Overview

Welcome to your Tuscany cycling trip! A two-hour shuttle will deliver you to your starting point for today's ride, a countryside trattoria set among the rolling hills of the Val d’orcia. After a delicious Tuscan lunch, your Trek Travel guides will ensure that you have an excellent fit to your Trek bicycle while offering specific cycling tips for riding in Italy. You’ll then start with a rolling, scenic loop ride among the cypress trees and olive groves to our first hotel in the charming medieval village of San Quirico d’Orcia. This evening, you and your companions will gather for an Italian aperitif on the hotel terrace before an exceptional dinner at our favorite restaurant in the heart of San Quirico. Enjoy a selection of traditional dishes with a modern twist, paired with a unique selection of regional wines.

Overview

This morning’s route lifts you high above the Val d’Orcia, a vista dotted with rolling hills blanketed with vines and rows of cypress. Your first stop is a tiny Roman spa town of Bagno Vignoni, known for its hot sulfurous springs. The town plaza is filled with a pool built by the Medici family centuries ago, where you can refresh your feet before you continue your ride to Abbazia di Sant’Antimo, a stunning 12th-century Romanesque abbey. If you're lucky, you may arrive to the choral harmonies of the monks' Gregorian chants—it is positively magical! Our lunch destination today is the walled village of Montalcino, whose 14th-century fortress and steep cobblestone streets dominate the surrounding countryside. Here you can discover the delights of Brunello wine, one of the finest Italian varietals together with lunch at the trattoria of your choice. Cycle back along winding roads or reward yourself with a shuttle and more time to enjoy yourself back at the hotel. This afternoon relax by the pool and perhaps order a sunset cocktail. This evening is yours to explore the cobbled streets of San Quirico to enjoy dinner at one of the many small bistros on your own.

Overview

Today you’ll head north into one of Italy’s most loved regions, Chianti. You will follow winding ribbons of road along cypress-lined ridges into the Crete Senesi, These hills, distinguished by the dramatic colors of the soil and blessed with some of the most stunning views in Tuscany, are sure to take your breath away. Our destination is the picturesque Chianti village of Villa Sesta and a charming bistro set in this historic village which dates back over 1200 years. Sit back, relax, and enjoy some local farm to table cuisine. From here, choose to ride or shuttle the last stretch to Il Borgo di Vescine our boutique hotel nestled amongst the Chianti vineyards. Check-in, relax and enjoy a dip in the pool or take a walk through the flowered pathways of this historic hamlet. This evening you’ll dine in the hotel’s La Torre Bistrot and relish another Tuscan sunset.

Overview

Don’t forget your camera today as you descend into the valley where vines and olive trees give way to shady chestnut trees as the landscape subtly shifts and changes. Stop to visit the Castello di Brolio and its famous L’Eroica caffè, home to great espresso and cool cycling memorabilia. For lunch we'll stop at Bar Dante in Radda in Chianti. Our hosts, Fabrizio and Carolyn pride themselves on serving the best bruschetta in Radda, if not all of Tuscany, washed down with a glass of local Chianti. Following lunch, continue your ride to the tiny village of Lucarelli and join the locals for the ritual of mid-afternoon espresso. Alternatively, choose to wander the tiny streets of Radda. Buy a local bike jersey or some delicious Tuscan olive oil before shuttling back to the hotel to relax and enjoy the pool. This evening is yours to explore Castellina in Chianti; wander the medieval cobblestone streets before discovering the Via della Volte, an impressive and historic tunnel that is now a fascinating walkway filled with artisan boutiques and restaurants. Enjoy a family-style dinner in town on the piazza, or perhaps something a little more romantic, while savoring the picturesque views and unique atmosphere of this charming village.

Overview

Following your morning cappuccino, get ready to enjoy stunning views of Siena’s towers amid the vine-covered hills on the route today. Surrounded by ancient stone walls, wildflowers, and the scent and shade of the forest, you leave the 21st century far behind. Along the way, you’ll pause to enjoy a fresh picnic lunch, featuring hand-cured prosciutto and local cheeses accompanied by delicious Frantoio olive oil. Once back on the bike, enjoy the impressive views of the walled town of Monteriggioni, perched on a hilltop and dominated by 14 dramatic towers. Stop for an espresso or mid-afternoon gelato on one of the many terraces lining the piazza, before embarking on an exploration of this enchanting city. Shuttle back to the hotel from here or continue riding through some of the leading wine-growing districts in Chianti. This evening, join your fellow travelers for a fun-filled private pizza-making session at the hotel. You will learn how to prepare a perfect Italian pizza, paired, of course, with the region's local wines. Under the guidance of an Italian pizza master, you'll use the original wood oven of the hotel, still functioning since the times when the hotel was itself a small village. Here we will toast to a week of great riding, warm fellowship, and truly phenomenal food!

Overview

It’s sadly time to bid farewell today as your Tuscany cycling trip comes to a close. Get up bright and early this morning to make the most of the stunning light and watch a bright new day unfurl over the classic Tuscan countryside. Or linger awhile over a hot cappuccino and enjoy a more leisurely paced morning in the hotel. However you say goodbye to Tuscany, you’re sure to take a little of this destination with you.