Tuscany including Siena and Florence

Pittsburgh International runway 28R

Off to Tuscany to visit the Italian countryside.

A little over a week exploring Tuscany by car. Our home base was Castiglion Fiorentino for most of the trip and finished with a few nights in Florence. Driving is very easy in Italy and there is ample parking in the shoulder seasons. High season parking reservations are recommended.

Flew in to Rome where we picked up the rental car headed to the seaside town of Porto San Stefano for a cappuccino to get the day started. Porto San Stefano lies on the west coast of Italy in the province of Grossetto, Tuscany. A favorite place for the Italians to head out to for the weekend.

A great place to start

Promenade

Harbor with boat rentals

Then it was off to Montalcino. Montalcino is a hilltop town renowned for producing Brunello di Montalcino, one of the world's most prestigious red wines made from the Sangiovese grape, it offers visitors stunning views of the Val d'Orcia historic sites like its fortress, and a rich culinary scene.

Entrance to the fortress

Fortress courtyard. Wine tasting and sales inside.

Montalcino town square

A walk through town

There are some steep hills but easy to manage

A great view

Lunch time, the Boar Ragu is a local favorite

A glass of Brunello di Montalcino

Bruschetta with basil grown in front of the restaurant

The next day started with Cortana. Cortona an Etruscan hilltop town in the province of Arezzo, Italy. Cortona was the setting for the movie Under the Tuscan Sun.

Piazza della Repubblica the heart of Cortona

Shops and cafes

The winding side streets

Fresh produce abounds

Picking up a snack

Piazza Garibaldini

The view from Cortona

There are escalators from the parking lots

Off to Passignano sul Trasimeno a commune in Umbria. Located on Lake Transimeno it is quiet town offering great food and wonderful views.

Lago Trasimeno

Aperol spritz lakeside

Quiet day on the lake

Making use of the terrain

Lakeside cafes and restaurants

Next stop on the tour of Tuscany was Montepulciano. Surrounded by vineyards the town is known for it's Montepulciano d'Abruzzo wine, local charm and great restaurants with one boasting a Michelin Star.

Piazza Grande Montepulciano

Piazza Grande Montepulciano

Sanctuary of the Madonna di San Biagio

Cypress tree lined street Montepulciano

Appetizer in Montepulciano

Aperol spritz with rosemary and peppercorns

One of the fountains to fill your water bottle

Canneto winery entrance

Enjoying a Vino Nobile di Motepulciano

And it comes with a view

Onward to Siena and San Gimignano. Two towns that should be high on Tuscany vacation planning.

Siena Cathedral

Palazzo Pubblico

Palazzo Pubblico

Bring a good pair of walking shoes!

Off the beaten path

What to do when it rains

Eat pizza!

Huge pizzas and a slice for a little over a Euro

San Gimignano the town of five towers

Travel tip... take the side roads away from the crowds

San Gimignano is home to the annual Italian gin festival

Castiglion Fiorentino our base of operation in Tuscany before heading to Florence. A medieval wall town that has a home town feel and with few crowds.

Castiglion Fiorentino

Entrance to the historical part of town aka the Roman gate or Porta Romana

Enjoy the city to yourself

Tight fit with a great view

Parrocchia Collegiata dei Ss. Michele e Giuliano

Torre del Cassero

Parrocchia Collegiata dei Ss. Michele e Giuliano

The seafood at the local market

Off to Florence and the rich history and fabulous food! There is a lot to do in Florence, from the Uffizi to the Duomo to the Galleria dell'Accademia and much more.

Ponte Vecchio

Neptune at the Piazza della Signoria

The Arno

Piazza della Repubblica

Piazza della Signoria

Porta Romana

The Duomo from the Uffizi

The Ponte Vecchio from the Vasari Corridor

The Duomo

Cathedral of Santa Maria del Fiore

The Ponte Vecchio from the Vasari Corridor. The spy window where the Medici family could check out the bridge

How the Medici went to church from the Vasari Corridor

The Arno from the Vasari Corridor

The Vasari Corridor

A great view from the Uffizi

Looking back at the Duomo from the Uffizi

Ponte Vecchio

Birth of Venus

Bistecca alla Fiorentina

A view from our accommodations in Florence

A last look at the Arno before heading home

I hope you enjoyed this blog. My specialty is putting together independent travel itinerates such as this whether it be Italy, France, the United Kingdom, Germany or anywhere else in the world. I have sent my clients from Africa to Antarctica to Bora Bora and everywhere in between. So if you are searching for a travel agent that cares about you and your vacation, you found me!