Ideas on how to spend 4 nights in Tuscany


New member
I would really welcome some suggestions about my trip which at the moment is very disorganized.
My husband and I are traveling to Italy and we want to spend 4 nights in Tuscany. this is what i have so far:

July 19 Florence – rent car. go to Ponte Veccio /san lorenzo market
drive to Tuscany to Greve in Chianti stay @Hotel castello Vicciomaggio

July 20 Tuscany region (We don't know where to stay)

July 21 Tuscany region close to Sienna overnight at Petriolo Spa Resort Reserved

July 22 Tuscany region (We don't know where to stay)

from here drive or take train to 5 Terre?

July 23 Drive to Cinque Terre overnight in Cinque Terre,
Hotel reserved. Cancel policy 20 days (7/2)
or skip Cinque Terre and spend 3 nights in Venice instead of two ?

July 24 depart 5Terre, train to Venice – (or drive? drop off car at train station) Overnight in Venice Hotel Paganelli reserved
July 25 Venice
July 26 Fly to Paris

I hope this is not too confusing, at this point I still need two nights in Tuscany, and to decide whether to go to Cinque Terre on the 23rd or go to Venice instead and spend 3 nights there instead of 2.



Well-known member
Hello Cecilsa!
I’m happy to give some suggestions for your Tuscan trip:)

Tuscany has so many beautiful things to see and to do that it can be difficult to plan the perfect itinerary! But 5 days are quite enough to get the best of Tuscany and visit the must see destinations:)

As you will move to the south of Siena on the 21st of July, once you depart from Greve, I suggest you stop along the route to visit the beautiful hilltop towns of San Gimignano and Monteriggioni, not to be missed from any Tuscan itinerary.
They are both perfectly preserved medieval hamlets: San Gimignano with its unique and incredible skyline of towers, that makes it one of the best known cities of all Italy, while Monteriggioni is characterized by the huge and imposing walls all surrounding the town center. Monteriggioni is a very tiny village and can be visited in a very short time, so you might then continue southward and visit the wonderful art city of Siena, so different from Florence, yet so beautiful and absolutely a must see! Here, you can admire the particularly shaped Piazza del Campo, where the famous Palio di Siena takes place!

As to accommodation for the night of the 20th of July I highly reccommend San Giovanni in Poggio, a wonderful country house located in the Crete Senesi, between Siena and the Valdorcia, amid stupendous Tuscan landscapes and stunning sceneries.

On July the 22nd, I suggest you drive east of Petriolo, towards the Valdorcia region. Here you should visit spectacular medieval villages atop hills, like the famous Montalcino and the impressive Sant’antimo Abbey, the lovely Pienza, renowned for the production of the exquisite “pecorino” cheese, Radicofani with its mighty watchtower, and the amazing Montepulciano.

All the area is beautiful and particularly renowned for its wine production; the Brunello di Montalcino and the Nobile di Montepulciano are just some of its superb wines.

I recommend you stay at Podere Cunina, that is a perfect base to explore all the various villages and attractions of the Valdorcia. Podere Cunina is a beautiful farmhouse, carefully restored in typical Tuscan style, offering fantastic panoramic views all over the Sienese countryside.

Finally, I suggest you stay in the wonderful Cinque Terre and spend there at least 2 nights. Here you can have a refreshing break at the wonderful seaside; July is rather a hot period!

You may then reach Venice, that is rather small and can be conveniently visited in one day or two.

Do not hesitate to contact us again for any other suggestion you may need:)
Enjoy planning your trip and have a great holiday!
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New member
Ciao Elena,
I am very excited with your suggestions, and I will start inquiring about San Giovanni in Poggio and Podere Cunina. We love wine and I appreciate the advise on that too. Would you suggest I make train reservations from the states, or can they be made there?
All the best


Well-known member
5 days Itinerary in Tuscany

Ciao Cecilia!
I’m very happy you like my suggestions:)
Both properties are really very good and have fantastic settings!

As to train reservations, if you already have an idea of the trains you’re going to take, then I suggest you book them ahead of time; you can check train timetables and buy tickets here.
In this way, you may avoid possible queues.

Please post again for any further help you may need!
I wish you a great stay!

Of course we’ll be waiting to hear about your Italian experience ;)


The Tuscan Expert ;-)
Staff member
cooking classes in Florence and Tuscany

As jmfell recommended, a cooking class is also a fun activity to enjoy while in Florence or Tuscany - you can look at this one or at the ones listed here.