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A seven-day luxury Tuscany itinerary works best from one hotel in Florence. Two days go to the city with a private guide and three to private day trips into Chianti, the hill towns and Pisa. The rest is a cooking class, a drive and a day with nothing booked. You unpack once.
The alternative is a week split between a Florence hotel, a Chianti villa and somewhere in Siena. That means three check-ins, three sets of parking rules and at least two mornings spent packing.
Building a seven-day luxury Tuscany itinerary around Florence
Most of what people come to see sits within about an hour of Florence. Siena is to the south, San Gimignano to the southwest and Pisa to the west. The Chianti Classico hills begin roughly twenty minutes past the city's southern edge.
Driving yourself is the other reason to stay put. Florence's historic centre is a ZTL, a limited traffic zone, with cameras at the gates that fine any car without a permit. A lot of the best hotels sit inside it, so a rental car often can't reach the hotel door at all. On a private tour the guide handles all of that.
Season makes a difference too. From mid-September into October the grape harvest is under way and the Chianti estates are at their busiest. In July and August the afternoon heat makes walking in Florence hard work, so keep the city days to the mornings. Spring is greener, and quieter in the countryside.
Still deciding on the length of the trip? Our guide to how many days in Tuscany compares shorter stays with longer ones.
Day 1 and Day 2: Florence
The Private Essential Florence Walking Tour runs about three hours with your own guide. It covers the main landmarks and includes a gelato stop. With a private guide the route can shift with your interests. If you saw the Duomo from the taxi, you can spend longer in the Oltrarno instead. Piazza della Repubblica is a good example of what a guide adds. It looks nothing like the medieval streets around it. In the 1880s the city demolished the old market and the Jewish ghetto to build it, and most visitors cross the square without knowing.
That idea of pace as part of the experience is something we covered in authentic luxury travel in Tuscany.
Day two is the Private Florence Duomo Tour with the dome climb. Brunelleschi's dome is 463 steps to the top, on narrow stairs between the inner and outer shells. Since March 2025 dome tickets carry each visitor's name, so they're issued for the exact people climbing. The cathedral asks for covered shoulders and knees, so plan the day's clothes around that even in July.
Do the climb in the morning and keep the rest of the day slow. Several of the city's top hotels have roof terraces facing the cathedral. An evening aperitivo up there, looking at the dome you climbed that morning, is a good way to end the second day.
Day 3: Chianti
The Private Tuscany Wine Tour, an off-road Chianti wine safari, starts at Villa Le Corti. The estate still belongs to the Corsini family. You walk through the cellars and reach the olive mill through tunnels under the villa, then taste cured meats with three wines.
From there the guide drives a specially adapted 4WD onto unmarked dirt roads through old woodland, past farms and small country churches. Lunch is at Rignana, a winery and restaurant with a long view over the valley. It's three courses with red wine, plus a blind olive oil tasting. The last stop is Poggio Torselli, a villa with around six hundred years of recorded history. There's time to walk the gardens before tasting three more wines with cheese.
Two things to know before booking. The menu can't be adapted for vegetarians or other dietary needs, and the terrain makes it unsuitable for anyone with walking difficulties.
Can Siena, San Gimignano and Pisa fit into Day 4?
They can, with a private guide. The Private Tuscany Tour in One Day to Pisa, Siena and San Gimignano with Winery Lunch covers all three towns. Lunch is at a winery along the way.
Three towns in one day gives you a proper visit to each, but not a whole afternoon in any of them. In Siena that means the shell-shaped Piazza del Campo, sloping down towards the Palazzo Pubblico. The Palio is run there every 2 July and 16 August. San Gimignano once had about seventy towers and fourteen still stand. In Pisa the cathedral and baptistery share the lawn with the Leaning Tower and deserve more than a glance. Climbing the tower works on timed tickets, so mention it early if someone in your group wants to go up.
If you'd rather see Siena slowly, you can split this into two separate days and give up the free day instead.
Day 5: nothing booked
It's tempting to fill every day of a luxury Tuscany itinerary. After Chianti and the three-town day, though, a late breakfast and an hour in the hotel spa are hard to argue with. If you do go out, the Oltrarno is where the city's workshops are. At Stefano Bemer in San Niccolò you can order made-to-measure shoes. The fitting happens during your stay, and the finished pair takes several months. The Boboli Gardens behind Palazzo Pitti are a few minutes away if you want green space afterwards.
Day 6 and Day 7: cooking and a vintage Fiat 500
The Private Florence Cooking Class and Lunch at a Farmhouse with Local Market Tour starts at a market. You shop with the chef before driving out to a farmhouse in the hills. You cook a four-course meal and then sit down to eat it, pork roast included. With only your group in the kitchen, there's time to ask about technique.
On the last day you drive a restored 1960s Fiat 500 on the Private Vintage Fiat 500 Tour. Your guide drives ahead, and there's a two-way radio in the car. The route follows a cypress-lined avenue out of the city and climbs to a viewpoint near one of Florence's oldest churches. Then it heads out through olive groves and narrow stone-walled lanes. Along the way there's a stop on a private terrace for local ham, cheese and wine. The tour's own advice is to stick to one glass, since there's more driving after.
The cars are manual only, and the driver needs a valid licence. Each car takes three adults, or two adults with two children aged three to twelve, and there are no rear seat belts. If nobody in your group drives a stick shift, look at the Private Vespa Tour in Tuscany from Florence. It covers similar countryside and starts with a riding tutorial.
If you're booking only one piece of the week in advance, make it the Chianti day. The Private Tuscany Wine Tour: Off Road Chianti Wine Safari from Florence takes you to two historic estates and a long lunch at Rignana. It's also the hardest part of the week to arrange any other way.
