There are many nice tour packages of Italy out there, from cruises to bus tours to city tours and even walking tours. It’s almost too much to comprehend. Why in the world do I feel it necessary to throw my two cents in? I don’t know; I guess it’s a lot like standing next to the Trevi Fountain. Who could resist tossing in a coin or two? So for what it’s worth, here are some shockingly random recommended itineraries.


Visiting Rome is a lot like being a mosquito in a nudist colony: You know what you’re there to do; you just don’t know where to begin! For starters, I would recommend breaking it up into two distinct parts: One is the Vatican City, and the other is Ancient Rome.

The Vatican

There are really two parts to this, as well. The first is St. Peter’s Basilica, and the second is the 4,763 museums attached to the Vatican. In a perfect world, you should allow a day for each of these. But since there is still no peace in the Middle East, we know it’s not a perfect world. Therefore, you likely have less time than you would ideally want in which to see these amazing sights. Therefore, start with what you like best because you will be tired and probably hot and sweaty by the time you get to the second half. If that is architecture and religious splendor, choose the basilica first. If it’s a mind-numbing cornucopia of museum artifacts (including, of course, the famous Sistine Chapel ceiling), choose the museums. Prepare to be blown away. Also, a word of preparation: You will need to be in modest dress for touring both of these sections. Another tip is that both these attractions get very crowded, so try to go during off-peak seasons and times, which is approximately never.

The Basilica

For architecture, history, and art lovers, as well as anyone interested in seeing a dead body in a glass casket, this is an incredible spectacle. On hot days, it is also nice because the Basilica is rather cool inside. I would highly recommend going below to see several of the popes’ tombs, and most rewarding is the climb to the top of the dome. Read up a little before taking your tour because there are so many interesting facts that will help you understand what you are seeing. This is, of course, probably true for any attraction you will ever see, but nowhere more so than St. Peter’s basilica.

Castle Sant'Angelo

This is one of the most fascinating, if not bizarre, attractions in Rome. Originally a tomb, it later was fortified as a place of safe refuge for popes in trouble, and was actually used for such by Clement VII when Rome was being sacked. The castle is also partly a palace with opulent rooms that have beautifully painted ceilings and views to an arsenal of cannon pointing off into the distance outside—quite a contrast. I would highly recommend this for anyone with enough time.

Ancient Rome

Reserve at least a day for this, maybe two. Get a decent map of the ancient city from the many nice men of Indian descent you’ll find on the sidewalks. Make sure to walk the forums, go up to Palatine Hill, and of course, go through the Colosseum. You can buy a ticket that allows you to do all three, and it comes complete with a guided tour of the Colosseum. (I would highly recommend this option. It’s relatively cheap, fairly informative, and it gets you past the big lines getting into the Colosseum.) Separately, you will also want to see the Mamertine Prison and right behind it (switching eras), the Piazza del Campidoglio that was designed by Michelangelo. For lunch or dinner, I would recommend walking across the bridge near Tiberina into Trastevere, where you can find many cheap but excellent restaurants, as well as street peddlers who want to make sure you get a stuffed monkey or clucking fur chicken for your trip home. There are also a couple of excellent restaurants directly across from the forums at the entrance to Via Cavour.

Various Other Attractions in Rome

There are so many other things to see and do in Rome that it boggles the mind. Perhaps you would enjoy a quick tour of the highlights by hiring one of the horse carriages to take you on a loop. Generally, this involves going from the Colosseum up past the forums to the Piazza Venezia (where Mussolini gave his famous balcony speech), up the Via del Corso to the Piazza Navona, to the Spanish Steps, the Trevi Fountain, and back down near the Pantheon. This is a relaxing way to get the lay of the land and determine what you’d like to walk back and see with more time. My favorite is the Pantheon and the small adjacent Piazza della Rotunda. (There are a couple of great pizza shops nearby.) Of course, one should see the Baths of Caracalla, and also the Appian Way (an original section is still a major thoroughfare for cars, while another section is cordoned off for a safer closer inspection). Finally (which is a lie because with Rome, there is no “finally”; there is always something more to see), there is the Circus Maximus, the famous chariot-racing stadium that is nothing more than a grassy area now. However, it is more likely that the vast number of Christians were sacrificed there rather than in the Colosseum, and when considering such a thing, it can be a sobering thought to stand there and ponder what took place on the now gentle, peaceful place.


I think it is best to arrive in Florence via train, thereby scooting past the bustling modern sections and beginning right downtown in the old section of town. However, if arriving by car, it is a fantastic view of the town (especially for the first time) across the Arno River from the Piazza Michelangelo.

