Pienza
For pecorino, pretty streets and quintessential Val d’Orcia.
Travel notes · Italy
A week in Tuscany
Hilltop towns, long lunches, beautiful hotels and wine tastings worth planning the day around.
My version of a week in Tuscany: seven nights across two bases, plenty of time in the countryside and enough left unplanned to actually enjoy it.
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The week
Two bases. Seven nights.
One suggested eight-day trip with seven nights, changing hotels on Day 4 and departing on Day 8. Tap a day below to see the plan. Use it as a rhythm, not a strict schedule.
My ideal pairing: three nights in Chianti or central Tuscany, followed by four nights in Val d’Orcia. Two different sides of Tuscany, without spending your entire trip packing and unpacking.
Where to stay
Six ways to do Tuscany.
Six of my favorite places to stay. Tap a hotel name below to compare it with the others, then choose the stays that suit your trip.
Choose your base
Tuscany isn’t one destination.
Three areas to consider for your stay. Tap an area to learn more, then choose one or two for your week.
Don’t choose your hotel first. Choose the part of Tuscany you actually want to experience.
The wine day
The day I’d splurge on.
Private driver.
Two wineries.
One very long lunch.
An example of how I’d plan the day
- 10:30First tasting
- 12:30Long lunch
- 3:30Optional second tasting, depending on how leisurely lunch runs
- 5:30Back to the hotel, whenever you’re ready
Towns worth your time
Pick two. Not all of them.
Montepulciano
For wine, views and a beautiful hilltop-town afternoon.
Montalcino
For Brunello and a slower wine-country day.
Siena
For art, architecture and a proper city day without going back to Florence.
San Gimignano
For medieval towers and one of Tuscany’s most recognizable skylines.
Florence deserves its own time. If it’s your first visit to Tuscany, consider adding a day there rather than squeezing it into an already full countryside itinerary.
The mistake: trying to string four towns together because they’re “close.”
The better trip: one or two towns, lunch and nowhere you need to be afterward.
Save this list
My Tuscany Shortlist
My perfect day
Private wine day
Two wineries. One long lunch. Private driver.
Don’t miss
Pienza + Montepulciano
One of my favorite pairings for a day out.
Need help choosing? Let’s plan your Tuscany trip →
Good to know
Before you go.
When to go
Spring and fall are my favorite windows for sightseeing, wine and countryside. Summer works beautifully when the hotel and pool are a major part of the trip.
Getting around
A car gives you freedom, but I prefer a private driver for wine days. Check travel time between towns before you plan the day.
One base or two?
For a week in Tuscany, I generally recommend two bases if you want to experience different parts of the countryside. For four or five nights, I’d stay in one place. One beautiful resort can also be a lovely base for a slower week.
Book first
Start with your hotels, then reserve the wineries, restaurants and experiences you don’t want to miss. Arrange transfers in advance, but leave room for spontaneity.