A Tuscany itinerary from Florence

How many days does Tuscany need? More than you have, always, but the honest answer depends on one decision: day trips from Florence, or nights in the countryside. Here are three plans that work, from one day to five.

One day: the highlights

With one free day, take the classic day trip: Siena, a Chianti farm lunch, San Gimignano and Pisa, about 12 hours from Florence, from about $100. It is a highlights reel, not a slow day, but it answers the question of what Tuscany looks like. Prefer depth to breadth? The small-group Siena and San Gimignano day trades Pisa for time.

Three days: Florence plus the hills

Keep Florence as your base and add two different day trips: day one to Siena and San Gimignano, day two to the Val d’Orcia or, for a shorter day, a Chianti wine tour in the morning and Florence in the afternoon. Pisa and Lucca make an easy third by train. Several operators sell “3-day Tuscany” packages, but three single day tours from the same hotel are usually cheaper and more flexible.

Five days: slow down

Two nights in Florence, then three in the countryside. The classic split is a base in Siena or a Chianti agriturismo (farm stay) with a car: day three in Chianti, day four in the Val d’Orcia with Pienza and Montepulciano, day five to San Gimignano and Volterra. Without a car, stay in Siena, which has buses to the hill towns, and add a tour for the Val d’Orcia. A week lets you add Lucca, Cortona or the coast.

Where to base yourself

Florence for the first visit: art, trains and nearly every tour starts there. Siena for medieval atmosphere and the south. A farmhouse in Chianti or the Val d’Orcia for the slow version, if you drive. Avoid planning a Tuscany trip around Pisa: the tower takes a morning, and the city is better as a stop than a base.