Guided Vacation in Tuscany

Hilltop Villages and Vineyard Valleys, History and Hospitality

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Chianti Classico          enlarge

San Gimignano          enlarge

Cortona Vista     by Patrick Denker (WC) *


This is a guided holiday, and your guide is the key to making it special.  Your guide is local and knows the places, stories, history, and art in detail – and loves sharing all that with you.

Renowned for its art, history, and evocative landscape, Tuscany is a region where the past and present merge in pleasant harmony.  Hill-towns gaze across the countryside from on high, many encircled by protective walls and cypress trees.  In the countryside, among the vineyards and olive groves, there are hamlets and farmhouses as well as fortified villas and castles.

Unlike in the big cities that can be reached by train and plane, and where guided tours are available and public transport is easy (if you speak Italian), here you have the chance to spend an Italian holiday like a local.

Your guide will be like a local friend who takes you to all those tiny villages and secret places that you would never find on your own.  (Or maybe you would find one, but then the day would be over.)  Your guide will pick the best spots, the best food, and make the best of your time.

* (WC) copyright note:  Images from Wikimedia Commons are marked (WC).   The clickable "by" lines link to tabbed pages with larger versions
   of the images, and details about the photographer and the terms of use.   Close the tabbed pages to return here.


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Day 1  –  MEETING


Meet your guide today upon your arrival in FLORENCE.  Whether you arrive by air or by rail or are already are in town, just let us know where and when to pick you up.  You'll have a private transfer to your resort.

 Your holiday begins now.  Spend the afternoon at leisure by the pool of your resort or Agriturismo.  Tonight have a fantastic welcome dinner at your place with a welcome drink, three-course meal, and Chianti wine.

We can make arrange ments to pick you up in Bologna or Pisa if that is more convenient.
If you would like us to arrange a pre-tour program, with or without a guide, we can do that for you as well.

>  Your vacation includes guide services, transfer, welcome dinner, and hotel accommodation.

>  Unlike most other tours, this vacation does not include a "departure" travel day before meeting.



Today your guide takes you on a full-day excursion driving through the Chianti Classico roads in the original heartland of the Chianti wine region.

We visit CASTELLINA IN CHIANTI, located atop a hill at the crossroads of important roads that cross the surrounding valleys.  The city's origins go back to Etruscan times, and it became an important outpost due to its strategic position on the route between Florence and Siena.  Stroll its medieval pathways and admire the breathtaking panorama of the surrounding Chianti countryside.

RADDA IN CHIANTI is a medieval village, situated on top of a hill and still surrounded by ancient city walls and warning towers.  Narrow streets open up to small squares.  The Palazzo Pretorio (municipal palace) was built during the second half of the fifteenth century.

GAIOLE IN CHIANTI has always played an important role as market center for the castles and towns nearby, and is known for its fine wines.  Its surroundings include beautiful castles and parish churches.  We enjoy wine tasting and lunch in a wine estate, and have dinner at the hotel.

>  Breakfast, guide services, transportation, entrances, wine tasting, lunch, dinner, hotel

Castellina in Chianti   by Frazione Fonterutoli (WC)


We begin our day driving through enchanting Valdarno and Val Tiberina (Tiber Valley).  We visit ANGHIARI, a small and elegant medieval hamlet, known for the Anghiari Battle in 1440, when Florentine troops won the battle against the army from Milano.  Anghiari is enclosed in massive 13th century walls, and preserves the ancient and original atmosphere of small medieval towns. Walking around its narrow streets, you can breathe the air of its history and glory.  The entrances and balconies of the houses are often decorated with flowers which color the narrow streets, making the town more beautiful and charming.  It's claimed to be among the most beautiful villages in Italy.  Lunch on your own.

In the afternoon we drive to CAPRESE MICHELANGELO, a tiny hilltop village in the province of Arezzo, to visit Michelangelo's birthplace and family house.  This quiet little part of Tuscany is home to beautiful old churches and a fine museum and library built in honour of its most famous son.  Dinner tonight in a typical Tuscan trattoria.

>  Breakfast, guide services, transportation, entrances, dinner, hotel


Today we take the ancient Pilgrims Route, the Francine Road, with short stopovers in several small villages.
MONTERIGGIONI is a mediaeval town surrounded by its virtually intact curtain walls and fourteen towers, conforming almost perfectly to the archetypal mental image most of us have of a walled village.  Inside there is almost no traffic, and the buildings are for the most part original and attractive.

ABBADIA A ISOLA is a village within sight of Monteriggioni where, in the 11th century, Benedictine monks converted marshland into an area ("abbey island") where they built a monastery, now dominated by a Romanesque church housing precious works of art.  And we visit SAN GALGANO, with the ancient small "pieve" (parish church) where the mysterious "sword in the stone" has been kept for centuries.

We reach SIENA in early afternoon and go for a walk with a local guide in this beautiful, gentle city built on three hills and still surrounded by its ramparts.  Its medieval centre has streets lined with majestic Gothic buildings in various shades known as burnt sienna.  You have free time later for shopping or more sightseeing.  Dinner on your own tonight in Siena, with great suggestions.

>  Breakfast, guide services, transportation, locally guided tour, hotel

Siena          enlarge



After you've spent a leisurely morning by the pool we'll leave for SAN GIMIGNANO, one of the prettiest and now most famous towns in Tuscany.

