The Insane Italy whirlwind tour: Italy's greatest hits in two weeks

A perfect two-week itinerary in Italy that includes a stop in the Italian lakes

Itinerary in brief

mapHere is an itinerary that takes in all three of Italy's great cities—Rome with its ancient ruins and 900 churches, Florence, the Cradle of the Renaissance, and Venice, that most sreen city of canals.

We'll visit Naples and the nearby ancient Roman ghost city of Pompeii.

Where to spend each night
Hotels in Rome (days 1-5)
Hotels in San Gimignano (day 6)
Hotels in Siena (day 7)
Hotels in Cinque Terre (days 8–9)
Hotels in Florence (days 10–11)
Hotels in Venice (days 12–13 or 14)
Hotels in Verona (day 14 option)
Hotels in Sirmione (day 14 option)
Hotels in Milan (day 15)
You'll get a chance to sample the best of the the hilltowns of Tuscany and Umbria, including Gothic Siena, the medieval stone towers of San Gimignano, the white wines and Etruscan tunnels of Orvieto, and climb the Leaning Tower of Pisa.

You'll hike the Cinque Terre fishing villages at the tip of the Italian Riviera, sample wine in the vinyards of the Chianti, and relax on the shores of Lake Garda after paying homage to Romeo and Juliet in Verona.

You end with a day in Milan to see Leonardo' Da Vinci's famous Last Supper.

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.

tip
If you want to take things a bit easier, there's a sane version of this itinerary that leaves out Pompeii and the Cinque Terre.
By all means, feel free to prune this itinerary down to something a bit slower paced. 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" section 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!

Insane Italy Whirwind Tour: Day by Day

Day 1 - Rome: The heart of Rome

The Pantheon
The Pantheon in Rome.
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.

Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at Viator.com 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)
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 looks to be packed with activity—is really not all that taxing.

Today is mostly about 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?

Continue north to stroll all the way to the lovely and lively Spanish Steps. Mingle for a while with the crowds on this tourism icon, 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.
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.

Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at Viator.com 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
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.
MORNING: Today we spend on the other side of the river from the bulk of old Rome.

tip
Early risers who want to cram in even more 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 perhaps some sights in Trastevere.
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 the Vatican Museums, drinking in its artistic and historic wonders such as:

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.

(Note that if you flew into Rome on a Friday night—as many people do—today would be a Monday and therefore the castello is closed. Unfortunate, yes—but that is also the very reason why you visited the Vatican on this day—the Vatican is one of the very few museums in Rome open on Monday.)

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

» Stay: Rome

Day 4 - Rome: Hidden treasures

Galleria Borghese
Bernini's Apollo and Daphne at the Galleria Borghese.
MORNING: Grab the 116 minibus to the Porta Pinciana (you'll see a park across the street; it's called the Villa Borghese).

Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at Viator.com that cover either of the sights featured on this day. Note that there are two times for the Borghese Gallery tour: 9am or 3pm. The Trastevere tour starts at 6pm in summer (3pm Nov-Mar):

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
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" tip at the end of this itinerary).

Tour the Borghese collections of amazing early Bernini sculptures and Raphael and Caravaggio paintings until your timed entry is up (90 minutes).

Wander through the Villa Borghese park for a while until it's time to rustle up some lunch.

Santa Maria in Trastevere
Santa Maria in Trastevere in Rome.
AFTERNOON: Take an afternoon off to do whatever the heck you feel like. You've earned it, and you're probably getting tuckered out from four days of wall-to-wall sightseeing.

Personally, I'd spend the afternoon 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 is time for dinner.

Again, Trastevere is positively packed with restaurants, from the traditional to the trendy, so there's no way you exhausted all the possibilities last night.

After dinner, take a nighttime stroll through Rome to say goodbye. My favorite destiantions include climbing the Gianicolo hill north of Trastevere (Rome's Lovers' Lane with great views of the cty), and crossing the Tiber back to peek at the Roman Forum lit up at night from behind the Campidoglio—and, of course, one last visit to the Trevi Foundtain to toss in a coin and ensure my return to Rome one day. (Yes, it's cheesy; yes, I do it anwyay.)

» Stay: Rome

Day 5 - Daytrip: Naples & Pompeii

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 Viator.com that cover many of the sights featured on

Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners at Viator.com that cover either of the sights featured on

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 Viator.com 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.

tip
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

. Note that ther are two tiems for the the Borghese Gallery tour: 9am or 3pm. The Trastevere tour starts at 6pm in summer (3pm Nov-Mar):

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: 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. Wander through the Villa Borghese park for a while until it's time to rustle up some lunch.

Santa Maria in Trastevere
Santa Maria in Trastevere in Rome.
AFTERNOON: 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 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 all the possibilities last night.

