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Being from Italy people often ask me advice and recommendation about Italy, where to go, where to stay, where to eat etc . . .
Here’s my opinion on the matter:
Traveling to Italy, just like traveling anywhere else is an adventure, an exploration, and especially in Italy you can create your own adventure.
First and foremost buy this book Eyewitness Travel Guide: Italy:

Eyewitness Guide: Italy

It’s very visual, very informative, it will save you time, and when you are on vacation saving time means enjoying it all more, and in a more relaxed way.

For each location it lists the MUST SEE/DO as far as attractions, hotels, and restaurants; as well as the off the beaten path attractions, the hidden gems for hotels, and the (almost) known to locals-only restaurants. And has a lot of self-guided tours that you can enjoy on your own time, at your own pace.

These are some of the places that I LOVE LOVE LOVE in Italy:

HOTELS

Venezia (Venice) Ca dei Dogi: The owner Stefano is an exquisite host, the hotel location is fabulous about 1/2 block from Piazza San Marco, and the amenities are what you would expect from a boutique hotel that doesn’t call itself a boutique hotel.  GO! Tell Stefano that Lorenzo from Boston sent you.

Cefalù/Sicilia (Cefalù/Sicily) Calanica Residence: quiet, nested in a private natural setting with individual bungalow-style rooms (they look like exotic bungalows but they are build in bricks and mortar) each with breathtaking views of the Mediterranean Sea, full bathroom, and large bedroom.  As a guest you’ll have access to the  private restaurant, a private beautiful swimming pool, and private beach. The staff is always helpful. The town of Cefalù is only a short car ride away (or taxi, or bus).  Last time I was there Matteo was the director, great guy!

RESTAURANTS

La Sassa/Toscana (Tuscany) La Grotta: this is way off the beaten path, and well worth it if you are looking for traditional Tuscan cucina and you are fond of wild game (wild boar, pheasant, venison etc…).  Call and make a reservation and ask to be seated in the “grotta” (cave).  And experience that you will remember for years to come.  Nothing, and I repeat, nothing like you would find in any “Italian” restaurant in the USA.

Anything in Bolgheri (photos) is an experience, from getting there (a bit off the beaten path), to the history, to the wines, to the food, to the sense of just BE-ing there.  Bolgheri is not only a place, Bolgheri is a state of mind.  Anything you eat in Bolgheri is fabulous, these are the 3 restaurants that I go to:
- Bolgheri/Toscana (Tuscany) La Taverna del Pittore: elegant dinner, no pizza. The owner Goffredo is a master restaurateur.
- Bolgheri/Toscana (Tuscany) Ristorante L’Uva Nera: elegant dinner, great place to also have pizza.  The owner Elena has her touch in the entire place.
- Bolgheri/Toscana (Tuscany) Enoteca Tognoni: somewhat a bit more casual, the food is still very good.  It’s a wine store AND a restaurant, so you’ll have the greatest selection of wines.

Firenze (Florence) : Osteria Vini e Vecchi Sapori Via dei Magazzini, 3-r 50122 Florence, Italy 055 293045 (no website as of today 3/25/2011). Call and make a reservation.  Father and son owners, the son Tommaso runs the front of the house (tell him I say “ciao”).   Small small small seats about 18 people (hence the need to call for a reservation), short menu that changes somewhat seasonally, always amazingly good, as close to typical Tuscan home cooking as you can find in a restaurant.  The location is 30 seconds from Piazza della Signoria (think: statue of David), and I mean 30 seconds!

PLACES

The must see:

• Rome
• Florence
• Venice

The “other” must see (in no particular order):

• Cinque Terre:  one of the few places in the world where the photos, although stunning, do not render it justice, Cinque Terre is BETTER than what it looks in photography.  Cinque Terre is not only a place, Cinque Terre is a state of mind.
• Milano: history, the Duomo, the Castello, the best contemporary art in Italy, the most fashion, the greatest nightlife, the most elegant contemporary Italian cuisine;
• Pisa: Leaning tower, the Duomo, the Baptistry.
• Sicily:  Sicily is the new Tuscany.  Uncontaminated natural beauty, amazing coastline, great artisan foods, great wines, mild climate.
• Sardinia: Uncontaminated natural beauty, amazing coastline, great artisan foods, mild climate.