Chianti is the Tuscany people picture when they close their eyes: rolling vineyards, stone farmhouses, cypress-lined lanes and medieval villages perched on ridges. It is also wonderfully central, sitting between Florence and Siena, which makes it a natural middle chapter in a wider Tuscan journey.
Vineyards, Hilltop Villages & Slow Roads
With ExpertoItaly you do not have to choose between wine estates, art cities and countryside walks – Chianti is where they all intersect. We help you pick a base (or two), then build a tailor-made, multi-centre holiday around it, with the right balance of slow days and gentle exploring.
Who Chianti Works Best For
If you recognise yourself below, Chianti is probably your natural base in Tuscany.
✓ Couples who want vineyard views and small villages, rather than a big resort
✓ Food and wine lovers keen to visit estates, cellar doors and traditional trattorie
✓ Travellers who like to mix Florence or Siena with countryside calm
✓ Drivers who enjoy scenic, slow roads – with clear, well-planned routes
Chianti as Part of a Multi-Centre Holiday
Chianti is rarely a stand-alone destination for our clients – it is the “in-between” chapter that ties your story together.
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DETAILSWhere to Stay in Chianti
We favour small, characterful places with a sense of history and a genuine welcome. No two are the same; we will match you to the right one based on how you like to travel.
Hotel Palazzo Leopoldo
Chianti
Stay at Palazzo Leopoldo in Radda in Chianti, a historic village palazzo for spring or autumn short breaks and tailored multi-centre Tuscan holidays with ExpertoItaly.
DETAILS
Castello del Nero
Chianti
Castello del Nero is a serene hilltop estate in Chianti, ideal for self-drive travellers seeking heritage, Michelin-star dining and restorative countryside calm between scenic explorations.
DETAILS
Relais Marignolle
Chianti
A charming Tuscan villa with pool, nestled in the Chianti hills but a stone's throw from Florence's centre. Ideal for a city/country break.
DETAILSGetting Around
With or Without a Car
A car gives you the most freedom in Chianti, especially for reaching smaller villages, viewpoints and wineries. We arrange car hire from Florence, Pisa or Rome, with clear driving notes and suggestions for half-day loops.
If you prefer to travel car-free, we can base you in or near a village with good services, weave in private drivers for key days and use trains for the city legs. It is more structured, but still entirely doable.
Chianti: the questions people ask us most
What is the best way to structure Chianti holidays?
Most travellers use Chianti as the central chapter of a wider Tuscany trip. A simple structure is Florence or Lucca first for city life, then three to five nights in Chianti for vineyards and villages, followed by a few days in Val d’Orcia or on the Tuscan coast. We adjust the rhythm to match how quickly you like to travel.
Do I need a car for a holiday in Chianti?
A car gives you the most freedom for visiting wineries, hilltop villages and viewpoints at your own pace. However, it is possible to enjoy Chianti without driving if you stay near a well-served village and use a mix of private drivers, local taxis and trains for the city legs. We will be honest about what is realistic for your travel style.
How many nights should I spend in Chianti?
Three nights is the minimum we suggest for Chianti holidays, giving you two full days to explore without rushing. Four or five nights works even better, especially if you want winery visits, a couple of scenic drives and at least one “do very little” pool day.
When is the best time to visit Chianti?
Late April to June and September to mid-October are ideal, with warm days, cooler evenings and colourful vineyards. July and August are hotter and busier, but still pleasant if you build in pool time and shorter drives.
Can you combine Chianti with other parts of Italy?
Yes. Many ExpertoItaly guests pair Chianti with Florence, Lucca and the Tuscan coast, or add Rome at the start or end. High-speed trains and a few well-placed transfers make it easy to link regions without stressful long drives.
Chianti travel guides & ideas
Want to read more before you decide? Explore a few of our favourite Chianti stories and guides below.
Tailor-made Chianti holidays by ExpertoItaly
Turn Chianti into the calm heart of your Tuscany holiday
Tell us how you like to travel – slow vineyard days, hilltop villages, time in Florence or Siena –
and we will design a Chianti itinerary that fits around you, not the other way round.
No rigid packages, no call-centre scripts. Just one-to-one advice and carefully chosen places to stay,
with all the logistics quietly taken care of.
Start planning your Chianti holiday
More Tuscan bases to mix and match
Tuscany works best as a gentle multi-centre. Explore our other favourite areas below – you can
combine any of them in one tailor-made holiday, with travel and timings stitched neatly together
for you.
Florence
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You’re in good hands
Clients often mention what matters most — care, precision, and the sense of travelling with someone who knows the way.
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