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Florence Day trips

Hi all! I have already posted about our trip coming up in May with the following itinerary :

1 night in Milan
2 Lake Como
2 Cinque Terre
4 Florence
2 Venice

I am planning our stay in Florence. We arrive from CT to Florence on the 22nd of May, then we leave Florence for Venice on the 26th. On the 25th, we have an event that ends around 1:30 - 2 pm so I don't think we'd be leaving the city that day. On the 22nd, we will only have around half a day so we will also stay around the city centre. I think those two days are more than enough for us and what we want to see and explore in the city.

However, on the 23rd and 24th, we are free and would like to explore the surroundings of Florence. We would like to visit the iconic Tuscan countryside and go to a winery. We were thinking of renting a car for that day. Do we go to a closer winery in the Chianti region, or is it worth the longer drive to go to the southern regions around Val d'Orica? Is it a good idea to stay there overnight for 1 night? (could be the first day we arrive in Florence)

Also, we would like to pay a quick visit to Pisa. Is it better to go there from CT (stop on the way, with our luggage) or go there as a day trip on our second free day, and possible include either San Gimignano, Lucca or Siena as well?

How would you suggest we plan our stay in Florence given the information I've provided? Any feedback would be much appreciated!

Posted by
68 posts

After doing some research, I have created a few possible options :

Options A
Day 1 : Private transfer from CT, stop at Pisa along the way
Day 2 : Day trip to Lucca or Siena
Day 3 : Rent car and day trip to Chianti winery (maybe stop at Siena on the way, and do Lucca on day 2)

Option B
Day 1: Train from CT to Florence
Day 2 : Guided tour to northern tuscany (12 hours, does Siena, Lunch at Chianti winery, San Gimignano, Pisa)
Day 3: Day trip to Lucca, or rent a car to another winery

Option C
Day 1: Train from CT to Florence
Day 2: Take train to Lucca, then Pisa
Day 3: Rent car and day trip to a winery in Chianti (maybe stop at Siena on the way)

Option D
Day 1: Train from CT to Florence, rent a car and sleep overnight at a winery (either Val d'Orcia region or Chianti)
Day 2: Visit different wineries and towns (if staying around Val d'Orcia)
Day 3: Drive back to Siena on the way
In this option we spend more time in the countryside, but don't see Lucca or Pisa