Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You'll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you'll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.
You’ll start with a scenic transfer to the medieval “town of towers,” San Gimignano. Enjoy views of beautiful Tuscany and take a detour to explore the fortress of Monteriggioni. This perfectly preserved castle features a complete ring of walls and turrets built in the 13th century and mentioned by Dante in his Divine Comedy.
Once in San Gimignano, you’ll stroll through the streets and admire the landmarks. Recognized as a UNESCO World Heritage Site, the entire town is a testimony to medieval architecture, with many austere towers that have survived the centuries. Follow your guide along the ancient Via Francigena route, the road that travelers and pilgrims from all over Europe once used to reach Rome and St Peter’s tomb. Stop to visit churches, towers, and museums, and enjoy free time to peruse artisanal boutiques filled with local products. Many shops sell saffron, known as the town’s “red gold,” and the centuries-old Vernaccia white wine, Italy’s first white wine to obtain DOCG status.
After lots of exploring, it’s time for lunch at a quaint family-run farm. Enjoy a spread of wholesome, traditional dishes prepared with seasonal products, including local saffron spice and Vernaccia wine. Afterward, head toward the Chianti region, where you’ll visit a winery and meet the local producer of Chianti Classico DOCG wines. Explore the cellars, discover the wine-making process, taste the various flavors and blends, and distinguish these traditional wines.
Read more about unique and interesting activities in Tuscany and culinary experiences in Italy.
Itineraries with Val D’ Elsa Wine Tasting in Tuscany
Off-the-Beaten-Path Greece & Italy Road Trip: Lake Garda, Bologna, Tuscany, Olympia, Nafplio, & More - 21 Days
Explore the back roads and small villages that characterize the countrysides of both Italy and Greece on this three-week road trip. You'll visit well-known highlights, like Florence, charming Tuscan hill towns, and the first Olympic site in Olympia, as well as some places a bit off the beaten path: Romeo and Juliet's Verona, the medieval villages of the Peloponnese, the wineries of Nemea, and more. With full control of the daily driving schedule, you'll have time to plan for spontaneous stops for coffee, for shopping at roadside markets, and for late-afternoon beach breaks.
Indulge your taste buds on this Tuscan tour, visiting beautiful vineyards and medieval towns like Siena, Volterra, and San Gimignano, where you'll enjoy the flavors of the region with wine tastings and traditional, locally-sourced cuisine. Explore ancient cobblestone streets and monuments, enjoy the old Cypress trees of Bolgheri, and sleep soundly in your cozy farmhouse accommodation. End your trip on the rocky coast of Cinque Terre where you'll enjoy more wine and regional foods, plus one last stop at the Leaning Tower of Pisa.