Italy in two weeks: The sane whirlwind (Tuscany & Cinque Terre edition)

A perfect two-week itinerary in Italy that includes stops in Rome, Florence, and Venice, Tuscan & Umbrian hilltowns (including Siena, Pisa, and Assisi), and a hike in the Cinque Terre

Itinerary in brief

Italy 2-week itinerary with Tuscany map
Click on the map to see a larger version and the itinerary-at-a-glance daily calendar.
Here is an itinerary that takes in the ancient sights of Rome and Pompeii, the Renaissance art of Florence , the canals of Venice, and (if you're interested) the city of Milan, home to Leonardo's Last Supper.

It also spend plenty of time exploring the hilltowns of Tuscany and Umbria: Gothic Siena, Pisa with its Leaning Tower, the wines of Chianti, the medieval towers of San Gimignano, the sheep's cheeses and perfect Renaissance architecture of miniscule Pienza, genteel Perugia, and mystical Assisi, home of St. Francis and his basilica frescoed by Giotto and other Gothic masters.

Oh, and there's a bit of beach time as well: a quick visit to the Amalfi Coast, and a day spent hiking the Cinque Terre fishing villages at the tip of the Italian Riviera.

Where to spend each night
Hotels in Rome (days 1-3 and 5)
Hotels on Amalfi Coast (day 4 option)
Hotels in Assisi (day 6)
Hotels in Siena (day 7)
Hotels in Florence (days 8–10)
Hotels in Cinque Terre (days 11-12)
Hotels in Venice (days 13–14 and/or 15)
Hotels in Milan (day 15 option)
Hotels on Lake Como (day 15 option)
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 (see the "tip" on the right) if you don’t want to spend so much time running around (say, leaving out a few hilltowns—Pienza or Orvieto—or perhaps the Cinque Terre, or maybe 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—and be sure to read the "Foolish Assumptions" page about how these itineraries are meant to work. Have fun!

Sane Italy Whirlwind—Hilltowns edition: Day by Day

Day 1 - Rome: The heart of Rome

The Pantheon
The Pantheon in Rome.
Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at that cover many of the sights featured on this day:

Best of Rome Afternoon Walking Tour
Baroque Rome Small Group Day Tour
Rome Photography Walking Tour: Learn How to Take Professional Photos
Classical Rome Morning Tour
Rome Angels and Demons Half-Day Tour
Private Tour: Classical Rome Art History Walking Tour
Ancient Rome Half-Day Walking Tour
Rome Hop-on Hop-off Double Decker Bus Tour (no site entries)
MORNING: Most transatlantic flights land in Rome in the early morning (around 8am), and by the time you collect your bags, go through customs/immigration, get downtown, and check into your hotel, it'll by 11am—plenty of time to check in, splash your face, and head out for an afternoon of sightseeing.

Just don't give in to the urge to lie down and take a cat-nap. Trust me. Those first-day "catnaps "have a nasty habit of lasting until 7pm, at which point it takes supreme willpower to drag yourself out of bed to find dinner. Best just to stay moving and stay awake.

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 (plus one small museum). Plan to spend only about 10–15 minutes inside each church—give yourself permission just to look at the highlights and not to try and appreciate every altarpiece and architectural element—and you will keep on schedule and not feel too overwhelmed.

Piazza Navona
Piazza Navona.
AFTERNOON: Sitting down to a leisurely lunch will only exacerbate the jet lag, so just grab a quick bite en route to Rome's prettiest square, the gracious, fountain-studded, cafe-lined Piazza Navona.

Pop out of the north end of the piazza to see the church of Sant'Agostino (works by Caravaggio and Raphael inside), then head south past San Luigi dei Francesi (more great Caravaggios) to the courtyard hiding the curly-cue dome atop Sant'Ivo alla Sapienza. Walk through the courtyard, past the church, and out the east side of the building to Piazza Sant'Eustachio, home to the most famous cappuccino in Rome at the Caffé Sant'Eustachio. Don’t linger too long, or the jet lag will start to catch up with you (an extra cappuccino or two helps).

Just a bit farther east is the noble Pantheon, the only ancient Roman temple to survive the millennia virtually intact and one of the best sights in all of Rome (if you skip everything else on this day, at least see the Pantheon).

The area around the Pantheon is the best spot in Rome for ice cream fans, so don't forget to try some gelato (Italian ice cream) in between the sights (gotta keep your strength up, after all).

