Tuscany and History - Best of Medieval Tuscany - Small Group Vacation

3 Days 3 Nights
Per person 580


Discover the city of Siena; learn about its history, traditions and culture on a guided tour within the city gates.
Tour the impressive castles of the Chianti while tasting the best wines of the region at historical wineries. Walk along the ancient roads of the hill towns of San Gimignano and Volterra surrounded by stunning scenery.

The order of the Tours on this vacation may vary according to availability.

Day 1

Small Group Chianti and Castles wine tour from Siena

Imposing castles and famous wines
  • Visit to the medieval castles of Brolio and Meleto
  • Tour a medieval Castle and Cellars
  • Meet small wine producers and learn about the Tuscan way of life
  • Stroll in a non touristy medieval village
  • Personal and laid back tour and chance of making new friends
  • No rushed schedule
  • Small group of maximum 8 people
  • Round trip transportation
  • Full lunch at a Winery
  • Chianti Classico and SuperTscan wine tastings
  • Led by expert English speaking Driver/Guide

Explore the ever contended hills between Siena and Florence. This wooded landscape opens up onto neat rows of vineyards dotted with many wineries and impressive castles.
This is the area of the famous Chianti wine. Learn about the history of the area, tour castles and wine cellars and taste Chianti wines in the company of the producers.

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Day 2

Small Group San Gimignano and Volterra tour from Siena

Two stunning historical hill towns
  • Visit to San Gimignano and Volterra
  • Beautiful panoramic roads
  • Visit to alabaster workshop
  • Personal and laid back tour and chance of making new friends
  • No rushed schedule
  • Small group of maximum 8 people
  • Lunch at an organic family run farm
  • Saffron and Vernaccia wine tasting
  • Round trip transportation in air conditioned minivan
  • Expert English speaking driver guide
Discover the roots of the Etruscans that inhabited these areas more than 2 millennia ago, and learn about the history of conflicts and economic triumphs of San Gimignano, the medieval hill town of towers.
See the art of sculpting the alabaster in Volterra and visit the town where a sense of ancient glory is still very tangible.

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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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The vacation includes

  • 3 nights in 4 star, or equivalent B&B in Siena centre
  • 2 full day Small Group tours
  • 2 farm lunches
  • 2 Chianti tastings
  • Visit of Alabaster workshop
  • Guided visit of Siena
  • Skip the line Duomo tickets
  • Transportation in air conditioned vehicle
  • English speaking driver/guide

Not included

  • Any extras not listed in inclusions
  • Pick up and drop off transfers other than Siena centre or bus/train station. (can be requested as an extra)
  • 3 In depth all-inclusive tours
  • Overnight in Siena's historical city centre
  • The company of professional English speaking guides
  • Meet the locals and taste the areas food and wine
  • Small Group Tours are a good opportunity for making new friends

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.