Tuscan landscape

Tuscany is on a lot of folk’s bucket list and for good reason. It is a beautiful place that offers it all. Great food, wine, history, art and landscapes are all at your fingertips when visiting this central Italian region which is home to just under 4 million people. Florence, the region’s capital, receives almost 2 million visitors each year making it one of the top 100 cities visited worldwide. No wonder it always seems crowded!

Tuscany is where the Renaissance started, dragging itself and the rest of Europe out of the Middle Ages. The region is home to seven Unesco World Heritage Sites. These include the centers of Siena, Florence, San Gimignano and Pienza, the Cathedral of Pisa, the Val d’Orcia and the Medici Villas and Gardens. It also has over 100 protected nature reserves.

There are thousands of wineries and vines are planted virtually everywhere you look. Tuscany boasts the second highest number of DOC/G wines in Italy, right behind Piemonte. These are considered the top of the quality pyramid. Some of them are the most famous wines in the world and include Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano, Vernaccia di San Gimignano and the Super Tuscans. If you are a wine lover, than Tuscany is a great place to visit and get your wine on.

I’ve visited Tuscany many times. In fact, I spent two months living and working in a small hamlet called Rendola which is in the hills just outside of a town called Montevarchi. (Tip: the Prada outlet is just outside of town) When someone comes to me for advice on visiting, the first thing I ask is where they are staying. Almost, but not always, I am told somewhere in or near Florence. Next, I ask how long they will be in the area. Almost, but not always, I am told 2 or 3 days. Then they will be on to Rome or Venice. I get it. For many it’s a trip of a lifetime and they want to pack in as much of Italy as possible. That’s fine. But, it’s well worth it to spend just a bit more time in Tuscany and seek out the not-so-touristy places.

First, I would suggest a more central location than Florence. Florence is fine but getting in and out is a nightmare most of the time and the hotels and apartments are expensive. Just outside Florence is better and less expensive. But there are better options. I like the area around the town of Poggibonsi. It’s near the main autostrada (highway) linking Florence and Siena. It’s also easy to get to the coast (Pisa, Lucca) and it’s on the edge of the Chianti region. There is no need to go into Poggibonsi itself except to use the market to stock your pantry.

A Tuscan Villa

I like to rent a villa. I know it sounds expensive but most are now chopped up into apartments so they are manageable. Also, if you have a large group, renting a whole villa is very affordable and tons of fun. We’ve done that several times. You can find them on Airbnb, Homeaway and my favorite Parker Villas. We’ve used them many times in the past and have always been happy.

Within Tuscany there are some must-see’s and do’s. Let’s get them out-of-the-way first. Go to Florence for the day. Go to the museums, the Boboli Gardens, the Ponte Vecchio, the Duomo and Baptistry. Then go to Pisa and see the leaning tower. On the way to Pisa visit San Gimignano with its’ medieval towers. See the walled town of  Monteriggioni, just down the road from Poggibonsi. And go to the Chianti hills for a half-day of wine tasting before heading back to the villa or apartment. You could do all of this in two and a half days. That leaves you plenty of time, if you’re staying put for 5 or six days, to see some other cool places.

This is by no means an exhaustive list of places to visit. There is so much to see and do in Tuscany. Ideally spending a month would be the thing to do. Unfortunately, most of us don’t have that luxury. So here are some of my favorites. Most of these visits are half-day affairs so you can do more than one town per day.

Siena from above


A lot of people skip Siena. Big mistake. It’s my favorite town in Tuscany. Think Florence without the crowds and, more importantly, the cars. Siena is a pedestrian city, no cars allowed in most of the city so you can leisurely stroll without the fear of being run over by a Fiat.

I could spend days in Siena. In fact, I have. The more time you have, the better. It’s the largest of the five I’m recommending and there are lots of things to see and do. Here are the highlights:

Piazza del Campo – This is one of the world’s most celebrated squares and certainly one of the most famous in Italy. Twice each summer the piazza is transformed into a racetrack for the famous horse race Il Palio. Crowds squeeze into every corner to see the action. Riders are chosen from 10 of the 17 contrada, or neighborhoods. Horses are then drawn randomly and the race begins. It is a spectacle. It happens once in July and then again in August. If you plan to attend book your tickets and a place to stay well in advance.

Piazza del Campo is a great way to spend a few hours just taking in the town and people watching. There are many cafes that line the square where you can get a coffee, glass of wine or something to eat. I prefer to grab something from one of the many salumeria that occupy the side streets that feed into the piazza. I always head straight to Pizzicheria de Miccoli for some salumi and formaggi and, if they have it that day, a porchetta sandwich. I then go to Il Campo and spend a leisurely couple of hours with my treats.

Fortezza Medicea (Medici Castle) – This is the old Medici fortress that guards the northwestern portion of town. It’s as interesting as any other old Medici fort but it has something the others don’t. The Enoteca Italiana is in the fortress. This is like a wine museum or library. You can visit the cellars and then taste wines from all over Italy. You can even buy some to take out. This is a must see for wine lovers.

Duomo – Visit Siena’s Gothic Cathedral above the Piazza del Campo. The exterior is magnificent. Inside there are works by Michaelangelo, Donatello, Pisano and Pinturicchio.

Piazza dei Salimbeni – This is not only a beautiful piazza but also home to the oldest bank on the planet, Monte dei Paschi di Siena. The bank was founded in 1472 and has been in the news lately. It may not survive much longer in its’ current form so you may just want to make a visit while it’s still around.

