Tuscany itinerary: The Tuscan Dream Vacation in 2 Weeks

A vacation blueprint for spending two perfect weeks in Tuscany


NOTE: This page is a work in progress. If it were in a physical place, it would have "caution" barriers around it keeping you from getting in. Feel free to read it, but realize that none of it is even close to finished—no links, for example (also, it peters out into a lot of "TKs" toward the end; "TK" is editorialese for "To Come"—and yes, I realize the irony that writers and editors abbreviate "come" with a "k," but that's just how it's always been done).

This itinerary assumes you won't want to waste a minute of that precious two-week vacation, so it includes the usual bracketing weekends, whose extra days give you back the two lost days (for travel to and from Italy) while leaving 14 days for your vacation. Of course this means not returning home until the following Sunday, a day before you have to report back to the office, jet-lagged but full of travel tales.

Don't forget to pay attention to the "Before you Leave Home " 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 work along with more time-planning tips.This itinerary assumes you won't want to waste a minute of that precious two-week vacation, so it includes the usual bracketing weekends, whose extra days give you back the two lost days (for travel to and from Italy) while leaving 14 days for your vacation.

Of course this means not returning home until the following Sunday, a day before you have to report back to the office, jet-lagged but full of travel tales.

Tuscany in two weeks: Day by Day

Day 1

Where to spend the night
Hotels in Florence (days 1-5)
Hotels in Lucca (day 6)
Hotels in San Gimignano (day 7)
Hotels in Siena (days 8–10)
Hotels in Montepulciano (day 11)
Hotels in Cortona (days 12–13)
Hotels in Arezzo (day 14)
Hotels in Rome (day 15)
Hotels in Milan (day 15)
Leave home. But before you do--preferably two weeks before--call 011-39-055-294-883 (or hit the Website www.arca.net/uffizi/reservation.htm) to reserve tickets and entry times at Florence's top two museums, the Uffizi Galleries and the Accademia, home to the David. This way, you can avoid the lines that can stretch for blocks and last for an hour or two in high season.


Day 2

Arrive in Italy (Rome or Milan) and train to Florence, arriving in the afternoon. In deference to jet lag, skip the big museums on the first day and instead spend your afternoon exploring the Duomo groups of buildings that make up Florence's religious core: The particolored cathedral topped by Brunelleschi's ingenious and noble russet dome (allow an hour to climb up between the dome's inner and outer shells for a fantastic Florentine panorama from the top); the octagonal baptistery, whose doors are graced with early Renaissance bronze panels so beautiful Michelangelo himself once dubbed them the "Gates of Paradise" and whose ceiling is carpeted with glittering medieval mosaics; and the Museo dell'Opera del Duomo, conserving all the statues removed from the exteriors of the Duomo buildings for preservations--including a Michelangelo Pieta and the original panels from the "Gate of Paradise."

End the day by tucking into a Tuscan feast under the legions of prosciutto hamhocks hanging from the beamed ceilings of rustic Il Latini, where crostini appetizers, stew-like soups, platters of grilled meats, tiramisu for dessert, and bottomless wine all fit into a $27 bill.


Day 3

The Accademia Gallery, starring the world's most famous statues, The David, as well as Michelangelo's unfinished (but powerfully evocative) Slaves, is always plagued by long lines, so either book your ticket ahead (see "Day 1" above) or be in line when it opens at 8:30 am.

Move on to San Marco, the monastery where the saintly early Renaissance painter Fra' Angelico lived and worked, decorating his brothers' cells with devotional frescoes and churning out the gorgeous altarpieces that fill the small gallery.

Stop by the Palazzo Medici-Ricciardi for a little-known treat--a tiny private chapel entirely frescoed with a courtly procession of the Magi by Benozzo Gozzoli (Fra' Angelico's student)--on your way to San Lorenzo, a church all but obscured by the stalls of Florence's outdoor leather market (save the shopping for after the church closes). Aside from the Donatello bronzes inside, you can also see Michelangelo's architectural genius in the Laurentian Library, and admire more of his sculpture in the Medici Chapel of the Princes.

NOW you can hit the leather market--stopping for a quick lunch at Nerbone, a 120-year-old eatery inside the Mercato Centrale food market--or sit down for a full meal at Trattoria Za-Za on Piazza Mercato Centrale.

Your art-appreciation energies fully restored, you're now ready for the shining star in Florence's constellation of museums: the Uffizi Galleries, the once private collection of the Medici and a virtual blueprint for the development of the Renaissance, featring such international icons as Giotto's Maesta, Botticelli's Birth of Venus, Leonardo da Vinci's Annunciation, and Michelangelo's Holy Family alongside masterpieces by Raphael, Caravaggio, Titian, and hundreds of others. You have until they kick you out at 7:30pm to enjoy it all.

