The last week of September and first half of October make up the grape harvest season in Tuscany, shared with local festivals and ripening figs. Spring brings green fields with poppies galore and pleasant temperatures for walks and riding bicycles. April/May evenings, along with evenings in October, can be chilly enough to light a fire in the fireplace.
Our favourite periods are in the spring and the autumn, with pleasant weather and few tourists. From late April to mid-June is when you can enjoy our beautiful green nature in abundance. From mid-September to the end of October is when Tuscany is green again and interesting with grape harvest, festivals and the outdoors. Winter can be cold and wet, but if you want to tour museums and immerse yourself in Italy’s culture, winter is perfect. Summer can be hot and crowded with all Europeans on holidays, but it’s the prime time for spending days on the beach or by the pool, and fun evenings out on the town. But of course, anytime in Italy is a good time when you are prepared.
During the pool season, from mid-June to early September, it is advisable to book accommodations well in advance. We suggest you book your villa at the same time as you get your plane tickets. If you are in Europe and close enough to drive, book at least 6 months ahead to get the villa you want. Some people book even a full year in advance, and especially if you have a large group that requires a big villa and specific amenities. Spring and fall are easier times for you to find good choices even just a few weeks in advance. Winter is when most villas in the countryside are closed up, so you might need to look around to find the right place – we are happy to help you with this.
A rental car is necessary. Without a car you can only stay in a large town with a train station, and when you are okay not to get around the neighbourhood much. You need a car especially if you intend to explore the Chianti or the Val d’Orcia areas and their wine regions. Consider how you get to your villa from the airport. Are you able to carry your luggage on and off crowded trains? There is no public transportation convenient for any villa in Tuscany’s countryside. We have a few villas that are within about a half an hour walk from a village with a restaurant and food stores, but still, you would need a car to bring your shopping back.
It’s best and easiest to rent your car from the arrival airport. Rome and Milan have huge airports that require much time to get through, but they also have every car rental agency represented. The regional airports in Florence, Pisa, Bologna, Venice and Naples are much smaller and easier to navigate. These regional airports come with the usual choice of car rental agencies. Florence Airport is closest to our villas, see the new location for rental cars, you need to take a short shuttle ride to get your car, here is a map for car rentals at Florence Airport. Europcar, Hertz and Avis have agencies in many towns, like Siena and near the main train stations, like at Chiusi but make sure you know their operating hours (closed Saturday afternoons and Sundays) and where they are exactly. In Siena, you need to take a taxi from the train station to the car rental agencies.
Our choice for the best times is in the spring and fall, for the best weather and the outdoors. During the summer it’s hot and busy, but then you go to Tuscany for the sun and the fun. Winter is best for culture in all of Italy.
Read here what the travel guru, Rick Steves says: … best travel months (also busiest and most expensive) are April, May, June, September, and October. These months combine the convenience of peak season with pleasant weather. The most gruelling thing about travel in Tuscany is the summer heat in July and August, when temperatures hit the high 80s and 90s.
Come to the countryside of Tuscany. Our first choice is the southern Siena Province, including the wide Orcia and Chiana Valleys and the wine regions of Brunello and Vino Nobile, around the towns of Montalcino and Montepulciano where the landscape opens up to panoramic views. The well-known wine region between Siena and Florence is of course Chianti, which gives you many towns but also more mountains and wilder scenery. Also visit San Gimignano, Volterra and the coast of Tuscany, with the island of Elba. Northwest of Tuscany has the famous riviera beaches at Versilia backed up by the Carrara marble mountains. Here you should see Lucca and Pisa, both wonderful small cities with lots to offer. On the eastern side don’t miss Arezzo and Cortona, both made famous by movies in the last decade.
Italy is generally considered to be a safe country. Most Italians are courteous and helpful, especially in the countryside and small towns of Tuscany. If you are ever in trouble, people would probably go out of their way to help you. The main concern for tourists is theft. In crowded cities, on the bus or train, at an open-air market, there could be pickpockets around and they can spot the tourists. These gangs are often children who work in teams, where one is trying to sell you something to distract you, while others are trying to get their hands into your bag or pockets. Backpacks are an especially favourite target. Keep your money safe; don’t put a wallet in your back pocket and don’t have it exposed in an open bag. The other easy target is your parked rental car. You shouldn’t leave any personal items visible inside the car, it’s best to put all your stuff in the trunk.