I only have 6 days in Italy…..
Hello, your site is great! Thank you for all the useful info. My wife and I are planning our 5 year anniversary trip this coming October. We will be doing a week in France, a quick 2 day trip to London for a friends graduation and then a week in Italy. We will arrive in Venice on October 20th in the morning. I am only planning on 1 night in Venice and then off. I know we want to visit Tuscany and Florence. I just don’t know the best route or towns to visit. I’d prefer to travel by rail rather than renting a car and driving. We love wine and are very into food. Should we do 2 nights in different villages or towns in Tuscany? Then 2 nights in Florence? or should we just do 1 night in Florence and visit another city? We have to be in Milan on Sunday evening Oct 25, to catch a flight the next day. Also, any hotel or villas recommendations would be great. We enjoy staying at higher end properties. One last thing, our anniversary will be on Friday Oct 23rd. I’d like to be somewhere very romantic for that evening. I completely understand that I am requesting a lot of information. Thank you so so so much for any help you can offer!!
Happy to give some advice for your special trip to Italy 🙂
Venice and Tuscany are really full of romance.
First thing you will have to decide is about the car; if you really are not willing to move by car, then you should base in Florence for most of your stay and then reach a romantic destination in the countryside and stay there. The fact is that Tuscany is all hills, villages atop hills, and touring it by rail or bus is not always convenient also in terms of loosing a lot of time to change train, wait for a bus, etc.
Just think about it and if you have any more questions on that, just ask. Also read this post dedicated to getting around Tuscany.
As for the best towns and villages to visit in Tuscany, in addition to Florence and Siena, I certainly recommend the scenic San Gimignano and its medieval towers, Montepulciano, Pienza, and Montalcino. Here is my list of the top villages to see in Tuscany 🙂
As for your itinerary, I would suggest 1 or 2 nights in Florence, maybe at a beautiful romantic hotel like Hotel Brunelleschi or the Jk Place.
As you love food and wine I would divide the rest of your stay between Chianti and Val d’Orcia with a visit to the beautiful Siena in between. Both these areas of Tuscany are popular for their unique landscape, fine wines, and delicious local specialities. That is true especially for the Val d’Orcia where the town of Montalcino gives the name to the prestigious Brunello di Montalcino wine.
In Chianti a great place to stay is Villa Bordoni, but also the scenic Castle of Spaltenna. In Val d’Orcia I’m in love with the Castle of Velona (thermal waters and much more), and Hotelito Lupaia in Montepulciano.
I would suggest you pass the Friday right at the Castle of Velona, but if you wish a different suggestion, let me know.
I remain at your disposal,
Enjoy planing your special Tuscan trip!
Thank you so much! So how does this sound:
Day 1 – Venice
Day 2 – Florence
Day 3 – Chianti
Day 4 – Val d’Orcia
Day 5 – Siena (or extra night in Val d’Orcia or Chianti)
Day 6 – Milan
I’m fine with renting a car. I realized that train travel would be difficult after I sent the original request. Would it be better to rent the car in Florence or Siena? We will be taking the train from Venice to Florence and a train to Milan as well.
As far as wine tasting at vineyards go, do I need a tour guide or can we just stop into places? Any specific vineyards that are a must in those area?
How about restaurants in Chianti and Val d’Orcia?
Thank you so much for all your help!!
thanks for getting back!
I would rent the car directly in Florence so you can first direct south to reach the Chianti region. After Chianti leave to visit Siena during the day before directing towards the Val d’Orcia, where I would pass 2 nights.
For wine tasting you can just stop at the many you’ll find along the route.
In Chianti I suggest you taste wine at the Castle of Brolio, at Badia a Passignano and Badia a Coltibuono. The last 2 are also serving excellent local food at their osterias.
In Val d’Orcia pay a visit to Fattoria Poggio Grande in San Quirico d’Orcia and Ciacci Piccolomini in Montalcino. This last one enjoys a panoramic terrace that will make wine tasting even a more pleasing experience. In MOntepulciano, Montalcino, and especially Pienza are a lot of good restaurants. In Pienza try the Osteria Baccus. In Montalcino you can try the elegant restaurants at Castello Banfi, that also produces prestigious wines.
I remain at your disposal,
Enjoy the weekend,
Elena, Looks like we are going to skip Chianti and just do 2 nights in Val d’Orcia. I was able to book at Castello di Velona. What is the travel time from Florence to the hotel? Is it necessary to have reservations for wine tastings at different local vineyards? Which restaurant would you recommend for our anniversary dinner? Thanks again!
Happy to hear from you 🙂
You can reach the castle of Velona from Florence in about 2 hours taking the fast Autostrada A1 Firenze-Siena.
It is usually not necessary to make reservations for wine tastings, but you like one winery in particular or for the names I suggested I would ask before.
The restaurant at Castello Banfi is a great option for an anniversary dinner 🙂
Have a great stay and then let me know about your stay,