Where to go and what to see around Tuscany - need help planning an itinerary


New member
I'm travelling to Tuscany for a wedding in June and I'm having trouble planning an itinerary for the trip. We are planning on flying into Pisa on Fri 19th June and depart either Fri 26 or Sun 28th. The wedding is based in Gaiole di Chianti on Monday 22 and we have accommodation from Sunday 21 to Tuesday 23rd morning. What to do to make the most out of our visit here and maximise what we see with out rushing is proving tricky as there are lots of options. My initial thought was land at Pisa and travel via train to Florence, stay Friday night to Sunday morning in Florence and then pick up a car hire from Florence (airport??) and drive to the wedding accommodation for Sunday night to Tuesday morning. This is where I'm getting stuck.... whether to travel down to Siena (stopping at a few places along the way such as the thermal spa for a few hours??) and stay in Siena for the rest of the week and drop the car hire off and on the final day get a train back to Pisa from Siena OR stay in a few different locations around Tuscany and drive to any places we want to visit such as a day trip to Siena and on our final day drive back to Pisa and explore Lucca before flying back on either the Friday or Sunday morning. I'm quite good at finding places to stay though airbnb and trip adv etc but it's the planning on what to see and do and whether to train or drive it etc... Another thing I'm concerned is the parking around Siena and if I'd need more than a day to see Siena ? I'm not overly into museums but I quite like a bit of art and love exploring buildings and back streets - maybe there are other towns or places to visit which I haven't found out about ?? Hopefully I can be guided in the right direction :) thanks


Well-known member
Car Rental


The first thing I would suggest you look at doing is putting Florence at the end of your stay. You could look into picking the car up immediately in Pisa - have a look at the tower (if you get in early enough) and then enjoy the trip tdown to Siena.

Your last stop can be Florence where you drop off the car - enjoy the city and then train it back to Pisa - I believe this will maximize your time. A suggested itin would be

Pisa - visit the leaning tower right away if you get in early enough.

San Gimignano area (you could look at staying in the city itself....I have stayed at Leone Bianco and loved it http://www.leonbianco.com/ ... think a glass of wine in their hot tub....wonderful!)

wedding (chianti area)

Siena (Val d'Orcia area) have a look at Podere Pietreta, they have suites and an abundant breakfast ... here you can truly appreciate the landscape http://www.tuscanyaccommodation.com/podere-pietreta.html



This would give you a wide range of views and experiences.

Buon Viaggio