Tuscany itinerary: The Best of Tuscany on Budget in 2 Weeks

A vacation blueprint for spending two weeks in Tuscany without breaking the bank


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).

You have a two week vacation, and you're determined to make the most of it, seeing as much as you can of Tuscany on a budget. But traveling frugally isn't necessarily shortchanging your experience. It merely means you'll enjoy 14 days of inexpensive family-run hotels, cheap transportation on Tuscany's excellent network of trains and public buses, and filling meals alongside the locals in inexpensive trattorie and osterie.

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 on a budget: 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 is 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," sorts a ceiling carpeted with glittering medieval mosaics. The Museo dell'Opera del Duomo conserves 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, tiramisù 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.

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

You're probably in artistic overload, so catch city bus no. 7 up to the hilltop Etruscan village of Fiesole, high above the crowds, heat, and relentless sightseeing of Florence but with great views back over the city. There are some modest Roman ruins, a fine little painting gallery, and a few churches to poke around in, but mainly you come up here to relax for a few hours.

Return to Florence for lunch, after which you can 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 6

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 7

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), and a few small but choice museums.
There is also, 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.

Getting to San Gimignano, a Medieval Manhattan still bristling with 14 tall stone towers, is never easy with public transportation, but the connections aren't too bad from Pisa. First take one of the frequent Florence-bound trains to Empoli (a trip of about half an hour), where you change for a train toward Siena, getting off at Poggibonsi (anther half hour), where you catch one of 19 daily buses to the Town of Towers.

Why all the trouble? It's worth it. Not only do they produce Vernaccia, Tuscany's best white wine, but there is no other hilltown that 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 La Mangiatoia--stick to their specialty dishes, which they do better than the standard Italian fare on the menu. Unfortunately, the cheapest hotel in town is the Bel Soggiorno at around $90 a night for a double. Or, you can shack up in the hostel (unlike most cities, actually inside the city walls) for around $15 per bunk.

Day 8

Finish off San Gimignano in the morning, then hop the bus back to Poggibonsi, where you catch that train for the rest of the short tip into Siena. Check into your hotel--the Cannon d'Oro or tiny Piccolo Hotel Etruria offer the best rates in the center--and grab some lunch at the dinky, laid-back spot for local shopkeeps' lunches, Il Grattacielo, which means skyscraper (since the ceiling is so low you almost have to duck).

Spend the afternoon relaxing, just wandering the streets, poking into neighborhood churches or shops, soaking in Siena's cloying medieval atmosphere. Many people who have never been to Tuscany before and are in full museum/Renaissance art mode ask why they should bother with Siena and its apparently few sights. When they get back from their trips, almost every single one laments having not spent more time in Siena, a city which mixes the best of a medieval hilltown with the best of low-key sightseeing and a cosmopolitan atmosphere.

After a leisurely passeggiata with the locals along shopping drag Via Banchi di Sopra, Dig into hearty Sienese dishes for a relative pittance at the Antica Trattoria Papei.

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 14th 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.

For lunch: half a block from the Campo lies La Torre, one of those local's joints with an open kitchen, huge portions, and low prices.

Spend the afternoon in the Pinacoteca, Siena's painting gallery, tracking the development of local painting from Gothic geniuses and proto-Renaissance masters, through the lull of the Black Death (which killed off more than two-thirds of the population), to local late Renaissance and Mannerist luminaries like Sodoma and Beccafumi.

Sienese often eschew the pricey tourist restaurants for a low-key trattoria/pizzeria like Da Roberto, where the fixed-price menu runs $13, and a pizza and beer will set you back only $9 or so.

Day 10

Spend the morning exploring the collection of buildings that make up Siena's cathedral group. The grandest of all is the massive, zebra-striped Gothic Duomo, with a Pisano pulpit inside and, off the left aisle, the Launrentian Library magnificently frescoed by Pinturrichio with scenes form the life of Sienese nobleman Enea Solvio Piccolomini, better known as the warrior pope Julius II (who, as a noted Renaissance humanist, commissioned Raphael to fresco his private apartments in Rome's Vatican and Michelangelo to paint the Sistine Chapel ceiling).

