Milan and Siena Recommendations

Posted by kcm617 (Boston) on 02/01/26 09:23 PM

Hello!

Thanks to the great thoughts and feedback of this forum, my best friend and I will be returning to Italy again this April. Our home base for most of the week will be Siena, with a few days in Milan at the end. We visited both very briefly last year as part of a larger Italy itinerary, and were so enchanted we had to return!
We would love to hear any restaurant/cafe/bar recommendations (or anti-recommendations!) for either place. We don't have dietary restrictions, and are both adventurous eaters who are open to trying anything! Additionally, if anyone has recommendations for wineries within driving distance to Siena that would be worth a visit while we are there we would love to explore those too.

As always, thank you for your time!

Posted by kmkwoo

Massachusetts, USA

02/01/26 10:04 PM

2179 posts

In Milan, we enjoyed dinner one evening at The Fisherman Pasta in the Brera district. Nothing fancy, but the food is delicious. There are lots of restaurants and cafes in Brera.

Another restaurant we liked in Milan is Trattoria Milanese 1933. They serve traditional dishes. Nice ambiance and great service.

We had many delicious meals in Siena. I don't think you can go wrong there. Our hotel recommended Trattoria Nona Gina. Superb food, ambiance, and service. We were able to get in without reservations our first night. However, we wanted to eat here our last night in Siena, but they were fully booked. So I advise making reservations.

Another night we dined at Vivace Restaurant. The food is delicious. We dined in the courtyard. Stunning views and sunset!

Our last night, when we couldn't get into Nona Gina, our hotel made reservations for us at Quatro Venti. Another delicious meal. Great service. They give a complimentary starter.

Regarding wineries, I can't recommend any near Siena because we weren't able to get into any wineries in Tuscany without advance reservations. So I strongly advise that you make reservations in advance (not sure how far in advance) for a wine tasting/lunch etc. We walked into a few and were turned away. I was so disappointed. But we did go on a wine tour in the Valpolicella region near Verona to make up for our disappointment. :-)

Posted by palmisanojm

02/02/26 01:29 AM

45 posts

Milan:

At the end of a three-week trip across northern Italy, our stay at Hotel Berna was luxurious! I highly recommend staying there.
https://uvethotels.com/hotelberna/

And I give a second vote for Trattoria Milanese Dal 1933 for traditional Milanese and Lombardian cuisine.
https://share.google/EdxsGiY1i1c8FPBMA

Note: The restaurant's menu was only printed in Italian. Google Translate saved the day. :)

Posted by Laurel

Forest Grove, OR

02/02/26 01:51 AM

12177 posts

We’ve been to Milan almost annually for the past 14 years. We have a couple favorites near the Hotel Berna but I encourage you to journey to Velvevodetto near the Duomo for some of the best Roman cuisine outside of Rome. Can reserve online and it is essential to do so.

Posted by charylm

Florida, USA

02/03/26 03:32 PM

313 posts

As stated, you will find many great places to eat in Siena. IL Vinaio di Bobbe e Davide at via Camollia #138 (website address is 167 but moved across the street) is an excellent place. Osteria al Palchetto at via dei Porrione #27 very traditional. For pizza recommend Trattoria L'Aquila at Casato di Sotto, 58. Paninii il Cencio in the Campo is very popular (you might find us sitting there in April).

Posted by Hallowed Way

Florida

02/04/26 12:07 AM

25 posts

Siena has an Old Wild West, great burgers. (but, I kid)

Montepulciano and Montalcino are driving distance from Siena. Hitting both would be a fantastic wine excursion.

Ercolani in Montepulciano has some excellent wines, give a good tour of their cellars and make shipping to the US too easy. https://www.ercolanimontepulciano.it/en/. I really enjoyed the Apostoli, a Vino Nobile.

In Montalcino (home of famous Brunello), we loved our tasting at La Sosta Bar. Ask for Flavio. We enjoy Brunello, but not 10 times as much as a good Chianti Classico. However, Flavio made an excellent show of the tasting, giving each glass a fun nickname. A fun splurge.

A little closer to Siena is Caparzo. https://www.caparzo.com/index-eng.html. We limited ourselves to 1 glass, as we were hiking through on the Via Francigena, and they advertised a "Pilgrims Lunch" for 8 Euros.