Discover the rolling hills of Tuscany, home to sprawling vineyards, medieval hill towns, and enchanting cities.

July 12-22, 2025

On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love. Explore the Etruscan hill town of Spoleto, where the gilded façade of the cathedral rivals with the silvery sheen of the olive trees, and stroll Assisi’s old city. Hunt for truffles in Umbria. In Siena, stand inside one of Tuscany’s most ancient piazzas. Visit Florence, the “Cradle of the Renaissance.” Admire the famous towers of San Gimignano. Delight in regional specialties and Italian wine with every dinner. Feel like a local as you discover the marvels of wine, cuisine, culture, and history.

Stay

Day: 1 Overnight Flight
On a journey through Italy’s roads less traveled, discover its endless treasures from Rome to Umbria to Tuscany, and the marvels of wine, cuisine, culture, and history in between.

Day: 2 Rome, Italy - Tour Begins Dinner Kolbe Hotel Rome
Italy’s dynamic capital city beckons. Get a taste of the local culture and start your journey at a delicious welcome dinner.

Day: 3 Rome - Spoleto – Umbria Breakfast & Dinner Antica Dimora Alla Rocca
Olive and cypress trees accent the Umbrian hill town of Spoleto. Stroll the historic streets with a local expert and see centuries of architectural history, from the ruins of the Rocca Albornoz castle to the gilded elegance of the Duomo of Santa Maria Assunta. Pause at an family-owned frantoio (olive presser), where olives are pressed each November.* After learning about the many varieties of trees and oil-making methods, join a tasting of the EVOO produced at the mill. Then, take in the splendors of country life in a pristine Umbrian hill town, your home for the next 3 nights.

Day: 4 Umbria - Assisi – Umbria Breakfast & Lunch Antica Dimora Alla Rocca
Travel to Assisi, birthplace of St. Francis. Set out on a walking tour of the old city with a local guide, learning about its history as you stroll the medieval streets. Visit the famous Basilica of St. Francis. Later, a local family welcomes you to their country home for lunch as their honored guest. Share stories and make an Umbrian friend (or two)

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Day: 5 Umbria Breakfast & Lunch Antica Dimora Alla Rocca
In the shadow of the Apennines, experience Umbria’s epicurean side. Join a local truffle hunter in search of the elusive fungi in the company of his trained, truffle-sniffing dogs. Sample the goods yourself during a rustic, home-cooked lunch before returning to your hotel in the late afternoon.

Day: 6 Umbria – Pienza Breakfast & Lunch Hotel Corsignano
Leave Umbria for the villages of Tuscany, nestled among the rolling hills and cypress trees of the Val d’Orcia region (UNESCO). Taste the flavors of the region at a local pecorino cheese farm. Snack on some of the cheesemaker’s creations and take in the views of the sparse farmhouses and open fields on your way to Pienza (UNESCO), a Renaissance village where flowers and plants adorn the cobblestoned streets.

Day: 7 Pienza Breakfast Hotel Corsignano
Embark on a culinary journey through the undulating landscape of the Orcia Valley. Begin your day with a visit to an artisanal pasta factory, producing the local specialty – pici – with its organically-grown wheat. Pause in the unique hamlet of Bagno Vignoni, whose central piazza is filled with thermal water once used to cure pilgrims who stopped here on their way to Rome. Then explore hilltop Montalcino, namesake to one of Italy’s great red wines, the Brunello. Tour a winery’s estate and cellar before indulging in a multi-sensory tasting, pairing wine with music. Back in Pienza for an afternoon at leisure, maybe you’ll explore the countryside along one of the many white roads that cut through the farmland.

Day: 8 Pienza - Siena - Chianti Region Breakfast Villa San Lucchese
Take a guided walking tour through Siena, delving into the local history as you learn about the world-renowned Palio Horse Race. Enjoy free time to explore more of this hilly town, perhaps visiting its cathedral or the town hall’s frescoes. An afternoon drive through Tuscany’s Chianti Region takes you to the restored Tuscan villa** where your hotel is located.

Day: 9 Chianti Region Breakfast Villa San Lucchese
Explore Florence, the “Cradle of the Renaissance,” during an extensive walking tour in the company of a local expert. View the Ponte Vecchio, the only Florentine bridge to survive WWII. Take in the Palazzo Vecchio, where, for over 300 years, the Medici Family ruled over the city. Admire the Piazza del Duomo, richly adorned by polychrome marble and gilded bronze doors. Take some time on your own*** to explore the city’s seemingly endless treasures, before returning to your Tuscan villa in the evening.

Day: 10 Chianti Region Breakfast & Dinner Villa San Lucchese
Spend your morning in San Gimignano, whose 13th-century medieval towers stand tall over the surrounding vineyards. Nicknamed “the Manhattan of the Middle Ages,” San Gimignano’s towers soar over the landscape making its distinctive skyline stand out against the rolling hills. Taste authentic Italian gelato from an award-winning ice cream parlor while you wander the cobbled streets and gaze up at the imposing towers during time at leisure in this Tuscan gem. Return to your hotel mid-afternoon. As the sun begins to set, gather with your fellow travelers for a farewell dinner of Tuscan specialties.

Day: 11 Chianti Region - Tour Ends Breakfast
Your journey through Tuscany and Umbria comes to a close today in your restored Tuscan villa.

Deposit:  $500 per person plus optional Travel insurance 

Ellen 516 248 3496
wisewomentravelellen@gmail.com

Rates are correct at the time of printing, and are subject to change unless under deposit.