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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.Well, if you've never been to Florence before, you'll spend at least a day or two there.
Then you have time to hit a few of the other major highlights of Tuscany—the Leaning Tower of Pisa, hilltown city of Siena, and/or the towers of medieval San Gimignano.
Here's how:
You could do just about anything you have your heart set upon. Here are a few sample itineraries of how you can spend a glorious week exploring Tuscany (with a few dips into neighboring Umbria):
If you prefer someone else to sweat the logistics details, take care of the driving (or train tickets), and provide a professional guide for all the sightseeing, consider an escorted tour.
Not just any tour, mind you, but one that allows you a measure of the kind of freedom independent travel offers—small groups (12 or fewer), trasnport usually on local trians and buses (rather than a giant tour bus), and the freedom to program some of your own sightseeing and meals (rather than being forced to do everything and eat everywhere as a group)—but still with all the support of a local guide.
Here are some of those kinds of independetly-spirited tours that cover Central Italy from trusted partners.
Destinations: Venice, Cinque Terre, Pisa, Florence, Perugia, Spello, Rome
Travel to Italy and savour the many flavours of this gastronomic haven on a journey from the canals of Venice to the cobblestone streets of Rome. Explore historic sites and picturesque villages on this special food-lovers' adventure through some of the most incredible places in Italy. There is plenty of time to indulge in everything from fresh seafood and hearty wines to the finest balsamic vinegars and pesto in the world. This 10-day trip is sure to tantalise all the senses....
Destinations: Venice, Gubbio, Assisi, Spello
Travel to Italy and explore the green heart of charming Umbria - mingling with pilgrims, eating delicious foods and seeing ancient sites along the way. Visit the most sacred places in Italy as you travel from Venice to Rome, via the ancient hilltop towns of Gubbio and Assisi. Encounter the religious and historical treasures of one of the most alluring regions in Europe on this delightful Italian adventure....
Destinations: Levanto, Punta Mesco, Monterosso, Riomaggiore, Manarola, Corniglia, Vernazza, Portovenere, Santa Margherita, San Fruttuoso, Camogli, Portofino
When entering this region of Italy, things can seem a little surreal. The houses are painted in vivid multi-coloured shades, the ocean’s brighter than the sky and the sun rains down so heavily that everything seems a little technicoloured – welcome to Cinque Terre. On this beautiful coastline tour of Italy, we hike from Levanto to Monterosso, Riomaggiore, Montenero and Portofino, finishing in Santa Margherita by foot, boat and train....
Destinations: Val d'orcia, Pienza, Monatelcino, Siena, San Gimignano, Pisa, La Spezia, Cinque Terre, Carrara, Lucca
Get to know gorgeous Tuscany and the UNESCO-listed Cinque Terre on this incredible 4-day tour from Rome! With 4-star hotel accommodation in Siena and La Spezia included, plus an expert guide, your tour offers everything you need to experience the best of these stunning regions. Discover charming hilltop towns like Pienza and San Gimignano, and then gaze in wonder at monuments like the Leaning Tower of Pisa. Head to Liguria and explore the five fishing villages that make up the beautiful Cinque Terre before returning to Rome...
Destinations: Florence, Pisa (or, Nov–Feb, Siena and San Gimignano)
Escape to the romance of Tuscany on a 3-day tour from Rome! The rolling hills of Tuscany continue to shape Italy's rich culture, be it through art, history or the finest Italian produce. Departing Rome, you will travel to the heart of Tuscany in Florence. The city is home to an abundance of paintings and sculptures housed in numerous galleries and public squares. Next it's onto Pisa with its biggest attraction, the Leaning Tower...
Destinations: Florence, Rome, and Venice
Destinations: Venice, Verona, Lake Como, Milan, Genoa, Pisa, Siena, Rome
See the most beautiful cities and towns of Northern Italy. See Verona, the town of Romeo and Juliet; see Lake of Como, famous for villas and mountain scenery; see the world famous Duomo in Milan; visit the most important ports in Italy in Genoa; see the bell tower of the Pisa'ss cathedral; and view the Piazza del Campo and the Municipal Palace in Siena...
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 two weeks? You bet. But there are three 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.)
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.
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