Florence ChiantiSienaMontepulciano

Embark on an unforgettable 8-day adventure through the enchanting Tuscany region and discover the hidden gems of Italian history, cuisine and countryside. This tour will take you to some of the most stunning locations in Italy, including Florence, Chianti, Pievascola, San Gimignano, Volterra, Siena, and Montepulciano. Get ready to indulge in mouth-watering local delicacies, explore ancient historical treasures and unwind in peaceful rural havens.

Itinerary Highlights

  • Explore historical towns and cities
  • Local Tuscan cooking class
  • Chianti tasting
  • Visit UNESCO World Heritage sites
  • Winery visits

What’s included

  • Private tours for most included activities
  • Meet & greet airport service
  • Luxury or boutique accommodation at your chosen level
  • Expert guides in each destination


This is an example itinerary. It is fully flexible; you can add or detract days and include hotels at your chosen budget. It departs daily.



Price Guide


Our quotes are bespoke for your customised trip. The prices displayed are indicative only, read more

Day 1

Fly to Florence

plan line
Day 1

Arrive Florence

Upon arrival at Florence Airport, your local representative will wait in the arrivals hall for your private transfer to your luxurious hotel in the heart of the city on Piazza della Republica.

Florence and Tuscany
Florence and Tuscany
Day 2

The Uffizi Gallery and Florence’s Lesser Visited Gems

Meet your guide in the lobby of your hotel, and enjoy a walking tour of Florence with your local English-speaking guide. This tour will include visits to the Uffizi Gallery, which houses some of the world’s most important art treasures, and the Church of Santa Croce, where many famous Florentines, such as Michelangelo and Galileo, are buried.

In the afternoon, explore some of Florence’s lesser-visited gems (3 hours). Walk by the impressive Duomo on to the lovely Piazza Santissima Annunziata, where the Spedale degli Innocenti, Europe’s first orphanage and a masterpiece of Classical design, is fronted by Brunelleschi’s colonnade. The Convent of San Marco is a delight with its frescoed monk cells, whilst the Scalzo Cloisters with frescoes by Andrea del Sarto depict scenes from the life of John the Baptist.

Day 3

Learn the Art of Tuscan Cuisine

It is often argued that Italy has the finest cuisine in the world; today, you can learn the skills of the Tuscan kitchen with a private hands-on cookery lesson at an important culinary institute with English-speaking instruction. Your morning begins at the Mercato Centrale where your chef will explain how to select the best produce before returning to the kitchen for a hands-on lesson and enjoying the fruits of your labour for lunch.
The remainder of the day is at your leisure.

Florence and Tuscany
Florence and Tuscany
Day 4

Florence – Chianti – Pievascola

Depart Florence today with your driver-guide and head into the famous Chianti region of Tuscany. Visit some lovely hilltop towns, such as Greve and Castellina, and enjoy two wine tastings at local vineyards. Renowned for its art, history and evocative landscapes, Tuscany is a region where the past and present merge in pleasant harmony. Hill towns gaze across the countryside from high, many encircled by Etruscan walls and slender cypress trees. In the countryside, among the vineyards and olive groves, there are hamlets and farmhouses, as well as fortified villas and castles that symbolize the violence and inter-communal strife that tore Tuscany apart in the Middle Ages. Stop for a ‘refuel’ of local Tuscan wine before heading to your beautiful hotel in the Tuscan countryside.

Day 5

Siena, San Gimignano & Monteriggioni

Today, your English-speaking local guide will meet you at your hotel for a 3-hour walking tour of Siena. The scenic Tuscan town of Siena was built on three hills and is enclosed by a set of walls and gates. Visit the Piazza del Campo, one of Italy’s finest main squares, and see the Palazzo Pubblico, which has served as Siena’s Town Hall since the 1300s. Siena’s Duomo is one of the finest Gothic cathedrals in Italy and well worth a visit; here, you can see the brilliant frescoes by Pinturicchio that adorn the Piccolomini Library.

This afternoon enjoy an excursion with private vehicle and English-speaking driver-guide to explore the countryside and visit San Gimignano, where you may wish to visit the Collegiata containing 15th-century frescoes, the Palazzo del Popolo, now the municipal museum containing Renaissance paintings, and the Church of Sant’Agostino, or wander the narrow cobbled streets with your driver-guide who will know where to go for the best local wild boar salami and Vernaccia white wine! Time permitting, enjoy a stop in Monteriggioni, a delightful example of a fortified medieval village.

Florence and Tuscany
Florence and Tuscany
Day 6

Tuscany – At Leisure

Today is a chance to relax and enjoy your fantastic surroundings.

Day 7

Montepulciano, Montalcino and Wine Tasting

Your English-speaking driver-guide will meet you this morning for a full-day excursion to some of Tuscany’s most picturesque towns, Montepulciano and Montalcino, and to enjoy wine tastings.

Montepulciano is an archetypal Tuscan hilltop town set 605 metres above sea level and offering superb views over the surrounding countryside. Inside the ancient city walls and fortifications, you will find winding streets and a wealth of Renaissance-style palazzi and churches. Montalcino, famous for the Brunello wine, is everything you hope for in a Tuscan hilltop town: winding narrow streets and charming flower-covered houses.

Vineyard Visit & Tastings:
Today, you will visit a renowned wine estate with its various vineyards, a medieval castle whose origins can be traced to the ancient Etruscans, the Glass Museum, and the famous enoteca, where you will be able to taste some of the area’s most celebrated wines.

Florence and Tuscany
dot joiner for itins
Day 8

Fly home

A note on price

The prices outlined above are a rough guide to give you an idea of costs and enable you to budget for your trip.

Guide prices are generally for private arrangements based on twin share, in well located, good quality accommodation (excluding international flights).

Please note costs are indicative and may vary due to a number of factors such as; travel date, hotel choice, room category, number of people travelling and prevailing exchange rates.

Price Guide $POA

When to travel

jan feb mar apr may jun jul aug sep oct nov dec

If you’re planning a trip to Italy, it’s important to consider the weather to ensure that you have an enjoyable experience. The best time to visit Italy in terms of weather is during the months of April to June and September to October, when the weather is mild and pleasant. However, if you’re looking for a winter getaway, January can be a good time to visit as long as you’re prepared for cooler temperatures. In Italy, January is typically one of the coldest months of the year, with average temperatures ranging from 3°C to 12°C depending on the region.

Add on’s

This Tuscan itinerary has many add-on holiday options; for example, you could head to Amalfi Coast, located in Campania. The Amalfi Coast is known for its breathtaking views of the Mediterranean Sea, colourful houses built into the cliffs, and delicious seafood. Another popular destination is Venice, a city built on water famous for its canals, gondolas, and historic architecture. Rome, the capital of Italy, is also a must-visit destination for history buffs and art enthusiasts alike. The city is home to iconic landmarks like the Colosseum, the Pantheon, and the Vatican, as well as countless museums and art galleries. Other popular destinations include the Italian Lakes region, known for its picturesque scenery and charming towns, and the island of Sicily, which has a unique culture and cuisine.

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