Tuscany

With stunning scenery, incredible art and architecture, and some of Italy’s best wine, Tuscany draws travelers back year after year. The rolling hillsides, ancient vineyards, and olive groves create a beautiful backdrop for the well-preserved medieval cities where you can truly enjoy the good life, Italian style.

The two largest cities in Tuscany, Florence and Pisa, attract tourists by the score. But it’s Tuscany’s smaller villages and towns that most captivate visitors. If you have the time, plan to visit several. Despite their proximity, each is unique – and special – in its own way. Use our map of Tuscany to plan your trip.

1) Lucca
No visit to Lucca is complete without a stroll or bike ride through the park that rests atop the 15th-century walls encircling the city. Walk along Lucca’s narrow streets, and you’ll run into a church almost immediately – there are 99 of them in Lucca. The gorgeous, crescent-shaped Piazza dell’Anfiteatro traces the lines of the old Roman amphitheater.

2) Volterra
Surrounded by quarries where the local alabaster was mined, Volterra sits perched on a rocky promontory. Its 3,000 year history is easy to explore with Etruscan, Roman, and Medieval sites and museums.

3) San Gimignano
With its medieval skyscrapers, San Gimignano has one of the most distinctive skylines in the region. Fourteen of the original 70 towers remain, but San Gimignano also boasts beautiful churches, museums, and convents from the Middle Ages.

4) Monteriggione
The only town in the region with intact walls, Monteriggione has a 14th-century parish church, a Romanesque abbey, and beautiful ceramics and leather goods.

5) Siena
Siena’s Campo is arguably the most beautiful public square in Tuscany. Little changed since the 14th-century, Siena seems almost lost in time. Thankfully, most of the city is closed to cars. Exceptional early Renaissance art and a vibrant local culture – best seen in the no-holds-barred Palio horse race run here twice a year – make Siena a must-visit destination.

6) Montalcino
Wine lovers must make a pilgrimage here to sample Brunello di Montalcino, one of Tuscany’s best red wines. Wine cellars are available in town for tastings or you can arrange to visit one of the wineries nearby.

7) Pienza
From the outside, Pienza looks like another Tuscan hill town. But thanks to its association with Pope Pio II, Pienza has a superb Renaissance complex designed by Alberti. While you’re here, be sure to sample the world-renowned Pecorino cheese.

Montepulciano

8) Montepulciano
A top destination for oenophiles, who come to taste the Vino Nobile wines made here, Montepulciano also has a beautiful Renaissance church just outside the town walls. The location, nearly 2,000 feet above sea level, provides sweeping views of the surrounding countryside.

9) Cortona
Best known from Frances Mayle’s book, Under the Tuscan Sun, Cortona is surrounded by vineyards and olive groves. In the town – which escaped damage in World War II – you can see exquisite paintings by Fra Angelico and Luca Signorelli. And there are beautiful views of Lake Trasimeno

10) Arezzo
For a town its size, Arezzo has a lot to see, including a Roman Amphitheater, the House of the poet Petrarch, an archaeology museum, and several fine churches. There’s a huge antiques fair here the first weekend of the month.

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Tuscany Image Flickr: echiner1
Montepulciano Image Flickr: lo.tangelini

Livorno Harbour

Livorno Italy is a cruise port that serves as the gateway for Tuscany.  As a result, for many travelers, Livorno is just a blur on the way to Pisa or Florence.  Which is too bad, because Livorno itself is worth exploring.

Located on a stretch of the Ligurian Sea known as the Etruscan Coast, Livorno has a charming ocean-front promenade, a series of navigable 17th-century canals, and some of the best seafood in Tuscany.

Getting to Livorno is simple enough.  It’s less than three hours by train ride from Rome or Civitavecchia (the cruise port for Rome).

Much of the city was laid out in 1567 by Medici architect Bernardo Buonatlenti.  He bounded the city with the five-sided Fossio Reale canal, anchored it with the Piazza della Repubblica, and added the Fortezza Nuova park for green space.

Here’s what to see and do in Livorno Italy:

1) Canal Cruise

Livorno’s canals, or fossi as they’re known locally, offer a unique view of the city.  The canals were originally defensive moats, and they connect the new and old fortresses with the Piazza della Repubblica, which is basically a big bridge spanning the Fosso Reale or Royal Canal.  This is the best way to see the city.

2) Terrazza Mascagni

Any town would be proud to have this wonderful, checkerboard promenade, which was originally built in the 1920s and restored in the 1990s.  It offers breathtaking views of the Tuscan archipelago.

Terrazza Mascagni, Livorno

3) Venezia Nuova

The New Venice quarter of Livorno is the most appealing area for tourists.  Here, you’ll find narrow bridges, winding lanes, canals, and merchants’ houses dating from the 17th century.  Stroll down charming Via Borra for a better look at the old storehouses that served the port.   In early August, there’s a cultural festival here with performances, street artists, and canal cruises.  In the evening, this is the liveliest spot in town with many popular bars and restaurants.

4) Mercato delle Vettovaglie

This large, covered market was built in the late 19th century in the Art Nouveau style.  Today, there are more than 200 stalls selling meat, fish, vegetables, cheese, and bread.  The market is open every morning but Sunday.

5) Mediceo Port and Fortezza Vecchia

Livorno’s Old Port is dominated by the Old Fort, which dates from 1534.  You can climb the Matilde Tower for great views of the sea and then reward yourself with a stop at the wine bar.

6) The Meloria

Rising from the sea across from the port, the Meloria is a watchtower first built by the Pisans in the 12th century.  The Medici rebuilt the tower  in 1598 after the Genoese destroyed it in 1286.  And the current tower dates from 1709.  Today, it is the symbol of Livorno.  You’ll see it on posters throughout the town.

7) Museo Fattori

Canal in Livorno

Housed in the Liberty style Villa Mimbelli, the museum has an interesting collection of 19th- and 20th-century Tuscan painting.

8) Mercatino Americano

Originally established to serve the American Military Base, today the Mercatino is the best flea market around.  After nearly sixty years in the Piazza XX Settembre, it recently relocated to the port.

After all this sightseeing in Livorno, you’re bound to work up an appetite.  Take the edge off with Cacciucco, a local rice and fish dish served on a thick slice of bread.

If you’d like to stay over, there are several good Livorno hotels to choose from.

The NH Grand Hotel Palazzo is the best Livorno hotel.   Just off the elegant Terrazza Mascagni promenade in a 19th-century palace, the hotel has beautiful ocean views, outdoor and indoor swimming pools, and a full-service spa.

Hotel Rex has a private beach, a marina, and several outdoor dining venues overlooking the sea.  It’s in a quiet neighborhood not far from Castello del Boccale.

With just 8 charming rooms, tiny Al Teatro – named for nearby Goldoni’s theater – is right in the heart of Livorno.  It provides easy access to all the city’s attractions and breakfast is served in the small, leafy garden.

Located on Piazza dei Quattro Mori, Hotel Gran Duca overlooks the harbor and the Monument of the Four Moors.   The hotel is walking distance to most of Livorno attractions, and you can dine on impeccably fresh seafood right on the plaza.  This is one of the most centrally located hotels in Livorno.

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Livorno Harbour Image Flickr: Matthias Ripp
Terrazza Mascagni Image Flickr: Eric Perrone
Canal in Livorno Italy Image Flickr: taver