This majestic medieval walled town stands on a hilltop in the heart of Tuscany, its profile bristling with tall towers that are famous all over the world.  It has retained all its old streets, its walls, gates, palaces, strongholds, and 14 of the original 72 towers.  San Gimignano is one of the most spectacular cities in Italy, and one of the best-preserved medieval cities in the world.  It has a quiet majesty about it, and its location on the top of a hill provides 360-degree views into the surrounding valleys.

After an orientation walk enjoy free time to explore the beautiful town.  Later a wine tasting in an organic DOCG wine estate / winery.

Tonight we have arranged a cooking class for you.  Buon Appetito!

>  Breakfast, guide services, transportation, wine tasting, cooking class dinner, hotel

San Gimignano     by Vignaccia76 (WC)


Spend a full day in the enchanting lands of Under the Tuscan Sun, the lands of Frances Mayes' 1997 book about falling in love with Tuscany and moving there.

First we visit CORTONA, a small charming town in the Valdichiana (Chiana Valley) in southern Tuscany.  The city, enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill about 600 meters (almost 2000 feet) above sea level.  This dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno.  The heart of Cortona is Piazza della Repubblica, with the Palazzo Comunale or town hall building overlooking the square.  Time at leisure and lunch on your own.

After we continue to AREZZO, one of the wealthiest cities in Tuscany.  Located in southeastern Tuscany, it sits atop a hill (where else?) at the crossroads of four valleys.  Its ancient origins are verified by archaeological discoveries that date back to the Paleolithic era, and it became one of the most important cities in Tuscany during the Etruscan era.

The Church of San Francesco is probably the most famous in Arezzo, with the incredible Early Renaissance fresco cycle by Piero della Francesca depicting the Legend of the True Cross.

Farewell dinner tonight in a Tuscan trattoria in the Tuscan Hills.

>  Breakfast, guide services, transportation, farewell dinner, hotel

Cortona View     by Wyzik (WC)

Day 7 – RETURN

After breakfast transfer back to Florence Airport or train station, or to your hotel or other destination to continue with your travels.

>  Breakfast, guide services, transfer


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Tour Features 

  • Private tour
  • All features as per itinerary
  • Door-to-door transportation (all modes).  Leave the navigating to us.
  • 6 breakfast buffets
  • 5 three-course dinners with menu choices, one beverage, and coffee or tea after dinner
  • 6 nights' accommodation
  • All entrance fees, taxes, and local guide fees paid
  • No hidden extras, no optional excursions – already included
  • The tour language is English only.
  • The days are well planned to offer you many highlights, but you are never rushed.
    Ideal combination of free time and planned activities.
  • All visits are inside, not drive-by.  Learn the stories that bring old buildings to life.
  • You will see not only the highlights but also the spots where only the locals go.
  • Tour director – Let our experts make every day and destination fascinating!
  • Satisfaction assured – backed up by our money-back guarantee.


Complete printable itinerary in PDF format >  Guided Vacation in Tuscany


View from San Gimignano          enlarge


Siena          enlarge

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Castellina Panorama     by LigaDue (WC)

Anghiari     by Adri08 (WC)

Caprese Michelangelo by Vincenzo Desiderio (WC)

Monteriggioni     by Zyance (WC)

Abbadia a Isola     by Mongolo1984 (WC)

San Galgano     by Massimo Civitelli (WC)

Siena          enlarge

Siena          enlarge

San Gimignano          enlarge


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We just came back from the Tuscany trip offered by European Castles Tours.  This was our 6th trip arranged by Astrid, and once again we could not have been more pleased.  Our driver and guide knew every corner of Tuscany, and his knowledge of the culture and history of the area provided us with unforgettable insight into the region.  The food, scenery and ambiance were just outstanding.  Our hotel was exceptional, and we give this trip a stellar recommendation.

        -  Arlene and Charles, Pennsylvania USA, May 2015

This is a elatively new tour offering so we are just beginning to gather comments from guests who have been this tour, but there are also dozens of recommendations from guests who have taken our other tours on our References Page.

Comments, experiences and recommendations from guests on past tours are featured in our  References Video .


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Accommodations, Prices and Reservations

Complete printable itinerary in PDF format >



Standard accommodations for his tour are in a First Class Tuscan villa hotel, with a private bath, beautiful pool, and garden with vineyards and umbrella pine and cypress trees.

It is possible to upgrade to a luxury hotel or economize somewhat.  Please contact us with dates and numbers of persons for these rates, as well as those for singles and children.

As we are using several hotels, depending on availability, we will provide specific details prior to requesting the booking deposit.

This tour is offered on the following basis:

This private tour is offered on a year-round basis, apart from scheduling conflicts.

Tour prices are for the land segment only.  Air fare is not included.

Prices are per adult, in U.S. dollars, based on double occupancy.
A child 8 to 16 years old sharing a room with two adults receives a 30% reduction.

A deposit of US $ 300 per person is required to secure a reservation.


Guided Vacation in Tuscany




2 persons (minimum)

4 persons

6 persons (maximum)


US $ 3,300 per person

US $ 2,990 per person

US $ 2,590 per person


Please contact us for Single and Triple Occupancy rates and special requests at this private tour email link


Reservation info and online form  >




Dates for all current multi-day Castles tours >

Tour Dates


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Contact Information

Email is fast, flexible, and free. You can write to us at  this email link .

You can call us in Germany  (Eastern Time + 6 Hours)

        U.S. Phone:  (202) 580 - 8732  /  Castles Office:  +49  8362  924 8800 


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