Just south of the Pantheon, on the piazza with the Bernini statue of an elephant carrying a tiny obelisk on its back, rises Santa Maria Sopra Minerva, a gothic church with Michelangelo's Risen Christ statue and Filippo Lippi frescoes inside.

Head north, past the baroque optical illusions in the church of Sant'Ignazio and the ancient Roman Column of Marcus Aurelius, then turn east across the Corso to find the iconic 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.

The evening passeggiata along Rome's Via del Corso.
The evening passeggiata along Via del Corso.
Head north again from the Trevi Fountain, perhaps pausing for another gelato at nearby San Crispino—after all, how will you know whcih is best if you don't try them all? You're aimig for the lovely and lively Spanish Steps. Mingle for a while, then window shop down fashionable Via dei Condotti and the surrounding streets.

By now, the evening passeggiata see-and-be-seen stroll will be in full swing, so you can strut your stuff with the Romans along main drag Via del Corso and Via del Babuino—both of which lead north to converge at Piazza del Popolo, home to the fabulous church of Santa Maria del Popolo at the far end of the square. If you manage to make it here before the church closes at 7pm, so much the better, as inside are works by Raphael, Caravaggio, and Bernini.

Passeggiata your way back south to find a hearty and well-deserved dinner somewhere in the Old City.

(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).

» Stay: Rome

Day 2 - Rome: Rome of the Caesars

The Roman Forum
The Roman Forum in Rome.
Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at that cover many of the sights featured on this day:

Skip the Line: Ancient Rome and Colosseum Half-Day Walking Tour
Private Tour: Ancient Rome and Colosseum Art History Walking Tour
Ancient Rome Half-Day Walking Tour
Imperial Rome Afternoon Tour
Private Tour: Imperial Rome Art History Walking Tour
• Private Tour: Ancient Roman Art History Walking Tour
Capitoline Museums and Origins of Rome Walking Tour
MORNING: Rome's all about Caesars, right? Start off day two in Rome by crawling around the ruins of the Roman Forum, where, two millennia ago, great orators held forth, senators debated, and Julius Caesar strode the streets.

Unfortunately, little is left to see in this dusty jumble of foundations, arches, and standing columns—and much left to the imagination. But so much the better, as this way 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.

AFTERNOON: After lunch (the old-school wine bar Cavour 313 is conveniently located nearby), 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 (save time in the often long lines by booking your entry ahead).

Now walk several long blocks farther south to tour the church of San Clemente, with medieval mosaics glittering in the apse, Renaissance frescoes in the chapels, and a door off the gift shop leading down to the first of several basements that provide an unparalleled tour through Rome's layer cake of history: below the current, medieval church is a 4th century church, and below that is a pagan temple to Mithras and the remains of several ancient Roman buildings, streets, and the splashing waters of a still-functioning aqueduct (go ahead and fill your water bottle; the water is clean, cold, and delicious).

Catch a bus to head back north 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.

» Stay: Rome

Day 3 - Rome: Vatican & St. Peter's

The Sistine Chapel cieling
The Sistine Chapel ceiling in Rome.
Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at that cover many of the sights featured on this day:

Skip the Line: Vatican in One Day
Private Tour: Vatican Museums and St Peter's Art History Walking Tour
Skip the Line: Vatican Museums, Sistine Chapel and St Peter's Basilica Half-Day Walking Tour
Skip the Line: Vatican Museums Walking Tour including Sistine Chapel, Raphael's Rooms and St Peter's
Skip the Line: Vatican Museums Tickets
Private Viewing of the Sistine Chapel and Vatican Museums
Private Tour: Vatican Museums Walking Tour
Skip the Line: Vatican Museums and Sistine Chapel Tour
Rome Angels and Demons Half-Day Tour
MORNING: 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. , which open at 9am.

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.

Early risers who want to cram more in can visit St. Peter's first—it opens at 7am—spend 90 min. there, then walk around the Vatican walls to tour the Vatican Museums when they open at 9am. This'll free up more time later for Castel Sant'Angelo and some sights in Trastevere.
AFTERNOON: 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 Castle Sant'Angelo on the river, which has a nifty museum of arms and armor. (If, however, you left for this trip on Friday, today would be a Monday and the castello is closed—which is why you visited the Vatican today; its one of the few museums open Mondays in Rome.)

Either way, spend the evening in the medieval neighborhood of Trastevere, where you can find lots of excellent Roman restaurants.

