Italy Guided Bike Tour / Best of Tuscany
This tour will be accompanied by Chuck & Judy Nichols
Riding across Italy is a rare chance to see, f eel and taste the wonderful differences that Tuscany has to offer. The food and wine is legendary and the scenery is the Italy you dream about. Beginning in Cortona, Tuscany, we ride through vast rolling hills covered with wheat fields and vineyards topped with picturesque hilltop towns all the way to Porto Santo Stefano, a picturesque Italian gem on the western coast. This town boasts a rich maritime heritage along with breathtaking natural scenery.
The classic charm of Italy is picture book perfect with stately farmhouses set amid a patchwork of green fields silhouetted with Cyprus trees. Vineyards line the quiet country roads and acres of sunflowers bathe in pastel sunlight. Our route passes through several renowned wine regions as it takes us to some of Italy’s most interesting hill top towns. Enjoy strolling the narrow winding streets that lead to magnificent cathedrals and grand plazas with charming shops and sidewalk cafes.
The accommodations we have selected reflect the warmth and hospitality of the region and feature a splendid assortment of charming country inns that provide a real sense of living history. The scrumptious meals served on the tour are made with local ingredients and seasoned with tasty olive oil and fresh herbs. You will have a chance to sample some of Italy’s best cheeses and most famous wines.
2026 Price: €3,450 Euros per person double occupancy
Price Includes:
- 7 nights lodging
- all meals lunches and dinners beginning with dinner on day 1
- van support and luggage transfers
- Chuck and Judy Nichols will accompany this tour
International flights, beverages, lunches
Tour Difficulty
This is a moderately difficult trip. Daily distances are between 50 – 85 km with elevation gains of 1,000 meters on several days
- Difficulty: Moderate
- Road Conditions: Paved
- Recommended Bike: Carbon Road bikes, Hybrid bikes, Electric Hybrid and Electric Road bikes
Tour Highlights
- Chianti vineyards to the Eturscan coast
- Upgraded inns with 2 nights in most villas
- 2 wine tastings
- Excellent gastronomy and renowned wine regions
- Tuscany’s most interesting hill top towns
- Medieval villages
- Shorter distances and relaxed pace
Itinerary
September 27, Day 1: Arrival in Cortona
The classic hill town of Cortona dates back to Etruscan times and was the home of Frances Mayes of “Under the Tuscan Sun” fame. Our hotel is situated just steps from the main Piazza in Cortona. We’ll meet in the late afternoon for a bike fitting, followed by dinner in the square.
Day 2: Cortona Loop ride (50 km, 1,000 m.)
Our ride today dips into Umbria where you’ll enjoy scenic overlooks of Lake Trasimeno. We’ll ride seldom used backroads returning to Cortona for one last night.
Day 3: Cortona – Montepulciano – Monticchiello – Bagno Vignoni (70 km, 850 m)
We ride through the iconic hilltowns of Montepulicano and Monticello. Cycling through the vineyards of Vino Noble, having lunch in a piazza iin Montepulicano, cycling down the famous switchbacks to Monticchiello for a gelato stop en route to Bagno Vignoni – life is good! Our home for the next 2 nights is in the countryside – a little paradise with a swimming pool just a short walk away from the hamlet of Bagno Vignoni.
Day 4: Bagno Vignoni – Montalcino – Sant Antimo Abbey loop ride (55 km, 1000 m)
Layover day. This will be a great spot to satisfy a variety of desires for the day. Bagno Vignoni is a short distance away and this is a spa town. There is also a wonderful loop ride to the vineyards of Montalcino, a 13th century paradise and the home of Brunello wine. The route continues to the abbey of Saint Antimo, a well preserved 12th-century monastery that still echoes with Gregorian chants. Then you’ll return to Bagno Vignoni for another night.
Day 5: Bagno Vignoni – Sorano (74 km, 1080 m)
You’ll cycle up to Arcidosso on the slope of Mt. Amiata and then enjoy a great downhill as you enter the Maremma region in the very southern tip of Tuscany where the vegetation and climate are greatly influenced by the Mediterranean. Your destination for the next 2 nights is the tiny hamlet of Sovana.
Day 6: Loop Ride Sorano – Ptigliano, Saturnia (75 km, 1100 m)
Cycle the splendid route in the Maremma region of Tuscany. This spectacular stretch of roads is literally carved into the tufa There are many options today to shorten the route if you prefer. Sorano is a very picturesque ancient city perched on a cliff. Saturnia is known for its thermal baths.
Day 7: Sorano to Port Santo Stefano, on the sea! (85 km, 800 m)
Our final ride takes us from the Maremma region of Tuscany all of the way to the Mediterranean. Our hotel tonight is on a small beach on the sea.
October 4, Day 8: Tour ends after breakfast
There is a train station in nearby Orbetello and private transfers can also be arranged.