The Experience

History, Hills & Heavenly Flavors in the Heart of Tuscany

You’ve found the sweet spot. It’s in that classic tableau of vineyard-draped hillsides and medieval villages. It’s on your table, tucked between the earthy flavors of pappardelle al cinghiale and the rich aroma of local porcini and tartufo nero. It’s in your glass – because you just discovered that a superb Chianti Classico tastes even better after a day of biking from one village to the next. It’s all around you, in the welcoming smiles of our local Tuscan friends, chefs and winemakers. This is how vacations were meant to be. Sweet indeed.

Return from your trip with actual know-how to create a Tuscan dinner for your famiglia back home – it’s the ultimate keepsake!

Journey into the heart of Chianti – and back in time – to sensational Siena and Radda

Shadow the hilly course of L’Eroica, Tuscany’s internationally recognized vintage bike race

In ancient cellars, taste superb Tuscan wines, from Chianti Classico to Vino Nobile di Montepulciano

Overnight in distinctive hotels where you’re welcomed like family



Days 1-2 Climb the ridges and cruise the downhills in the beautiful Val di Chiana Kick off the week in true Tuscan style with a grigliata mista under the stars Flex your cycling muscles on a ride through the Val d’Orcia’s rolling hills Explore the Renaissance gem of Pienza, pausing to taste pecorino cheese and southern Tuscan wines Prepare a traditional meal, from l’antipasto to i dolci.

Day 3 An exclusive wine tasting at Fèlsina estate, one of the finest producers of Chianti Classico View the bare chalk hills rising above woods and vineyards as you approach quintessential Chianti Stroll through grand piazze and alleyways, soaking up the medieval charm of Siena Treat yourself to a slice of Sienese panforte and local vin santo.

Day 4 Pedal through oak-shaded valleys and castle-crowned hills, watching the landscape alternate between perfectly symmetrical vineyards, gnarled olive trees and ancient forests Admire hand-painted pottery at Ceramiche Rampini, then explore the shops and markets of Radda in Chianti At a private olive oil tasting, learn why Tuscany’s “liquid gold” is beloved around the world Create a four-course Tuscan spread in a local kitchen.

Days 5-6 World-famous Chianti vineyards provide a stunning backdrop for our ride Relax over a cappuccino in lively Castellina While your handmade pizza bubbles in the wood-fired oven, gaze across the valley to the villa where Mona Lisa once lived Visit the famed butcher shop of Dario Cecchini, who stocks specially prepared salts and medieval seasonings Enjoy a traditional osteria experience at Il Papavero, where our friends introduce you to classic Tuscan dishes with an elegant twist Treat yourself to a morning spin before returning to Florence


The Route

Start with our vacation planner so we can match you with our most suitable travel advisor. We do it all for you, air, car, accommodations, tours, you name, it in a seamless luxury vacation experience you will treasure for a lifetime.