The Internet's most comprehensive Travel website for Italy
Use quote marks to search for exact names eg "Hotel Florence"

Self Guided Tour
Pick up your car in Milan, Rome or some other arrival point.

Suggested tour length:

7 days, 6 nights
Suggested travel periods:
April 1 to October 31
Price for this tour
Includes compact car , all hotel accommodations , breakfast
(based on double occupancy)
Jul-Sep 15:
USD $ 1699/person
Off season:
USD $ 1399/person

Tour car rentals from AutoEurope
included in tour price

(7 days)
Alfa Romeo 147 or similar: 4 door, Manual  Transmission with AC
Add $85/day for extra days

Pix and upgrades

Click to enlarge

Route mileage and MapQuest maps (approx distances)
Click on links for maps

Rome - Cortona - 203 km
Cortona - Siena - 71 km
Siena - Greve - 43 km
Greve - San Gimignano - 48 km
San Gimignano - San Miniato - 41 km
San Miniato - Montecatini - 34 km
Montecatini - Florence - 47 km
Montecatini - Pisa - 63 km

Print maps and driving directions from these MapQuest maps

Book this tour
Contact: IV Travel

Tour includes all hotel costs and  car rental for 7 days and 6 nights. Hotel costs are based on a bed and breakfast plan.

Hotel costs are based on one suite, or one room with double occupancy, and either double bed or twins.

Costs may vary slightly depending on hotel and car selections available during your travel period.

No hassle booking:
Contact (by email) and let us know the dates of your tour, how many are traveling in your party. 

We'll contact you within 24 hours to offer you a selection of hotels and cars.   We can also assist with flights to and from Italy and any other needs you may have.

20% deposit on booking
remainder within 45 days
of your departure date

We will confirm all hotel and car bookings and forward all the vouchers and other material you need for the hotels and your car.

Contact: IV Travel


Rates are highest in July and August.
Car  rental:
Included in tour cost, but varies according to tour level.
Other  Transportation:
Air fare, gas, road tolls, ferry's etc not included.
Breakfast is included in all recommended accommodations; the cost of other meals is extra.  Meals in Italy are priced to include the tip.
Entertainment, entrance fees:
Entertainment costs and the cost of entry to museums, galleries, tourist sites, etc are extra
Cost of tours or guiding services is extra.
Extra of course.
Equipment rental costs (bikes, boats, etc) are extra.
Of all the regions of Italy, Tuscany is the region that is best known throughout the world.  Here are the fabled cities of Florence, Siena and Pisa, and here the rolling, verdant hills where vintners produce some of the most famous wines in the world.  Tuscan landscapes, Tuscan architecture, Tuscan wines, cheeses and olive oils, and, of course, the fabulous flavours of Tuscan cuisine await the open-hearted (and hungry!) traveler.

This self-guided driving tour lets you penetrate to the heart of Tuscany's "art cities", but it also takes you into the countryside, well-off the beaten track, where you can immerse yourself in immemorial time, and savour the deep pleasures of real Tuscan life and real Tuscan hospitality.

Click the links for more info from
Booking this tour:
IV Travel

Arrival in Italy

We suggest you arrive in Rome, pick up your car at either Fumicino or Ciampino airport and head straight for Cortona.  But, arrive as you wish and pick-up the trail as you wish.

Day 1 - Cortona
(1 night)

This is the small Tuscan city that Frances Mayes put on the map with her smash best-seller "Under the Tuscan Sun".  Inhabited since Etruscan times, Cortona was conquered by the Romans, and became an important medieval city.  Take time to explore the centro storico - the historical center - and enjoy the city's utterly unique character.  

Hotel in Cortona *

3 Star Hotel
(Superior Double)
Hotel Oasis
Things to do

See: Cortona on

Taverna Pane e Vino - Via Piazza Signorelli 27 - light dishes, good prices
Osteria del Teatro and Caffe del Teatro - Via Maffei 5 - warm welcome, meat dishes, pastas
Tonino - Piazza Garibaldi - great view, good food
Caffe La Saletta - Via Nazionale -  up-scale, excellent crepes, good wine list - pricey
Route 66 - Via Nazionale 78 - happening place for young folks
Day 2, 3 - Siena - Montepulciano - Montalcino - Arezzo
(2 nights)

Your accommodations are just outside the city of Siena where you will have the freedom to go in a number of different directions.  You might spend one of your days visiting the heart of old Siena and stroll through the Campo di Fiori, the large square which is the stage for the rollicking annual medieval horse race called the Palio, or amble through the ancient streets where you can still hear the echos of ancient times - while you shop in some of Tuscany's finest stores.

You've got wheels, so next day you might want to drive south to the famous wine districts of Montepulciano or Montalcino and have a full-on experience of the Tuscan countryside - far off the fast-moving Autostrada.  Or perhaps, drive east to Arezzo, another of Tuscany's vibrant hill-top walled towns.  No matter which way you can't lose!

