At Your Own Pace
Tuscany from Place to Place
Val d'Orcia, Chianti, Maremma
Short drives, long lunches — the landscape sets the timetable.
Tuscany rewards no speed. Two hotels are rarely more than ninety minutes apart, and the finest stretches run along unsignposted gravel: cypress avenues, a wine estate, a village with one bar and three tables.
We build these journeys around three bases: Chianti for wine and workshops, the Val d'Orcia for light and distance, the Maremma for coast and quiet. Between them, time for whatever you find.
The car is part of it. If you like, a vintage Alfa or Lancia — not as an attraction, but because these roads were built for them.
The Pure Voyage view
Why we recommend it
Because Tuscany takes two bases, not seven.
The best roads lie between Siena, the Val d'Orcia and the Maremma, and all of them work as a day out. Change property every other night and the trip becomes an exercise in luggage. We suggest two bases of four or five nights each, a car with a short wheelbase, and lunch as the fixed point of the day. May, June and September are considerably better here than high summer.
- Who it suits
- Couples and friends who enjoy driving themselves
- What stays
- The cypress avenue in late afternoon, with no hurry
Suitability
Who it is for
Ideal for
- Couples and groups of friends
- Wine and food as the reason to travel
- Seven to ten nights
- May, June, September, October
Less suited for
- Travellers who do not want to drive
- Guests with a dense museum programme
- August stays
What travellers often underestimate
Two bases over ten days beats five. Driving times on country roads are twice what the map suggests.
If this is not the right fit
You may also want to consider
If Italy stays but the driving does not:
01 · Val d'Orcia
Rosewood Castiglion del Bosco
One address as a base, with day trips rather than daily packing.
See more02 · Spanien
Andalusien im Auto
The same idea, longer distances and quieter roads in spring.
See more03 · Kampanien
Amalfiküste
For travellers who want coast and would rather leave the car.
Not better, not a step up — simply different, and right for different travellers.
Our view
Why we recommend it
Because with your own car Italy stops being a list of places. You stop where you want, and the best hours are almost always unplanned.
- Best time to travel
- Late April to June and September to mid-October. August is hot and busy; November brings truffles and empty roads.
- Suggested duration
- Ten to fourteen days, three to four nights per base.
- Who it is best for
- Couples, families with older children, travellers who enjoy driving. Less so if narrow hill roads unsettle you — then we drive you.
Pure Voyage note
Set out early on market days. Between nine and eleven the whole year is gathered in a few streets in Pienza, Montalcino or Greve — after that the coaches have it.
Along the way
Retreats along the way
The addresses we suggest most often for this journey — as a starting point, not a fixed route.
And then
Journeys that sit well beside it
Andalusia by Road
White villages, olive slopes and cities that wake in the evening.
Greek Islands under Sail
Bays reached only from the water — and harbours that empty in the evening.
The Scottish Highlands
Single-track roads, passing places and light that changes by the hour.
Whether this journey suits you is settled fastest in conversation.
Season, length and the hotels before and after shape the result more than the route ever does.
Speak with the conciergeWhat is the most common mistake here?
Too many stops. Three bases across ten days beat six — Tuscany rewards returning, not ticking off. Watch the ZTL zones in historic centres; the cameras are unforgiving. And book lunch rather than dinner: the good country addresses are calmer at midday and better placed in daylight.
Noted by Pure Voyage
Common questions
What guests ask us about this
- Self-drive or with a driver?
- Self-drive when the road itself is part of the pleasure — Tuscany, the Alentejo, the Highlands. With a driver when hairpins, cities or long stages would otherwise eat the day.
- How many nights per stop?
- Two at least, three ideally. One night per hotel means luggage rather than travel — and the best hours almost always come on the second morning.
Pure Voyage Signatures
Themes that run through our work
Recurring thoughts rather than categories. They appear where they explain something.
Related travel thoughts
What this brings to mind
Not the most similar, but the most natural next step: places, routes and essays that belong to this way of travelling.
- HouseAman VeniceCanal Grande, VenedigA house we would mention in the same conversation.
- DestinationItalyThe country most often planned badly — and the most rewarding when it is right.The country behind it — how everything connects.
- RecommendationFirst Time ItalyFor a first journey to Italy — the one that sets the tone for all the others.Our selection for travellers with this outlook.
- JournalWhich Aman Is Right for You?9 minutesAn essay that carries this thought further.
Continue through Pure Voyage
Where to go from here
Not a catalogue, but a next step: the retreats, routes, countries and essays we would mention at this point in a conversation.
Hotels
Addresses that belong beside this page.
Destinations
The country at a glance.
Recommendations
What we suggest for this occasion.
Journal
Further reading before you decide.
Further reading
What we have written on this
Destinations
Tuscany Beyond Florence
Val d'Orcia, Maremma, Casentino: three landscapes that carry a second Tuscan journey.
Destinations
Puglia, Beyond the Postcard
Where travelling in Puglia genuinely rewards you, and why May and October make the difference.
Guest Voices
What stays with you
Not stars or ratings — but what you remember afterwards.
We had two retreats in mind and booked a third in the end. The reasoning was so clear that the decision became easy.
M. K. — HamburgAmalfi Coast, May The advice on which weeks to avoid changed our journey. We went two weeks later — and had the river to ourselves.
Dr. A. S. — MünchenTanzania, family journey
Published with consent, shortened and anonymised.
A Personal Enquiry
Shall we plan Tuscany from Place to Place for you?
Tell us when you would like to travel and with whom — we check availability, cabins or rooms and the right opening to the trip.
A first assessment is without obligation and free of charge.
Why book through Pure Voyage?
- Personal luxury travel advice
- Carefully chosen hotel recommendations
- Tailor-made itineraries
- Partner benefits wherever they apply
- Direct personal contact from start to finish
An Invitation
Once a month: hotels, new openings and travel ideas
One hotel that convinced us. One new opening we are watching. And one travel idea for the right season. Carefully selected and reduced to the essentials.