An Italian Fortnight

A perfect two-week itinerary in Italy

Rome—Pompeii—Hilltowns of Tuscany & Umbria (Orvieto, San Gimignano, Siena, Pisa)—Cinque Terre—Florence—Venice—Verona—Lake Garda—Milan

First thing you should know: you can't see all of Italy in just two weeks. Trust me. I've spent approximately six years of my life there, and have yet to scratch the surface (and three of those years were spent writing guidebooks and being, for all intents and purposes, a professional tourist).

However, that doesn't mean we can't have a great time trying to cram in as much as possible! Here is an itinerary that takes in Rome and Pompeii, Florence and the hilltowns of Tuscany and Umbria (Siena, Orvieto, San Gimignano, Pisa), the Cinque Terre fishing villages at the tip of the Italian Riviera, Venice and the best of the Veneto (Verona and Lake Garda), and Milan.

A tall order for just two weeks? You bethca. But there are two tricks to fitting all you can into such a short time here.

Two week actually lasts 16 days (figuring you leave on Friday night for your overnight flight, and you don’t return until two Sundays after).
You're going to fly "open-jaws" into Rome and out of Milan. This'll save you a full day of traveling back to where you started to pick up the return flight.

Here's the basic itinerary. It's pretty packed—a lot of early morning wake-ups, a lot of churches and museums—because there's simply so much to see and do in Italy. By all means, feel free to prune this itinerary down to something a bit slower paced if you don’t want to spend so much time running around (say, leaving out Orvieto, Verona and/or Lake Garda, or Pompeii). Think of this more as a blueprint to squeezing in the maximum possible. You should, above all, have fun.

Don't forget to pay attention to the "Before you Leave" box at the end of the itinerary covering all the details you need to take care of before leaving home. Have fun!

Day 1

Most transatlantic flights land in Rome in the early morning (around 8am), and by the time you get you bags, get downtown, and check into your hotel, it'll by 11am—plenty of time to check in, splash your face, and head out sightseeing.

Now I know the first day can be rough, what with jet lag and the fact that you probably didn't sleep well on the plane, so today, though it seems packed with activity, is really not all that taxing. It's mostly just poking around the greatest churches of the Tiber Bend, the center of the old city.

First stop is perhaps my favorite single sight in all of Rome: the Pantheon, the only ancient Roman temple to have survived the centuries intact, and an amazing space inside. The nearby church of Santa Maria Sopra Minerva hides Michelangelo Risen Christ statue and Filippo Lippi frescoes.

After a quick bite to eat, head to Rome's prettiest square, Piazza Navona. Station yourself at Tre Scalini's outdoor cafe tables to enjoy their famous tartufo dessert while watching children play soccer under the shadow of Bernini's fountains. Don’t linger too long, or the jet lag wil start to catch up with you (an extra cappuccino or two helps).

Swing by a trio of overlooked churches near Piazza Navona—Sant'Ivo alla Sapienza, with its soft-serve ice cream of a dome, and Sant'Agostino and San Luigi dei Francesi, both housing great Caravaggio paintings—on your way to grab the 116 minibus head up the Via del Corso toward Piazza del Popolo and the church of Santa Maria del Popolo, packed with paintings, sculpture, and architecture by Caravaggio, Rapheel, Bernini, Bramante, and others.

Join the Romans in their evening passeggiata stroll up and down the Corso and its sidestreets. Turn left eventually on Via dei Condotti, lined with top-name fashion boutiques, to the lively Spanish Steps to mingle for a while.

Rejoin the passeggiata to strut your stuff with the Romans until it's time for a hearty and well-deserved dinner (I know you're exhausted, but Italians eat late, so try to hold out until at least 6:30 or 7pm before heading to a restaurant).

Day 2

Rome's all about Caesars, right? Start off day two in Rome by crawling around the ruins of the Roman Forum, where orators once held forth, senators debated, and Julius Casear strode the streets. Unfortunately, little is left to see, but so much the better so you can be out by 11:30 and on your way to see Michelangelo's Moses in the church of San Pietro in Vincoli before it closes at 12:30pm.

After lunch, pay a visit to the Colosseum (you just kind of look at it, take a peek inside at the floor plan, and you're done) then walk several long block further to tour the church of San Clemente, with medieval mosaics glittering in the apse, Renaissance frescoes in the chapels, and a door leading to the first of several basements that lead you through Rome' layer cake of history: below the current church is a 4th century church, and below that a pagan temple to Mithras and the remains of several ancient Roman buildings and streets.