Across from the cathedral is a worthy new addition to Siena's sightseeing scene, the Ospedale Santa Maria della Scala, still used as a hospital up into the 1990s but now restored as a museum so the public can see up close the quirky early Renaissance frescoes in the main ward celebrating the confraternity that founded and originally funded this hospital.

When Florence built it's giant new cathedral, rival Siena couldn't sit by and be outdone, so they undertook to turn their huge Duomo into merely the nave of a new, gargantuan church that would have dwarfed every other in the world, including St. Peters. The human and financial toll of the devastating 1348 Black Death, though, put an end to Siena's grandiose dreams, and all that remains of their hubris is a massive side wall and the beginnings of a towering nave, with an open piazza in the middle where the new nave would have been. The wide space within that side wall has been converted to house the Museo dell'Opera Metropolitana, a collection (as usual) or all eh statues and other art removed over the ages for replacement or for safekeeping, including statues by Giovanni Pisano and Donatello, and the cathedral's former altarpiece, Duccio's brilliant Maestà, a glittering work which founded the Gothic Siena School of painting. You can also climb to the very top of that unfinished facade wall for a spectacular panorama over the city.

From the museum's entrance, a set of stairs spills down to wrap you around the back of the Duomo and the Baptistery (which is located directly below the Duomo's main altar), home to some idiosyncratic frescoes and a gem of a baptismal font whose gilded bronze panels were crafted by the likes of Donatello and Jacopo della Quercia.
Hidden in the streets just north of the cathedral, the excellent new Antica Osteria da Divo offers ristorante-class food at trattoria prices.

After lunch, head to the Casa di Santa Caterina to pay your respects to St. Catharine of Siena, a saintly woman who, in between mystical visions, acted as a brilliant stateswoman and ambassador (it was largely her strident letters and visits to the papal court at Avignon, France that convinced the popes to return to Rome). Nuns of her order tend her pretty little house and chapel. Above it on the ridgetop, the brick bulk of San Domenico church houses her highly venerated shrunken head and thumb as relics in a chapel frescoed by Sodoma.

Having had you fill of religion, head to the bulky Medicean Fortress that dominates the north end of town. In its brick vaults Italy has installed the national Enoteca Italian Permanente, a repository of almost every wine made in Itay--most available for purchase, and dozens at a time available by the glass for only $2 to $6 so you can perform your own taste tests of Italy's best vintages.

Suitably inebriated, head off to dinner a few doors up from St. Catharine's old digs at Osteria La Chiacchera, a simple little osteria hat's long been a stand-by for local students and budget travelers of all stripes.

Day 11


Day 12

am/lunch - Pienza

evening/night - Cortona

Day 13


Day 14

am - Cortona


Hop a train heading north along the wide Chiana Valley. Anyone who's seen the Oscar-winning film "Life is Beautiful" will recognize the Tuscan town where it was filmed, Arezzo, hometown to Giorgio Vasari (architect of the Uffizi, mediocre painter, and author of the world's first art histories).

Dine at La Buca di San Francesco, an antique cellar restaurant serving time-tested Aretine dishes with some of the friendliest service in town.

Day 15

I've saved one of the best for your last full day. Piero della Francesca--one of the early Renaissance's masters of composition, perspective, and probing psychology--left his greatest work, the Legend of the True Cross fresco cycle, in Arezzo's San Francesco church. Under restoration for years, the first half of this marvelous chapel has recently reopened to the public--and since the scaffolding is still up while they restore the other half, your ticket (wise to book ahead at tel. +39-011-39-0575-355-668 or www.bpel.it/piero) lets you clamber up to the frescoes' level so you can marvel at them up close, just as Juliette Binoche got to, using a movie set reproduction of the chapel of course, while holding a torch and swinging on a rope in "The English Patient."

In the afternoon, it's time to return to 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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