Much like Rome, you need several days to get even a glimpse of Florence. If you really want to see it properly, you should probably just move there. There is no way you can take it all in. If you like art at all, you should allow a whole day (much of which will be spent waiting in line and fighting crowds) for the Uffizi art gallery. And you can’t miss the statue of David by Michelangelo in the Galleria dell’Accademia. However, for me, the starting point should be the Duomo. My favorite thing is to climb to the top of Brunelleschi’s dome, from the lantern of which one is rewarded with the best view of Florence possible. The baptistery where Dante was baptized is usually pretty easy to get into, and the bronze doors of Ghiberti (replicas) are amazing. If you like shopping, you’ll love the hawker’s stalls set up around the church of San Lorenzo (and yes, this is where I get my three-euro ties). For hanging out and people watching, resting while eating a gelato, or whatever, the Piazza della Signoria is the best, and a quick tour of the Palazzo Vecchio (Florence’s town hall) is also worthwhile. For sure, cross over the Ponte Vecchio (old bridge) and get a gelato at the shop on the corner entrance of the bridge. And hit several of the churches, such as the Orsanmichele (which bears a striking resemblance to a grain dispensary) and Sante Croce (which houses the tombs of Machiavelli, Michelangelo, and Galileo). If you have extra time, cross over the Arno to the Palazzo Pitti and tour its innards and the Boboli Gardens.

There is a ton of history of almost all types in Florence, and I would, as always, recommend having a history book or two at hand so you will understand what you are seeing. Also try the pizza; my kids promise that it is the best in the world. And the gelato (look for stainless bins and places that declare it is made on sight) is fantastic. Finally, when you see the pregnant Gypsy lady showing a photo of her kids and begging for money, don’t be fooled. She’s been the same-amount-pregnant every time I’ve ever been there. Go ahead and give her some money anyway, though, as you have to admire her guts (or desperation?).

Montepulciano and Pienza

These two hilltop medieval towns are nearby each other just on the west side of the Valdichiana in Tuscany. Montepulciano is famous for its wines; Pienza, for its cheeses. What a great combination, eh? I would recommend beginning with tiny Pienza, where you could take a light lunch, and then driving over to Montepulciano before the crowds show up to hit its many shops as you wait for dinner. Several photos from this area ended up in my (and my co-author Orrin Woodward’s) book entitled LIFE, and a copy of the book may be seen in one of the wine shops. (See if you can spot it.)


The best way to see Siena is to drive your minibus smack dab into the center of town. This, however, you can really only do once, as it’s illegal. (See the book for the complete story.) Begin with the Piazza dell Compo. From there, you can go into the Palazzo Pubblico (town hall) and climb the Torre del Mangia (tower). The views from the top of the tower are magnificent. Have some pizza in one of the restaurants adjoining the piazza and watch the pigeons around the Fonte Gaia. Don’t miss the duomo, either, and its ambitiously-planned original dimensions as indicated by the still-standing but never-utilized façade (one side of which has been turned into the Museo dell’Opera del Duomo). Siena is awesome and deserves at least a full day, if not a lifetime.

Lago Trasimeno

Spend a day near the lake, taking an early morning drive around its fifty-some-kilometer perimeter (best on a motorcycle, of course). Then hop a ferryboat for the Issola Maggiore, the lake’s biggest island, where there are several delectable places to have lunch. In the afternoon, visit Castiglione del Lago for gelato and an awesome meal. I recommend the Stucchio wine. If possible, take in a concert in the old castle overlooking the lake—wonderful!


One of Italy’s most famous wine towns and certainly one of the towns offering the most beautiful panoramas of Tuscany’s countryside, Montalcino deserves at least a day. Begin with a visit to nearby Banfi winery. Even if you have no interest in wine, the old castle and surrounding 7,000 acres of vineyards are breathtaking. There is a neat museum inside and a wonderful shop. Then, if you can arrange it in advance, visit the Máté winery hidden in the nearby hills down a little gravel trail. Ferenc Máté is the author of three fabulous books on Tuscany, and his little winery is friendly and makes his books come alive. End the day by visiting the town of Montalcino for dinner and gelato, and, if you have time, visit the Medici fortress.


Orvieto makes for a nice day visit on the way from Rome up to Tuscany. Absolutely beautiful from afar, as it sits atop an atoll, it’s almost like Italy’s version of Israel’s Masada, except there’s no history of a Roman siege here, but instead quaint shops, a marvelous duomo, and fantastic restaurants. The Etruscan caverns underneath are also well worth a visit.

Horsepower History

For this, one will have to drive north, across the mountains, and into the flat productive industrial zones of Italy. These are still quaint regions, however, and the drive itself will be beautiful. You can probably hit both Ferrari in Maranello and Lamborghini in Nonantola in a single day (we did), but if you want to throw in nearby Ducati, you’ll need to spend the night and stretch it into two.