» Stay: Rome

Day 4 - Pompeii, Amalfi Coast, & Capri

Take a tour
If you prefer an expert guide and no-hassle transportation (and not have to bother switching hotels but rather continue to be based out of Rome), here are some Pompeii and Amalfi Coast day trip tours from Rome from our partners at that cover many of the sights featured on this day:

• Pompeii Day Trip from Rome
Pompeii and Amalfi Coast Small Group Day Trip from Rome
Rome to Pompeii Shuttle Bus & Independent Day Trip
Pompeii and Vesuvius Day Trip from Rome
Naples and Pompeii Day Trip from Rome
Pompeii and Amalfi Coast Small Group Day Trip from Rome
• Sorrento and Pompeii Small-Group Tour from Rome
A street at Pompeii
A street at Pompeii.
ALL DAY: While it's possible to do Pompeii and the Amalfi Coast in a single day—and even to do so on your own—the train connections are confusing and time-consuming, so this is one trip where it pays either to take a direct shuttle, or best left to a group bus tour through Viator (—which offers both a Pompeii-and-Naples day trip from Rome as well as a popular Pompeii-Amalfi Coast trip—or some outfit like Enjoy Rome (

It'll take all day, include lunch, and probably also 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.

If you take a tour, great; it means you get to spend all of tomorrow (Day 5) in Rome. If you decide to go it alone, however, I highly recommend staying the night down in the Amalfi Coast (or Capri), which does mean you'll spend the next morning simply returning to Rome, leaving only the afternoon for sightseeing.

OK, so to go it alone: Grab an early morning train (earliest you can drag yourself out of bed for; seriously: try the 7:34am IC, which will have you in Naples by 9:30am, then run downstairs, since the Pompeii train leaves at 9:40am) to Naples. At the Napoli Centrale train station, head downstairs to switch to the separate Circumvesuviana commuter line (a more-complicated-than-it-needs-to-be procedure detailed here). The ride takes 36 minutes. You should aim to get to Pompeii between 10am and 11am.

Spend the remainder of the morning and early afternoon amid the ruined city (either have packed a bag lunch, or grab a panino from one of the stands across from the entrance). Make sure you bring plenty of water, sunscreen, and a hat. Try to be out of the Pompeii site by 2pm.

Continue on the Circumvesuviana to the end of the line at Sorrento (about another 30 minutes). If you're staying here, drop your bags at your hotel before hopping the Amalfi Coast bus. If not, either leave the train station either to (a) hop one of the Amalfi Coast–bound buses parked just out front, or (b) catch the local city bus down to the docks and a ferry over to spend the night on the island of Capri.

If you choose to go the Amalfi Coast route, you have your pick of where to spend the night: posh Positano, historic Amalfi, or (via another bus from the Amalfi) the garden hilltown of Ravello. (If you're staying in Sorrento, after you've wandered around Amalfi a bit and seen its handful of sights, hop the return bus back up the coast.)

Real gung-ho types might even be able to swing hopping a ferry (in summer only) from Positano or Amalfi over to Capri to spend the night there—I wouldn't necessarily recommend this, as you're squeezing your time a bit too tightly, but some folks just dream of visiting Capri.

Real, real gung-ho types might even be able to ride the bus to Amalfi, then switch to another bus to continue down the (more scenic and less-developed) southern half of the Amalfi Coast to Salerno, and once there get aboard a late train all the way back to Rome. You can do it, but you'd have to be sure to be on the 7pm bus from Amalfi to Salerno at the latest; that gets into Salerno at 8:15pm, leaving you precious little time to make the 8:42pm train back to Rome—last one of the night, arriving at 11:15pm.

» Stay: Amalfi or Positano or Ravello or Sorrento or Capri or Rome

Day 5 - Rome: Hidden treasures

Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at that cover either of the sights featured on this day—you can even do both, as the Borghese Gallery tours are at 3pm, and the Trastevere one starts at 6pm (except in winter):

Skip the Line: Borghese Gallery and Gardens Walking Tour
Private Tour: Borghese Gallery and Baroque Rome Art History Walking Tour
Skip the Line: Borghese Gallery Tickets (no tour; just the tickets)
Trastevere and Rome's Jewish Ghetto Half-Day Walking Tour
Santa Maria in Trastevere
Santa Maria in Trastevere in Rome.
MORNING: Get up early and make your way back to Rome(or, if you did Day 4 as a day trip from Rome, feel free to sleep in and spend the morning as you wish).

