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  1. Destination
  2. Italy: The Tuscan Hills
  • Live Away
  • Italy

Italy: The Tuscan Hills

Cypress lanes, hill towns, and a long lunch every day.

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Two weeks living in one Tuscan farmhouse, with day trips to Florence, Siena and the hill towns, and evenings that start with the local wine.

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Italy: The Tuscan Hills

Destination overview
  • Watch first
  • From the founder
  • Upcoming departures
  • The moments
  • Photographs
  • In their words
  • Practicalities
  • Keep exploring
On this page
  • Watch first
  • From the founder
  • Upcoming departures
  • The moments
  • Photographs
  • In their words
  • Practicalities
  • Keep exploring

Watch first

The Journey

Fifteen minutes of the trip as our members find it: the cities, the roads, and the quiet in between. Worth watching before you pick your dates.

Italy: The Tuscan Hills, a Wheel & Anchor journey.

From the founder

Why we love Italy

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Gordon

Ireland has been one of the most in-demand programs in our travel community. So what is it about Ireland that captivates the imagination of so many of us?

The humour and charm of the Irish people is certainly part of it, as well as the subconscious pull of heritage for those of us with Irish descendants. And of course there are the landscapes, and that marvellous, iridescent shade of green that covers the hills dotted with sheep.

It's that green that stands out most to me. There is something about the aliveness in those shades that speaks to the mysterious allure of Ireland, where the stories of the fae and other elemental energies have seeped into the landscapes and communities across the island. To hear it from the Irish, they are not just stories; they are often presented more as memories.

Perhaps Ireland is one of those places where you can reawaken that child-like sense of wonderment that, just maybe, there really is magic out there in the world. After all, this is why we travel, is it not?

Upcoming departures

Italy: The Tuscan Hills

Dates Price from: Status View Details

May 14–28, 2027

Price from:CAD $9,890

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View Details

New departures for this trip are being planned. Talk to a specialist to hear about them first.

The moments

Six moments to look forward to

  1. 01

    Florence

    The Duomo, the Uffizi, and the view from Piazzale Michelangelo at sunset.

  2. 02

    San Gimignano

    A medieval skyline of stone towers above the vineyards.

  3. 03

    A Tuscan table

    Pecorino, salumi, olive oil and Chianti, straight from the farms around us.

  4. 04

    Siena

    The shell-shaped Piazza del Campo and its striped cathedral.

  5. 05

    Pienza

    A Renaissance town famous for its pecorino.

  6. 06

    A cooking class

    Fresh pasta with a local nonna, then eating the results.

Photographs

Memories from past trips

In their words

What past travellers said

  • Rated by 27 members who travelled this trip
  • Solo traveler favorite
  • 11 repeat travelers

Two weeks in one place was exactly right. We felt like locals by the end.

BBarbara, Ottawa

The farmhouse was lovely and the food was better.

G&AGerry & Anne, Winnipeg

I didn't want to come home.

HHelen, Saskatoon

Practicalities

Things you'll want to know

Why stay in one place?

No packing and unpacking. You get to know the village, and the village gets to know you.

Can I skip a day trip?

Of course. The pool and the terrace are there for exactly that.

Will there be wine?

Yes. Chianti, Brunello and Vino Nobile, mostly with dinner.

Ready to look at timing?

Check out the dates for this trip

Keep exploring

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Small-group journeys for Canadian travellers who would rather arrive than tour. Fifteen years, one community, and a lot of long tables.

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Markham, Ontario L6G 1B3
1-888-247-1480
info@wheelandanchor.ca

TICO Reg. 1817786

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