We are planning a family trip to Tuscany in June for my fathers 60th and are a little overwhelmed by the location options and would appreciate any suggestions. We are 6 adults and a 20 month old child. We would like a villa or farmhouse in beautiful countryside but not too secluded. We plan to explore local areas and visit wineries and local restaurants etc. We also like to spend time relaxing so a pool or beach nearby would be good.
Any area suggestions would be much appreciated.
If for you spending the complete holidays on the beach is not important and you want to check out Tuscany sightseeing and culture we'd recommend renting a villa or a farmhouse in the area of Florence or between Florence and Siena. This area is rich in places to see and to visit (like wineries, historical objects and typical Tuscan restaurants).
Florence, Siena and San Gimignano are three objects protected by UNESCO and are must-see, in my opinion, when traveling in Tuscany in any time of year. Only exploring Florence can take you at least three days if you want to do it right. Keep in mind the city of Florence in rather crowded in June.
When you go south-east from Siena you'll meet Montalcino and Montepulciano world famous for its great wines - Brunello di Montalcino and Vino Nobile di Montepulciano. Make sure to take a few bottles with you, these are high quality Italian wines known and appreciated in the whole world.
Other interesting objects in the area are Volterra (near San Gimignano), Pienza, Val d'Orcia, Abbey of San Galgano (with its sword in the stone), Monteriggioni and Greve in Chianti.
Although Tuscany bus and train connections are very well organized having a car (or renting one) is necessary when you are staying in countryside and have a busy holiday schedule. There are many villas with pool in the area of Florence and Siena since it's a bit away from the Tuscan coast and beaches.