Siena and Tuscan Villages

As stated in the Florence Guide, we thought our stay in Siena was more memorable and we felt it was a better home base for a Tuscany experience. Our reasoning:

• Less crowded than Florence, with less tourists. While tour groups will still descend on Siena, especially during the summer, if you avoid the main tourist sites during the mid-day hours, you can experience Siena without the crowds
• Closer to most of the villages you want to visit. We went to Volterra, San Gigminano, Greve in Chiante, and Montalcino
• Streets are more enjoyable to explore. One of our favorite things to do is to just walk around a European city, especially those that still maintain that authentic, historical feel. Siena’s narrow stone streets, its stairways and winding neighborhoods, and it’s views were, to us, far superior to exploring Florence.

Wine Overview

There are plenty of blogs and websites that can go into details of Italian wine classifications, regions, grapes, best vintages and more. For me, it’s overkill. If you just want to drink wine and maybe have a short conversation with your waiter, here are some high-level Tuscany basics.

Sangiovese is the main grape grown throughout Tuscany, and like other grapes the flavor of the Sangiovese and the wine it produces can vary dramatically from wine to wine depending on a number of factors. So, if you don’t like one 100% Sangiovese wine, definitely just try another! This is the grape that made Tuscany such a renowned wine destination!

Go!Go! Brunello di Montalcino is one of Italy’s most famous and revered wines. It is required to be 100% Sangiovese grapes and be grown within a certain distance of Montalcino. It’s a very bold, dry/tannic wine. Be sure “DOCG” is on the label signifying it’s a true Burnello di Montalcino. My favorite wineries and bottles I’d recommend are: Biondi-Santi, Conti Costanti, Giodo (small producer), Casanove di Neri, and Altesino. Drinking Brunello in Montalcino, just an hour drive south of Siena, is a bucket list wine experience! Sure some vintages are technically better than others, but if you don’t drink Brunello all the time, you probably won’t tell the difference.

Go!Go! Nobile di Montalpulciano is the same concept with two important differences. First, to be a Nobile (pronounced “nobile-a”), the wine must only be 70% Sangiovese. While some Nobile wine makers choose to use 100%, there is some variety. Personally, I generally prefer the taste of Nobile blends over that of most Brunello wines.

Go!Go! Vernaccia di San Gimignano. If you are looking for white wines, GO TO SAN GIMIGNANO! The white Vernaccia grape is light and delightful, we loved it! There are only a few bottle options available in the United States, so look for it while you are there! Try it!!! This is a definite treat while visiting Tuscany!

Go! Chianti wine. If the only Chianti wine you’ve had was in a bottle with a basket at an Italian chain restaurant, you’ve never had Chianti. Simply look for any bottle with a black rooster on the label and you can rest assured it’s the real deal. Meaning, an authentic Chianti must be at least 80% Sangiovese in addition to being made in the Chianti region.

Go!Go!Go! Saving the best for last, the “Super Tuscan”. If the bottle has “IGT” on it, that likely means you’re holding a Super Tuscan, meaning all the rules for minimum amounts of Sangiovese grapes go out the window. In fact, Super Tuscans use a lot of grapes commonly used in Bordeaux blends. Super Tuscan’s tend to vary in quality more than the others, since there are less guidelines, but the good ones are, in my opinion, the best wines in the World. The best are Tignanello, Sassicaia, Ornellaia, and Solana, but there are also numerous less expensive Super Tuscans that are incredible. Antinori makes a number of mid-range Super Tuscans that have become regular bottles for me at home.

Finally, as always, keep an eye out for “reserve” or “selection” on the label, meaning the grapes are hand-picked instead of pulled by machine, typically resulting in a higher quality wine.

Food Overview

There aren’t any surprises here… you can’t find prosciutto or parmesan cheese in the US that tastes like it does here. Eat as much of it as you can. Gelato of course. Don’t eat anywhere that has pictures of the food on the menu, and be careful eating at places nearby tourist attractions or on the main square. Don’t go all the way to Tuscany and not eat authentic, homemade pasta. Truffles are everywhere, enjoy them.

Two comments you may not expect to read: 1. pizza in Tuscany was unimpressive – probably the easiest food to get fooled on, thinking you’re going to get something better than you can find in the US. You can, but this isn’t pizza country. Most pizzas put all of one ingredient on each slice, it’s weird. You order a mushroom, bell pepper and olive pizza, and you get all the mushrooms on one piece, all the peppers on another, and so on; 2. ORDER GRILLED VEGGIES! Amazing!

SIENA

SIENA HOTELS

As for where to stay, the first decision you need to make is what type of stay are you looking for on your trip? To clarify, you can stay in Central Siena, you could stay in a somewhat remote winery hotel to get away from it all and really experience the countryside, or you can find a middle ground – a place that’s close to the larger town of Siena but also feels like you’re out in the country. For example, the Hotel Certosa Di Maggiano, which gets wonderful reviews, is only 1 mile from Siena but gives you the feel of being out in the countyside. We stayed several nights at a small hotel just a block away from the Piazza del Centro in the heart of Central Siena, and then two nights in a Tuscan Villa just outside of Greve in Chianti.

