Tuscany itinerary: Six days of wining and dining

A vacation blueprint for spending a week touring the vineyards and feasting in the great restaurants of Tuscany

FlorenceThe ChiantiMontalcino— Montepulciano—Orvieto

Six days of wining and dining Tuscany: Day by Day

Day 1-3 - Chianti

Where to spend the night
Hotels in Florence (day 0)
Hotels in the Chianti (days 1-3)
Hotels in Montalcino (day 4)
Hotels in Montepulciano (day 5)
Hotels in Orvieto (day 6)
Spend your first few days getting to know Tuscany’s legendary Chianti Classico red and its siblings in the sun-kissed valleys and craggy hills of the Chianti region between Florence and Siena.

You can do much of this vineyard visiting and sightseeing in three days’ time.

The absolute don’t-miss vineyards for buying include Villa Vignamaggio, Castello da Verrazzano, Castello di Ama, Castello di Volpaia, and the granddaddy of them all: Castello di Brolio, where modern Chianti was invented.

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.If you didn’t have a chance to plan or phone ahead to arrange degustazione (tastings), Castello da Verrazzano and the Rinaldi Palmira shop for Castello di Ama all welcome degustazione drop-ins.

I recommend basing yourself for the first night or two in a mini-apartment at Villa Vignamaggio, a gorgeous Renaissance villa where the real Mona Lisa was raised and where Kenneth Branagh filmed Much Ado About Nothing. It is near Greve in Chianti, the “capital” of the region and home to the most wine shops (there’s another good shop at the bend in the main road as it passes through Castellina in Chianti; good snacks, too).

There are also some fine meals to be had in the Chianti. None is overly fancy, but La Cantinetta in Spedaluzzo serves some of the best-prepared versions of local specialties, and is good for lunch or dinner.

You can also get a sophisticated meal at the osteria at Castello di Fonterutoli, with each course paired with one of this ancient estate's excellent wines.

La Cantinetta di Rignana is the Chianti’s lunch spot par excellence, with good, simple food and a killer vista, tucked way out in the wonderful middle of nowhere (excellent agriturismo, too).

For at least one night—perhaps two—stay in the southern Chianti at Podere Terreno, a homey little country house turned agriturismo that serves some of the most fabulous dinners you'll have in Italy—all done family-style with all the guests seated around a big table along with the proprietors.


Day 4 - Montalcino

Please take a minute to read the section on how to use these itineraries, which explains some of the shorthand and contains all sorts of tips on making these trips work for you.
It’s time to up the stakes from the fun-loving but lightweight Chianti and get into some serious Italian wine and food. South of Tuscany lies Montalcino, home to one of Italy’s most powerful and respected red wines, Brunello di Montalcino.

In the morning, stop by the local wine consortium’s office to pick up their vineyard map, then ensconce yourself in the Enoteca La Fortezza, a wine cellar installed in the bastions of the town’s medieval fortress and manned by a very knowledgeable staff.

Here you can cozy up to glasses of some of the best Brunellos, try out the less heavy-duty Rosso di Montalcino red and Moscadello dessert wine, and make a list of which labels produce the elixirs you want to bring home with you and tuck it away for later.

Brunello goes perfect with a rare bistecca Fiorentina or Tuscan game dishes, and there’s no better place to test it out than at the fine restaurant on the estate of one of Brunello’s premiere labels: Poggio Antico.

Now you could return to town to pick up your favorite Brunellos at the Entoeca, but purchasing direct from the vineyard itself is so much more fun. So armed with your map and your list, set off in search of the perfect Brunello among the vine-crossed hills of Montalcino. After a light dinner, sleep off all that wine by spending the night in Montalcino.


Montepulciano is a hilltown of Renaissance palazzi and Tuscany’s #2 red, Vino Nobile di Montepulciano. Its a more versatile wine than its neighbor Brunello, lighter weight and fruitier, and good with just about any food.

You can try its at any of the dozens of cantine scattered about town—many of them storefronts above vast networks of Etruscan tunnels where the wine is stored— and even have lunch farm hand-style at one of the estates, Fattoria Pulcino. But for the best “noble wines,” drop by the estates northeast of the city.

Poliziano (tel. +39-0578-738-171, www.carlettipoliziano.com), near Gracchiano, has some powerful wines, but perhaps the best Vino Nobile is produced at the La Cappezzini vineyards of the Avignonesi outfit (tel. +39-0578-724-304, www.avignonesi.it), across the Chiana canal near the village of Valiano. Their special reds are to set aside for aging, and be sure to pick up some of their pricey, velvety Vin Santo.

Return to Montepulciano for a celebratory dinner at the Trattoria Diva & Matteo and turn in for the night—your tour of Tuscan reds is over. Spend the night in Montepulciano.


Day 6 - Orvieto

Now that the cellar back home will be well-stocked with Tuscan reds, it’s time to cross the Umbrian border and revel in one of the few Italian white wines worth troubling over, the dry, straw-colored Orvieto Classico.

Orvieto is a stony city, rising implacably on its mesa of tufa. Spend the morning with its major sight, the jewel box of a Duomo with horribly fascinating carvings on the facade and ground-breaking frescoes inside.

Orvieto has been producing its famous white wine probably since Etruscan times, and has made an industry out of getting everyone from the Celtic French to the Roman emperors to the invading Goths and Renaissance popes more than tipsy on the stuff.

There are a couple of good cellars to help you get intimate with the semi-dry and sweet varieties of the Orvieto Classico that are seldom exported, but the best way to warm up to an afternoon in Orvieto is to let yourself imbibe a bit at the lunch table, and there’s no better place for that than at the Trattoria Tipica dell’Etrusca.

After lunch, you can hit a few of the outlying vineyards for direct sales—the best are recommended in the Orvieto chapter—or relax in town and do your shopping, and perhaps a bit more tasting, at the enoteche.

Spend the night in Orvieto.



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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