Tuscany and lesser-known Umbria are two of Italy’s most beautiful—and bountiful—regions. Sitting next to each other in the center of Italy, both boast cypress trees, olive groves, medieval hill towns, and vineyards galore. That said, both are also famous for their fantastic food and wine.
On this 11-day tour, you’ll soak up Rome’s passionate street culture and then travel to the laid-back Umbrian region to wander the cobbled lanes of Orvieto. You’ll ogle the medieval fortress in Spigeto and get an Umbrian cooking lesson inside of a 16th-century farmhouse. Next, you’ll be whisked to Montefalco and sip the region’s most prized wine, Sagrantino, and visit a family-run frantoio (olive presser). The beauty of Assisi will simply beguile you, and then it’s on to Tuscany’s Val d’Orcia region where more wine tasting awaits. Feast on Tuscan cuisine and world-class art in Florence, and then explore the charming Tuscan villages of Siena, Monteriggioni, San Gimignano, and Volterra.
Itinerary / 11 days
PLAN YOUR TRIP
DAY 1Night Flight to Rome
Slip on your eye pillow at 30,000 feet—you’re on your way to one of the world’s most romantic cities: Rome. Few cities can rival Rome’s ancient statues, world-class museums, Byzantine mosaics, and Renaissance frescoes. Oh, did we mention the food and wine? Rest up, it’s going to be a tantalizing 11-day journey.
DAY 2Rome's Dolce Vita
A trip to Rome is as much about living the dolce vita lifestyle as it is about gorging on art and incredible food. Wander around Rome’s picturesque streets, ogle the Baroque fountains, lounge at street-side cafes, and people-watch on pretty piazzas. In between cappuccinos and Chiantis, admire ancient icons such as the Colosseum, Pantheon, and St. Peter’s Basilica.
Later, join the stylish aperitivo (pre-dinner drinks) crowd and then move on to meet your travel group over a delicious welcome dinner.
Later, join the stylish aperitivo (pre-dinner drinks) crowd and then move on to meet your travel group over a delicious welcome dinner.
DAY 3Cinematic Umbria: Orvieto
Today, you’ll travel 1.5 hours north into the Etruscan hills and to Orvieto, a town riddled with vines and olive trees. Nestled in the Umbrian region, this area has kept many of its charming old-world traditions. Stroll the historic streets as a local expert points out the city’s treasures such as Piazza Duomo, the Medieval Quarter, and the soul-stirring Gothic cathedral.
In the afternoon, you’ll be free to wander solo. Eat, drink, and soak up the local culture with a glass of Pinot Nero in hand and a tartufo (truffle) on your fork. Take it in slowly, you’ll have the next four nights to embrace these rustic Umbrian splendors.
In the afternoon, you’ll be free to wander solo. Eat, drink, and soak up the local culture with a glass of Pinot Nero in hand and a tartufo (truffle) on your fork. Take it in slowly, you’ll have the next four nights to embrace these rustic Umbrian splendors.
DAY 4Culinary Umbria: Spoleto
On day four, you’ll travel about 1.5 hours to ancient Spoleto. This stunning town is presided over by a formidable medieval fortress and the Apennines—and it’s also a historical picnic. Take a walking tour through the city’s streets and ogle centuries of architectural history, from the Ponte delle Torri aqueduct to the gilded elegance of the Duomo of Santa Maria Assunta. In the afternoon, explore Spoleto’s shops and cafes at your whim.
Few travelers get to experience a country restaurant nestled inside of a 16th-century farmhouse, but this evening, after exploring the farm’s herb garden and cheese-making process, you’ll join the restaurant’s chef for a hands-on cooking lesson and then dine in the countryside.
Few travelers get to experience a country restaurant nestled inside of a 16th-century farmhouse, but this evening, after exploring the farm’s herb garden and cheese-making process, you’ll join the restaurant’s chef for a hands-on cooking lesson and then dine in the countryside.
