Southern Tuscany

Small Group Vacation - 3 Days 3 Nights
Per person 580


Enjoy rich wines and savour the local cuisine at family run farms, spend your evenings in the historical centre of Siena after having been on a walking tour that brings the city and its traditions and monuments to life.

Breath in the clean air and breathtaking views in the Val d'Orcia and visit the pretty hill towns.

Sip on the world famous Brunello wines on the wine hill of Montalcino in the company of the producers and learn about the passion put into the pruduction of this fine wine.

  • Visit must see sights and wine regions in southern Tuscany and spend your evenings in Siena's city centre

  • Enjoy meals on farms and wineries tasting some of Italy's finest red wines and savouring the tasty and fresh cuisine

  • Small group tours ensures personalized attention from your guide but also between fellow travellers

The order of the Tours on this vacation may vary according to availability, you may have a look here .

Day 1

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.

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Day 2

Small Group Pienza & Montepulciano Tour

Picture perfect Tuscany
  • See the magical landscapes of the Crete Senesi and Val d’Orcia
  • Visit the hill towns of Pienza and Montepulciano with free time for exploring
  • Personal and laid back tour and chance of making new friends
  • No rushed schedule
  • Small group of maximum 8 people
  • Lunch on organic dairy farm with spectacular view on the Val d'Orcia with cheese tasting
  • Visit to historical wine cellars and tasting of the Nobile di Montepulciano wine
  • Expert English speaking Guide
Roll along clay hills in the Crete Senesi. Climb characteristic hill towns and walk the streets of Pienza in the morning.
Enjoy a traditional Tuscan lunch on a farm and taste the famous pecorino cheese of the area.
In the afternoon visit the town of Montepulciano with its elegant churches, palaces, piazzas and high walls and visit cellars hewn out from the ground beneath the city.

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Day 3

Small Group Brunello Wine Tour

A collectors favorite wine and a delightful area
  • Tour of wine cellars
  • Meet the producers
  • Visit to Montalcino and the Abbey of San Antimo
  • Personal and laid back tour and chance of making new friends
  • No rushed schedule
  • Small group of maximum 8 people
  • Brunello wine tastings
  • Relaxed lunch at a family run winery
  • Expert English speaking Guide
Internationally recognized as one of the best Italian red wines, Brunello is a collectors’ favorite!
Tour cellars where they are aged, meet and have lunch with the producers and learn about the makings and the passion behind these wines.
Visit the hill town of Montalcino and the Abbey of Sant'Antimo and take in the breath-taking landscapes.

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The vacation includes

  • 3 Nights in 4 star or equivalent central Siena hotel
  • 1 2 hour Siena walking tour
  • Duomo entrance tickets
  • 1 Lunch at dairy farm with cheese tasting
  • 1 Nobile di Montepulciano wine tasting
  • 3 Brunello wine tastings
  • 1 Lunch at winery
  • Round trip transportation from Siena
  • Expert English speaking driver guide

Not included

  • Dinners and lunch on first day
  • Any extras not listed in inclusions
  • Pick up from hotel (Meeting point for tours)
  • Gratuities

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.