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Tour · Collette · 9 nights

Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns

  • Three nights in a restored Tuscan villa in the Chianti region
  • Local expert guides for walking tours in historic towns
  • Truffle hunting experience with a local expert and his dogs
From
$7,649 pp twin share
$9,199 pp solo share
9 nights
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When & how much

Choose your departure

14 departures

  1. Sun 11 Oct 2026 → Tue 20 Oct 2026 9 nights · Rome → Tuscany from $7,649 pp twin share Departs todayGuaranteed Enquire
  2. Wed 14 Oct 2026 → Fri 23 Oct 2026 9 nights · Rome → Tuscany from $7,649 pp twin share Departs in 3 daysGuaranteed Select
  3. Sun 18 Oct 2026 → Tue 27 Oct 2026 9 nights · Rome → Tuscany from $7,649 pp twin share Departs in 7 daysGuaranteed Select
  4. Wed 21 Oct 2026 → Fri 30 Oct 2026 9 nights · Rome → Tuscany from $7,649 pp twin share Guaranteed Select
  5. Sun 25 Oct 2026 → Tue 3 Nov 2026 9 nights · Rome → Tuscany from $7,649 pp twin share Guaranteed Select
Departs Sun 11 Oct 2026 Returns Tue 20 Oct 2026
Duration9 nights
OperatorCollette
StyleTour
HighlightDiscover Umbria and Tuscany's hill towns, countryside, and Renaissance treasures on a ten-day Italian journey
Stroll medieval streets in Assisi, Spoleto, Siena and San Gimignano. Hunt for truffles with trained dogs in the Umbrian countryside. Explore Florence and tour a Chianti winery with tastings

On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love. Stroll Assisi’s old city, and explore the Umbrian hill town of Spoleto, where the gilded façade of the cathedral rivals with the silvery sheen of the olive trees. Visit Florence, the “Cradle of the Renaissance.” In Siena, stand inside one of Tuscany’s most ancient piazzas. Admire the famous towers of San Gimignano and hunt for truffles in the Umbrian countryside. 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.

Day by day

Itinerary

  1. 1

    Rome, Italy

    Sun 11 Oct
    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.
    Dinner
  2. 2

    Rome - Spoleto - Umbria

    Mon 12 Oct
    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 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.
    BreakfastDinner
  3. 3

    Umbria

    Tue 13 Oct
    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).
    BreakfastLunch
  4. 4

    Umbria

    Wed 14 Oct
    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.
    BreakfastLunch
  5. 5

    Umbria - Pienza, Southern Tuscany

    Thu 15 Oct
    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 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.
    BreakfastLunch
  6. 6

    Pienza, Southern Tuscany

    Fri 16 Oct
    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 Brunello. 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.
    Breakfast
  7. 7

    Pienza - Siena - Chianti Region, Northern Tuscany

    Sat 17 Oct
    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 the Chianti countryside takes you to the restored Tuscan villa where your hotel is located.
    Breakfast
  8. 8

    Chianti Region, Northern Tuscany

    Sun 18 Oct
    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 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.
    Breakfast
  9. 9

    Chianti Region, Northern Tuscany

    Mon 19 Oct
    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.
    BreakfastDinner
  10. 10

    Chianti Region - Tour Ends

    Tue 20 Oct
    Your journey through Tuscany and Umbria comes to a close today.
    Breakfast
What you get for the price

Inclusions & exclusions

What’s included

  • Enjoy three nights in a restored Tuscan villa.
  • Behold the unique water-filled piazza in the village of Bagno Vignoni.
  • Hunt for truffles with a local expert and his truffle-sniffing dogs.
  • Surround yourself in the mystery of the Umbrian hill town of Spoleto.
  • Discover Florence, the "Cradle of the Renaissance.".
  • Explore historic Siena and see the famous piazza of the Palio Horse Race.
Where you’ll stay

Accommodation

  • Kolbe Hotel, Rome
  • Hotel Dei Duchi, Spoleto, Umbria
  • Hotel Corsignano, Pienza, Tuscany
  • Villa San Lucchese Hotel, Chianti Countryside, Tuscany
From the operator

Common questions about this voyage

How long is this journey?
This itinerary runs for 10 days and 9 nights.
When can I travel?
Departures are currently scheduled between 11 Oct 2026 and 29 Jun 2027, subject to live availability.
Are there different departure options?
Yes, multiple departures may be available depending on your preferred travel period.
Can I travel solo?
Solo pricing may be available on selected departures, and final options can be confirmed at enquiry.
Are discounts available?
Seasonal or loyalty discounts may be available on selected departures at the time of enquiry.
Ready to lock in?

Book this tour

Send us an enquiry and a consultant will be in touch, or call 1300 414 198 for personal help choosing a departure.

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Travel at 60 Social Getaways

Travel further when you're not travelling alone

Our Social Getaways are small-group holidays designed especially for over-60s Australians who want the freedom of a great trip without the work of planning every detail. A Travel at 60 host travels with the group, the operator handles the logistics, and you get to focus on the bit that matters — the people, the places, and the stories you'll bring home.

Open to solo travellers too. Many of our travellers book on their own and find their feet quickly in a friendly group of like-minded Australians. Reduced single-supplement options are available on most departures — ask one of our consultants and we'll talk you through what's offered on this trip.

  • A friendly Travel at 60 host — an Australian face on the ground, looking out for the group from day one.
  • Curated local guides & boutique suppliers — the same operators we'd book for our own families.
  • Real itineraries, not whirlwind tours — comfortable transfers, breathing room, and the “off the beaten track” stops the big bus tours skip.

Want to talk it through? Call 1300 414 198 7 days a week, Queensland time, and one of our consultants will walk you through it.

— The team at Travel at 60

A Travel at 60 host with travellers on a Social Getaway
From (twin) $7,649 pp
From (solo) $9,199 pp
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