If you choose to stay in Central Siena be warned you could run into some noise issues, especially on weekends or during peak travel season, as well as having to deal with parking and lugging around your luggage. Siena is built on several hills and you have to park in one of the outside lots to walk into the center of town. The pro’s of course is you can explore Siena and relax at the Piazza del Centro as late as you’d like with just a short stroll back to your hotel. Siena also offers a ton of incredible dining and wine drinking options all within walking distance. If you do want to stay inside the gates, so to speak, we’d recommend looking at the Grand Hotel Continental.

SIENA THINGS TO DO

Go!Go!Go! Cathedral, Biblioteca, Facciatone, Piazza del Centro: All are amazing. You can learn more about each of these attractions in literally any Siena guidebook. Don’t forget to buy tickets in advance, go early or late if staying in Siena area to avoid tour bus crowds, and try and go when the mosaic floors are uncovered!

Siena has the standard trifecta of European tourist attractions: beautiful cathedral, incredible central square, and panoramic viewpoint awaiting up a bunch of stairs. Siena’s “Big 3” are truly special and worth visiting. However, they are also the first 3 items listed in every guidebook and on every tour so be prepared for crowds. As usual, you can minimize the crowds by going early or late and buying advance tickets where possible.

Don’t miss the library – the Biblioteca Piccolomini – found inside the Cathedral. If you like ornate details and color, this is the library for you. It feels like this is where they created “Once Upon a Time”…if you go you’ll know what I mean. Also, the Cathedral is famous for it’s remarkable mosaic tile floors. They keep them covered most of the year but do uncover them at times – usually during summer months. Overall, I thought the Siena Cathedral was more impressive to view than the one in Florence.

While we have climbed the main tower at almost all the European cities and towns we’ve visited, we skipped the Torre de Mangia and its 400 steps raising up from the very center of Siena. While I’m sure the views are beautiful, you should also look into the Facciatone. The Facciatone is a section of wall in what would’ve been the new wing of the Cathedral had the black death not hit Siena in the 1300s. You can see the walls that were put up, and even climb up one of them for some fantastic views. They only let a dozen or so people up at a time, for about 5 minutes per group, then you have to squeeze by them as you both go up/down the stairs. So, if the lines are long do not expect them to move quickly. However, if you can make it up, it makes for a very unique and memorable viewing platform!

Beyond the main tourist attractions, we were truly mesmerized just walking around Siena and exploring. There aren’t a lot of tips or suggestions needed for Siena – just walk around, especially at night! If you’re looking for that magical European experience where you feel like you are in a different world, Siena is right up their with Bruges, Colmar, Dubrovnik and others that frequently make those kinds of lists. One of our favorite evenings was just sitting in the main square, enjoying some wine, and soaking in the size, scope and beauty of the Piazza del Centro. Pictures cannot put it into proper perspective. You can turn 360 degrees and literally see the architecture change through the decades. Walking down into the plaza through the giant, arched entrances will give you travel chills.

The other obvious activity is wine tasting! You can go to a wine store to taste wines from all over the region, including smaller wineries that aren’t found in the US or special vintages. Don’t just wonder into any wine store, look for places with good reviews such as Cantina del Brunello di Montalcino or Enoteca Sotto al Duomo.

One last note: Siena is VERY hilly, with lots of steep stairs. Keep an eye out or get a map that shows where the escalators are located. They have 6-7 escalators hidden away, out of sight, that take you throughout Siena.

SIENA FOOD AND DRINK

Go! Osteria La Mossa

Go!Go! The Masgalano Gelateria: By far the best gelato in Siena and (bonus) it’s right around the corner from the best view of the Siena skyline. Grab a gelato then get your IG pic!

Of course, you should always be wary of eating at any restaurant located withing a main square or plaza, and Siena is no different. Many of the restaurants (and gelato places, cafe’s, etc.) with tables outside where you can enjoy the views of the Piazza are overpriced and with disappointing food. This doesn’t really matter if you’re just ordering a glass of wine, but if you do want some food, I’d recommend Il Bandierino, Te Ke Voi, San Paolo Pub, or Ristorante Pizzeria Spadaforte. We didn’t eat at any of these – we drank at San Paolo Pub and had an appetizer – but these appear to be the best reviewed options in the Piazza.

We did have dinner on the Piazza at Osteria La Mossa, which overlooks the Piazza del Centro. We thought the meal was fabulous. Fresh, homemade Italian with a great wine selection. We would definitely recommend it based on our experience, but it gets a few mixed reviews on both Google Reviews and TripAdvisor.

TUSCANY VILLAGES

Below is how we would rate our favorite Tuscan hilltop towns.

