride our bikes along footpaths and back streets where we meet fellow cyclists and pilgrims traveling the path on foot. The slow pace of the ride really allows you to see a part of Italy that cannot be experienced by car or train. See the little old Italian ladies hanging up their laundry as you greet them with a hearty “Buon Giorno!” Today is a good warm-up to the day that follows which is a bit more hilly. Lunch will be at a local eatery along the way and lodging for the night is in the town of San Miniato, internationally known for its amazing white truffles! Dinner will be a group outing at a very local Trattoria.

Meals: Breakfast, Lunch, Dinner

San Miniato to San Gimignano: 42 kilometers; welcome to the Tuscan hills! Moderately difficult to difficult. Our morning starts out with a downhill experience… after that, it’s up and down as we make our way over and through the Val D’Elsa to the Manhattan of Tuscany: San Gimignano with all its remaining medieval towers and a UNESCO World Heritage Site! A challenging uphill section from Castelfiorentino to Gambassi Terme will stoke our appetites for a lunch stop at the top of the hill. After lunch, the terrain is still a bit rolling but we have the vineyards of Vernaccia wine grapes to feast our eyes upon and we will perhaps even stop to snack on some grapes. We reach our destination in the late afternoon, time enough to wander the city and maybe have a gelato…but we don’t want to ruin our dinner!

Meals: Breakfast, Lunch, Dinner

San Gimignano to Siena: 51 kilometers; from one UNESCO World Heritage Site to another! We continue up and down through the breathtaking scenery of the Tuscan hills to Colle Val d’Elsa where we can stop for a cafe. The itinerary takes us through another beautiful section of the Via Francigena; a meditative bike path along the Elsa river where you will be surrounded by the silence of the river valley away from any traffic noise and the hustle and bustle of daily life. Our next stop is Pieve di Strove with its Romanesque interiors, then on to the splendid Abbadia at Isola, with its imposing abbey that has been a pilgrimage resting stop for centuries! The lunch stop today is at a long-standing eatery for Sienese locals that is located in the shadow of medieval walls, Monteriggioni. We will then reach Siena through some dirt roads, passing by the medieval hamlet of Cerbaia. An unforgettable way to celebrate your arrival! Maybe with a glass of wine and a wedge of panforte (a local Sienese specialty fruitcake) in the illuminated Piazza del Campo. We suggest you book a hotel in Siena a spend at least a day exploring this other important destination in Tuscany.

Meals: Breakfast, Lunch