After dinner, take a nighttime stroll through Rome to say goodbye. My favorite destiantions include climbing the Gianicolo hill north of Trastevere (Rome's Lovers' Lane with great views of the cty), and crossing the Tiber back to peek at the Roman Forum lit up at night from behind the Campidoglio—and, of course, one last visit to the Trevi Foundtain to toss in a coin and ensure my return to Rome one day. (Yes, it's cheesy; yes, I do it anwyay.)

» Stay: Rome

:

• 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:Don’t check out of your hotel (you'll be returning to spend one final night). Just leave everything but a daypack filled with your guidebooks, a hat, sunscreen, and lots of water. It's time to head to Naples and the ancient Roman ghost city of 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 where it pays either to take a direct shuttle, or best left to a group bus tour through Viator (www.viator.com) or some outfit like Enjoy Rome (www.enjoyrome.com).

A huge benefit to these tours is that they will also take you to the Naples Archaeological Museum (which houses most of the best statues and mosaics from Pompeii), and in some cases will even give you a quick visit to the Amalfi Coast if you sign up for one of the ever-popular Pompeii-Amalfi Coast tours—which woudl be nearly impossible to do on your own using public transportation in just one day.

No matter which tour, it will take all day, likely 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.

Don’t expect to be back in Rome until 8 or 9pm.

» Stay: Rome

Day 6 - Tuscan & Umbrian hilltowns: Orvieto & San Gimignano

The towers of San Gimignano
The towers of San Gimignano.
Take a tour
If you do not want to bother renting a car, you can piece together a pretty good Tuscany tour using short escorted tours one of two ways:

Option 1) Take the train from Rome to Siena to spend two nights there. On the first day (Day 6) take the following afternoon/evening escorted daytrip from Siena to see San Gimignano and the Chianti. On the second day (Day 7) see Siena as outlined in thus itinerary. On the third day (Day 8) continue on to Pisa and the Cinque Terre by train (having already seen the Chianti on Day 6):
• Chianti and San Gimignano Sunset Trip

Option 2) Take the following escorted 4-day Tuscany & Cinque Terre trip that will take you not only to Siena, the Chianti, Pisa, San Gimignano, and the Cinque Terre (all the sigths covered on Days 6–8 of this itinerary) but also to the Tuscan towns of Pienza, Montalcino, Carrara, and Lucca—and it takes care of all the driving, provides professional guides, breakfast and dinner, and lodging in 4-star hotels in Siena and La Spezia. The bus heads back to Rome from Lucca at the end of the last day (Day 9 of our larger itinerary here), but you can just leave the tour in Lucca and take the train from there into Florence to pick up the rest of the itinerary on Day 10 as planned. Neat.
• 4-Day Tuscany and Cinque Terre Tour from Rome
MORNING: 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.

AFTERNOON: 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.

» Stay: San Gimignano

Day 7 - Tuscany: Siena

Piazza del Campo in Siena
Piazza del Campo in Siena.
Take a tour
If you prefer an expert guide for your sightseeing, here are some walking tours from our partners that cover many of the Siena sights featured on this day (note that the guided walk leaves at 11am, so you'll have to be settled into Siena by then):

Skip the Line: Siena Duomo and City Walking Tour
Palazzo Pubblico Audio Guide (self-guided)
MORNING: It's not a long drive (about an hour) 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 wondrously frescoed rooms of the Palazzo Pubblico town hall on the main square, the gorgeous sloping scallop-shell of Il Campo.

AFTERNOON: 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.

» Stay: Siena

Day 8 - Chianti vineyards & Pisa's tower

The leaning tower of Pisa
The leaning tower of Pisa.
MORNING: Drive north of Siena along the S.S. 222 Chiantigiana road 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 one of the shops along the arcaded triangular main piazza of Greve in Chianti, a tiny market town that serves as the unofficial capital of the region (the huge and famous butcher shop Falorni is particularly good for slapping together memorable picnics).

AFTERNOON: Continue north on the SS> 222 until you hit the A1 Autostrada south of Florence at Ponte A Ema; get on the highway and follow it north (toward "Bologna") just 13.5km to the Firenze-Scandicci exit for the Florence-Pisa highway.

Follow this highway west through the Arno valley past Pisa—stop for obligatory ogle of the Leaning Tower and, if you have the time and the fancy, to climb it—though it would be wise to book that ahead.

From Pisa, hop the A12 headed north up the coast past Viareggio, Massa, and Carrara 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. Get off in La Spezia to follow the local road to Riomaggiore, , the southernmsot village of the famous Cinque Terre ("The Five Lands").

tip
Budget-crunchers will save themselves two days of car rental fees—and of parking—by dropping off the car in La Spezia (a larger port town just south of the Cinque Terre villages, and the closest drop-off spot for most rental companies) and taking the train up to Riomaggiore and then from there on to Florence—which will cost only about $15 total, and save you the hassle of driving into and around Florence.
Park in Riomaggiore and 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. For dinner have some fresh pesto pasta—which was invented here in Liguria—and turn in early at your apartment overlooking the Thyrrhenian Sea.