Catch a bus to head back to Piazza Venezia, at the north end of the Forum. Nearby is the elevated square Piazza del Campidoglio, where the Capitoline Museums will entertain you with ancient sculpture and Renaissance and baroque painting until 7pm. Make sure that before sunset you nip around the back of the right side of the central building on Piazza del Campidoglio where you're treated to a surprise panorama of the Forum from above, with the Palatine Hill and the Colosseum as a backdrop. Have dinner in the Old City tonight.

Day 3

Today we spend on the other side of the river from the bulk of old Rome. Be up bright and early (I know, you never seem to get to sleep in) so that you beat the legions of tour buses to the Vatican Museums. Spend all morning in there, drinking in such artistic wonders as Raphael's Transfiguration, Caravaggio's Deposition, the Raphael Rooms, and Michelangelo's incomparable Sistine Chapel ceiling.

They shoo you out in early afternoon, so grab a snack on your way around the Vatican walls to visit the grandiose church of St. Peter's. See Michelangelo's Pietà and tour the tombs of popes under the basilica before climbing its dome for a panoramic sweep of the city across the river.

If you finish with St. Peter's quickly, you may want to head to the pope's nearby Renaissance fortress, the Castel Sant'Angelo on the river, which has a nifty museum of arms and armor. Either way, spend the evening in the medieval neighborhood of Trastevere, where you can find lots of excellent Roman restaurants.

Day 4

Grab the 116 minibus to the Porta Pinciana (you'll see a park across the street; it's called the Villa Borghese). Enter the park and take the first path on your right (Viale di Museo Borghese) to get to the Galleria Borghese by your scheduled entry time (TIP: you will need to purchase tickets in advance for this; see the "Before You Leave" sidebar at the end of this itinerary). Tour its collections of amazing early Bernini sculptures and Raphael and Caravaggio paintings until they kick you out and it's time to rustle up some lunch.

Take an afternoon off to do whatever the heck you feel like. You've earned it, and you're probably getting tuckered out. Personally, I'd spend it in the medieval artisans district across the Tiber known as Trastevere, visiting its little churches, hanging out in a café, and soaking up the roman lifestyle until it was time for dinner—Trastevere is positively packed with restaurants from the traditional to the trrendy.

After dinner, make your way back across the river to the famous Trevi Fountain, into which it's tradition to toss a few coins and will ensure that, one day, you'll return to the Eternal City.

Day 5

Don’t check out of your hotel, just leave everything but a daypack you’re your guidebooks, a hat, sunscreen, and lots of water. It's time to head to Pompeii for the day. While it's possible to do it on your own in a single day, the train connections are confusing and time-consuming, so this is one trip best left to a group bus tour from some outfit like Enjoy Rome (www.enjoyrome.com) or Green line (www.greenlinetours.com). It'll take all day, include lunch, and probably a stop to see some of the sights of Naples on your way south, past Mt. Vesuvius, to the ancient Roman ghost town of Pompeii. Don’t expect to be back in Rome until 8 or 9pm.

Day 6

It's time to explore the hilltowns and vineyards of Tuscany and Umbria, and the only way to do that properly is with your own set of wheels. Pick up your rental car in Rome (arrange this rental for days 6-10 before you leave home to ensure the best rates), and head north on the autostrada to Orvieto. This Umbrian hilltown is renowned for its white wine and its Duomo decorated by Signorelli and other early Renaissance greats.

Keep heading up the road into Tuscany and San Gimignano, a Medieval Manhattan still bristling with 13 stone towers. It tends to get packed out with bus tours, which is why I have you spending the night here. After 5pm, when the bulk of the tourists leave, the locals come back out of the woodwork and reclaim their streets, and the city of towers regains a magical air in the moonlight.

Day 7

It's not a long drive from San Gimignano to the granddaddy of the hilltowns, Siena, so you should be in by late morning. That'll give you time before lunch to wander through the wonderously frescoed rooms of the Palazzo Pubblico town hall on the main square, the gorgeous sloping scallop-shell of Il Campo.

After lunch, walk through the medieval streets to the zebra-striped 12th century Duomo (cathedral), with its medieval carved pulpit inside and a library frescoed in bright, Fujifilm colors by Umbrian master Pinturicchio (helped by his young apprentice Raphael).

As huge as it is, Siena's Duomo was actually meant to be much larger (turning the present church into merely the transept of what would have been the largest church in the world). The Black Death of 1348 put an end to those plans, but two mighty walls of the would-be expanded cathedral survive, and are now installed with the Museo del Opera Metropolitana, a magnificent collections of art from Duccio's seminal Maestà to carvings by Donatello and Jacopo della Quercia (and a great city panorama from the top of the wall).

Take the rest of the afternoon off to wander the nearly-car-free streets, pop into the shops (Siena does good ceramics) and cafes (mmm, cappuccino), and join the locals in their passeggiata evening stroll along Via Banchi di Sopra and Via di Città.