You should arrive back in Rome in time for lunch.

AFTERNOON: After lunch, 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.

Take whatever time you have left in the day to do whatever the heck you feel like. You've earned it—and you're probably getting tuckered out. Personally, I'd spend it back 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—again, Trastevere is positively packed with restaurants, from the traditional to the trendy, so there's no way you exhausted the possibilites when you ate here back on Day 3.

» Stay: Rome

Day 6 - Umbria hilltowns: Orvieto & Assisi

Take a tour
If you prefer an expert guide for your sightseeing, you can take the train straight up to Florence and then tour Tuscany and Umbria with guided day tours from our partners at (Since tours start in the morning, to do this you'd move day 9's Florence activities here onto Day 6, to be done after you pull into town on an early train from Rome, then proceed with a series of Tuscan and Umbrian day trips on Days 7–9.) Here are a few that cover Assisi:

• Private Tour: Perugia and Assisi (11 hr.)
• 5-Day Best of Italy Trip (5 days/4 nights)
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 6–8 before you leave home to ensure the best rates) as early as the office opens, then head north on the autostrada to Orvieto. This Umbrian hilltown rising from the plateau atop a low volcanic mesa is renowned for its fantastic white wine, its Duomo decorated by Signorelli and other early Renaissance greats, and the Etruscan tunnels that honeycomb the tufa underneath he buildings (tunnel tours leave from the tourist office).

After lunch, strike out east, then north, to the famed pilgrimage hilltown of Assisi, where hometown hero St. Francis began his monastic career and the massive, two-story basilica erected in the saint's honor was covered inside, floor to ceiling and in all the chapels and nooks, with masterful frescoes by the Titans of pre-Renaissance Gothic painting—Giotto, Cimabue, Simone Martini, and the Lorenzetti brothers.

Assisi is a popular place for pilgrims (of both the religious and artistic varieties), so there are plenty of hotels—not to mention scores of religious guesthouses—where you can spend the night.

» Stay: Assisi

Day 7 - Tuscany I: Pienza & Siena

Piazza del Campo in Siena
Piazza del Campo in Siena.
Take a tour
If you prefer an expert guide for your sightseeing, you can take the train straight up to Florence and then tour Tuscany and Umbria with guided day tours from our partners at Here are a few that cover Siena (though not Pienza):

• Tuscany in One Day Sightseeing Tour (Siena, Monteriggioni, Chianti, San Gimignano, Pisa; 12 hrs)
• Siena and San Gimignano Small Group Day Trip from Florence (8 hrs)
• Private Tour: Siena and San Gimignano (8.5 hrs)
• Siena and San Gimignano Day Trip from Florence (8.5 hrs)
• 5-Day Best of Italy Trip (5 days/4 nights)
In the middle of the Crete Senese—the picture postcard Tuscan landscape south of Siena—rises the tiny town of Pienza, with a central piazza laid out by a Renaissance architect to be the "perfect Renaissance city," and a half-dozen little shops selling the region's wines and a dozen variations on Pienza's true claim to fame: The finest pecorino cheeses in Italy.

It's not a long drive from Pienza to the granddaddy of the hilltowns, Siena, so you should be in by mid-afternoon. If you hustle, that will give you enough time to wander the wondrously frescoed rooms of the Palazzo Pubblico town hall on the main square, the gorgeous sloping scallop-shell of Il Campo.

Then scurry 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 evening 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 stroll along Via Banchi di Sopra and Via di Città.

» Stay: Siena

Day 8 - Tuscany II: San Gimignano & Chianti

The towers of San Gimignano
The towers of San Gimignano.
Take a tour
If you prefer an expert guide for your sightseeing, you can take the train straight up to Florence and then tour Tuscany and Umbria with guided day tours from our partners at Here are a few that cover San Gimignano and the Chianti:

San Gimignano
• Tuscany in One Day Sightseeing Tour (Siena, Monteriggioni, Chianti, San Gimignano, Pisa; 12 hrs)
• Siena and San Gimignano Small Group Day Trip from Florence (8 hrs)
• Private Tour: Siena and San Gimignano (8.5 hrs)
• Siena and San Gimignano Day Trip from Florence (8.5 hrs)
• 5-Day Best of Italy Trip (5 days/4 nights)