Chianti Wine Region

Even if you don’t drink wine, this gorgeous area of Tuscany is quite nice as a simple day drive. Make a loop of it beginning around Siena and making your way up to Brolio Castle. There are many good guidebooks available which recommend several additional stops along the way. For those who love wine, there is no end to the places to stop along the way and have a taste. If you have extra time (or get lost as we did), I would highly recommend a drive through the desolate, but intriguingly picturesque, Crete Senesi (Tuscan Desert) to the south of Siena. I predict your time spent in this region will be one of your most memorable, especially if you like photography. You will also likely see bikers and motorcyclists touring through here because of the area’s preponderance for winding roads and stunning vistas.

San Gimignano and Monteriggioni

You can see these two towns in one day. Begin with San Gimignano, and arrive early in the morning before the tour buses get there. Climb to the top of the tallest remaining medieval defensive tower that is accessible from the Museo Civico. Be prepared for stunning views—one of my favorites in the whole world. The Museo Civico and the Palazzo del Popolo are both excellent. You will also have no trouble finding an excellent lunch.

Next, make your way to the tiny fortress outpost called Monteriggioni, which many feel inspired Dante’s description of Hell. There is not much here, but it is still worth it to scale the walls and look out across the Tuscan countryside, and you can have a quiet dinner in the piazza. Crowds here are normally not too bad.


This famous town is really a must-see for any visitor to Italy, mostly because if you don’t come home with pictures in front of the leaning tower, people won’t really believe you made it to Italy. The Campo dei Miracoli, which contains the leaning tower, Baptistry, Duomo, and cemetery, is magnificent. You will not be disappointed. However, get there early in the morning for two reasons: 1. You will avoid the massive crowds (mostly) and 2. The morning light is absolutely fantastic on the white marble of the structures. There is really not much else in Pisa, so plan this as part of a trip to somewhere else.

Assisi and Perugia

I am really doing a disservice to many of these locations because, of course, there are almost an infinite number of attractions at each. It really depends upon the traveler and what he or she is most interested in. However, for the average first-timer, both Assisi and Perugia can be experienced in about a day. Begin with Assisi in the morning and have lunch there, walk the main streets, and hit some of the shops (being sure to buy a St. Francis figurine—I think it’s some kind of requirement), and then make your way into the old, central part of Perugia. The night life and people on passeggiata (promenade) will welcome you, as will the many gelato shops and fine restaurants with seating right out in the street. There are usually festivals and music performances and all kinds of stuff to do here in the evening.

Amalfi Coast

Take several days down here if at all possible. There is a marked difference between southern Italy and the regions to the north. Actually, each region is special in its own way, but to me, the most distinct difference is between the coastal southern regions and the rolling hills of the central-central region (how’s that for a term?). Take a drive (if you’re brave) or ride on a bus along the coastal road of SS-163, which often hangs out over a cliff or squeezes between two houses so closely you’ll be sucking in your breath. The views of the Mediterranean and mountains are wonderful. The lemons are huge, the food is delicious but different than that of the north, the pizza is incredible, and the heat even hotter. As you take this drive, be sure to stop in the town of Positano. There are beautiful walks to be taken in the narrow spaces between buildings built on the steep hillside. Take your time here. Then make your way to Amalfi for lunch and, perhaps, to Maiori for dinner and a stroll along the beach. There are crazy-cool hotels and resorts along this area, each perched on a crag or hanging out over a cliff. Be prepared to drop some bucks, but I promise, it will be worth it for the experience (and view) alone.

If you have time, take a ferryboat over to the island of Capri and spend the day. If you can spend the night on the island, you’ll be rewarded with smaller crowds and a peaceful atmosphere in the central piazza. The views from the island are extraordinary. (I wonder, how much can one talk about the views? It’s a broken record when attempting to describe Italy, for which, I am sure, many an author has struggled to find enough adjectives.)

Drive a little further south past Solerno to Posidonia (Paestum) and see some of the finest Doric temple ruins in the world. This is one of my favorite spots in all of southern Italy, and the crowds don’t seem to make it down here in such density.

Further north, don’t miss Pompeii and Herculaneum (Ercolano) for the best preservation of the Roman way of life at roughly the time of Christ. (Both cities were destroyed by the eruption of Mt. Vesuvius in 79 AD and preserved in slightly different geological ways.)

And of course, pizza in Napoli (Naples) is a must.


There is more, so much more, and perhaps some day, I’ll add more attractions to this list. (Several places not covered here are given extensive treatment in the A Month of Italy book.) But if one were to take only what I’ve provided in this little section, he or she would be getting a wealthy dose of Italy’s finest attractions. So set out, try a few of these itineraries, and enjoy. Of course, don’t be afraid to cut out on your own and find your own way—and when you do, be sure to come back to this website and tell us all about it!

Bon Viaggio!