Tuscan Hill Towns

7 days/6 nights

Maximum number of participants on tour is 14

Tuscan Hill Towns small group tour

Tuscan Hill Towns Small Group Tour overview:

The name Tuscany means “land of the Etruscans“. These were the ancient peoples who controlled a large part of the Italian peninsula prior to the rise of the Romans. They were great builders and engineers. Many of their temples and roads and burial chambers can still be seen today. They drained swamps, had indoor plumbing and painted frescoes. Etruscan women were allowed to own property and drive chariots. The ancient Etruscans and their successors constructed their towns on hilltops for defense. They also wanted to avoid lowland swamps and malaria-carrying mosquitoes. The location of  the Tuscan hill towns has not changed so be prepared for winding roads and wonderful vistas.

The tour begins with a transfer from Florence to Renaissance Pienza, featuring the fabulous landscapes of the Orcia Valley.  Brunello and Vino Nobile wines await our visits to nearby cantinas in Montalcino and Montepulciano. We’ll walk down a 2,500 years old road and explore ancient Etruscan sites in Sovana and Pitigliano. Medieval San Gimignano, the city of beautiful towers features lovely evenings and the best gelato. Siena is home to Italy’s most beautiful square, the Piazza del Campo, and an amazing cathedral.

Michelangelo’s David at the Accademia Museum and a pre tour exploration of Florence are included!

Read what our travelers say about our Tuscan Hill Towns small group tour!

Day 1

Your Tuscan Hill Town tour begins with our afternoon transfer from Florence airport where you’ll be met by your tour manager. Heading south into the heart of Tuscany our first stop is the 13th century walled fortress of Monteriggioni; the ancient hamlet within still retains its original appearance and counts just 42 inhabitants.

Then we’ll arrive to one of the most charming towns in Italy, Pienza, the Renaissance “ideal city”. Constructed in the latter part of the 15th century at the behest of native son Pope Pius II Pienza overlooks the rolling cypress-lined hills of the stunning Orcia Valley. Our lodging is Hotel Corsignano (3 nights) located just outside the town walls. Introduction to the delicious local cuisine at our welcome dinner.

Tuscan Hill Towns small group tour

Day 2

Cortona, one of the original 12 Etruscan city-states, is reputably the oldest continuously inhabited town in Italy. Situated on a commanding hill overlooking Lake Trasimeno, it has cyclopean walls – huge boulders roughly fitted together without mortar – that date back 3,000 years.

Cortona was conquered in the 16th century by Florence. We’ll begin our morning with a look at the Medici fortress after which we’ll learn about Cortona’s earliest residents at the Museum of the Etruscan Academy.  Winding lanes, medieval squares and great small restaurants await your midday break.

Montepulciano, which has its roots in Roman times, is home to grand piazzas, noble palazzos and ancient alleys. After a guided walking tour we’ll complete our visit with a tasting of Vino Nobile wine.

Tuscan Hill Towns small group tour

Day 3

This morning we go to the very south of Tuscany passing through mysterious landscapes to visit the tiny town of Sovana and the nearby Archaeological Park where we’ll have a fascinating guided tour of the 2,700 year old Etruscan necropolis and the profound experience of walking along ancient Etruscan roads.

Pitigliano is one of the most unusual towns you can imagine, sitting atop a sheer cliff lined with holes that were once Etruscan tombs and now used as cantinas, stables and storehouses. It has a lovely medieval center with 16th century fortress, massive aqueduct and old Jewish ghetto.

Included dinner in Pienza.

Tuscan Hill Towns small group tour

Day 4

An early morning visit to the vineyards and cantina of Il Casato to have a taste of their Brunello wines. Then we’ll take in the hill-town and castle of Montalcino, with some of the most scenic settings on our tour.

Afternoon visit to the 9th century abbey St. Antimo, one of the most beautiful Romanesque structures in Italy.

San Gimignano, originally an Etruscan settlement, became an important medieval town due to its location along the Francigena Way – the famous pilgrim route from northern Europe to Rome. It’s known as the city of the beautiful towers – once there were 72, now 14. In 1353 it was overpowered by the might of Florence and was forbidden further construction. In addition, the Francigena Way was relocated – diminishing the city’s importance. The result is that, today, San Gimignano retains its same charming 14th century appearance. We’ll be staying at the 13th century Hotel La Cisterna , set in the main square of town.

