I’m planning my first trip to Italy. There are 4 of us going. We have 2 of three legs of the trip planned and I’m looking for recommendations for the 3rd.

The first part of the trip is Florence and we plan to spend 4 days there.

The last leg of the trip is Chianti. We’ve rented an apartment in a villa in the Classico region.

We’re trying to decide where to go for the intervening 3 days. My wife wants to go to Sienna and I’d like to go someplace like Perugia in Umbria.

Does anyone have experience in either of these cities? I know that Perugia is smaller but that’s why I like it as a choice.

Any help would be appreciated.



We’ve been to Tuscany a few times, most recently in 2017. The overwhelming memory that I have of the larger cities, such as Florence and Siena, is of the hordes of other tourists. Florence of course has so many compensating pleasures and attractions that I would still recommend, but I would hesitate to recommend Siena (perhaps its charms become evident in the evening when many of the tourists have gone away?) For the 3 day gap that you are looking to fill, I would suggest taking a look at the Val d’Orcia, a region just to the south of Sienna. The landscape is very different from the rest of Tuscany and a joy to take a walk or a drive through. There are small towns to visit, or to stay in. Lots of wine in that area too. Good luck in your planning and have a great trip.
P.S. We liked the Chianti region.

I agree that the cities in Tuscany are over run with tourists.

We spent a week on the Tuscan coast in the Maremma. We stayed in Talamone which is a particularly cute town on a peninsula jutting into the sea. We did not see or interact with a single American, Canadian or Brit during the entire week.

You need a car but there is a lot to do in the region including visiting Bolgheri, the Maremma and tasting the next generation of interesting winemakers.

We had the best meal in Italy at small outdoor plce just outside of Talamone callled Ristorante dell’Agriturismo Buratta. Set inside a horse farm, you order at a counter and find a picnic table outdoors and watch the horses train. Right below the restaurant are vineyards that the owner said were owned by Batali and Joe Bastanich. The wines are supple and amaxingly cheap. We paid about $30 for 3 people with 2 bottles of wine made within a few miles of the farm .

Coincidentally, the ship that sunk a few years ago was right off the coast from Talamone .

Thanks for the information on Sienna. We’re checking out options in Meremma now. I think she likes the idea of being on the coast for a few days.

Hi Paul
I must admit that Perugia jumped out as somewhere to give a glimpse of Italy without the tourist hordes. If your wife likes chocolate, then that might help influence her towards Perugia.

FWIW I didn’t enjoy Siena, as whilst we found it reasonably easy to escape the obvious tourist concentration (the campo and the old pedestrianised street leading to it), the rest of the city just didn’t excite.

Tuscany certainly is typically welcoming to 1st time tourists, without any experience in the Italian language.

Lucca appeals to many, so worth reading up to see if it appeals. It also lacks the endless slopes in Siena that can become draining. Colle val d’Elsa also impressed us, and it has smaller scale charm without excessive tourism and a thriving glass making industry that might appeal.

Nearer the border with Umbria, Montepulciano might also be worth a look. Much smaller than Siena, but with steeper slopes, but at least here the slopes offer the chance of lovely rural views. Very easy place to taste wine, with plenty of drop in tasting rooms, and genuinely historic cellars, including huge ancient barrels.

Plenty more besides, but I’m trying to find that balance between touristy enough to make it feel ok, but not so touristy it gives a false (and IMO poor) image of the country.


You’ll be quite close to Siena so it’s an easy day trip. Montalcino is about an hour away, and if you wanted to book some wine tours/tastings, Altesino in is quite accessible. We found Montalcino to be less flooded than many of the cities we visited and really enjoyed dinner at Hotel Giglio. Perhaps the best meal we had on our trip.