Go!Go!Go! San Gimignano

Go!Go!Go! Volterra

Go!Go!Go! Montalcino

Go!Go! Greve in Chianti

Go! Palzano

SAN GIMIGNANO:

This popular hilltop town is on every tour group list but it’s still worth a visit. The towers give it a unique look compared to its peers and the streets are truly magnificent.

Go!Go! D!Vineria – perfect for lunch, wine, charcuterie or all of the above.

Go! Divinorum – go for the back tables!

Go! Geleteria Dondoli – very good, interesting flavors.

Go!Go! Rocca di Montestaffoli – peaceful, away from crowds at main square, amazing views!

There will be a line to get into Gelateria Dondoli in the main square. It’s a famous place known for their creative flavors. It’s good, but not bucket list gelato so don’t wait too long in line.

The main things to try in San Gimignano are the cinghiale (wild boar) and the Vernaccia di San Gimignano, one of the few white wines in Tuscany.

From the town square, walk about two minutes to the D!Vineria for lunch. Then, stop at the Vernaccia di San Gimignano across the street. It’s hard these days to find food or drinks to try that you cannot find in the US, but Vernaccia is one of those. At least, the US only has a couple options that are imported. After tasting some Vernaccia, wonder into the beautiful and serene olive grove at the entrance to Rocca di Montestaffoli. Then, climb up to enjoy dream views of the Tuscan Countryside.

Another perfect place to enjoy wine and those Tuscan hill views is at Divinorum Wine Bar. It’s a bit tricky and we almost missed it – the inside of Divinorum is nice and atmospheric, but if you make your way through several rooms to the very back, you emerge outside where a half dozen tables await with perfect views.

VOLTERRA

Volterra was my personal favorite. I liked the historical remains, including the Etruscan Gate dating back to the 3rd Century – the oldest in Italy. The town also looked more authentic than others – maybe because it just recently hit the tourist radar when it was featured in the Twilight movies. Maybe it’s changed since we’ve been there, but it didn’t seem like the Twilight fame resulted in any changes to its character. The steep streets, the charming main Piazza, the local restaurants, and the truffles everywhere made for a truly wonderful half-day stop.

MONTALCINO

As mentioned, Tuscany is of course one of the most well respected and famous wine regions in the World, and Brunello di Montalcino. To be considered a Brunello, the wine must be 100% Sangiovese grapes and be grown/produced within a certain diameter of Montalcino. In short, a trip to Montalcino is going straight to the source!

I was delighted to see the famous Centro Storico in the center of town that I had seen on so many wine bottles through the years.

Even non wine-drinkers should consider Montalcino. It is perhaps the most dramatic of the Tuscan towns we visited in terms of steep rises and expansive views. It’s a narrow street, cobblestone, Medieval feeling town that is magical on its own…and then you add the food and wine to it which puts it on another level.

There are several exceptional restaurants in tiny Montalcino. We ate at Taverna del Grappolo Blu and recommend it highly. You should also consider Il Moro or Il Gallo Stuzzicheria if you just want a quick but absolutely delicious sandwich.

Our half day in Montalcino went like this: Ate lunch, hiked up and enjoyed the views, then went to an enoteca to taste Brunello. It was perfect.

GREVE IN CHIANTI

“Greve” is a cute little town primarily made up of a small square with restaurants, shops and a wonderful wine tasting shop. While popular now in the US, Greve is where we first discovered wine tasting via pre-paid card. You buy a card for 50 Euro, then select whichever 3oz pour you want from the incredible, can’t miss selection behind the glass. The tasting room is located in the same store as a butcher shop, so you can pair your wine with some of the very best charcuterie in the area.

We did stay two nights at Villa Vignamaggio just outside of Greve in Chianti. We loved it. Our “Mona Lisa” room was enormous and beautiful, but also dated. It felt like something out of a Scoobi Doo cartoon, but in a fun way. However, Villa Vignamaggio is currently (mid 2023) closed and is being renovated for a grand reopening in summer of 2024. My guess is it will be spectacular. The restaurant onsite was amazing and our wine tasting in their cellar was one of our all-time favorites. We still have a few bottles in our collection at home. Best of all, just wondering their grounds is THE QUENTISENTIAL TUSCANY EXPERIENCE. If you’re looking for the Tuscan Villa experience with the rolling hills full of gorgeous grape vines and hilltop villages sprinkled all around you, this is the place. If you are looking for that movie-like setting, well this place WAS actually a movie. The 90s movie “Much Ado About Nothing” was filmed in part the Vignamaggio. Of course, there are many, many other spectacular villa hotels in the area so while this is far from a “you have to stay here” recommendation, take a look at the pictures and see how their renovation comes out. My guess is you will not regret choosing the Vignamaggio as your Tuscan Villa experience. Below are some of our pictures, knowing their renovations may make these obsolete.

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