DAY 5Montefalco and Bevagna
Today, it’s a short hop to the medieval town of Montefalco—and it’s a giant step back in time. Montefalco is called the “Balcony of Umbria” because of its unobstructed views of the countryside, so soak in the vistas. Next up: the region’s most-prized wine, Sagrantino, as you head to a local winery for a tasting and sampling of authentic Umbrian dishes. Then you’ll head about five miles north and to Bevagna for a walking tour that highlights the town’s Roman and medieval architecture. Cap the day off at a family-run frantoio (olive presser).
DAY 6Assisi
Prepare to be enraptured by the town of Assisi, the birthplace of St. Francis. The mere sight of it is beguiling—with its pristinely preserved medieval Centro Storico and UNESCO-listed Franciscan structures—and today, you’ll take a walking tour of the old city with a local guide. Explore the medieval streets and wander into the famed Basilica of St. Francis.
Later, a local family will welcome you into their country home for a delicious homemade lunch. Prepare to make an Umbrian friend or two.
Later, a local family will welcome you into their country home for a delicious homemade lunch. Prepare to make an Umbrian friend or two.
DAY 7Tuscany: the Val d’Orcia Region
On day seven, travel a few hours northwest and to the sunflower-covered hills of Tuscany’s Val d’Orcia region. With lyrical landscapes, rolling vineyards, olive groves, and a superb cucina contadina (farmer’s kitchen), Val d’Orcia is a UNESCO World Heritage Site worth savoring.
In Tuscany, locals spend an inordinate amount of time talking about food and wine. Join the conversation during a tour of a local winery’s family estate and enjoy a Tuscan lunch, created by the winery’s chef and paired with the vineyard’s own wines. Afterwards, relax at a restored Tuscan palazzo.
In Tuscany, locals spend an inordinate amount of time talking about food and wine. Join the conversation during a tour of a local winery’s family estate and enjoy a Tuscan lunch, created by the winery’s chef and paired with the vineyard’s own wines. Afterwards, relax at a restored Tuscan palazzo.
DAY 8Feast on Florence
Today, you’ll visit legendary Florence, the “Cradle of the Renaissance.” Romantic, enchanting, and utterly delicious, Florence is a place to feast on world-class art and gourmet Tuscan cuisine—and you’ll do both today. Explore the city with a local guide on a walking tour to Cathedral of Santa Maria del Fiore in the religious center of the Piazza del Duomo. You’ll also visit the Palazzo Vecchio and tap into Florence’s creative side at a local artisans’ botteghe (workshop). Afterwards, wander off on your own and get lost in the boutiques, trattorias, and museum
DAY 9Siena and Monteriggioni
Today is yet another incredible adventure, this time to the medieval Siena. Take a guided walking tour of this stunning town, visit the Piazza del Campo, and learn about the world-famous Palio Horse Race. After the tour, you can decide if you’d like to explore Siena’s Gothic cathedral or if you’d rather experience local life by visiting a contrada (a small local community). Later on, take a trip back in time with a walk through the walled town of Monteriggioni.
Day 10Volterra and San Gimignano
On day 10, you’ll wake up and be whisked 1.5 hours southwest to the “City of Alabaster,” Volterra. A former Etruscan city, this walled town perched high above the countryside dates back to the 7th-century BC. You’ll spend time inside the Guarnacci Museum, one of the oldest public museums in Europe, and then watch a live alabaster-carving demonstration. Next, you’ll travel to the nearby San Gimignano to see for yourself why it’s called the “City of Beautiful Towers.” Stroll the Piazza del Duomo and Piazza della Cistema in the shadows of 13th-century medieval towers, and later, enjoy a delicious farewell dinner and wine presentation from an expert sommelier.
DAY 11Head Home
On your final day, you’ll venture up almost 1,000 feet and to the medieval village of Montaione. Set on a hill, the village is surrounded by vineyards and olive trees. In short, it’s an idyllic Tuscan setting and the perfect place to spend your last morning. Meditate on all the greenery, art, and delicious food and wine you’ve savored over the last days. Remember the people you’ve met, the history you’ve witnessed, and the farm-fresh pastas and Sagrantino you’ve sipped. As you head back to Florence for your flight home, your cup truly overfloweth.