Hotel in the Siena area *

4 Star Hotel
(Deluxe double)
Villa Sciacciapensieri
Things to do

See: Siena, Montepulciano, Montalcino, Arezzo and on

Restaurants in Siena
Al Marsili - Via del Castoro 3 - up-market elegant
Cane e Gatto - Via Pagliaresi 6 - expensive
Da Divo - Via Franciosa 29 - Below street dining - cool
Due Porte - Via di Staloreggi - Piazza and Tuscan foods
Gallo Nero - Via del Porrione 65 - vaulted restaurant - neat
Tullio ai Tre Cristi - Vicolo Provenzano 1 - great meals since 1830
Renzo - Piazza Indipendenza - light simple meals
Netto - Via del Porrione 28 - Sienese food done very well
La Campane - Via delle Campane 6 - high quality Sienese food
La Taverna di Cecco - Via Cecco Angiolieri 19 - fab food - good service
Day 4 - Greve in Chianti
(2 nights)

If you like wine, you've heard of the Chianti wine district, where some of the world's most popular wines are grown.  Greve is the busy, charming little town in the center of the district, so plan to have lunch in Greve.  But spend most of your time getting lost on the country roads that wind their way around the area.  On the top of every hill you will see jaw-dropping vistas over the vineyards, olive orchards and cypress bordered fields that have been under the hand of man for centuries.  Walk, ride a bike, golf, go horseback riding.

Hotels in the Chianti area *

4 Star Villa Hotel
(Deluxe double)
Villa Vignamaggio
Things to do

See: Greve in Chianti on

Da Verazzano - Piazza Matteotti 28 - good Tuscan food
Gallo Nero - Via Cesare Battista 9 - great pizza
La Cantina - Piazza Trento - pizza and light meals
Torre delle Civette - Via Veneto - light menu, good prices
Day 5, 6 - San Gimignano - San Miniato and Montecatini Terme
(1 night)

We're not taking you into Florence...not yet.  When you leave the Chianti area we want you to head Montecatini Terme and Alta but we insist you make a couple of longish stops to see two of Tuscany's great old cities.  First, make your way across country to San Gimignano, the "city of the towers" and spend the morning strolling it's evocative medieval precincts.  After lunch, drive to the pretty little town of San Miniato, home of the incredibly tasty - and very expensive - white truffle.  Maybe splurge and have a Tuscan dish incorporating a sliver or two of this justifiably famous truffle.

Later in the day - before or after dinner (your choice) - you'll drive into Montecatini Terme, a beautiful spa town featuring gorgeous Liberty Style architecture from the 1800s.  You don't have to just kick-back and relax in one of the city's fabulous spas (although you can!), you can enjoy a trip up the cable car to Montecatini Alta, a medieval fortress town perching on the mountain behind the city that offers stunning views in just about every direction.

Hotels in Montecatini Terme *

4 Star Hotel
(Deluxe double)
Grand Hotel Tettuccio
Things to do

See: San Gimignano, San Miniato, Montecatini Terme and Alta on

Il Granduchi - in the Grand Hotel Tamerici - elegant dining - upscale
Corsaro Verde - Piazza XX Setembre 11 - Tuscan dishes, pizza
Lo Stuzzichino - Corsa Roma 45 - elegant dining, reasonable prices
Restorante Egisto - Corso Roma, 101/A - fun place, good food, good value
Day 7 - Departure
  • Drop your car at Florence or Pisa.  If you want to extend your visit and the time for use of the car, let us know.

* reserves the right to select hotels within the same class depending on availability at the time of booking.


Looking for suggestions to extend your journey to Tuscany and Central Italy?
  • A visit to spectacular, interesting, stylish, historical  Florence!  It's not far from Montecatini so getting there by car is not the problem.  The problem is one of time - because Florence is too wonderful to be seen in a few hours, or even a day.  If you want to see Florence, do everything you can to spend at least 2 days. has a selection of hotels, apartments and B&Bs in Florence or we can offer you a variety of accommodations near the city.  Just ask!
  • How about a side trip to Pistoia, Lucca or Pisa?  Pistoia is just a few short kilometers from Montecatini - and worthy of at least a day's attention.  Lucca is a beautiful walled city just jammed to the gunnels with things to see and do - and some fab restaurants too!  Pisa has that famously leaning tower that you've got to see at least once, right?
  • Via Reggio, Camiarori, Lierici, Livorno and other coastal towns of Tuscany.  This is a part of Tuscany that a lot of people don't think of as being in Tuscany.  But it is.  These sea-side towns and villages have lots to offer.
  • Not in Tuscany, but within striking distance, you'll find the ever astounding Cinque Terre - five little seaside villages that are strung together like pearls.  Find a place in one of the villages to sit and ponder, or do what a lot of people do - hike the trails between the towns.

Want to extend your tour for a few more days? can customize your tour.

Contact: IV Travel