The Chianti
• Small Group Chianti Wine Region Day Trip from Florence (8 hrs)
• Chianti Region Wine Tasting Half-Day Trip from Florence (5 hrs)
• Private Tour: Chianti Region Wine Tasting (5–9 hrs)
• Chianti Region Wine-Tasting and Dinner Half-Day Trip (8 hrs)
• Tuscany in One Day (12 hrs)
• Horse Riding in Chianti Day Trip (6 hrs)
• Vespa Small Group Day Trip to the Chianti Wine Region (6 hrs)
• Tuscany Bike Tour in the Chianti (7 hrs)
Just northwest of Siena rises the picture postcard hilltown of San Gimignano, a Medieval Manhattan still bristling with 13 stone towers. It tends to get packed out with bus tours, but if you can ignore the crowds and cheesy souvenir shops, it is a magical place.

Take the time to visit the Collegiata church, swaddled inside with Technicolor Gothic frescoes, and to climb the tallest of the towns towers for a panorama across this miniature cityscape of medieval skyscrapers surrounded by the crazy quiltwork of stitched-together fields in postage stamps of green and yellow.

Try to get out of town before lunch, which is best had on the road in Italy's most famous wine region lying just to the east: the fabled Chianti, which stretches 30 miles between Siena and Florence. My vote: Grab lunch 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.

Spend the afternoon slowly making your way north to Florence, pausing at a vineyard or two to take free samples, free tours of the cellars, and perhaps buy a bottle or twelve.

Continue north toward Florence, stopping at vineyards that catch your eye and exploring the small towns. Drive into Florence, drop your bags by the hotel, then drop off the rental car; you won't be needing it anymore on this trip. Find a nice place for dinner and gear yourself up for tomorrow's sightseeing in the cradle of the Renaissance.

» Stay: Florence

Day 9 - Florence: Renaissance 101

The Duomo
The Duomo in Florence.
Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at that cover many of the sights featured on this day (as a bonus, many include the Accademia, which would free up tomorrow morning):

All sights:
• Florence Half-Day or Full-Day Sightseeing Tour
Private Tour: Florence Sightseeing Tour

• Skip The Line: Best of Florence Walking Tour including Accademia Gallery and Duomo
Skip the Line: Florence Renaissance Walking Tour with Accademia Gallery
• Private Tour: Florence Walking Tour
• Florence Walking Tour

 • Skip the Line: Florence Uffizi Gallery Tickets
• Skip the Line: Florence Uffizi Gallery Tour
• Skip the Line: Uffizi Gallery and Vasari Corridor Walking Tour
• Skip the Line: Small Group Florence Uffizi Gallery Walking Tour
• Skip the Line: Florence Accademia and Uffizi Gallery Tour
MORNING: Grab an early train to Florence and drop your bags by the hotel.

Head directly to the Duomo(cathedral) to climb Brunelleschi's ingenious and noble dome for a panorama across the city, then duck into the adjacent baptistery to marvel at the mosaics inside and the massive bronze doors outside—the ones facing the Duomo are so beautiful they became known as the Gates of Paradise.

AFTERNOON: Be sure you extricate yourself from the cathedral group by 1pm 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, Raphael, Caravaggio, and Titian until they boot you out the doors at 7:30pm. Have a Tuscan feast at Il Latini before bed.

» Stay: Florence

Day 10 - Florence: Michelangelo & The Medici

Michelangelo's David in the Accademia
Michelangelo's David in the Accademia
Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at that cover many of the sights featured on this day:

• Skip the Line: Accademia Gallery Tickets
Skip the Line: Accademia Gallery Tour
• Skip the Line: Accademia and Uffizi Tour
• Skip The Line: Best of Florence Walking Tour, incl Accademia Gallery and Duomo
• Skip the Line: Florence Renaissance Walking Tour with Accademia Gallery
• Florence Half-Day or Full-Day Sightseeing Tour
Private Tour: Florence Sightseeing Tour
MORNING: Florence rule #1: Be in line at the Accademia when it opens to see Michelangelo's David before the crowds arrive. (Avoid the hour-long wait altogether by reserving your tickets.)

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.

AFTERNOON: After a quick lunch, and while the city is shut down for the mid-day riposo, make your way over to the Giotto frescoes in Santa Croce church (it stays open all day), Florence's version of Westminster Abbey and the final resting place of Michelangelo, Galileo, Rossini, and Machiavelli with an excellent 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 48 hours in Florence, and avow a return.