If you do end up going from Florence to Perugia, a worthy detour along the way is Abbazia di Monte Oliveto Maggiore, where you can hear Gregorian chants in a medieval abbey. This is in a region called the Crete Sienese, with rolling hills and rows of cypress trees.
Another good detour along that route is the Felsina winery, just east of Siena.

if it’s your first time you have to do Florence and Siena. They are the two most beautiful towns and full of people for a reason. Also San Gimignano , Volterra and Arezzo are a must see

It’s funny to read your note - I’ve never been to Tuscany, but just spent the evening holding up the Hemingway Bar at the Ritz in Paris. I randomly sat with a nice, older gentleman who runs the bar program at Il Pellicano in Porto Ercole… and could not stop talking about me visiting his hotel in Tuscany. So, I feel compelled to post, in the event fate is trying to intervene.

Hotel is Hotel Il Pellicano, Luxury Hotel Porto Ercole, Argentario, Tuscany and the bartender was Federico Morosi. Take it for what it’s worth, but we spent an hour talking about making negronis, living in Tuscany and bartending life. I’m totally trying to find an excuse to visit now :slight_smile:

I’m a huge Sienna fan. Yes, it’s more charming after the day trippers leave.

The key, besides it’s beauty, is there are no cars allowed inside the city walls. For me, that helps balance the crowds. Plus the times I went, I was out of town during the day at wineries.

I’ve been to Perugia and Sienna and prefer Sienna significantly.

If you are going to the coast, you’ll have a great time but not much of the history that makes Italy unique.

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We had a similar itinerary on our first Italy trip. I would recommend Siena as well. The city of Siena is quite nice, but more importantly it is an easy drive from there to San Gimignano, Montalcino, Volterra, etc. If you go to Siena, dine at https://www.tavernasangiuseppe.it/. Simply amazing meal!

I adore Il Pellicano. Go when it’s warm and don’t plan on leaving the property often during your stay.

And I agree with Barry; Siena is best at night after the day tourists leave.

Well if you’re thinking of getting a place there don’t bother. There’s really nothing available.

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Here’s an old post I wrote a few years ago, some may be out of date:


I’ve been to Umbria a few times, based in Perugia. Also, in Tuscany many more times, and have been based everywhere.

First major difference you will notice when driving from Tuscany into Umbria is that the latter is not nearly as manicured, and without the clean lines, as the former’s prettied-up countryside. Umbria will be much more rugged, with (yes) less tourists. Perugia is actually quite a big city, but is also a great one to use as a base to do your day-drives around the region. No, chocolates is not what we’d go there for, we get Perugia’s chocolates products here (and everywhere) and ignore them for others that are better.

In addition, the contrast in wines (sagrantino-based wines are good if you carefully choose producers) and foods, where Umbrian foods are terrific with more “soul” and rusticity, make the case for us to try for a few days stay whenever we plan for Tuscany. Pork products are better in Umbria than in Tuscany, imo. Plus, Perugia only a 2-hour drive (or train) from Florence.

edited to add: Have stayed at Orvieto a couple of times before, too. A good base, too.

Great thread. I’m going to Tuscany the last week of May - doing Florence for a few days, Bolgheri for two days, then 4-5 days in Tuscany.

Does anyone know how to get an appointment at Biondi Santi? I thought it was open to visitors but got an email from them today rejecting my request. They said they only host tastings through their partners…

Any one tasted or planned tastings at wineries in Bolgheri that I should visit?

the new ownerships stopped doing tastings and only does them for press or trade. If you are ITB you might want to reach out to their US importer

Florence is wonderful. Lots of tourists including my wife and me. So much to see. David and the Duomo are worth it alone. Get an apartment with a terrace. A light dinner of wine, cheese and salami is wonderful in the warmth of sunset.

San Gimignano is fabulous after the tour buses leave. Magical at night. Reservations start at 7:30 PM. Had a great dinner at La Mangiatoia, Via Mainardi, 5, phone +39 3479699414.

There’s a great little hotel in Montalcino - Il Giglio Hotel and Restaurant. Run by an older husband and wife. Excellent dinner there too.


Hi, Michael
as with all things, it depends what you like. My personal highlight last week was a visit with Michela at Grattamacco. Full transparency, I’ve been a fan of Piermario for decades, and simply had to see where it all started.

Also, depending on when you will be visiting, I recommend Biserno, just outside the village of Bibbona, my base for 4 days, and just 15 minutes from la strada del vino in Bolgheri.