First trip to Tuscany! Please help!


New member
My friend and I will be traveling to Tuscany in mid-October, arriving from Naples and leaving out of Rome. We have a total of 4 days (leaving for Rome on the last day): arriving Saturday 16 Oct (afternoon/evening) and leaving Wednesday 20 Oct (evening), taking a train to and from the area.

We'd like to spend time in Florence, but also get in wine tasting, and sight-seeing in the Chianti region - we want to eat and drink and really experience the area. In our native New Hampshire, we buy almost all of our food from local farmers, and my friend is an incredible cook (I'm learning). As such, these are things that mean something to us. We also adore wine. And hiking. And history.

We were thinking about staying in the Greve in Chianti or surrounding area. The only other thing is we are on a bit of a budget - we could splurge a little, but generally would like to keep costs down. Basically, we want a very special trip, but we do have limitations; cheaper alternatives are welcome, but if something is worth the money, we'll consider it.

My questions are:

1. Our original idea was staying in Florence 1-2 nights (2 real days), then the remainder at a base in Chianti (i.e. Greve in Chianti - or alternative?) Is this a good idea?

2. If this sounds like a good general plan, should we train to Chianti first, then on to Florence, then on to Rome? Or head straight to Florence, then Chianti, then Rome?

3. The more I hear about Chianti, the more I want to stay and explore there - but sounds like buses are difficult. Is renting a car a good idea if you're on a budget? Or a scooter? If we are constrained to public transit by money, what should we definitely see? And, if not and we rent transportation, would you recommend one of the Gaiole in Chianti's Castles of Chianti route ?

4. What about when things are closed, such as castles, wineries, and museums? I see museums are often closed on Mondays...

5. I also saw this: "dining with a family". Have you heard about this? What do you think?

Thank you SO much for your time - I was really impressed by the feedback you provided to others! This is a great source! :D



Well-known member
4 days in Chianti

Dear Emily,

it sounds like you have a clear idea on what you want to do and to see in your vacation in Tuscany and I think you got it right :).

Since you arrive in Naples in the afternoon/evening and move by train, you necessarily head to Florence and I suggest you spend your first night in Florence and then move to Chianti. You should consider that: Naples-Florence by Frecciarossa train (the fastest train) about 2 hours and half, then Florence-Greve in Chianti by bus about 30 minutes, but the last bus departs at 8.30 pm.

You can think about splitting your stay in the city and spending there the first and last night. In fact moving from Florence to Rome by train is much easier and faster than from anywhere in Chianti, since there are not direct buses or trains.

I think that 2 days in Florence are perfect to visit the city, main museums and monuments. Of course I suggest you book Florence museums in advance, especially for the Uffizi and Academy Gallery.

Greve in Chianti is a good destination, because it's close to Florence, but still centrally located in Chianti. As you said moving around Chianti by public transports can be a challenge. Of course renting a car or a scooter would be better, but it's up to you. I suggest you read these articles about moving around Chianti and about what to see in Chianti. I also recommend you search the forum for other threads about wine tastings in Chianti by bus.

Regarding the castles' itineraries, there are so many castles and fortresses, as well as beautiful churches, all around Chianti. I suggest you visit the Castle of Montefioralle, the Parish Church of San Cresci and the Castle of Lamole, near Greve; Vertine, the Coltibuono Abbey and the Castle of Brolio near Gaiole in Chianti. Of course I named just the most famous destinations. If you want to visit these places you'll need a scooter or better a car, since most of them are out of the main roads and there is no bus service.

I'm sorry but I cannot help you about the "dining with a family" thing. I've never heard about it. Anyway you don't have to worry, you will certainly find lots of places where to eat good Tuscan food, as well as taste excellent wine.

My last recommendation is to keep an eye on our guide to Chianti, because we will soon publish new articles about the main destinations ;)

I hope these suggestions will help you planning your vacation in Tuscany! Don't hesitate to come back with any other question :)


New member
Thank you!

Dear Valentina,

Thank you so much for your help! The only other thing I am wondering is about when things are closed because we'll be in the area over Sunday-Monday.

I know museums are often closed on Mondays - is there a day when castles/wine tastings/tours are typically closed, too?

Thank you again!



Well-known member
Since I am not going to Chianti until next month the only thing I can help you wit his to let you know that we are renting a car...mainly because we are flying into Rome and staying in Castellina in Chianti and are going to be very touristy in the region and if you are looking for a place to stay in Chianti we are staying here which is centrally located in the region and the contact I have had with the owners have been VERY positive.


The Tuscan Expert ;-)
Staff member
Emily, you'll find practically everything closed on Sunday in terms of shops. Many museums are open on Sundays in Florence, but in smaller towns since the weekends are when there is most visitors in town, actually are open Saturday and Sunday. Truly depends on where you want to go, you should search for and look for opening times. As for shops, many are also closed Monday mornings but open in the afternoon.