Italy in two weeks: The sane whirlwind (Tuscany & Cinque Terre edition) - in brief

A perfect two-week itinerary in Italy that includes stops in Rome, Florence, and Venice, Tuscan & Umbrian hilltowns (including Siena, Pisa, and Assisi), and a hike in the Cinque Terre

A map of the sane two-week Italy itinerary: Tuscany edition

Itinerary highlights

Here is an itinerary that takes in Rome and Pompeii, Florence and the hilltowns of Tuscany (Siena, San Gimignano, Pienza, Pisa) and Umbria (Orvieto, Assisi), the Cinque Terre fishing villages at the tip of the Italian Riviera, Venice, and (if you're interested) Milan.

This is the quick, just-the-facts-ma'am version of the itinerary, laid out as if on a calendar (which is why the "Day 1" is placed where Saturday would be, assuming most folks will be flying over to Italy on a Friday night; click here for more such foolish assumptions about how these itineraries work).

If you want a longer, text version of the daily plan—complete with transportation details and descriptions of (and how much time to spend at) each of the sights and destinations, click on either the "Day #" at the top of any given day or the "» more" at the bottom. (Or you can just scroll through the whole thing at once on this page.)

Day 0
Fly to Italy in the evening (it's an overnight flight)
Day 1

[arriving, getting downtown]
Lunch: [Quick]
Piazza Navona, Sant'Agostino, San Luigi dei Francesi, Sant'Ivo alla Sapienza, Pantheon, gelato, SM Sopra Minerva, Galleria Borghese, Villa Borghese, Spanish Steps, Santa Maria del Popolo, passeggiata
Dinner: [Old city]
Stay: Rome

» more
Day 2
Roman Forum, San Pietro in Vincoli
Lunch: Cavour 313
PM: Colosseum, San Clemente, Campidoglio, Capitoline Museums
Dinner: [Old city]
Stay: Rome

» more
Day 3

AM: Vatican Museums, Sistine Chapel
Lunch: [snack]
PM: St. Peters, Castel Sant'Angelo, Trastevere
Dinner: [Trastevere]
Stay: Rome

» more
Day 4

Pompeii, Amalfi Coast, Capri
Stay: Rome or Amalfi Coast

» more
Day 5
Free [sleep, shop, sightsee, whatever]
Villa Borghese, Galleria Borghese, Trastevere, Trevi Fountain
Stay: Rome

» more
Day 6
Lunch: Orvieto
PM: Assisi
Stay: Assisi

» more
Day 7
Lunch: Pienza
PM: Siena
Stay: Siena

» more

Day 8

AM: San Gimignano
Lunch: Chianti
PM: Chianti
Stay: Florence

» more

Day 9
AM: Duomo, Brunelleschi's Dome, Baptistery
Lunch: I Fratellini
Piazza della Signoria, Uffizi
Dinner: Il Latini
Stay: Florence

» more
Day 10
Accademia/ Michelangelo's David, Santa Maria Novella
Lunch: [Florence]
PM: Santa Croce, gelato at Vivoli, Ponte Vecchio, Pitti Palace
Dinner: [Oltrarno]
Stay: Florence

» more
Day 11
Lunch: [Pisa]
PM: Cinque Terre
Dinner: [Cinque Terre]
Stay: Cinque Terre

» more
Day 12

ALL-DAY: Hiking the Cinque Terre
Dinner: [depends]
Stay: Cinque Terre

» more
Day 13
Getting to Venice
Lunch: [on the go]
PM: Grand Canal, Accademia Gallery, Peggy Guggenheim, gondola ride
Dinner: [Venice]
Stay: Venice

» more
Day 14
Piazza San Marco, St. Mark's Cathedral, Bell tower, Doge's Palace
Lunch: [Venice]
PM: Free time [shopping, Ca' d'Oro, getting lost, etc.]
Dinner: [Venice]
Stay: Venice

» more
Day 15
OPT #1:
Stay in Venice and tour the outlying islands - Murano, Burano, and Torcello)
OPT#2: AM: Transport to Milan
Lunch: [Milan]
PM: Da Vinci's Last Supper, Duomo, Pinacoteca di Brera, Pinacoteca Ambrosiana, La Scala, Navigli
Dinner: [Milan]
Stay: Venice or Milan

» more

Day 16
Flying home
Lunch: Airline food (sorry)
PM: Still flying home, getting to your house, deciding to leave the unpacking until tomorrow
Dinner: Order take-out
Stay: Your own bed

» more


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)

Useful links
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