Overview

You'll meet your guides in Florence, a marvel of Renaissance art and where you'll find the Uffizi galleries, the Duomo, and the Galleria dell'Accademia, home of Michaelangelo's David. From here you'll take a one-hour private shuttle to the charming town of Villa a Sesta. After a delicious Tuscan, picnic-style lunch, you'll be fit to your Trek Checkpoint gravel bike, and then we're off on a rolling, scenic ride through stunning cypress trees and to the impressive Abbadia a Monastero, a monastery dating back to the 9th century. We'll arrive at our hotel where you can relax, unpack, and prepare for our first night's dinner and social hour at the hotel.

Overview

Buongiorno! We arise in Chianti with an appetite for a hearty breakfast and a menu of adventure. Today you will cover some of the most beautiful roads in the area. After a brief warmup on the pavement, you'll turn onto the gravel roads toward the historic, medieval towns of Vagliagli and Radda. In centuries past these limestone-white, unpaved roads, known by their Italian name strade bianche, were the only connections between those villages! We'll stop for lunch at a cafe of your choosing in Gaiole, a small Tuscan village with a unique history of vintage cycling. Don’t miss a visit to the Eroica cycling store to learn more about the local cycling event with riders decked out in full vintage regalia, and pick up a souvenir and signature caffè latte. After lunch, we'll continue winding through fragrant vineyards to the cypress-lined entrance of Castello di Brolio, the famous castle that has been the home of the Ricasoli family for 800 years. The afternoon is yours for relaxing at the hotel before we gather for a chef-inspired pizza dinner in the evening.

Overview

It's another spectacular day of cycling discovery and adventure as you follow the white gravel routes featured in one of Italy’s most famous pro races, taking you to beautiful Siena, the start and finish point to the race. In this picturesque town you can enjoy the views while sipping your macchiato in the vibrant Piazza del Campo, Siena’s main historic square and local meeting point. From Siena, you'll head south through the almost lunar landscape of Crete Senesi to Buonconvento, where we'll stop for a special lunch with incredible, sweeping views of Tuscan rolling hills. With 360 degree vistas, you can appreciate the contrast between the dense vineyards of Chianti and the vast, rolling fields of Val d'Orcia. We arrive this afternoon at our destination, an elegant luxury agriturismo, that has a unique perspective on the traditions of this beautiful region. Tonight, your guides will shuttle you to the nearby walled fortress of Montalcino for a dinner of your choice.

Overview

Rise today with a cappuccino in preparation for some of the region's most stunning views. Our ride today takes us to the hills of Val d'Orcia. The Val d'Orcia is an incredible agricultural landscape that is a UNESCO World Heritage site due to its continued adherence to Renaissance layout and aesthetic. It is like cycling inside a painting! You'll continue through the medieval villages of San Quirico d’Orcia and Pienza, with buildings dating to the 15th century and epic views from every hilltop. Don't forget to stop and savor the scenery and maybe even take a few pictures before we head back to the hotel. We'll gather this evening for a private wine tasting and immerse ourselves in the captivating world of superb Tuscan wines. Tonight, we celebrate a week's worth of memories with a special dinner prepared with seasonal ingredients sourced straight from the hotel farm and perfectly paired with select local vintages. We'll toast together and recap the highlights of an incredible week!

Overview

It's sadly time to say farewell to this Signature Tuscan unpaved adventure. Choose to rise early for one last glorious spin at the base of Montalcino through lush, fragrant vineyards as a warm sun rises over the Tuscan countryside. Or, skip the ride and savour a cappuccino at the hotel, recounting the memories of a week well-spent. However you say goodbye to the sumptuous heart of Italy, you'll be sure to take a small bit of it in your soul as you leave.