Sample Itinerary…

All tours are custom designed by our experts based on your travel dates and desired destinations, with your specific interests in mind. Please contact Plan-it Italy by phone or email, or complete the online form, to receive a no-obligation proposal, including a preliminary itinerary and estimated travel costs.

Tour of Tuscany & Umbria

The timeless beauty of Tuscany and Umbria has been spoken of, and seen, in many forms in our culture. You can experience these two extraordinary regions for yourself with visits to charming hill towns, wineries, villas and sumptuous gardens. Take part in a cooking class, visit an olive oil and cheese-producing farm, and follow the footsteps of Italy’s most famous artists and saints as you journey through breathtaking countryside..

• Arrive at Rome’s Leonardo da Vinci Airport. Meet your tour escort and driver and transfer to the beautiful hill town of Spello in Umbria. Stroll through the charming center and relax with amazing countryside vistas in every direction.

• On day two, depart for Assisi. Meet your local guide and follow the footsteps of St. Francis as you stroll through the medieval walkways, drawing in the breathtaking views of the surrounding countryside and a visit to Basilica di San Francesco. An afternoon departure takes you to the olive groves where you will meet another guide who shares a demonstration and tasting on the types of olive oil.

• Transfer this day to Southern Tuscany to the village of Pienza. En route is a visit to Cortona, made famous by Frances Mayes’ novel, Under the Tuscan Sun. Pienza is in the middle of sheep country; a village of refined art in a setting of pastoral charm.

• Spend the morning of day five ingesting more sites of Pienza. In the afternoon depart for the Abbey of Sant’Antimo, where the angelic chanting of the monks can be heard each day – a heavenly experience in an amazing setting. Continue to Bagno Vignoni, where you can enjoy the peace and serenity of this village with only 30 inhabitants

• Day six of your tour will start at the village of Montalcino. Situated in a blanket of vineyards, this charming village is known for its world class Brunello wine. Visit a winery to taste select vintages. Continue in the afternoon to Montepulciano. This town of walls and fortifications winds through streets crammed with Renaissance palaces. Return to Pienza with a stop at another local winery for a tasting.

• Day seven transfers you to Tuscany’s Chianti district, the most prized area of the region, known for its beautiful villages, rolling vineyards and olive groves.

• Start day eight with a scenic drive to a private villa, where you will participate in a cooking class to learn the secrets of Tuscany’s cuisine. Enjoy an authentic lunch of local specialties, and then spend the afternoon visiting area villages and a beautiful villa with lovely gardens

• Set your sites on day nine to one of Italy’s most beautiful medieval cities, Siena. Meet your local guide and make your way to the stunning Duomo. Continue through the winding streets to Piazza del Campo, where the famous Palio horse race happens twice a year. Continue in the afternoon to one of Italy’s most beautiful hill towns, San Gimignano, known for its famous towers and smart boutiques.

•• Transfer on the last day to Florence, Amerigo Vespucci Airport or extend your stay in Florence.