Tuscan Hill Towns small group tour

Day 5

Early morning free in San Gimignano followed by a drive into Chianti wine country. Our first stop is Castellina in Chianti, an attractive hill-town that was once the fortified border between Florence and Siena. It still retains its 15th century defensive look with imposing walls and fortress but these days is more inviting with shops vending wine, olive oil and other local products.
This afternoon we’ll have a guided tour of a local vineyard and taste their Chianti wines.

Tuscan Hill Towns small group tour

Day 6

Our last excursion is to the enchanting Gothic city of Siena, home to one of Italy’s most beautiful squares, the Piazza del Campo and a marvelous cathedral. Originally founded as a Roman military colony, Siena flourished during medieval times as an important banking center and was a powerful rival to Florence. In the mid 14th century the Black Death put a halt to cathedral construction as Siena lost 70% of its population. The combined might of Spain and the Medici family put an end to the Republic of Siena in 1559.

Our local guide will walk us through the contrade (wards) of Siena with an entertaining explanation of their role in contemporary social life and the competition of the famous horse race, the Palio. After which we’ll leave you on your own for shopping, lunch and, perhaps, to climb the 503-step Torre del Mangia.

Our San Gimignano farewell dinner restaurant is located in the historic center with stunning views over the valley.

Tuscan Hill Towns small group tour

Day 7

Morning transfers to Florence airport, train station & hotels; Pisa airport.

Tuscan Hill Towns small group tour

2023 Single supplements


Principal towns & villages

1-3Monteriggioni, Pienza, Cortona, Montepulciano, Sovana, Pitigliano
4-6Montalcino, St Antimo, San Gimignano, Castellina in Chianti, Siena


  • Pickup Florence & Pisa airports at scheduled times
  • 6 nights accommodation in charming hotels
  • Tourist accommodation tax
  • All breakfasts, 3 dinners, beverages included
  • All activities and admissions listed in Highlights
  • Full-time professional tour manager
  • Porterage
  • All ground transportation Days 2 - 6
  • Morning transfers to Florence & Pisa airports, station or hotel
  • All activities and admissions listed under Highlights


  • Etruscan Museum at Cortona
  • City walking tour with local guide in Montepulciano
  • Vino Nobile wine tasting at Montepulciano
  • Guided visit to the Etruscan necropolis at Sovana
  • City walking tour with local guide in Pitigliano
  • Brunello cantina tour & wine tasting near Montalcino
  • Visit to the 9th century Sant'Antimo Abbey
  • Chianti cantina tour & wine tasting
  • City walking tour with local guide in Siena
  • Siena Duomo

Getting there

Tour begins: Florence

Day 1 transfer from Florence airport is at 14:00.

Upon request we can transfer you from Pisa airport (morning only) to Florence airport.

Tour ends: Florence

Morning transfers available from 04:00-10:00 to Florence airport, train station and Pisa airport

How to get there: Book round trip tickets into Florence or Pisa airports.

Pre tour: We recommend arriving to Florence a day or more prior to tour start. The city center/historic district is just a 10-15 minute taxi ride from the airport.

Take advantage of our free Florence city tour including Michelangelo’s David at the Accademia Museum the afternoon prior to tour start.


Day 1 — Pienza, SI, Italia

Day 2 — Cortona, AR, Italia

Day 2 — Montepulciano, Siena, Italy

Day 3 — Sovana, Grosseto, Italy

Day 3 — Pitigliano, GR, Italia

Day 4 — Montalcino, Siena, Italy

Day 4 — San Gimignano, SI, Italia

Day 5 — Castellina In Chianti, SI, Italia

Day 6 — Siena, SI, Italia

Activity level

Most medieval towns were built as hilltop fortifications, so you will find some of your walking to be uphill.

The Day 3 visit to the Necropolis near Sovana includes walking on uneven ground.

Be prepared to spend a few hours a day on your feet. This tour is not suited for anyone who has problems with knees, back, heart, obesity or those who cannot manage steps and moderate inclines.  Age is not important as long as you are reasonably fit and a good walker. If you have mobility issues this is not the right tour for you. Please call us if you have questions.


  • Prices shown are per person, double occupancy, in euro.
  • The deposit is 400 euro per person.
  • Balance payments are due 70 days prior to tour start.
  • Deposits and balance payments are accepted by Visa and Master Card or by bank wire. After your deposit has been received we will send you an invoice with the due date and amount for the balance of payment. Should you fail to make final payment by the date specified on your invoice, we reserve the right to cancel your booking without refund.
  • Cancellations and refunds: in the unlikely event that we would cancel your tour, you would be entitled to a 100% refund within 2 weeks after the tour’s cancellation.