» Stay: Florence

Day 11 - Tuscany III: Pisa

The leaning tower of Pisa
The leaning tower of Pisa.
Take a tour
If you prefer an expert guide for your sightseeing and want to stay based in Florence, you can take a day tour of Pisa from Florence (and then another day tour to the Cinque Terre the following day) with our partners at (Home-basing in Florence has the added benefit of making the transfer to Venice on Day 13 much easier.) Here are a few tours that cover Pisa:

• Private Tour: Pisa and the Leaning Tower from Florence (4 hrs)
• Pisa and the Leaning Tower Half-Day Trip from Florence (5.5 hrs)
• Private Tour: Lucca and Pisa from Florence (10 hrs)
• Tuscany in One Day Sightseeing Tour (12 hrs)
The faster trains to Pisa take between 60 and 90 minutes to shoot down the Arno Valley to this famous old University city famous for its off-kilter bell tower.

Yes, everybody comes to Pisa for the obligatory ogle of the Leaning Tower (if you want to climb it, book that ahead of time, since tour groups snap up most of the tickets), but the other sights on this grassy Field of Miracles are just as impressive, including the cathedral (the Leaning Tower is actually simply the Duomo's bell tower), the baptistery with its intricately carved pulpit and perfect acoustics, and the lovely Camposanto cemetery with its frescoes damaged by WWII firebombs (and the fascinating Museo delle Sinopie museum dedicated to those frescoes across the square).

Grab lunch on the run (Bar Il Canguro, just down the street leading south from the tower, makes excellent panini) then head back to the train station to grab a northbound train to La Spezia—past what look year-round like snow-capped mountains (the "snow" is actually open marble quarries; these are the Apuan Alps, producing the world's purest white marble for sculptors from Michelangelo to Henry Moore), La Spezia lies at the very southern tip of Liguria, the Italian Riviera, and is an utterly uninteresting port city. It is, however, where you have to change trains for the local rail line to Le Cinque Terre ("The Five Lands").

Your goal tonight is the southernmost of these five fishing villages, Riomaggiore, where you'll rent an apartment for two nights—it'll be easier, cheaper, and more atmospheric than a hotel. 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 Thyrrhenian Sea.

» Stay: Cinque Terre

Day 12 - Hiking the Cinque Terre

Vernazza in the Cinque Terre
Vernazza in the Cinque Terre.
ALL DAY:If you want to hit all five villages and still have time to enjoy youtself along the way (leisurely lunch, sitting at cafe tables sipping sweet shiacchetrà wine, etcc), set out as early as you can to hike the coastal trail that links all five of the colorful fishing villages that make up the Cinque Terre.

Walking is the main way to get from town to town, most of which are inaccessible by car—though they are linked by a regional rail line that spends most of its time tunneling from town to town through the sea cliffs.

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 largely level path above a beach Manarola and Corniglia (the only cliff top village of the five), to a scenic mix of moderate-to-tough trails and one long staircase between Corniglia and Vernazza (the postcard village of the bunch, picturesquely curved around a cove), and finally the tough, two-hour steep ascent and descent between Vernazza and Monterosso, the northernmost of the Cinque Terre. Or, you know, vice versa. You can hike it either way.

My vote: Take the train all the way to Monterosso and start the morning with the two workout stretches. Besides, coming in this direction, the first view of Vernazza as you come around the cliff is unforgettable (and if you do forget, it's plastered on postcards everywhere). Also, this way lets the going get easier as the day winds down, allowing you to finish with a sunset stroll back into Riomaggiore.

» Stay: Cinque Terre

Day 13 - Venice: Paintings & gondolas

The Grand Canal
The Grand Canal in Venice.
Take a tour
Though no tours of the Accademia are offered, you can book a gondola ride with our partners at

• Venice Gondola Ride and Serenade
• Venice Gondola Ride and Serenade with Dinner
• Venice Walking Tour and Gondola Ride
MORNING: There's really no way around this: to get from the Cinque Terre to Venice requires some tiresome train changes and long journeys. The best option leaves Riomaggiore at 7:27am and arrives in Venice at 1:17pm (with changes at La Spezia and Bologna.

(Another option for die-hards who don't want to waste a second of sightseeing is taking off the night before on the overnight train that leaves Riomaggiore at 8:52 and arrives in Venice at the yawningly early hour of 5:26am the next day, though note that the train changes—11:08pm at Parma, 12:54am at Bologna—aren't terribly convenient for sleeping.)