Mangia Tower – This tower, over 100 meters high, sits next to the town hall in Piazza del Campo. Construction was begun in 1325 and completed in 1348. The climb is well worth it. You will be rewarded with a commanding view of the city and surrounding countryside.

There is more to Siena but that should get you started. It’s one of my favorite European towns for just wandering around and getting lost. And if you do get lost, just make your way back to Il Campo and start all over again.

Volterra high on its’ perch


The most underrated Tuscan town in my opinion. This Etruscan town dates to at least the 7th century BC. In fact, it is believed that the surrounding area has been continuously inhabited since the 8th century BC. It was one of the most important Etruscan settlements and largest with almost 25,000 inhabitants. The whole town stands perched on a hill 1700 feet above sea level. The area is rich in alabaster and the local artists do wonders with this translucent mineral.

Volterra is a treasure trove of riches from both the Etruscan and Roman periods. There is  an unparalleled collection of Etruscan antiquities from this ancient civilization on display in the Guarnacci Museum. The Porto all’Arco is still intact after 2,000 years. Its’ 3 badly eroded heads keep watch on all who enter the city. The Roman theater just outside the walls dates to the 1st century BC.

I like to just take my time and stroll through the narrow streets and take in as much of the atmosphere as possible. Visit the Duomo (Cathedral), enlarged after an earthquake in the 13th century, to see its’ many paintings, wood carvings and statues from some of the best artists of the time. For a unique experience visit the Fortezza Medicea or Medici Fortress. Part of it is now a prison. At certain times of the year you can have a meal cooked by famous chefs helped by the inmates. Enoteca Scali is a great place to stop for lunch. Very friendly staff and great food and wine.


This hilltop town is a must-see for all wine lovers. It was hard to choose between here and Montepulciano due east on another hill. For pure charm this wins out. The town is small and can be done in half a day. I would  combine this with a visit to one of the wineries that surround the hill. I cannot guarantee which take visitors and which charge for tastings but some of my favorites are: Biondi-Santi; Siro Pacenti; Ucceliera; Pian dell’Orino; Il Palazzone; Carpazo and Sassetti. Here is a handy reference for the producers with a map.

Stroll the narrow streets and take in the view of Val d’Orcia. Try and have lunch at Osticcio. This is an enoteca in the true sense. It’s a wine shop, wine bar and restaurant serving small plates, sandwiches, cheese and salumi. Sit in the back room for stunning views of the valley below.

Sant’Antimo Abbey

Time permitting visit the Sant’Antimo Abbey just south of town. It is one of the best examples of Romanesque architecture in Tuscany. It was a powerful monastery in the middle ages. The abbey fell into disrepair and remained that way until the 1980’s when efforts were started to restore it. Today there are about a dozen monks who call Sant’Antimo home.


Panzano is a small town located on a ridge along the Chiantigiana (Chianti road) exactly halfway between Florence and Siena. This is one of the smaller Chianti towns that is often overlooked but it should not be. There is not much to see and do but stroll the town and look at the remains of a Roman road here and there. It’s a great way to really see and appreciate the small towns of Chianti.

Try to go on a Sunday as you will be in for a treat. Sunday is market day so the piazza is humming with activity. Before you go make a reservation for lunch at Solociccia. Lunch starts at 1PM sharp and the seating is communal. For 30 Euro, you get a 7-course meal. Each course consists of meat from various parts of the cow, cooked using various methods. There is even a tartare version called Tuscan Sushi. And you can bring your own wine. The world’s most famous butcher Dario Cecchini owns the restaurant. His butcher shop is just across the street where it has been for several hundred years. Visit the shop and you’ll be welcomed with a glass of wine, some bruschetta with lardo and other bites to whet your appetite before heading over for lunch.

Talamone, Porto Ercole and Porto Santo Stefano – Yes, I know that’s three towns but they are all worth visiting and are within a couple of minutes drive of each other.

Many people skip the coast. This is another big mistake. In the warmer months the coast is a cool respite from the hot interior of Tuscany. Why not take a day trip and spend some time in a small fishing village or seaside resort town?

Porto Ercole by Petitverdot: Matteo Vinattieri

Talamone is small. It’s really small. But what it lacks in size it makes up for in charm. It’s located on the very southern edge of the Maremma regional park. Park your car and take a walk up to the main piazza which overlooks the Mediterranean and the rest of the town. Wander through the marina with its mix of fishing boats and mega-yachts. There are two hotels and a handful of cafes in the town. An hour or two is more than enough time to see everything there is to see.

Porto Ercole and Porto Santo Stefano are both located on the Monte Argentario promontory on southeastern Tuscany. It is linked to the mainland by a few causeways. The area has been a vacation spot for wealthy Italians since Roman times.

Pass through the town of Orbetello on your way to Porto Santo Stefano. Park the car and walk along the harbor where fishing boats, pleasure craft and ferries are coming and going. Have lunch at one of the many restaurants that line the water. It’s a great spot for super-fresh seafood and a bottle of Vermentino.

After lunch drive around the promontory to Porto Ercole. It was here in 1610 that the famous Italian Baroque painter Caravaggio died of malaria on his way back to Rome after being exiled by the Pope. He is buried in the Cathedral.

There you have it. 5 Tuscan towns that a lot of tourists don’t visit but should. If you have any other hidden gems in Tuscany or beyond I’d love to hear about them in the comments section. Happy travels!