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Here is an itinerary that takes in Rome and Florence plus the best of Tuscany (Siena, San Gimignano, Pisa, the Chianti).
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. Think of this more as a blueprint to squeezing in the maximum possible. You should, above all, have fun.
Where to spend each night
Hotels in Rome (days 1–4)
Hotels in San Gimignano (day 5)
Hotels in Florence (days 6–8)
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!
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.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 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 which 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).
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 TourUnfortunately, 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.
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.
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 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 destinations include climbing the Gianicolo hill north of Trastevere (Rome's Lovers' Lane with great views of the city), 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 Fountain to toss in a coin and ensure my return to Rome one day. (Yes, it's cheesy; yes, I do it anyway.)
Piazza del Campo in Siena.MORNING: It's time to explore the hilltowns and vineyards of Tuscany, and the only way to do that properly is with your own set of wheels.
Take a tour
If you prefer an expert guide for your sightseeing and don't want to fiddle with renting a car, you can take the train straight up to Florence and use it as a homebase to tour Tuscany on guided day tours from our partners at Viator.com. Here are a few that cover Siena and 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)
Pick up your rental car in Rome (arrange this rental for days 5-7 before you leave home to ensure the best rates), and head north on the autostrada, into Tuscany and the granddaddy of the hilltowns, Siena, so you should be in by late morning.
This will 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).
The towers of San Gimignano.By mid-afternoon, have wrapped up Siena and wend your way north on the Firenze-Siena Autostrada, exiting at Poggibonsi to get to San Gimignano, a Medieval Manhattan still bristling with 13 stone towers.
If you arrive in time, go into the magnificently frescoed Collegiata church, then climb the tallest of the towers—the Torre Grossa—for some great medieval art inside and spectacular countryside views from the top (if you get in too late, no worries; you can do it all in the morning).
San Gimignano 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.
The grape vines around the Badia di Passignano in the Chianti.MORNING: Do any San Gimignano sightseeing you didn't get in yesterday first thing, then get back in the car and head back through Poggibonsi and cut due east into the heartland of the Chianti, that fabled wine region that stretches 30 miles between Siena and Florence.
Take a tour
Again, if you prefer an expert guide for your sightseeing and don't want to fiddle with a car, you can take the train straight up to Florence then tour the Chianti with guided day trips from our partners at Viator.com. To stick roughly to this itinerary's schedule, you'll want to tour the Uffizi in the morning, then take the Chianti Region Wine Tasting Half-Day Trip which leaves Florence at 2pm. Or you can take a full day in the Chianti now, and do the Uffizi and Accademia together on Day 8 with another tour.
Chianti:
• Chianti Wine Tasting Half-Day (5 hrs)
• Small Group Chianti Wine Region (8 hrs)
• Private Tour: Chianti Wine Tasting (5-9hr)
• Chianti Wine-Tasting and Dinner (8 hrs)
• Tuscany in One Day (12 hrs)
• Horse Riding in Chianti Day Trip (6 hrs)
• Vespa Small Group Chianti Day Trip (6 hr)
• Tuscany Bike Tour in the Chianti (7 hrs)
Uffizi:
Uffizi:
• Skip the Line: Uffizi Gallery Tickets
• Skip the Line: 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
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 into Florence, check into your hotel, drop off the rental car (you won't be needing it anymore on this trip), then plunge right in with one of Italy's greatest hits: the Uffizi.
This is the world's premier gallery of the Renaissance, and you'll want to 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. (TIP: The Uffizi is another museum for which you'll want to purchase tickets before leaving home.)
The Uffizi opens off of the stage set of Piazza della Signoria, filled with statues and lined by buildings the Medici would still recognize. Wander through it on your way to a Tuscan feast at Il Latini before heading for a well-deserved night's rest.
The Duomo in Florence.MORNING: In the morning, 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.
Take a tour
If you prefer an expert guide for your sightseeing and transportation, take a half-day tour of Pisa from Florence with our partners at Viator.com:
• 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 Tour (12 hrs)
You can also tour the Duomo with a guide:
• Florence Half-Day Sightseeing Tour
• Private Tour: Florence Sightseeing Tour
• Skip The Line: Best of Florence Walking Tour including Accademia Gallery and Duomo
• Private Tour: Florence Walking Tour
• Florence Walking Tour
You'll also have time to go around to the back of the cathedral, cross the street, and pop into the little-visited (well, for Florence) but excellent little Museo dell'Opera del Duomo, filled with statues from the Duomo group by the like of Michelangelo, Donatello, and Giotto—not to mention Ghiberti's original gilded panels from the Gates of Paradise (the ones on the baptistery itself are copies).
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.
The leaning tower of PisaAFTERNOON: After lunch, hop the train to Pisa and your obligatory ogle of the Leaning Tower—if you have the yen to climb it, book your entry time ahead of time). The famous Leaning Tower, however, isn't the only great sight here on Pisa's Campo dei Miracoli, the grassy "Field of Miracles" studded with Gothic buildings. You'll have to hustle to fit them all in, so visit the other sights in order of how interesting each is:
Return to Florence late for a well-deserved dinner.
Michelangelo's David in the AccademiaMORNING: 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.)
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 Day 8:
• 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
• Florence Half-Day Sightseeing Tour
• Private Tour: Florence Walking Tour
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.
ALL DAY: Most flights back to the U.S. leave either in the morning or early afternoon—and, since you most likely have to get to the Rome airport from Florence first, definitely try to arrange an afternoon return flight!
Either way, your last day is largely a wash. You'll spend the entire morning getting to the airport.
Remember: Even if you have a 3pm flight, you have to check in by 1pm, which means the absolute latest train you can catch leaves Florence at 10:38am, which means you have to leave your hotel for the station by 10am, which means you need to be checking out by 9:45am... The day's pretty much shot by the time you wake up.
Still, take a few minutes to run out to a cafe or bakery to grab one last amazing Italian snack to bring with you on the plane—way better than airline food. My favorite in-flight, make-everyone-else-jealous food is pizza bianca (focaccia), but you should get whatever you like best. (No, sadly, gelato will not last long enough—though there is a San Crispino gelato stand in the upstairs dining area of Rome's Terminal A, just beyond the McDonald's.)
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.
Lodging: Booking.com, Bedandbreakfast.com, Airbnb.com, Rentalo.com, Vrbo.com, Belvilla.com, Hostelworld.com, Hostelbookers.com, Couchsurfing.com, Homeexchange.com
Packages: SelectItaly.com, Gotoday.com, Orbitz.com, Expedia.com, Travelocity.com
Maps & guides: Amazon.com, Maps.google.com, Tuttocitta.it
A tall order for just one week? You bet. But there are tricks to fitting all you can into such a short time here.
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.)
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:
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Lodging: Booking.com, Bedandbreakfast.com, Airbnb.com, Rentalo.com, Vrbo.com, Belvilla.com, Hostelworld.com, Hostelbookers.com, Couchsurfing.com, Homeexchange.com
Packages: SelectItaly.com, Gotoday.com, Orbitz.com, Expedia.com, Travelocity.com
Maps & guides: Amazon.com, Maps.google.com, Tuttocitta.it
This article was written by Reid Bramblett and was last updated in March 2013.
All information was accurate at the time.
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