If you cancel your tour reservation:


1. are 50% refundable up until 180 days prior to tour start date.

2. are 100 % non-refundable less than 180 days prior to tour start date.

Balance payments

3. are 98% refundable 70 days or more prior to tour start date.

4. are 48% refundable 70 to 31 days prior to tour start date.

5. 30 days or less prior to tour start date: no refund.

Physician documented emergency medical reasons or police documented cases of accident, flood, fire or crime are required for refunds.

We do not provide refunds for: non-medical personal problems; air carrier delays or cancellations; inability to obtain passports; business problems or emergencies; etc.


We strongly recommend that you purchase a travel protection plan to help protect you and your travel investment against the unexpected. Travel protection plans can include coverage for Trip Cancellation, Trip Interruption, Emergency Medical and Emergency Evacuation/Repatriation, Trip Delay, Baggage Delay and more.

For information on available plans or to enroll, go to insuremytrip.com 

It is not possible for Amber Road Tours to provide protection coverage of any sort and you agree to buy insurance or travel at your own risk.


Transfer from Florence Airport on Day 1 (available only at scheduled time). Morning transfer from Pisa airport to Florence airport available upon request. All ground transportation Days 2 to 6, including tour manager and drivers. Transfers on Day 7 from San Gimignano to Florence airport or train station. 6 nights hotel accommodations with breakfast, 3 dinners including beverages (wine, beer, soft drinks and water). Admissions to all sites visited as a group, as listed in bold in the tour itinerary.


Air transportation, all meals not listed above, room service, phone calls, etc.


The transfers from Florence Peretola airport to our first hotel destination in Pienza on Day 1 will be at 2pm.


You are allowed one suitcase and one carry-on bag. If you exceed this limit there may not be space in the coach to transport your excess luggage and it will be at your own expense to have it transported throughout the tour. We suggest that you bring a daypack for carrying water, guide books, jacket, rain gear, etc.


Most medieval towns were built as hilltop fortifications, so you will find some of your walking to be uphill. Be prepared to spend a few hours a day on your feet. This tour is not suited for anyone who has problems with knees, back, heart, obesity or those who cannot manage steps and moderate inclines. Age is not important as long as you are reasonably fit and a good walker. If you have any difficulty walking this is not the right tour for you.


Days 1 – 5 by air-conditioned coach

Days 6 & 7 by air-conditioned maxi-van taxi


Are located in quiet locations within historic districts or a short distance outside the city walls. European hotel rooms are generally smaller than those in the U.S., and have one queen bed or two single beds, with private bath.


We have space available for two singles on each of our tours. They are provided with single-use double rooms. The additional single room supplement cost can be found on the Calendar page of our website.


For our recommended tours and dates, as listed in our web site, are guaranteed. We do not sell optional excursions or take you on shopping expeditions. Your additional expenses will be for non-included meals, moderate tipping where appropriate, and personal sightseeing or shopping.


We have a no smoking policy on all tour buses, at group meals and at all sites visited. The same policy applies to the use of cellular phones.


For the enjoyment of all our guests on tour we ask those who choose to travel with Amber Road Tours to be congenial, lighthearted and to take small issues in stride. Should you have any issues please address them to your tour manager – he or she is your Amber Road Tours’ representative during your time on tour. Once your tour is finished you will be emailed a link to our website where you can leave comments about your experiences and suggestions about how we can improve our services.


No responsibility is accepted for any loss, expense, accident, injury, or damage to any person or property due to the actions or omissions of any person, or any cause, including but not limited to acts of God, acts of terrorism, war, strikes, defects in machinery, breakdown of equipment, weather, quarantine, or other causes beyond our control.


Amber Road Tours reserves the right to accept, reject, or not retain any person as a tour participant whose condition or general deportment impedes the operation of the tour or, in the opinion of the tour manager, affects the rights and enjoyment of other guests. A guest not retained on tour shall have no cause for complaint or refund, and shall bear any and all extra expenses that ensue.


All information on this website is, to the best of our knowledge, correct. However, we reserve the right to make changes in accommodations, visits, and itineraries at any time should it become necessary or desirable. Delays or itinerary changes caused by strikes, bad weather, traffic, or other unforeseen circumstances are beyond our control and we are not obliged to pay guests compensation.