Day 8

Drive north through the fabled wine region that stretches 30 miles between Siena and Florence: the Chianti. Pause at a vineyard or two to take free samples, free tours of the cellars, and perhaps buy a bottle or twelve. Grab an early lunch on the go from a shop along the arcaded triangular main piazza of Greve in Chianti, a tiny market town that serves as the unofficial capital of the region.

Continue north to the outskirts of Florence, then cut west to drive through the Arno valley past Pisa (stop for obligatory ogle of the Leaning Tower and, if you've the fancy, to climb it—though it might be wise to book that ahead) and the Apuan Alps (preferred by sculptors from Michelangelo to Henry Moore for the world's purest white marble) to the southern tip of Liguria, the Italian Riviera and the Cinque Terre ("The Five Lands").

Park in the southernmost of these five fishing villages, Riomaggiore, and rent an apartment for two nights—it'll be easier, cheaper, and more atmospheric than a hotel—from the Fazioli brothers (tel. +39-0187-920-822) or Mar Mar (tel. +39-0187-920-932). Drop your bags, then just relax. There's a pebble beach off to the left of the little fishing port at the bottom of the hill. Have fresh pesto pasta in the region where it was invented, and turn in early at your apartment overlooking the Thyrrenian Sea.

Day 9

Set out in the morning to hike the coastal trail that links all five of the colorful fishing villages that make up the Cinque Terre, inaccessible by car (though linked by a regional rail line that spends most of its time tunneling from town to town through the sea cliffs) and as yet only moderately touched by tourism (except June through August, when its packed with Rick Steves' fans—Damn you, Rick!).

The trails from town to town get progressively steeper and more challenging as you move north—from and easy 45-minute Via del Amore stroll between Riomaggiore and Manarola, to the tough, two-hour steep ascent and descent between Vernazza (the most picturesque) and Monterosso, the northernmost of the Cinque Terre.

My vote: Take the train all the way to Monterosso and start the morning with this work out. The first view of Vernazza as you come around the cliff is unforgettable (and if you do forget, it's plastered on postcards everywhere), and this way the going gets easier as the day winds down, allowing you to finish with a sunset stroll back into Riomaggiore.

Day 10

Drive to Florence, check into your hotel, drop off the car, and head directly to the Duomo (cathedral) to climb its ingenious and noble dome for a panorama across the city, then marvel at the mosaics inside the adjacent baptistery.

Be sure you extricate yourself from the cathedral group by 1pm or so that you can wander a few blocks south for a lunch on-the-go at I Fratellini, a traditional fiaschetteria, a hole-in-the-wall joint with no seats, just a counter selling wine by the glass and scrumptious sandwiches to patrons who stand in a crowd on the flagstones of the sidewalk and pedestrianized street.

Then continue a few more blocks to the stage set of Piazza della Signoria, filled with statues and lined by buildings the Medici would still recognize.

Opening off the south side of the square is world's premier gallery of the Renaissance, the Uffizi (TIP: another museums for which you'll want to purchase tickets before leaving home). Spend the rest of the afternoon communing with Giotto, Botticelli, da Vinci, Michelangelo, Rapahel, Caravaggio, and Titian until they boot you out the doors at 7:30pm. Have a Tuscan feast at Il Latini before bed.

Day 11

Florence rule #1: Be in line at the Accademia (avoid the hour-long wait by reserving your tickets) when it opens to see Michelangelo's David before the crowds arrive.

Don't linger since before lunch you need to swing by Santa Maria Novella church for a look at the first Renaissance painting to use perfect perspective and a Ghirlandaio fresco cycle on which a young apprentice named Michelangelo helped out.

After a quick lunch, and while the city is shut down for the mid-day riposo, take an hour to wander the stalls of the outdoor leather market around San Lorezno, then make your way over to the Giotto frescoes in Santa Croce church (it stays open all day), Florence's version of Westminster Abbey—the final resting place of Michelangelo, Galileo, Rossini, and Machiavelli—with a great leather school in the back.

On your way back over to the heart of town, stop by Vivoli for the best gelato (ice cream) the world has ever known. Licking your cone, head back toward the center of town to cross the jewelry shop–lined medieval bridge Ponte Vecchio over to the artisans' quarter known as the Oltrarno. Here you'll find the Medici's grand Pitti Palace, whose painting galleries will keep you occupied until closing time at 7pm. The Oltrarno is full of good, homey restaurants where you can kick back, toast your 36 hours in Florence, and avow a return.

Day 12

There's an 8:37am train from Florence that pulls into Venice around 11:30am so you can dive into the city of canals (not literally). Have a snack on your way to check into your hotel in the early afternoon, then spend the mid-afternoon perusing the masterpieces of Venice's Accademia Gallery. Take a gondola ride before dinner, and wander the quiet, romantic streets a while after your meal.

