Italy: The Tuscan Hills
Ten nights at home in the Tuscan hills, then Florence.
May 14–28, 2027
See other dates- Rated 4.9 / 5
- 15 days, 14 nights
- 4 to 18 travellers
- Live Away
Ten nights living in a Tuscan farmhouse, then four in Florence, with day trips to Florence, Siena and the hill towns, and evenings that start with the local wine.
- Proudly Canadian
- TICO Reg. 1817786
- Small group travel
- Carefully curated journeys
- A community of like-minded explorers
At a glance
Quick facts
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Duration
15 days, 14 nights
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Group size
4 to 18 travellers
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Activity level
Basic
Activity levels explained -
Cities and stops
Montepulciano, with day trips to Siena, Pienza and San Gimignano, then Florence
Where you'll stay, in this order:
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Montepulciano
10 nights
A restored farmhouse among the vineyards, ten minutes from town.
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Florence
4 nights
In the centre, a short walk from the Duomo.
The route
Map of the trip
The fine detail
What's included, and what's not
Included:
Private transfer from Florence Airport (FLR) to the trip's first hotel on arrival
Transfer to Florence Airport (FLR) on the last day
All transportation as described in the itinerary
14 nights' accommodation with daily breakfast
Most lunches and dinners, as listed in the itinerary
A Wheel & Anchor host for the whole trip, plus local guides
Entrance fees for every visit in the itinerary
Not included:
- International airfare and air taxes
- Arrival or departure transfers for members travelling on dates other than the trip's start and end dates
Trip cancellation and travel medical insurance, which we strongly recommend and can quote depending on your province of residence
All programs are subject to our detailed terms and conditions, provided automatically upon booking.
Pricing & availability
We hope you'll join us
Dates
May 14–28, 2027
See other datesStatus Go
- Pending – dates are being finalized and booking isn't open yet
- Go – the departure is confirmed to run; book with confidence
- On Request – contact us and we'll confirm whether space can be opened
- Sold Out – the departure is full; join the waitlist
Availability Double and single rooms available
- Sold out – no places remain on this departure
- One spot left – a single place remains
- A few spots left – a small number of places remain
- Double rooms only – remaining places are double-occupancy only
- Double and single rooms available – both room types are still open
- On request – contact us and we'll confirm what's available
Double occupancy
CAD $9,890
per person
Single occupancy
CAD $11,990
per person
Deposit
CAD $1,500 per person at booking
Second instalment CAD $3,000 six months before departure
Balance due 90 days before departure
Prices may differ based on room / cabin category selected.
Companions for the Road
Travelling solo?
Our Companions for the Road program helps solo travellers find a roommate or a travel companion, so you can share the trip, and the single supplement, with someone likeminded. Travelling on your own? You'll be in good company: ask us about finding a companion for the road.
Next steps
Ready when you are
Love this trip? Let's get you started with the details you need.
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Get the itinerary
A detailed day-by-day for this departure, ready to download.
Get the itinerary -
Book now
Reserve your place with a deposit.
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Speak to a specialist
Call 1-888-247-1480 and dial 1 from the welcome message, or send us a message.
Your host
Your Host on this departure
Antoine Tremblay
Patrick has hosted Wheel & Anchor journeys through Ireland, Scotland and Portugal since 2019. A Dubliner by birth and a Galwayman by preference, he knows which pub has the session worth staying up for and which headland is worth the early alarm. He'll be with the group from the first morning in Dublin to the last evening in Galway.
The Host currently scheduled for this departure is Antoine Tremblay. Host schedules may change; the assigned Host will be confirmed prior to departure.