Tuscany tours are mostly countryside experiences: wine estates, hill towns, food workshops and slow-moving days by car, bike or balloon. This page compares the best regional tours by type, operator and price, rather than repeating city sightseeing, which our Florence tours and Siena tours pages already cover.
Most departures start in Florence or Siena and return the same evening, so the real choice is which part of the region you want: the Chianti Classico hills between the two cities, the Val d’Orcia to the south, or the truffle country around San Miniato. Prices are indicative for 2026. Our Tuscany region guide covers where to stay and how to link towns.
Chianti Classico Wine Tour from Florence
Duration: 5-6 hours | From: approximately 85 per person
Small-group half-day tours from Florence visit two family estates in the Chianti Classico area, with tastings of Sangiovese-based wines and olive oil. Larger estates such as Antinori nel Chianti Classico at Bargino and Castello di Brolio, the Ricasoli family seat since the 12th century, also take direct bookings for cellar visits and tastings. Group tours usually include a driver and lunch, so check the number of tastings listed. Harvest season, September and October, is lively but books out early.
Val d’Orcia, Pienza and Montalcino Day Trip
Duration: 9-10 hours | From: approximately 120 per person
The Val d’Orcia is a UNESCO World Heritage landscape of cypress-lined roads and ridge-top towns. Full-day tours from Florence or Siena usually combine Pienza, known for pecorino, and Montalcino, home of Brunello. Castello Banfi is a well-known stop for tastings. The drive between stops is part of the pleasure, so expect long viewpoint breaks rather than museum visits.
Hot Air Balloon Flight over Tuscany
Duration: 3-4 hours | From: approximately 260 per person
Flights take off at sunrise in the Val d’Orcia or near Siena, drifting for around an hour over farmland and villages. Operators serve a breakfast or a glass of local sparkling wine on landing. Weather decides everything, and flights are often rescheduled for wind or fog. This is the priciest option on the page, so book flexible dates and avoid your last day.
Truffle Hunting and Lunch
Duration: 4-5 hours | From: approximately 95 per person
Guided hunts with a trained dog take place in woods around San Miniato, a centre for white truffles, and Crete Senesi. The white truffle season runs roughly from October to December, with summer and black truffles available at other times. Tours end with a lunch built around the finds, and hunters explain how prices are set. Wear boots and expect uneven, sometimes muddy ground.
Tuscan Cooking Class with Market Visit
Duration: 4-5 hours | From: approximately 90 per person
Classes in Florence and farmhouses nearby combine a market trip with hands-on lessons in fresh pasta, ribollita or bistecca alla fiorentina side dishes. Farmhouse classes cost a little more and include countryside views and wine. Group size ranges from 6 to 12, and vegetarian menus are common on request.
Strade Bianche E-Bike Tour
Duration: 4-5 hours | From: approximately 100 per person
The white gravel roads south of Siena are the setting for the cycling race that gave them fame. E-bike tours make the climbs manageable on routes through Crete Senesi clay hills, with stops for wine or lunch. Helmets are included, and routes suit moderate fitness. Spring and autumn have the best temperatures.
Book a Strade Bianche e-bike tour
Practical Information
Best season: April to June and September to October for weather and harvest. Truffle hunts run mainly October to December. For official regional information, see Visit Tuscany.
Booking: Book wine days and balloon flights 1 to 2 weeks ahead in peak months. Most Chianti and Val d’Orcia tours include hotel pickup in Florence or Siena, and tastings mean that an organised tour is safer than driving.
Prices: Prices are approximate as of 2026 and vary with group size, season and whether lunch or tastings are included. Compare the region with the coast in Tuscany vs Amalfi Coast.
Browse all Tuscany tours and activities
Where to stay: see our hotel guide for Tuscany for the best areas and options at every budget.
For bookable options, see our best tours in San Gimignano.