If, however, you've done the Cinque Terre as a guided day trip and are leaving from Florence, there's an hourly bullet train called the Frecciargento that makes the trip in a cool 2 hrs. 3 min.—leave Florence at 8:30am, you're in Venice at 10:33am; sleep in and leave on the 9:30am and you're still in Venice by 11:33am, with loads for time to check into your hotel and get a proper lunch.

OK: assume you're arriving from the Cinque Terre directly. At least those six hours on the train will give you plenty of time to rest up, grab lunch from the cart or restaurant car, and prepare, once you arrive in Venice, to dive into the city of canals (not literally). Luckily, the vaporetto (ferry—kinda the public bus system of Venice) from the train station to all sights in the historic center cruises right down the famous Grand Canal.

AFTERNOON: Check into your hotel as quickly as possible then spend the balance of the afternoon perusing the Renaissance masterpieces in Venice's Accademia Gallery(yes, it has same name as a museum in Florence; this is because both are part of their city's "Academy" of Fine Arts).

If you have time (and for a chance of pace), also try to fit in an hour or so admiring the modern art—yes! Italy has modern art, too!—at the lovely Peggy Guggenheim museum nearby.

Take a gondola ridebefore dinner (yeah, it's a bit cheesy—and expensive—but you wouldn't want to have come all this way and not done it, either), and wander the quiet, romantic streets a while after your meal.

» Stay: Venice

Day 14 - Venice: St. Mark's & Secrets of the Doges

The mosaics of San Marco
The mosaics of San Marco.
Take a tour
If you prefer an expert guide for your sightseeing in Venice, here are some walking tours from our partners at that cover many of the sights featured on this day:

San Marco:
Skip the Line: Venice Walking Tour with St Mark's Basilica
• Skip the Line: St Mark's Square Highlights Tour
• Skip the Line: Venice in One Day

Palazzo Ducale:
Skip the Line: Venice Walking Tour with Doges Palace

Outlying islands:
• Murano, Burano and Torcello Half-Day Sightseeing Tour
• Private Tour: Murano, Burano and Torcello Half-Day Tour
MORNING: 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 San Marco cathedral and ride the elevator up the bell towerfor 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.)

AFTERNOON: Spend the afternoon however you’d like: shoppingfor Venice's famous glass trinkets, popping into more museums (my vote: 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.

If any of your days in Venice happens to be a Sunday, do not miss the 6:345pm mass in the Cathedral of St. Mark's—the only time they throw on all the light switches to illuminate all of those amazing gold mosaics.
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 fishing 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.

If you time things just right, you should be motoring back to downtown Venice (and a celebratory canal-side final dinner) right as the setting sun sends sparkling streamers across the waters of the lagoon with the bell towers of Venice as a backdrop. Perfect.

» Stay: Venice

Day 15 - Choice: Venetian islands or Milan

Take a tour
If you prefer an expert guide, here are some tours from our partners at that cover many of the sights featured on this day:

If you stay in Venice:
• Murano, Burano and Torcello Half-Day Sightseeing Tour
• Private Tour: Murano, Burano and Torcello Half-Day Tour

If you continue to Milan:
• Skip the Line: Small-Group Milan Walking Tour with Da Vinci's Last Supper Tickets
• Milan Half-Day Sightseeing Tour with Da Vinci's Last Supper
• Private Tour: Milan Walking Tour
• Milan Brera Museum Walking Tour
• Milan by Night Tour
The Venetian island of Murano.
The Venetian island of Murano.
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 above 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, before you head home, try to squeeze in Milan, capital of the north. My thinking here is this: even if your flight back home leaves from Venice, it's going to stop first in Milan—or maybe Rome—before crossing the Atlantic anyway, so you might as well save them the trouble and make your way to Milan on your own a day early so you can at least squeeze in some sightseeing.

So: grab a—you guessed it—early train and get to Milan by late morning. The ride takes about 2.5 hr.; I'd try for the 7:50am or 8:32am train. The latest train you can catch that gives you enough time in Milan to make it worthwhile leaves Venice at 8:50am and gets in at 11:25am, after which there's a two-hour gap until the next train (which wouldn't get you to Milan until mid-afternoon—too late to do much).

The two biggies in Milan 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, Caravaggio, Titian, Botticelli, and Raphael's cartoon sketch for the famed School of Athens in the Vatican).

If you're really lucky, you might be able to nab 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 (or after the show), 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.

» Stay: Venice or Milan

Day 16 - Heading home

ALL-DAY: 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: Even 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.

