Tuscany Destination Guide

Four Different Tuscanies And Only One Is On The Postcard

People book Tuscany as a single idea and then discover it is four countrysides that look and behave nothing alike. Chianti, between Florence and Siena, is vineyard and oak forest, the closest to the city and the most visited. The Val d'Orcia, south of Siena around Pienza and Montalcino, is the wide bare hills, the cypress lines and the road everybody photographs. The Maremma, on the southwest coast, is flatter, wilder and far emptier, with the Bolgheri wine estates and a real coastline. The Crete Senesi east of Siena is clay hills and almost no tourism at all. Choosing wrongly between them is the most common way this trip goes sideways, because they are two hours apart and the drive is not the holiday.

The planning decision: which hills, and a villa or a hotel

Decide the landscape first, then the accommodation. Chianti is the safe answer for a first trip and for anyone who wants Florence and Siena close. The Val d'Orcia is right if the scenery is the reason you are coming. The Maremma suits repeat visitors and anyone who wants a beach in the same week. Then choose the product: villa rental with a cook and a housekeeper is what most families end up in, agriturismo is the honest middle, and country hotels give you service and a spa without the catering logistics. A car is not optional here; without one you will see a swimming pool and a driveway.

Harvest, heat and the months that actually work

May, June, September and October are the season, and September is the best month of the year: warm days, cool nights, the vines still in leaf and the harvest under way. The vendemmia usually starts in early September for the whites and runs through October for Sangiovese, with the Brunello pick in Montalcino often last, so an autumn trip puts you in working cellars rather than empty ones. Olive harvest follows in November and new oil is worth planning around. July and August are hot, regularly into the high nineties, with Florence and Siena at capacity. The Palio runs in Siena on the second of July and the sixteenth of August and turns the city upside down for days either side. From November into March many country properties close.

Where to base, and how far apart things really are

Chianti sits about forty minutes from Florence and thirty from Siena, which makes both cities easy afternoons. The Val d'Orcia is roughly ninety minutes south of Florence, and from a base near Pienza you have Montalcino, Montepulciano, San Quirico and Bagno Vignoni inside half an hour. The Maremma is two hours out and closer to Rome than people expect. Fly into Florence for the shortest transfer or Pisa for more choice, or take the fast train and collect a car outside the center. Every historic town has a restricted traffic zone with camera enforcement, so park outside the walls and walk in. A two base trip beats one base with long drives.

Stay strategy in the country

Rosewood Castiglion del Bosco sits on a large estate inside the Brunello zone with its own vineyard and golf. Borgo Santo Pietro near Chiusdino is a restored villa with serious gardens, a working farm and one of the best kitchens in the region. Castello di Casole occupies a restored castle estate outside Siena with an enormous amount of land around it. Il Borro, in the Valdarno east of Florence, is a whole restored hamlet. COMO Castello Del Nero sits in Chianti in a fourteenth century castle. Above all of these, the private villa market here is deep and well run, and for six or more travelers it is usually both better value and a better week.

When to begin

Six months for September and October, and longer for a villa, because the good houses with a pool, a view and a cook are booked a year out for the harvest weeks. Six to eight months for a summer villa. Cellar visits at the reference estates in Montalcino and Bolgheri are by appointment and the well known names have limited slots, particularly during harvest when the winemaking team is busy, so those get held early. Restaurant tables in Florence and Siena for the same trip should be arranged at the same time.

Four experiences worth building the days around

• A morning in Montalcino tasting Brunello at two estates, one large and one small, with a vertical rather than a walk through the barrel room.
• The Bolgheri cypress avenue and a tasting on the coast, where the Cabernet based wines look nothing like the rest of Tuscany.
• The Val d'Orcia at dawn on the road between San Quirico and Pienza, before the cars and with the mist still in the valleys.
• A truffle hunt with dogs in the Crete Senesi in autumn, followed by lunch cooked from what you found.

Who this trip suits

This suits families and multi generational groups better than almost any destination in Europe, because a villa absorbs everybody. It suits wine travelers, and couples on a second Italian trip who already did the cities. It pairs perfectly with three nights in Florence at the front and works as the middle of a route with Venice or Rome.

When another plan may fit better

If nobody in the party will drive, this is the wrong destination and no amount of transfers will fix it. If you want a beach holiday, the Tuscan coast is pleasant rather than remarkable and Puglia or Sardinia will serve you better. And if your window is August, understand that the towns are full, the heat is real and the villa terrace is where you will spend the afternoons.

Plan it with one accountable advisor

Tell us the month, the group size and whether the trip is scenery, wine or a house with a pool, and we will pick the right corner of the region before anything is held. Our luxury leisure travel planning covers the villa market and the estate appointments together.