Day 13

In the morning, head straight to one of Europe's prettiest squares, the canalside Piazza San Marco. Wander the glittering mosaicked wonderland of its Byzantine St. Mark's cathedral and ride the elevator up the belltower for a sweeping view across the city and its canals.

Take the "Secret Itineraries" tour of the Doge's Palace at 10:45am for a behind-the-scenes look at Venetian history and intrigue from its Renaissance days as the world's trading and shipping powerhouse. (It’s wisest to book this tour ahead of time, but not necessarily from home before you leave. Dropping by the afternoon before or even first thing in the morning before touring San Marco, should be sufficient. Still, just in case you want to be sure you get a ticket by booking in advance, I've spelled out the process here.)

Spend the afternoon however you’d like: shopping for Venice's famous trinkets, popping into more museums (my votes: the Peggy Guggenheim of 20th century art and the Ca' d'Oro, the grandest of the Renaissance palazzi along the Grand Canal) and churches, or simply have fun getting lost in the twisting, confounding, unspeakably beautiful back streets of Venice .

Another option (and a personal favorite): take off on a ferry for the outlying islands of Murano, where the glass industry started and a bit like a Venice in miniature, and Burano, a finishing village of riotously colored houses along miniature canals. It’s about an hour's ride out and back, and you should spend about an hour on each island.

Day 14

Now you really have a choice today. You've been going pretty pell mell for two weeks straight, so feel free to spend another day in Venice just relaxing—perhaps taking that tour of Venice's outlying islands I mentioned and doing it today, taking a bit more time on each and also heading to a third island, Torcello, wonderfully undeveloped, with simple, swampy canals and a gorgeously mosaicked church.

Or you can keep going full throttle and squeezed in a bit the Veneto's highlights. The main train line from Venice to Milan (where you need to end up tomorrow) has trains every half hour which stops at two equally compelling places where you might want to get off, Verona (of Romeo and Juliet fame) and Desenzano (gateway to Lake Garda).

You could try to squeeze in both, if you limit yourself in Verona to just taking a peek at "Juliet's balcony" (in short: Shakespeare chose approximations of the names of two real rival families in Verona for his play, but the plot is, of course, made up—or, rather, stolen from the Greeks), the nearby bustling marketplace on Piazza delle Erbe, and a visit to the Arena (a midget Colosseum—and most perfectly preserved ancient Roman amphitheater in Italy—where they still perform operas—well worth sticking around to do if one is on for the night and you can get a ticket).

No Opera? No problem. Hop back on the train and continue to Desenzano del Garda, where you can get a half-hourly bus to Sirmione, built at the tip of an impossibly skinny peninsula that juts up into the massive Italian lake. Twenty minutes later, you'll be walking over the bridge, under the guard tower, and past the pocket-sized castle that guards this little medieval island-village. Find your hotel, drop your luggage, and take a stroll to eat gelato or simply sit at a café and watch the sun set beyond the lake's shores, the Alps glowing purple off to the north in the distance.

Day 15

Before you leave home:
Book plane tickets
Book hotels
Check train times
Book entry tickets:
    Rome: Galleria Borghese
    Florence: Uffizi, Accademia (David)
    Venice: "Secret Itineraries" tour
    Milan: Last Supper
Learn more about Italy
Practice your Italian

Whatever you did yesterday, today it's time to continue on into Milan, capital of the north. The two biggies here are Leonardo da Vinci's faded by still mighty Last Supper (yet another thing you really should book ahead), and the massive Gothic Duomo, its exterior studded with hundreds of statues bristling with pinnacles and spires (climb to the roof for a chance to step through and around the buttresses and spires, admire the statues up close, and get a great city panorama).

If you've the time (and you're not all museumed out by now), check out Milan's greatest painting gallery in the Brera. I also love the smaller but choice collection in the Pinacoteca Ambrosiana (Da Vinci, Carvaggio, Titian, Botticelli, and Raphael's cartoon sketch for the School of Athens in the Vatican).

You might get last-minute tickets for a performance at Milan's famed opera house La Scala tonight (lines form along the lateral arcade to the left of the main entrance; ask at the tourist office for details).

If not, head out for a last supper of your own in the southern Navigli district of canals, once a big part of Milanese commerce but today turned into a hopping nightlife district, the old canals lined by dozens of restaurants, trendy bars, and nightclubs.

Day 16

Most flights back to the U.S. leave either in the morning or early afternoon. Either way, the day's largely a wash. You'll spend the morning getting to the airport and the day in the air.

(Remember: if you have a 3pm flight, you have to check in by 1pm, which means you have to head to the airport by noon, which means you have to leave your hotel by 10:30... The day's pretty much shot by the time you wake up.)