If you only have one day to explore Chianti, I won’t argue that driving the La Chiantigiana highway (SS222) from where it starts just south of Florence to where it descends into Siena is a fairly decent agenda. You get stupid-beautiful scenery, quick walk-throughs of the major hill towns, and plenty of small shops and vineyards to see along the way.

But I’ll tell you right now, you should do whatever you have to do to carve out at least two days, and more if possible, to detour off that highway. Because, while the hill towns are charming and colorful and have some great places to get souvenirs, it’s getting off the mainline and going sideways down the smaller roads that you’ll find the experiences and memories that no souvenir can deliver.

While this list could be much longer, I’ve narrowed it down to seven of my favorites that inhabit a crooked but navigable route north to south. This should take you at LEAST two days, and that’s what I’ll describe here. But as with everything in Chianti, the more time you can spend there the better.

You will need a car. Assuming you’re starting in Florence, a good place to rent one is from a Europcar place down near the Arno, off Borgo Oggnisanti. If you have a navigation system in the car (and you should definitely request a car with a navigation system!), type in “Florence American Cemetery.”

Operated by the American Battle Monuments Commission, this fascinating memorial is the resting place for 4,402 American soldiers who fought and died for the Allied forces in Italy during World War II. Stretching across 70 acres of beautiful green hills and surrounded by trees, the white crosses stand at attention in long rows.

Even if your father, or grand- or great-grandfather, didn’t fight in WWII, it is still sobering to walk down those rows and contemplate the kind of heroism and sacrifice that most of us will never know.

13466217_10153681750223873_6129417897155710941_nBack on the road, follow the signs (or your nav) to Greve in Chianti. If you’re tempted to stop here, grab a cappuccino at Caffe le Logge, and hunt for the perfect prosciutto at Macelleria Falorni. For this itinerary, I’m sending you straight through the town, because it’s close to lunchtime.

This is my hands-down favorite eatery in this area: Ristoro di Lamole. However, get ready for one of the most “interesting” drives you’ve ever taken.

As you come down the SS222 out of Greve, keep your eyes open for a sign pointing left to LAMOLE. The first part of this drive is narrow and winding, but nothing too strenuous. The trick here – as on any road in Chianti – is to keep to the right, pay attention, and don’t speed.

That advice will be crucial as you climb the hill to Lamole. The road gets narrower at spots, with drop-offs to the right, but just take it easy and you should be fine. On some of the blind corners, where another car could be coming in your direction, a quick HONK of the horn is a nice warning that will alert that driver a “negotiation” is eminent. One of you will have to back up to a spot on the road where you can pass each other.


Finally, you’ll find the Lamole sign, round the corner, and see the town. “Town” may be a bit generous. There is a church, a few houses behind the church, and the restaurant. You can park in the church parking lot, or along the roadside – just be sure you’re far enough off to the side that cars and buses can pass.


“Ristoro” means “rest stop.” Lamole is a place for travelers to stop for a meal, fortify with some wine, and enjoy the INCREDIBLE view.


The menu is simple and includes some not-to-miss items. There’s a Warm Red Onion Pudding that sounds strange, but is so very, very yummy. The Bruschetta (pronounced “broo-sketta”) and Crostini are also good choices. Chianti is “boar” country, so order the Pappardelle with Wild Boar Sauce as a tasty primi. And if the pasta with truffle oil is anywhere on the menu, order it.


After that, ask your waiter what’s good that day. It’s all fresh, and the preparation is flawless. And don’t forget the dolce!

The blue label Lamole di Lamole wine is delicious, or you can order a Vignamaggio. That is an estate you’ll pass on the way up, and it’s where the movie “Much Ado About Nothing” (with Kenneth Branagh, Denzel Washington and Keanu Reeves) was filmed.


So, now that you’ve had one of the best meals ever, time for some more sightseeing. Instead of going back down the road you came up, take the “high road” past the ristoro and follow what-will-soon-become an unpaved road to Volpaia. There are signs at crossroads.

You’ll come into town from the outskirts. Go slowly and you’ll soon pull into the town square. You can’t park there, but continue through to your left to find parking spaces down the hill to the right.


