Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - 2025

11 days
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Group Tour
On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love.
29% OFF
$4,857
From$3,449
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Overview

Trip type
Group Tour
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

    • Experience a home-cooked meal in one of Umbria's country homes.
    • Sample pecorino sheep-milk cheese at a local farm in the Orcia Valley.
    • Savor the famous Brunello red wine during a musical tasting at a winery in Montalcino.
    • Hunt for truffles with a local expert and his truffle-sniffing dogs.
    • Behold the unique water-filled piazza in the village of Bagno Vignoni.
    • Enjoy 3 nights in a restored Tuscan villa.
    • Surround yourself in the mystery of the Umbrian hill town of Spoleto.
    • Explore historic Siena and see the famous piazza of the Palio Horse Race.
    • Discover Florence, the "Cradle of the Renaissance."

What's this trip about?

    On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love.

Details

Itinerary focusClassic Highlights
Group sizeSmall Group - 24 max
Age range36 years and up
Flights and transport
Start CityRome
End CityTuscany

Travel Themes

  • Cultural

Destinations

Attractions

  • Assisi
  • Florence
  • Rome
  • San Gimignano
  • Siena
  • Tuscany
  • Umbria

Activities

  • Culture
  • Historic Sightseeing
  • History

Itinerary

Travel Map

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

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

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 a...

Day 4 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 honored guest. Share stories and make an Umbrian friend (or two).

Day 5 Umbria

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

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 dairy farm producing prized sheep-milk pecorino cheese. Snack on some of the cheesemaker’s creations an...

Day 7 Pienza

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 ce...

Day 8 Pienza - Siena - Chianti Region

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

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 Signoria Square and its imposing Palazzo Vecchio, where, for over 300 ...

Day 10 Chianti Region

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...

Day 11 Chianti Region - Tour Ends

Your journey through Tuscany and Umbria comes to a close today in your restored Tuscan villa.

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Dates & Availability

Price From $3,449
Price per day$314
Last Updated: 2/22/2025
Departure Date
Finish Date
Double Share
Single Standard
Triple Share
Availability
07 Jun 2025
18 Jun 2025
$4,299
$4,899
21 Jun 2025
02 Jul 2025
$4,299
$4,899
12 Jul 2025
23 Jul 2025
$4,299
$4,899
26 Jul 2025
06 Aug 2025
$4,299
$4,899
09 Aug 2025
20 Aug 2025
$4,299
$4,899
06 Sep 2025
17 Sep 2025
$4,399
$4,999
09 Sep 2025
20 Sep 2025
$4,399
$4,999
13 Sep 2025
24 Sep 2025
$4,399
$4,999
16 Sep 2025
27 Sep 2025
$4,399
$4,999
20 Sep 2025
01 Oct 2025
$4,399
$4,999

Check current availability, prices, specials & more.

The total tour cost includes the tour price (regular or promotional) and the compulsory local payment. The promotional price is subject to change. Check directly with the operator for the latest price offer. The tour operator requires you to pay only the tour price to purchase your travel. The compulsory local payment will be paid when you join the trip. All prices are based on double, twin or triple share occupancy. Solo passengers will be accommodated in a double, twin or triple room according to availability with a passenger(s) of the same gender. Single supplement only needs to be paid if the passenger does not want to share and requests their own room. Discounts can only be applied at the time of booking and cannot be added at a later date, regardless of any changes made to the original booking.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

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Collette Reviews & Ratings

4.8/5  Excellent
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Worst and most poorly planned guided tour I have evr taken

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Do not travel with Collette They area subpar company

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Logistics

What's excluded

    • The land price does not include air travel, airline fees, airport or departure taxes, transfers, visas, customary end-of-trip gratuities for your Tour Manager, driver, local guides, hotel housekeepers, cruise ship waitstaff, and any incidental charges.

Accommodation

Travel Insurance
We strongly recommend purchasing travel insurance alongside your travel package to safeguard against unforeseen circumstances such as medical expenses, trip cancellations, and other contingencies. It offers you peace of mind and ensures you are prepared for unexpected events that may occur before or during your journey
Visa requirements
Visa requirements vary depending on your country of origin and your country of destination. It is your responsibility to familiarize yourself with the relevant requirements. For a handy tool that can help you quickly find the requirements, please visit this link .
Meals Included
15
Age Requirements
36 years and up
Optional Activities
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Additional Information
[object Object]
Trip ID
collette-16085

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