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 medieval villages and famous hill towns.
Taste the robust flavors of the food and wines that these mineral rich soils have been offering up since centuries, enjoy meeting and learning about the habits, thoughts and traditions of the locals.

All this, combined with a happy dose of Tuscan sunshine, assures yourself a relaxing and sensory four days filled with great food, wine and many sights.

  • In depth tours of the most characteristic hill towns of central Tuscany

  • Evenings in the Medieval city centres of San Gimignano and Siena with many restaurant options in walking distance of your accommodation

  • Four different days focusing on food, famous wines and meeting local producers

  • The company of professional English speaking guides to tour you privately thoughout your vacation

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.

Pricing for groups larger than 2, will need to be quoted separately.

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

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 Siena and Florence visiting 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.

More details

Day 2

Cooking Class & Volterra food tour

Hands on Tuscan Cooking and a beautiful Hill Town
  • Hands on cooking class with preparation of a full Italian meal with fresh pasta
  • Indulge in the lunch you have prepared served with local wines
  • Afternoon visit to alabaster workshop
  • Visit of Volterra
  • Meet and interact with the Tuscan 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 views and many sights.

More details

Day 3

Small Group Siena & Duomo Walking Tour

Tour the main attractions and Duomo interiors
  • 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 medieval centre in the company of your guide and discover the fascinating history of Siena and its proud people.
Arrive to the beautiful shell shaped Piazza del Campo and learn about the traditional Palio horse race. Finally, marvel at the art and detail in the gothic masterpiece that is the Duomo of Siena.

More details

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.

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

  • Dinners
  • Any extras not listed above
  • Pick up and drop offs than Siena centre or bus/train station (can be requested as an extra)

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.