Help please! 7 days in Tuscany & Cinque Terre


New member
Hi Everyone!

I am in desperate need of some help because every part of Tuscany looks beautiful and since I only have a week, I want to make sure I see the best parts.

I get in on 15th June and am spending 15th and 16th in Florence. And then I've also planned to go to Cinque Terre on the 20th for 2 nights. However, in between from the 17th to the 19th, I have rented a car as I want to cover a medieval town and also some countryside/ . The initial plan was to do Siena on the 17th and stay a night there and then go to a region in Chianti and spend 2 nights there, on 18th and 19th.

My question is:
1) Is Siena better or San Gimignano better for a visit and a 1 night stay? Or is there somewhere else I should be looking. Basically I'm looking to experience something unique.

2) Also, do you think that it is worth staying a night in Siena/ San Gimignan, or am I better off just driving through these towns for day trips and staying an extra night in Cinque Terre instead?

3) From the Chianti regions, which is the best one to stay at? What I'm looking for from Chianti is to be able to find accommodation where I can enjoy some great views of the hills and vineyards, be able to do some wine tours and also be able to spend some time experiencing a small town. So far, I'm thinking Radda is a good option, but I'm not sure.

4) Which Cinque Terre town would you recommend staying at? I would like to stay in a place that is scenic, with those typical Cinque Terre coastal views, and also has some restaurants/ bars.

Sorry for the numerous questions! Any help at all would be greatly appreciated!


Well-known member
A few days in Tuscany


Oh my goodness, if you really want to see the best of Tuscany you would have to stay months and months! really there is just so much!

From the 17th to the 19th gives you three days, and if you have a car that means lots you are pretty free to drive around, enjoy the scenery and some off the beaten track opportunities.

On the first day, I would actually take the car down to Montepulciano (about an hour and a half on the main highway) and then work your way north. Make your first night outside of Siena in the Val d'Orcia area. Here you will find hot springs, excellent wine & cheese, and awesome little towns.

This article may give you a few towns to look into:

Then the next morning I would head towards Siena and spend the day - great town with so much to see! If you are there for a full day, then don't skip out on the museums and churches.

Read here for the more details on the many places to visit:

That evening you could either sleep in Siena or take the car for a twilight stroll through Monteriggioni and stay in San Gimignano or head over to Chianti. Any place is going to be fairly touristy during the day, but in the evening places like Radda, San Gimignano, and others calm down and it is a softer mix between locals and tourists. I suggest you have a look at the accommodations in San Donato:

Then the next day you can casually head north towards 5T (Cinque Terre) and maybe stop at Lucca along the way. :cool:

Buon Viaggio,

Donna Denise


The Tuscan Expert ;-)
Staff member
Yes, you've only got 3 days for Tuscany at this point, considering 5T is not Tuscany. I second the recs Donna gave you, to try to fit in the best of the region.

As far as 5T, I would recommend staying in either Vernazza or Manarola, those are in my opinion the most scenic and picturesque to enjoy in the evening too. All the towns have places to eat at so you don't run into a problem from that point of view. Consider June is a busy month so get going with accommodations so that you find availability at the ones you like!

Here's more info on CT:

Here's a link for places in CT for those two nights on (disclosure: affiliate link).