Volpaia means “den of foxes” and the whole town sits comfortably on the top of a hill, affording expansive views in every direction. The winery tour here is great as it takes you through a lot of the small streets and eventually to the tasting room. To buy bottles of Volpaia wine, olive oil or vin santo, visit the Bell Tower on the main piazza.

Next, drive down the hill and follow the signs to Radda in Chianti. If you have time and energy, continue on into the town and walk down its main street, where you’ll find several shops with handmade clothing, shoes, jewelry, wine and more. But for a place to spend the rest of the day – and the night – veer off before you get into the town and follow the signs to LUCOLENA.

About half a mile from that turnoff is a sign on the left for the road to La Penisola. There’s a little goat on the sign, and here’s why.


La Penisola is a goat farm, and home to Chianti Cashmere. Go SLOWLY on this road and follow it up to the farmhouse. By now, you should already have made a reservation for La Penisola’s vacation rental through the website. Stop at the farmhouse and you’ll be greeted by Nora Kravis.

Originally from Long Island, Nora moved to Chianti in 1972 and started raising cashmere goats. She processes the wool and creates wonderful scarves, shawls and baby booties, along with other unique gift items.


Staying on the farm, you’ll have plenty of time to observe, feed and interact with some of the goats. If you’re there at the right time, you can even take part in Goat Camp! (see the website for details)


The nights are quiet here, and your alarm clock is the soft ‘bahs’ of the goats. After a lovely breakfast overlooking the gorgeous countryside, leave the goats behind and get back on the road for the short drive to Gaiole in Chianti.

This small town is well known for two things. One is the giant “Gallo Nero” (black rooster) statue. The Gallo Nero is the official symbol for Chianti, so it’s nice to get a photo with the mascot. The other is a fantastic event for bikers.

Gaiole is the site for Chianti’s L’Eroica, an annual cycling event that celebrates the “Beauty of Fatigue and the Thrill of Conquest.” Usually scheduled in October, the ride brings hundreds of cyclists to the town, ready to explore the strade bianchi (white roads) of Tuscany.

A must-stop for every bike enthusiast while in Gaiole is Ramuzzi, a shop famous for the sale, repair and hire of bicycles, mopeds and motorbikes. The place is full of biker gear, clothes, plus bike-themed accessories and gifts.

20160612_154933Outside of Gaiole, and above it all by way of a long road up a high hill, is an old abbey where Benedictine monks lived for about 700 years, until 1810. Today, Badia a Coltibuono (“the Abbey at Coltibuono”) is known for its gardens and fabulous views, which you can enjoy as a guest at its equally fabulous restaurant.


Italian families come here for very special occasions, but since being in Chianti at lunchtime is a special occasion in itself, do treat yourself to the scrumptious food and excellent service. There’s a shop at the bottom of the hill where you can buy wine, olive oil (which they will ship) and other goodies to commemorate your visit.

The last stop on my Seven Faves of Chianti Tour is the town of Monteriggioni. A fully walled town atop a hill just north of Siena, Monteriggioni is called a “gateway to the middle ages” as the wall and most of its buildings are original to its founding in the 13th Century.

images-4There are several rooms and hotels where you can spend the night (see the website above), but in your waking hours, start your exploration of the town by walking around the top of its walls. The views are breathtaking, including the skyline of Siena in the distance.



The “Monteriggioni in Arme” Museum contains reproductions of medieval and Renaissance weapons and armour. Each room takes on a different time in the town’s history, with models of weapons and siege techniques. Visitors familiar with the video game “Assassin’s Creed” will find Monteriggioni somewhat familiar. That’s because the town’s outer walls and many of its buildings served as models for Ezio Auditore’s feats and follies.

One other stop I love in Monteriggioni is the Pieve di Santa Maria Assunta, an ancient church that graces the main square. Built along with the town’s founding – the bell dates to 1299 – the interior is a simple rectangular space that is elegant in its simplicity and stillness.


In fact, that’s what I love about this church. So many of the duomos and cathedrals in Italy are massive, ornately decorated affairs. And while they’re beautiful in their own way, this church here in Monteriggioni is humble, barely decorated and peaceful.

I think of it this way… When Jesus makes it back to earth, and walks into the splendor of St. Peter’s Basilica, he might slap his head and say, “No, no, you got it all wrong!” But if he wanders into the Pieve di Santa Maria Assunta, he’ll feel right at home.