Perfect Tuscany itineraries

Vacation blueprints for your trip to Tuscany so you can get the most out of your trip, no matter where you want to go and how much time you have

If you only have a few days to spend in Tuscany

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:

If you have about a week to spend in Tuscany

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):

Guided tours of Tuscany

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.

Duration: 10 days
Cost: from $2,412
Book: Reserve it

Italy Experience

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....

  • Included activities: Cinque Terre day pass, Enoteca wine tasting and lunch, Pesto class, San Giorgio Bell Tower, Traghetto across the Grand Canal, Welcome dinner in Venice
  • Accommodation: Guesthouse (2 nts), Hotel (6 nts)
  • Meals: 9 breakfasts, 1 lunch, 3 dinners
  • Transport: Bus, Ferry, Metro, Taxi, Train
  • Group size: Max 16
Duration: 8 days
Cost: from $1,355
Book: Reserve it

Umbrian Discovery

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....

  • Included activities: Enoteca wine tasting, Guided tour of Basilica di San Francesco, Hike and cable car ride, Orientation Walk Assisi
  • Accommodation: Hotel (7 nts)
  • Meals: 1 lunch; budget €280 for meals
  • Transport: Bus, Cable car, Metro, Train
  • Group size: Max 12
Duration: 8 days
Cost: from $1,790
Book: Reserve it

Active Cinque Terre

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....

  • Included activities: Guided Walk to Portofino, Guided Walk to the Abbey of San Fruttuoso, Levanto to Monterosso Guided Walk, Riomaggiore to Portovenere Guided Walk, 'Sentiero dell’Amore' Guided Walk, The Wild West Coast Guided Walk, Welcome dinner, Farewell Dinner
  • Accommodation: Agriturismo/farmstay (7 nts)
  • Meals: 7 breakfasts, 3 dinners
  • Transport:Boat, Public bus, Train
  • Group size: Max. 16
Duration: 4 days
Cost: $577
Book: Reserve it

4-Day Tuscany and Cinque Terre Tour from Rome

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...

  • Included activities: Professional guide, transport by air-conditioned coach, 5 Terre Card
  • Accommodation: 4-star hotels (3 nts)
  • Meals: 3 breakfasts, 3 dinners
  • Transport: Coach, Boat
  • Group size: N/A
Duration: 3 days
Cost: $378
Book: Reserve it

3-Day Italy Trip: Florence and Pisa

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...

  • Included activities: Profeesional guide, entrance fees, transport by air-conditioned coach
  • Accommodation: 3-star hotels (2 nts)
  • Meals: 2 breakfasts, 1 lunch
  • Transport: Coach
  • Group size: N/A
Duration: 5 days
Cost: $1,086
Book: Reserve it

5-Day Italy Private Tour: Rome, Florence and Venice

Destinations: Florence, Rome, and Venice

Discover the three most famous and visited cities of Italy with this private 5 days tour around the “Bel Paese”. Starting from Rome, the Italian capital, this tour will stop in Florence and Venice. Enjoy the magical atmosphere of these cities, walking through their narrow alleys and visiting their top attractions.

  • Included activities: guided tours, transport by train
  • Accommodation: 3-star hotels
  • Meals: Lunch and dinners not included
  • Transport: Train
  • Group size: N/A
Duration: 3 days
Cost: from $389
Book: Reserve it

Up North from 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...

  • Included activities: Entrance fees, tours of Verona, Lake Como, Milan, Genoa, Pisa, and Siena
  • Accommodation: 4-star hotels in Venice (1 nt), Como (1 nt), Pisa (1 nt)
  • Meals: 3 breakfasts, 3 dinners
  • Transport: Coach
  • Group size: N/A

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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