» Stay: Cinque Terre

Day 9 - 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 10 - 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 Viator.com 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

Duomo:
• 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

Uffizi:
 • 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: Drive to Florence, drop your bags by the hotel, then drop off the rental car; you won't be needing it anymore on this trip.

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 11 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 Viator.com 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 36 hours in Florence, and avow a return.

» Stay: Florence

Day 12 - Venice: Paintings & gondolas

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

• Venice Gondola Ride and Serenade
• Venice Gondola Ride and Serenade with Dinner
• Venice Walking Tour and Gondola Ride
MORNING: There's an 8:37am train from Florence that pulls into Venice around 11:30am so you can dive right into the city of canals (not literally). Luckily, the vaporetto (ferry—kinda the public bus system of Venice) from the train station to all the 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 13 - 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 Viator.com 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.

tip
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 14 - Choice: Venetian islands or Verona & Lake Garda

Take a tour
If you prefer not to hassle with the public transportation (or a rental car) and want an expert guide, you have the option to visit Verona, Lake Garda, and Lake Como entirely on escorted tours. There are two options:

OPTION 1: Escorted daytrips: These all leave from Milan, so on Day 13 you would take a train there first thing, spend the rest of Day 13 seeing Milan itself—as outlined for "Day 14" (below)—then take the following escorted tours from our partners at Viator.com, one each on Day 14 and Day 15:
• Verona and Lake Garda Day Trip from Milan
• Lake Como Day Trip from Milan

OPTION 2: Three-day tour: There is also a three-day tour of Verona, Lake Garda, Lake Como, and Milan that leaves from Venice (actually, day 1 of this tour is just free time in Venice, so bascially it is a two-day tour—but it includes that hotel night in Venice, which is nice)—saving you ever more hassle:
• 3-Day Northern Italy Tour from Venice: Verona, Italian Lakes and Milan

OPTION 3: On your own: If you do choose to do it all on your own, you still might want to take one of these tours of Verona once you are there:
• Verona City Hop-on Hop-off Tour
• Verona Segway Tour
The Venetian island of Murano.
The Venetian island of Murano.
ALL DAY: You really have a choice today.

Option 1: 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 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.

Option 2: 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 in the bustling marketplace on Piazza delle Erbe and a peek at nearby "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; all the Romeo and Juliet–associated "sights" in Verona are fanciful, but fun). Also take a look at the Arena, a midget Colosseum—and most perfectly preserved ancient Roman amphitheater in Italy—where they still perform operas. It's well worth sticking around town and getting a hotel if there's a performance on for the night tickets are still available (not an issue, in my experience, and I've been three times).

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, a pretty little medieval village-turned-resort (with the scenic ruins of a Roman villa) perched near the tip of an impossibly skinny peninsula jutting up into the massive Lago di Garda, largest of the Italian lakes. 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.

» Stay: Venice or Verona or Sirmione

Day 15 - Milan

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

• 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
MORNING: Whatever you did yesterday, today it's time to continue on into Milan, capital of the north.

From Sirmione: The total ride (bus plus train from Desenzano del Garda) takes about 2 hr. The latest train you can catch that gives you enough time in Milan to make it worthwhile leaves Desenzano at 9:52am and gets in at 10:55am, after which there's a 2.5-hour gap until the next train (which wouldn't get you to Milan until early afternoon—too late to do much of use).

From Venice: The ride takes about 2.5 hr. I'd try for the 7:50am or 8:32am train. As above, the latest useful train leaves Venice at 8:50am and gets in at 11:25am, after which there's a two-hour gap until the next train.

From Verona: The ride takes 1.5 to 2 hrs. There are 2–3 trains per hour starting around 6am, but the latest useful run is the 10:05am, which get into Milan at 11:25.

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).

AFTERNOON: 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: 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.

What you need to do before you leave home
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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Highlights
  • 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 5)
  • Touring that Medieval Manhattan town of towers SAN GIMIGNANO (Day 6)
  • Sipping wine in the CHIANTI (Day 8)
  • Climbing the Leaning Tower of PISA (Day 8)
  • Hiking the Cinque Terre on THE ITALIAN RIVIERA (Day 9)
  • Boticelli's Birth of Venus at the Uffizi in FLORENCE (Day 10)
  • Climbing Brunelleschi's Dome on the cathedral of FLORENCE (Day 10)
  • Michelangelo's David at the Accademia in FLORENCE (Day 11)
  • Crusing the Grand Canal of VENICE (Day 12)
  • The glittering cathedral of St. Mark's VENICE (Day 13)
  • A day in VERONA and on LAKE GARDA (Day 14)
  • Leonardo da Vinci's Last Supper in MILAN (Day 15)
 


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