Off-the-Beaten-Path Tuscany and Umbria Exploration Itinerary

Begin your day with a scenic drive to Montalcino. Visit the Montalcino Fortress (Fortezza di Montalcino) and enjoy panoramic views of the vineyards. Have a light breakfast at a local cafe.

Delight your taste buds with a From Florence Small Group Wine Tasting Tour to Tuscany in the renowned wine region. Pair the wines with local cheeses and cured meats. For lunch, savor the flavors of Tuscany at Il Canto del Maggio.

Relax in the evening with a leisurely walk through the charming streets of Montalcino. Enjoy a dinner featuring the region's specialties at La Grotta di Montepulciano.

Explore the Basilica of Santa Maria Assunta (Duomo di San Gimignano) and the Medieval Criminal and Torture Museum in San Gimignano. Grab a quick breakfast at a local cafe.

Enjoy a From Florence Day Trip Pisa, Siena & San Gimignano w/Lunch with a stop in this medieval hilltop town. For lunch, taste the local cuisine at La Taverna di San Giuseppe.

Witness the sunset from the Rocca of Montestaffoli and have a relaxed dinner at Antica Trattoria Botteganova, known for its traditional Tuscan dishes.

Explore the charming town of Pienza, known for its Pienza Cathedral (Duomo) and Palazzo Piccolomini. Enjoy a leisurely breakfast at a local cafe.

Take a scenic drive through the Val d'Orcia and visit the Abbey of Sant'Antimo. Stop for a rustic Tuscan lunch at La Bottega del Nobile.

Return to Pienza for a relaxed evening. Dine at Ristorante Il Falconiere, a Michelin-starred restaurant offering a refined dining experience.

Journey to the picturesque town of Orvieto and visit the Orvieto Cathedral (Duomo di Orvieto) and the Pozzo di San Patrizio. Enjoy a traditional Umbrian breakfast at a local cafe.

Explore the Orvieto Underground and the National Archaeological Museum of Orvieto. For lunch, taste the local specialties at Ristorante La Torre.

Take a leisurely stroll through the medieval streets of Orvieto. Enjoy a dinner with panoramic views at Cibrèo Ristorante Firenze.

Discover the Etruscan and Renaissance heritage of Cortona with a visit to the Diocesan Museum (Museo Diocesano) and the Fortezza del Girifalco. Enjoy a cappuccino at a local cafe.

Stroll through the Piazza della Repubblica and the Medieval Quarter. For lunch, savor the local cuisine at Osteria La Porta.

Relax in the evening with a glass of wine at La Bottega del Nobile. Enjoy a dinner at La Grotta di Montepulciano, known for its traditional Tuscan dishes.

Explore the Siena Cathedral (Duomo) and the Piazza del Campo. Have a classic Sienese breakfast at a local cafe.

Visit the Museo dell'Opera del Duomo and the Palazzo Pubblico and Torre del Mangia. For lunch, enjoy the traditional Tuscan flavors at Trattoria Da Burde.

Conclude your trip with a memorable dinner at Enoteca I Terzi, known for its extensive wine selection and Tuscan dishes. Enjoy a leisurely evening in the historic center of Siena.