Hill towns of Tuscany - Private Vacation

4 Days 4 Nights
Per person 1.250


Discover the ancient heart of Tuscany, the province of Siena, tour its stunning countryside and many medieval villages and hill towns. Taste the robust flavors of the products that these mineral rich soils have been offering up since centuries and enjoy meeting and learning about the habits, thoughts and traditions of the locals.
Combine this with a happy dose of Tuscan sunshine and it provides for a relaxing and enthralling four days filled with great food, wine and many sights.

The Itinerary may change a little according to availability but will maintain the same general imprint.

This vacation will start with a minimum of 2 participants and needs to be booked 1 month in advance, we will contact you in case of modifications required due to availability and/or location/type of accommodation.

Day 1

Chianti and San Gimignano transfer tour

Visit Tuscany's highlights and taste great wines

  • Farm lunch with wine tasting
  • Cellar tour and Chianti wine tasting
  • Visit San Gimignano and Monteriggioni
  • Get the best of your travel between destinations
  • The company of an expert English speaking driver guide
Travel between destinations and visit the medieval hill town of San Gimignano and the fortress of Monteriggioni and spend leisure time. Savour a seasonal lunch at family run farm and taste the areas wines. Visit a Chianti Classico winery, tour the cellars and enjoy tastings of this famous red wine.

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Day 2

Tuscan Cooking class and Volterra tour food tour.

Hands on Tuscan cooking and a beautiful hill town
  • Hands on Cooking class with preparation of full italian meal and fresh pasta.
  • Enjoy eating the lunch you prepared served with local wines
  • Afternoon visit to alabaster artisan
  • Visit of Volterra
  • Meet and have fun with the locals
Bring back some interesting new ideas and recipes to impress your friends, learn how to prepare tasty recipes that will remind you of your time spent in Tuscany!
Enjoy the afternoon visiting an Alabaster workshop and the historical hill town of Volterra with its beautiful vioews and many sights.

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Day 3

Small Group Siena and Duomo Walking Tour

Tour the main sites and city Duomo
  • Tour of all the main city sights
  • Small group ensures a more personalized experience
  • Tour in only English avoids lengthy waits for translations
  • Skip the line Duomo entrance tickets and tour of interiors

  • Duomo entrance tickets
  • Expert English speaking guide
Visit the historical medieval centre in the company of your guide, discover this fascinating ancient city and its proud population.
Walk down the main road to the beautiful shell shaped Piazza del Campo and discover the traditions of the Palio tournament.
Marvel at the art and detail in the gothic masterpiece that is the Duomo of Siena.

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Day 4

Pienza and Montalcino, Organic Cheese and Wine tour

Cheese and wine, a great combination
  • Visit of the Val d'Orcia
  • Visit the hill towns of Pienza and Montalcino
  • Enjoy a tour of dairy farm and cheese tasting
  • Tour wine cellars and taste of Brunello wines
  • Enjoy the company of an expert English speaking driver guide
See the beautiful Val d'Orcia and enjoy a tour of organic dairy farm followed by percorino cheese tasting on a panoramic terrace.
Visit the renaissance gem Pienza and Montalcino the high hill-town famous for its wines.
Taste the rich flavours of Brunello wines and tour wine cellars producing the famous nectar.

More details

The vacation includes

  • 2 nights in 3 star hotel in San Gimignano
  • 2 nights in 3 star hotel in Siena
  • Farm lunch near in Chianti
  • Guided Chianti wine tasting in cellar
  • Cooking class and full lunch
  • Guided tour of Siena and Siena Duomo
  • Tasting of local products
  • Cheese tasting at organic dairy farm near Pienza
  • Guided Brunello di Montalcino wine tasting
  • Private transportation in air conditioned vehicle
  • English speaking driver/guide

Not included

  • Any extras not listed above
  • Dinners
  • Pick up and drop off transfers other than Siena centre or bus/train station. (can be requested as an extra)
  • In depth tours of the main sites of central Tuscany
  • Overnights in historical city centres
  • 4 very diverse days of activities
  • The company of professional English speaking guides
  • Meet the locals and taste the areas food and wine

Personalize your itinerary


For all Vacations it is possible to change the budget range of your accommodation. You can either decide to increment the budget to include nights at 4 or 5 star Hotels and Resorts, or if you prefer to save on accommodation you may also decrease the budget to include more affordable B&B’s or Hostels.

You may also personalize your itinerary to include different locations for your accommodations for example, choose to stay in the countryside or self catered apartment, or split the nights between different hotels and accommodation types and locations.


The Vacations offered are just indications of a packaged tour, all packages can be customized to your specific needs ad can be either made to include more nights and additional activities or shortened to your liking.

If you are not planning on touring every day but plan to have some days off in your itinerary and would like for us to hold your hotel reservation for extra nights after your package with us or are arriving earlier and require accommodation you may lengthen or shorten you nights at chosen hotels to your requirements.

Start - End destination

Say for instance that you are going to be travelling from Florence to Rome, but would like to spend a few days in Tuscany on the way. You can change your private tours to transfer/tours that have different pick up and drop off locations.

If you have chosen a itinerary that is comprised mostly of shared tours with set start and end destinations, you may like to consider including private transfers between destinations to pick you up on arrival or transfer you to your next destination.