Tuscan & Umbrian Countryside

The adventure

See another side of Italy. Explore Tuscany and Umbria’s smaller, more authentic towns. Learn the secrets of Tuscan and Umbrian cuisine. Journey to Florence, the “Cradle of the Italian Renaissance.” Visit a family owned winery for a tasting and have a home-hosted lunch in a charming country home. Stop in Siena, a medieval town with one of Tuscany's most beautiful squares. Venture to Assisi for a guided walking tour of the old city. Travel to the Etruscan hill town of Orvieto, known for its white wine and Gothic cathedral. Spend time in the hill town of Volterra to visit the Guarnacci Museum and witness an alabaster carving demonstration at a local workshop. Explore San Gimignano, known as the "City of Beautiful Towers." Along the way, savor regional specialties and enjoy Italian wines with every dinner.

At a glance

Day by day

Your journey through

Italy

Showing Days 1-7

11-day itinerary

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

Overnight Flight

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

Day 2Rome, ItalyItaly’s dynamic capital city beckons. As arrival times will vary, there is no scheduled sightseeing today. Spend the day as you wish, exploring independently. Get a taste of the local culture and start your journey at a delicious welcome dinner.

Italy’s dynamic capital city beckons. As arrival times will vary, there is no scheduled sightseeing today. Spend the day as you wish, exploring independently. Get a taste of the local culture and start your journey at a delicious welcome dinner.

Day 3Rome - Spoleto - UmbriaOlive 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 a family-owned <I>frantoio</I> (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.

Rome

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 a family-owned <I>frantoio</I> (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 4UmbriaTravel 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 honoured guest. Share stories and make an Umbrian friend (or two).

Umbria

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 honoured guest. Share stories and make an Umbrian friend (or two).

Day 5UmbriaIn the shadow of the Apennines, experience Umbria’s epicurean side. Join a local truffle hunter in search of the elusive <i>fungi</i> 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.

Umbria

In the shadow of the Apennines, experience Umbria’s epicurean side. Join a local truffle hunter in search of the elusive <i>fungi</i> 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 6Umbria - Pienza, Southern TuscanyLeave Umbria for the villages of Tuscany, nestled among the rolling hills and cypress trees of the Val d’Orcia region (UNESCO). Taste the flavours of the region at a dairy farm producing prized sheep-milk <i>pecorino</i> cheese. 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. The evening is yours to eat, drink, and explore the local scene.

Umbria

Leave Umbria for the villages of Tuscany, nestled among the rolling hills and cypress trees of the Val d’Orcia region (UNESCO). Taste the flavours of the region at a dairy farm producing prized sheep-milk <i>pecorino</i> cheese. 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. The evening is yours to eat, drink, and explore the local scene.

Day 7Pienza, Southern TuscanyEmbark on a journey through the undulating landscape of the Orcia Valley. 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 <i>Brunello.</i> Tour a winery’s estate and cellar before indulging in a tasting of these noble red wines. 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.

Embark on a journey through the undulating landscape of the Orcia Valley. 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 <i>Brunello.</i> Tour a winery’s estate and cellar before indulging in a tasting of these noble red wines. 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.

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