Are we doing too much? Help!


New member

First time posting, but I've been enjoying the site. It's been a great resource.

My wife and I have booked a trip to Italy from May 29 to June 10. We've both been to Italy before, but not together. We're starting in Venice for a few nights and then heading over to Florence and the Tuscany area until the 7th when we'll head down to Rome for the last leg of our trip. We're a bit overwhelmed by the options in Tuscany and could use some advice on what to do and if we are moving around too much.

Here's what we have scheduled so far:
May 31: arrive in Florence by train from Venice. See the sites in the city.
June 1: Full day in Florence to see more of what the city has to offer. Some museums, etc.
June 2: Train to Cinque Tere. Explore and overnight in one of the towns.
June 3: Explore some more in Cinque Tere, and then train back to Florence.
June 4,5,6, and 7: Explore Tuscany. We don't have much planned for this section yet. But have looked into staying at a hotel that is a converted Castle. It has a winery. But we also wanted to possibly do an organized wine tour. See Sienna, Chianti, Luca, and the countryside. I also saw that there is a food and wine festival going on in one of the towns in the area that we were hoping to check out too.
June 7: Head to Rome by train and arrive in the evening.
June 8: Pompeii day trip
June 9: Explore Rome all day
June 10: head home.

Thoughts? What would the best way be to make the most of the days exploring Tuscany. Should we stay in one location and drive around? Or should we book a few places? I'd like to minimize changin hotels as there are already quite a few planned. We would be renting a car for the Tuscany exploration bit.



The Tuscan Expert ;-)
Staff member
Ciao Kirshy,

Glad you're finding the site useful so far!

I agree with you doing Florence first, separating out from the rest of Tuscany. Consider though that you likely have to go through Lucca on your way to CT - or on the way back. So there is no definite need to head back to Florence before starting on Tuscany. So you could do:

May 31- June 2: Florence
June 2-3: CT
June 3: Lucca on way back from CT, by evening head to Pisa where you can spend the night.
June 4: Explore Pisa, then head to airport to rent a car from there. Then head to your base.

June 4 - 7: Where is the winery/castle you found so far? If it is in Chianti, then it is very central and you can use it as a base for all of the days. You can roam around the hilltowns, Siena, the Val d'Orcia to the south of Siena.

You already moved between Florence-CT-Lucca, so that's another good reason to stay put in one place for a few days later.


New member
Ciao Lourdes!

We ended up booking at Villa Casagrande Resort & SPA, Figline Valdarno. Which I think should be nice and central for our exploration of Tuscany.

We had not considered staying overnight in Pisa or Lucca instead of coming back to Florence. You suggest exploring Lucca during the day and then heading to Pisa later in the evening and staying there. What would we do with our luggage during they day in Lucca? Do you know where we could store it? And what would be the best way to get to Pisa from Lucca?

Any recommendations for wineries in the Chianti region we should consider?

Also for the train. Should we purchase tickets ahead of time or can they be bought on the day of travel? I was looking at this site: Do you know if this is a good site for tickets? Or is there a better more official one we should use?