Tours & Vacations
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Italy vacation idea
Tuscany & Umbria: Hill Towns, Assisi & Rome
An 8-day premium small-group journey through Tuscany and Umbria with hill towns, food, wine, Assisi and a finish in Rome.
Italy
Guided / Escorted
Luxury
Small Group
Culture
Food & Wine
Length8 days / 7 nights
FormatPremium small-group regional Italy journey
ActivityPace 3; full sightseeing days with some downtime
Route
Florence / Chianti • Gubbio • Perugia • Assisi • Torgiano • Arezzo • Rome
Why This Trip Stands Out
This 8-day small-group Italy journey skips the standard Venice–Florence–Rome loop and spends its time in Tuscany and Umbria. The focus is hill towns, wine country, local food, crafts and smaller hotels before finishing in Rome.
- Stay in the Tuscan countryside and explore Chianti.
- Spend time in Gubbio, Perugia and Assisi.
- Include wine, food and artisan experiences that fit the region.
- Finish in Rome without turning the trip into another generic first-time Italy itinerary.
Sample Itinerary
Days 1–2 | Florence & Chianti Country
Begin near Florence in the Tuscan countryside with time among vineyards, hill towns and regional food and wine experiences.
Days 3–4 | Gubbio & Central Italy
Continue into Umbria for medieval Gubbio, countryside experiences and a closer look at the crafts and traditions of the region.
Days 5–6 | Perugia, Assisi & Wine Country
Use Perugia as a base for Assisi and surrounding Umbrian towns, with local wine and cultural experiences woven into the itinerary.
Days 7–8 | Arezzo & Rome
Continue through central Italy toward Rome, with a final night in the capital before departure.
What You Get
What’s Included
- 7 nights in premium smaller hotels and historic properties
- Small-group touring averaging 24 guests
- Guided sightseeing in Tuscany and Umbria
- Wine and culinary experiences
- Visits to regional hill towns including Gubbio, Perugia and Assisi
- Professional the tour operator direction and local guiding
Your Stay
Where You’ll Stay
Seven nights are included in premium smaller hotels and historic properties across Tuscany, Umbria and Rome. Exact properties can vary by departure.
Getting Around
Transportation
Transportation between included destinations is arranged as part of the guided journey.
Food & Dining
Meals & Dining
Selected meals and regional culinary experiences are included. I’ll confirm the exact current meal plan for your departure.
More to Add
Optional Experiences
The itinerary is highly structured. Any optional choices vary by departure.
Stay a Little Longer
Extensions Available
Extra nights can be added before the trip in Florence or after the trip in Rome.
Make It Yours
Ways to Customize It
I can coordinate international airfare and additional Italy travel around the fixed small-group itinerary.
Group Details
How the Group Works
All departures operate as small groups averaging approximately 24 guests.
A Good Match?
Who This Trip Is Best For
Travelers who have already seen Italy’s headline cities or want a more regional trip focused on Tuscany, Umbria, food, wine and smaller towns.
Before You Choose It
A Few Things to Know
This itinerary includes full sightseeing days, historic hill towns, cobblestones and uneven streets. Some experiences take place in rural settings and older properties.
Interested in This One?
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Pricing & availability: Prices shown are starting prices from the applicable tour operator and were available when last verified. Unless noted otherwise, pricing is per person based on the occupancy shown above. Availability, taxes, fees, supplements, promotions, and supplier terms can change. Your exact price and availability will be confirmed before booking. Nothing is confirmed until payment is applied.