Here are the details for getting to the airport from downtown Milan.

I hope you had a great trip. Try to catch up on your trip journal on the plane—oh, and be sure to grab some good plane snacks before you head to the airport (foccaccia's my favorite)—Italian food beats airline food any day of the week.


Tips & links

Consider a tour

I'm all for planning your own trip‚ and this website is set up to help you do just that—but some people might just as well prefer to leave all the planning, logistics, transportation, lodging, and gathering of information to the professionals and simply sign up with a guided tour.

Nothing wrong with that. Just take my advice and choose a tour that emphasizes small groups over large crowds, local transport over big tour buses, and fun cultural experiences over sightseeing checklists. You'll have a better time, and probably spend less for it. Here are a few of my favorite tour companies who emphasize just that.

1-5 days

1-2 weeks

Useful links
How it all fits into 2 weeks

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

  1. Two weeks actually lasts 16 days (figuring you leave on Friday night for your overnight flight, and you don’t return until two Sundays after). » more 

  2. You're going to fly "open-jaws" into Rome and out of Milan.This will save you a full day of traveling back to where you started to pick up the return flight» more 

Don't forget to pay attention to the "What to do before you leave" section (next) covering all the details you need to take care of before leaving home—and be sure to read the "Foolish Assumptions" page about how these itineraries are meant to work. (Note that there's also a brief, calendar-view of this itinerary with a much larger map available.)

What you need to do before you leave home
How to use this itinerary

The basic itinerary above is 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 a few hilltowns—Pienza or Orvieto—or perhaps the Cinque Terre, or maybe Pompeii). I've even gone ahead and whipped up a sane version of this itinerary that leaves out Pompeii and the Cinque Terre.

Think of this more as a blueprint to squeezing in the maximum possible. You should, above all, have fun.

Don't overplan

I will freely admit to being as guilty as anyone of this, but: Please try not to overplan your trip to Italy. That's a two-fold plea:

  1. Plan everything, but don't feel compelled to stick to the plan. I think it's a fine idea to work out all the details of what you plan to do—if nor no other reason than it will help you get a handle of what you are able to get done, and start making the hard choices of what you have time for and what you should leave for the next trip to Italy. (Always assume you will retrun!)

    But then do not book absolutely every second in advance (that leaves no room to adjust things as you go to accommodate changing interests, sudden festivals, or unexpected invitations), and please do not attempt to stick to the schedule if it turns out to be overly ambitious and startrs making you miserable.

    Rememeber Clark W. Griswold, the Chevy Chase dad in the Vacation movies, always bound and detemrined to get to WallyWorld come hell or dead aunties? Yeah, don't be that guy. No one in that family was having any fun.
  2. Don't try to pack too much in. A vacation is not meant to be all about checking sights off a list or dashing from place to place to fit in as much as humanly possible. It's about enjoying yourself.

    So do that. Enjoy yourself. Take a hint from the Italian concept of la bel far' niente—the beauty of doing nothing—and take a break from the sightseeing every once in a while.

    Leave some time to stop and sip the cappuccino.

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  • Reliving the ROME of the Caesars at the Colosseum and Roman Forum (Day 2)
  • St Peter's, The Sistine Chapel, & the Vatican Museums in ROME (Day 3)
  • ROME's Pantheon, Trevi Fountain, and the Spanish Steps (Day 1)
  • The ancient ghost city of POMPEII (Day 4)
  • The towns of the AMALFI COAST (Day 4)
  • Giotto's frescoes in ASSISI (Day 6)
  • Touring Gothic SIENA and Renaissance PIENZA (Day 7)
  • Sipping wine in the CHIANTI (Day 8)
  • Exploring that Medieval Manhattan town of towers SAN GIMIGNANO (Day 8)
  • Boticelli's Birth of Venus at the Uffizi in FLORENCE (Day 9)
  • Climbing Brunelleschi's Dome on the cathedral of FLORENCE (Day 9)
  • Michelangelo's David at the Accademia in FLORENCE (Day 10)
  • Climbing the Leaning Tower of PISA (Day 11)
  • Hiking the Cinque Terre on THE ITALIAN RIVIERA (Day 12)
  • Crusing the Grand Canal of VENICE (Day 13)
  • The glittering cathedral of St. Mark's VENICE (Day 14)
  • Leonardo da Vinci's Last Supper in MILAN (Day 15)

Useful links
Train tix

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