Have dinner at Cibreo, perhaps Florence's finest traditional restaurant. They reach back centuries for recipes here; no pastas or grilled meats appear on the menu, but what does in invariably excellent. If you want to halve your bill (and the menu selection), you can book at the lower-key Cibreo trattoria next door, which shares the same kitchen.


Day 4

Start off the morning with the first painting ever to use true perspective, Massacio's Trinita fresco in Santa Maria Novella church, which also features frescoes by Ghirlandaio, the man who taught a 14-year-old Michelangelo how to paint.
Cap the morning off with a trip to the Bargello sculpture gallery, with its ranks of statues by Michelangelo, Giambologna, and above all Donatello. For a quick lunch, grab a fresh roll stuffed with creamy caprino goat cheese and spicy boar salami at I Fratellini, once of the last hole-in-the-wall fiaschetteria wine bars.

On your way to barn-like Santa Croce church--with chapels frescoed by Giotto, a high class leather school where you can watch the artisans at work, and the tombs of local notables like Michelangelo, Rossini, Machiavelli, and Galileo--pop into Vivoli, the premier parlor in Florence for rich, hand-crafted gelato (ice cream).

Cross the Ponte Vecchio bridge, lined for centuries by tiny goldsmith shops, to the Oltrarno neighborhood to seek out Santa Maria della Carmine church and its groundbreaking frescoes by Masaccio. Step into the neighborhood's other great church, Santo Spirito, to admire the harmonious Brunelleschi-designed interior. The Oltrarno is one of Florence's culinary hotbeds, and you'll find restaurants a-plenty, from the convivial brick-vaulted former wine cellar of Il Cantinone to Il Cinghiale Bianco, an informal trattoria so good cooks from other restaurants go to eat there.


Day 5

Catch a morning train to Lucca, a musical town that gave us Puccini and Boccherini. It's a gem of a city that Tuscany lovers are still trying to keep secret from the tourism industry. Car traffic is scare, and everybody, from tykes on trikes to grandmothers with the days' shopping, gets around by bicycle.

Both Lucca's central San Michele church and the Cathedral of San Martino are graceful examples of Tuscan Romanesque architecture, with facades that stack story after story of lithe colonnades in white and pale gray stone. Inside the latter is the breathtaking marble tomb of Ilaria Guinigi, carved with unearthly realism and grace by Jacopo della Quercia and undoubtedly his masterpiece.

Lucca is still entirely encircled by its broad brick 16th century ramparts, the top of which is lined with trees as a public park, always busy with parents pushing strollers, stately matrons tooling about on their bicycles, lovers smooching on benches, and cadres of old men still playing the same inscrutable Italian card game they started in 1951.

On the north side of town, at the end of the shopping and evening passeggiata (stroll) drag Via Fillungo, lies a curious ellipse of medieval houses with a oval piazza in the center--look closely at the outer perimeter of these houses and you'll see they're built into the yawning, half-crumbled marble arches of an ancient Roman amphitheater.

Make sure you climb the medieval Torre Guinigi, sprouting with ilex trees, for a stupendous panorama of the town and the nearby Apuan Alps, whose mighty peaks hide the snowy white marble preferred by every sculptor from Michelangelo to Henry Moore.


Day 6

Just 10 minutes by train south of Lucca is its far more famous (but less rewarding) neighbor, Pisa. Conveniently, the best sights are all gathered in on spot, the aptly-named Campo dei Miracoli (Field of Miracles), so you can easily see them in one morning. This grassy square just inside the city's northern walls encompasses a massive baptistery and Romanesque Duomo (both of which contain incredible gothic pulpits carved by the Pisano clan), a few small but choice museums, and, of course, a cylindrical stack of marble columnets officially designated as the cathedral bell tower but far better known as the Leaning Tower of Pisa. Legend holds that a curious local fellow named Galileo Galilei used to drop balls of differing weights off the tower to prove his theories on gravity. (To climb it, you really need to book in advance.) Stake out a spot of grassy under the Tower for a picnic lunch, or head just north of the city walls for a proper Pisan feast at rustically refined da Bruno.

Don’t linger too long over lunch, rather train it back to Florence early so you have time to hit the city's other great art museum, the Galleria Palatina in the massive Pitti Palace. It picks up where the Uffizi left off, running through room after sumptuously decorated room of paintings by Renaissance and baroque masters Raphael, Titian, Caravaggio, Rubens, and many others. The Pitti also contains museums of costume, decorative arts, tours of the royal apartments, and the tranquil Boboli Gardens (where the world's very first opera premiered, written in honor of a Medici wedding).

You could easily spend the rest of the day here, or call it quits on museums and simply wander the medieval streets of the historic center where Dante once lived, or head to Via de' Tornabuoni and its tributary streets to shop (or at least window shop) the high fashion boutiques in the city that gave the world Gucci, Ferragamo, Beltrami, and Pucci. Cap off you Florentine stay with a splurge dinner at La Giostra (run by a bona-fide Hapsburg prince) or a juicy, two-inch Florentine steak at Ristorante Vecchia Firenze.


