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Day trip recommendations please

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Durham, United...
Level Contributor
1,138 posts
85 reviews
Day trip recommendations please

Hubby and I are staying in the Palazzo Squarcialupi apartment for 4 nights in September and as well as relaxing we'll also want to get out and about a bit.

We'll start our trip in Florence for 4 nights, then 2 nights in Siena before moving onto Castellina.

We'll be picking up a hire car before we leave Siena so getting around won't be a problem. As well sampling the local culture, our other interests on holiday are food and wine (well in Italy, it would be rude not to!) so any recommendations would be appreciated.


north carolina
Level Contributor
5,596 posts
118 reviews
1. Re: Day trip recommendations please

Your hotel and your town are both lovely, so don't worry much about what to do. I would very definitely plan to drive to Radda and Gaiole, either same day or two separate trips. San Gimigniano is perhaps 45 minutes drive. There are, as you anticipate, many fine wineries around, both within Castellina and within a comfortable drive. You could very easily visit three or four wineries, if that appeals to you, and have choices of some wonderful wines, if Sangiovese appeals to you. - (it does to me)

The people who own the hotel also own the "La Castellina" vinyards and factory, within an easy walk from your hotel. I happen to think that their "Squarcialupi Reserva" is the best Chianti I have ever had, but there is ample opportunity for critical comparison near-by.

Plan to visit the restraurant Albergaccio di Castellina, drive, do not walk, it is very fine, slightly expensive.

restaurant Antica Trattoria la Torre, close to the hotel is good, not great.

the pizzeria, Il Fondaccio Pizzeria Bar, is, IMHO, the best pizza place we have ever visited in Italy. (we have not been to all of them);

and there is a gelato place on Via 4 Novembre, just south of the hotel, that we visited repeatedly and we thought it was the best gelato we had anywhere.

As you see, i am a big fan of Castellina, but Radda and Gaiole are lovely towns, too.

you can not fail to have a great time.

Idaho Falls, Idaho
Level Contributor
131 posts
6 reviews
2. Re: Day trip recommendations please

Oh we love Radda and Gaiole and that part of the world. We stayed in Radda for years and now we are in Gaiole.

Our goal most days is a great lunch with wine and to tour wineries. With that in mind here are our favorites, but if you want our complete list then email us at jnjfraz@cableone.net

Restaurants: Many of these are out of the way so you need a good driver or a good map.

Ristoro di Lamole is in a little town above Greve and is just amazing food and a full afternoon experience.

Cantenetta di Rignana is up over the ridge from Panzano toward S2 and is also amazing

Badia a Coltebouno is wonderful... located on the road from Gaiole to Montevarchi.

Ristoro la Antica Scuderia is at Badia a Passignano (again up and over to the west from Greve)

Osteria del Castello Brolio is just below Castello di Brolio and is wonderful. This is a very historic place as Baron Ricosoli standardized the Chianti formula and was one of the first Prime Ministers of Italy..


We think one of the very best tours is Castello di Monsanto but you need to contact them and arrange a tour

Dievole does a good job

Castello Fontorutoli is good

and there are so many more that you can just stop to tast

Durham, United...
Level Contributor
1,138 posts
85 reviews
3. Re: Day trip recommendations please

Thank you both for your replies, that's great and really helpful

Castellina In...
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99 posts
17 reviews
4. Re: Day trip recommendations please

You'll have a great time in Castellina I'm sure.

I live nearby and have my own list of local restaurants which I update constantly: http://www.patrignone.com/56/local_food.html

Everyone has different tastes, but from where you're staying you can definitely walk to Albergaccio, and La Torre is the best in Castellina IMHO. Best tasting pizza at Tre Porte. But with a car you have dozens of brilliant restaurants to choose from, I promise you!

The same page has my list of favourite local wineries, most of them small properties that make superb wine.

Durham, United...
Level Contributor
1,138 posts
85 reviews
5. Re: Day trip recommendations please

Thank you so much. I will keep a close eye on that before we go

Level Contributor
69 posts
5 reviews
6. Re: Day trip recommendations please

My husband and i stayed at the Palazzo a few years ago and loved it. Our favorite day was spent at Castello di Verrazzano, their wine tasting luncheon is one of the best, with 5 courses and 5 wines, not sips but bottles!. We also tasted their olive oil and balsamic vinegar. About a half hour drive from Castellina.

My girlfriends and I are also staying at the Palazzo Squarcialupe this Sept. from the 27th to oct 2nd. and plan on doing the same tasting luncheon.

Level Contributor
2,873 posts
158 reviews
7. Re: Day trip recommendations please

We stayed there for a week exactly a year ago! We did daily excursions to Greve/Montfioralle, Radda/Gaiole, Volterra/San G, Siena and Florence. Castellina is the perfect place for exploring the Chianti Classico region.

Our favorite vineyard was Vignamaggio just outside of Greve, we did the tour with lunch and it was the best meal we had in all of Italy! I would gladly visit there again.

Have a wonderul time, you'll love the Palazzo Squarcialupi!

Barberino Di...
Level Contributor
85 posts
5 reviews
8. Re: Day trip recommendations please

Since you are in Castellina in Chianti I strongly recommend the following places in the surroundings:

- Radda in Chianti is a small village, enclosed in massive walls, famous for its wine's production. Nearby visit the Brolio Castle, owned by the Ricasoli famiy, one of the most famous producer of Chianti Classico wine. In fact the Barone Ricasoli was the first to create the original recipe for the wine Chianti Classico, that is still used today. Included in the visit to the castle you have a wine tasting - http://www.ricasoli.it/ .

- Gaiole in Chianti surroundings such as the medieval village of Vertine and the Badia of Spaltenna, a stunning Romanesque church.

- The small village of San Gusmè that is almost unknown. It is famous for its funny statue and the legend about it, that in English cannot be translate since you'll loose the word pun. I recommend you eat at the restaurant "Sira e Remino". Try the "pici cacio e pepe", handmade past with cheese and pepper that is a must for this area.

- I also suggest you visit San Gimignano and the museum 1300, where I've last week. It's amazing!

Hope it helps

TooMuchVale http://www.toomuchtuscany.com/

Durham, United...
Level Contributor
1,138 posts
85 reviews
9. Re: Day trip recommendations please

Wow! Thanks so much for your replies

10. Re: Day trip recommendations please

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