Itinerary
- Day 1
Rome to Umbria to Tuscany
Your Italian adventure begins as you travel through Rome, Umbria, and toward Tuscany, discovering the country's hidden treasures, wine, cuisine, culture, and history along the way.
- Day 2
Rome
You'll arrive in Rome at your own pace with no scheduled activities today. Spend your time walking around independently and getting a feel for the local culture before joining a welcome dinner this evening.
- Meals
- Dinner (Welcome dinner)
Included Activities
- Welcome dinner
Optional Activities
- Independent exploration of Rome
- Day 3
Spoleto
A guided walk through Spoleto takes you through historic streets where you'll see the Rocca Albornoz castle ruins and the Duomo of Santa Maria Assunta. After that, head to a family-owned olive mill to learn how oil production works and try some EVOO. You'll then check into your accommodation for the next 3 nights.
- Meals
- Breakfast
Included Activities
- Guided walking tour of Spoleto with local expert
- Visit Rocca Albornoz castle ruins
- Visit Duomo of Santa Maria Assunta
- Tour family-owned frantoio (olive presser)
- Extra virgin olive oil (EVOO) tasting at the mill
Landmarks/POIs Rocca Albornoz Duomo of Santa Maria Assunta - Day 4
Assisi
Travel to Assisi this morning, the birthplace of St. Francis. A guided walking tour takes you through medieval streets and you'll visit the famous Basilica of St. Francis. Later, lunch happens at a local family's country home where you'll be their honored guest.
- Meals
- Breakfast, Lunch (Lunch at local family's country home)
Included Activities
- Travel to Assisi
- Guided walking tour of old city with local guide
- Visit Basilica of St. Francis
- Lunch at local family's country home
Landmarks/POIs Basilica of St. Francis - Day 5
Spoleto
This morning brings truffle hunting in the shadow of the Apennines with a local expert and his trained truffle-sniffing dogs. You'll sample truffles during a rustic, home-cooked lunch, then head back to your hotel in the late afternoon.
- Meals
- Breakfast, Lunch (Rustic, home-cooked lunch)
Included Activities
- Truffle hunting with local expert and trained dogs
- Rustic, home-cooked lunch featuring truffles
- Day 6
Spoleto to Pienza
You'll leave Umbria today and head to Tuscany's Val d'Orcia region, a UNESCO site. Start by visiting a dairy farm to taste and sample prized sheep-milk pecorino cheese. After that, walk through the Renaissance village of Pienza (also UNESCO) with its flower-adorned cobblestoned streets. Your evening is yours to explore.
- Meals
- Breakfast
Included Activities
- Travel to Val d'Orcia region
- Tour dairy farm producing pecorino cheese
- Sheep-milk pecorino cheese tasting and snacks
- Explore Pienza
Optional Activities
- Evening dining and exploration of Pienza
Landmarks/POIs Pienza - Day 7
Orcia Valley and Montalcino
Journey through the rolling Orcia Valley this morning, making a stop in Bagno Vignoni to see the thermal water-filled piazza. Next, head to hilltop Montalcino for a winery tour and tasting of the famous Brunello wine. Return to Pienza in the afternoon where you'll have time at leisure to explore the countryside.
- Meals
- Breakfast
Included Activities
- Journey through Orcia Valley
- Visit Bagno Vignoni
- Winery estate and cellar tour in Montalcino
- Brunello red wine tasting
Optional Activities
- Explore countryside along white roads
Landmarks/POIs Bagno Vignoni Montalcino - Day 8
Siena
A guided walking tour of Siena shows you the history behind the well-known Palio Horse Race and local stories. You'll have free time to check out the city's cathedral or the frescoes in the town hall. In the afternoon, drive through the Chianti countryside to your restored Tuscan villa hotel.
- Meals
- Breakfast
Included Activities
- Guided walking tour of Siena with local expert
- Learn about the Palio Horse Race
Optional Activities
- Visit Siena Cathedral
- View town hall frescoes
Landmarks/POIs Siena - Day 9
Florence
Florence awaits with an extensive guided walking tour of its Renaissance heritage. You'll see the Ponte Vecchio, Signoria Square with Palazzo Vecchio, and the Piazza del Duomo with its polychrome marble and gilded bronze doors. Afterward, you'll have free time to explore on your own before returning to your Tuscan villa.
- Meals
- Breakfast
Included Activities
- Extensive guided walking tour of Florence with local expert
- View Ponte Vecchio
- Visit Signoria Square and Palazzo Vecchio
- View Piazza del Duomo
Optional Activities
- Self-guided exploration of Florence's treasures
Landmarks/POIs Ponte Vecchio Signoria Square Palazzo Vecchio Piazza del Duomo - Day 10
San Gimignano
Spend your morning in San Gimignano, the 'Manhattan of the Middle Ages,' where you can see its distinctive 13th-century towers standing tall over the surrounding vineyards. Grab authentic Italian gelato while wandering the cobbled streets at your own pace. You'll return to your hotel mid-afternoon for a farewell dinner featuring Tuscan specialties.
- Meals
- Breakfast, Dinner (Farewell dinner of Tuscan specialties)
Included Activities
- Visit San Gimignano
- Gelato tasting from award-winning ice cream parlor
- Farewell dinner of Tuscan specialties
Optional Activities
- Leisurely exploration of San Gimignano's cobbled streets
Landmarks/POIs San Gimignano - Day 11
Departure
Your journey through Tuscany and Umbria comes to a close today.
- Meals
- Breakfast