Day 7

Pick up your rental car (which you already booked from the States for 10 days) and hit the TK Chianti.

lunch at La Cantinetta di Spedaluzzo

Dinner at La Piazza

Day 8

am - Chianti

Lunch at TK.

pm - Siena. Duomo. Ospedale Santa Maria della Scala. Baptistery. If it's summer, you can also visit the Museo dell'Opera Metropolitana this afternoon [TK why] (if it's winter, when the museum is open only morning, you'll have to return tomorrow).


Day 9

Siena's core is the felicitous Pizza del Campo, a sloping scallop of herringbone-pattern bricks on which the city's struts its stuff and suns itself. It's anchored at the bottom by the imposing 13th century Palazzo Pubblico, the seat of civic government since the Middle Ages and today also home to the Museo Civico. The museum is really no more than the public rooms of the palace, frescoed during Siena's early 14h century heyday by local greats Simone Martini and the Lorenzetti Brothers, who produced here the storybook-like Allegory of Good and Bad Government and Its Effect on the Town and Countryside, the most important painting to survive from the medieval era.

Head toward the cathedral, and then past it to lunch at the highly recommended new joint, Antica Trattoria da Divo.


Day 10

Get up early to drive to the ancient Etruscan city of Volterra, perched impossibly high above the surrounding countryside, Its major industries these days are carving alabaster into gorgeous craft objects, and tourism--which means visiting the unparalleled collection of Etruscan funerary urns and other artifacts in the Museo Archeologico Guarnacci. The city's Roman era peeks out in the evocative Roman Theater and Baths visible from a windswept promenade off Via Guarnacci. Also make sure you swing by the church of San Francesco for its marvelous Croce del Giorno chapel off the right aisle, frescoed in medieval Technicolor with the Legend of the True Cross cycle. Lunch at TK.

Make the short (but torturous) drive over to neighboring San Gimignano, a Medieval Manhattan still bristling with 14 tall stone towers and producers of Vernaccia, Tuscany's best white wine. It may be inundated with guided tour daytrippers in high season, but no other hilltown preserves its medieval appearance and atmosphere better than San Gimignano. And, since you're spending the night, you'll get to enjoy it after all the tour buses depart at 5pm, when the locals creep back out into the streets and the cobbled alleyways are illuminated by moonlight.

See how much sightseeing you can fit into the afternoon. There are two main activities: touring the magnificently frescoed Collegiata church, and climbing the tallest remaining tower, Torre Grossa (after checking out the small painting gallery inside), for a stunning panorama of the city and the idyllic Tuscan countryside of green swatches of fields stitched together just beyond the walls.

If you get both done today, great. If not, save one for tomorrow morning, a morning which should also include a jaunt over to the ruins of the fortress, which gives you the perfect postcard shot of San Gimignano's towers.

Have dinner at the excellent Dorando, where traditional dishes are prepared with consummate skill, and shack up at L'Antico Pozzo, converted from a 15h century building, or at La Cisterna, where rooms overlook either the triangular piazza centered on the town's medieval well or the rolling countryside beyond.


Day 11

Finish off San Gimignano in the morning, then push on to TK

pm - Montalcino

Day 12


Day 13

am - Pienza

pm - Chiusi

night - Cortona

Day 14


Day 15

am - [TK???? Pitigliano/Saturnia????]


In the afternoon, it's time to drive back to the gateway city (Rome or Milan) from which you'll be flying out the next day to spend the night.


Day 16 - Heading home

Leave plenty of time on this final day to get to the airport and fly home.


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 three 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 

  3. You are going to take some guided daytours to visit the towns and sights outside the big cities in order to (a) pack as much sightseeing as possible into a limited amount of time, (b) get a professional guide, and (c) provide all transportation so you can spend your time seeing the sights and not waiting on train and bus connections.

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
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)
  • Capri & the AMALFI COAST (Day 4)
  • Boticelli's Birth of Venus at the Uffizi in FLORENCE (Day 6)
  • Climbing Brunelleschi's Dome on the cathedral of FLORENCE (Day 6)
  • Sipping wine in the CHIANTI (Day 7)
  • Climbing the Leaning Tower of PISA (Day 7)
  • Touring that Medieval Manhattan town of towers SAN GIMIGNANO (Day 7)
  • Michelangelo's David at the Accademia in FLORENCE (Day 8)
  • Giotto's frescoes in ASSISI (Day 9)
  • Hiking the Cinque Terre on THE ITALIAN RIVIERA (Day 10)
  • Crusing the Grand Canal of VENICE (Day 11)
  • The glittering cathedral of St. Mark's VENICE (Day 12)
  • Leonardo da Vinci's Last Supper in MILAN (Day 14)
  • A day on LAKE COMO (Day 15)

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