If you have 3 days to spend in Tuscany

A vacation blueprint for how to spend your time if you have just three days in Tuscany (Florence + Pisa or Siena)

Florence—Tuscan Day trips (Pisa, Chianti, Siena, San Gimignano, Monteriggioni)


Days 1-2

Where to spend the night
Hotels in Florence (days 1-2)
Hotels in Pisa (day 3)
Hotels in Siena (day 3)
Spend the first two days in Florence:


Day 3 - Day trip: Best of Tuscany (Siena, Monteriggioni, The Chianti, San Gimignano, Pisa)

Day 3 - Day trip: Best of Tuscany (Siena, Monteriggioni, The Chianti, San Gimignano, Pisa)

Il Campo
Piazza del Campo in Siena. (Photo by Zyance)
Take the tour!
The only way to fit it all in on an all-day escorted tour with partners at Viator.com:

• Tuscany in One Day Sightseeing Tour (12 hrs)

There are other day trip options if you want to take things more slowly and do just a few of the towns:

Siena/San Gimignano:
• Siena and San Gimignano Small Group Day Trip from Florence (8 hrs)
• Private Tour: Siena and San Gimignano (8.5 hrs)
• Siena and San Gimignano (8.5 hrs)

• Private Tour: Pisa and the Leaning Tower from Florence (4 hrs)
• Pisa and the Leaning Tower Half-Day Trip from Florence (5.5 hrs)
• Private Tour: Lucca and Pisa from Florence (10 hrs)

The Chianti
• Small Group Chianti Wine Region Day Trip from Florence (8 hrs)
• Chianti Region Wine Tasting Half-Day Trip from Florence (5 hrs)
• Private Tour: Chianti Wine Tasting (5–9 hrs)
• Chianti Region Wine-Tasting and Dinner Half-Day Trip (8 hrs)
• Horse Riding in Chianti Day Trip (6 hrs)
• Vespa Day Trip to the Chianti (6 hrs)
• Tuscany Bike Tour in the Chianti (7 hrs)

• 5-Day Best of Italy Trip (5 days/4 nights)
Take the third day to make some day trips.

You could conceivably fit in two or three of those towns listed above on your own using public transportation—maybe four if you rent a car and do everything at a dead run.

But honestly, the only reasonable way to cram this much Tuscany into one day is to let someone else do the driving—and the parking, and the guiding, and the entry tickets, and the taking care of finding everything and knowing all the background information...

That's why I highly recommend the Tuscany in One Day Sightseeing Tour offered by our partners at Viator.com. It is a long one—12 hours, getting up at 8:30am and not returning to Florence until 8:30pm—but you get a lot for your $108.

Cruise past the walled hilltown of Monteriggioni en route to the king of the Tuscan hilltowns, Siena, which you can tour with the guide or on your own. (If you opt for the latter, try to squeeze in both the wondrously frescoed rooms of the Palazzo Pubblico town hall on the main square, the gorgeous sloping scallop-shell of Il Campo, and a quick spin around the zebra-striped 12th century Duomo, with its medieval carved pulpit and a library frescoed in bright, Fujifilm colors by Umbrian master Pinturicchio—helped by a young apprentice named Raphael).

The towers of San Gimignano
The towers of San Gimignano.
After a drive through the Chianti—and lunch and a wine-tasting class at a Chianti vineyard—you check out the Medieval Manhattan of San Gimignano, a picture-postcard hilltown bristling with stone towers.

Last stop: Pisa, with its gorgeous gaggle of Gothic buildings on the Campo dei Miracoli (The "Field of Miracles"), and a chance to climb the famous Leaning Tower of Pisa.

The tour drops you back off in Florence around 8:30pm—exhausted, but with loads of famous Tuscan sights added to your list of vacation accomplishments. Time for a celebratory dinner—and early bed time.

» Stay: Florence



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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