6-Day Tour: Quintessential Tuscany Expedition

Discover why Tuscany is famed throughout the whole world for its spellbinding scenery, artistic masterpieces, scrumptious local fare and superb wines.


Day 1 Highlights:

  • Private Guide, Driver and State-of-the-Art Minivan throughout the day
  • Visit to Farmers’ Market
  • Private Visit, Olive Oil Tasting and Cooking Class at Countryside Olive Oil Mill
  • Welcome Champagne and 4-course specialty dinner at Relais Villa Olmo’s restaurant

Day 2 Highlights:

  • Private Guide, Driver and State-of-the-Art Minivan throughout the day
  • Visit and wine tasting of two famed Chianti Classico wineries
  • Explore and shop: free time in Greve in Chianti
  • Tantalizing organic meat lunch at “Officina della Bistecca”, owned by a celebrity butcher
  • Private Pizza and Gelato Cooking Class, and Pizza-based dinner

Day 3 Highlights:

  • Private Guide, Driver and State-of-the-Art Minivan throughout the day
  • Explore and shop: free time in Volterra and San Gimignano
  • Private truffle hunt led by a local tartufaio (truffle hunter) and lunch based on truffle
  • Taste the best local specialties: sweets and gelato in Volterra and San Gimignano’s best gourmet shops
  • Private Wine-Making Experience led by an expert sommelier

Day 4 Highlights:

  • Private Guide, Driver and State-of-the-Art Minivan throughout the day
  • Visit and Lunch at a charming local farm
  • Explore and shop: free time in Montepulciano and Cortona
  • Visit and wine tasting at a historic Montepulciano winery
  • Choose your trattoria: free dinner in a Cortona restaurant

Day 5 Highlights:

  • Private Guide, Driver and State-of-the-Art Minivan throughout the day
  • Visit, insight on Cheese and Lunch at an organic typical podere
  • Explore and shop: free time in Pienza
  • Visit and wine tasting at an innovative Brunello di Montalcino winery
  • Michelin-star dinner with a view in the hillside

Day 6 Highlights:

  • Private Guide, Driver and State-of-the-Art Minivan throughout the day
  • Visit and wine tasting at a castle winery


Every first Monday of Every Month at 9:00 AM


Approx. 6 days


From April to October




A bountiful sun-kissed region blessed with breathtaking natural beauty and a mild climate.  Rich in centuries-old traditions and charm, Tuscany is famed throughout the whole world for its spellbinding scenery, artistic masterpieces, scrumptious local fare and superb wines.

Enjoy the privilege of traveling in a small group aboard a comfortable minivan, and dive into Tuscan flavor and tradition. Savor memorable wines, sample mouth-watering local specialties, roam picturesque medieval towns and learn the art of Tuscan cooking hands-on!

From Florence and Chianti to Volterra and San Gimignano, from the hills of Brunello wine to Montepulciano, Cortona and Pienza our 6-day small-group Quintessential Tuscany tour takes you down country roads and through vineyards, into ancient olive oil mills and behind the scenes of stunning wineries and farms, allowing you to relish Tuscany’s authentic flavors and discover its soul.

DAY 1 – Farmers’ market, Olive Oil, Cooking Class and Champagne: Welcome to Tuscany!

Meet your dedicated private guide and driver in Florence and enjoy a stroll through the fascinating Farmers' Market. Browse through the stalls, get to know the products, and taste a selection of scrumptious specialties.

Then set off for a scenic drive to a charming ancient olive oil mill in the rolling countryside for an insider’s viewing, tasting and cooking class. Learn about the centuries-old olive oil tradition and pressing process and sample the full-flavored estate oil; then don your apron and follow your chef's lead to master the art of making an exquisite traditional Tuscan meal.

Savor the delicious lunch you prepared hands-on before travelling to your hotel, to check in and relax before enjoying a memorable welcome dinner including Champagna welcome toast.

Sweet dreams at Relais Villa Olmo



DAY 2 – Steak, Wine, Pizza and Gelato: the Florentine Chianti hillside

After a delicious breakfast meet your dedicated private guide and driver and set off to explore Florentine Chianti, fairytale-like hills studded with golden-hued farmhouses and vineyards. Your first stop will be a famed historic winery set on the premises of an evocative age-old hamlet.


Enjoy an enlightening visit of the cellars, discover the secrets of world-acclaimed Chianti Classico wines and savor the best blends of the estate wines, and then journey on, for a memorable lunch in charming Panzano in Chianti. Relish choice cuts of delicious meats, and ruby-red Chianti wine, at “L’Officina della Bistecca” (namely the “steak workshop”!), a friendly joint owned and personally managed by Dario Cecchini, a real celebrity butcher.


After lunch stop for a stroll through picturesque Greve in Chianti, and for a visit to an outstanding award-winning organic winery. Enjoy the privilege of visiting this unique estate, and sample a range of its exquisite biodynamic blends.


Crown your day with an iconic Italian evening: a pizza and gelato cooking class held in an authentic Tuscan farmhouse/ at your hotel! Meet your friendly dedicated chef in the country kitchen and follow his lead to master the secrets of making pliable paper-thin yeast dough and zesty tomato sauce. Aprons on! Get your hands floury, measure, mix and knead your dough. Learn about Italian gelato’s history and heritage while your dough rests, then roll out your pizza, season and flavor it, raise it with the flat pizza-shovel and slide it into the oven.  Finally relish the unique taste of the scrumptious pizza you made yourself.


Sweet dreams at Relais Villa Olmo



DAY 3 – Truffle, Alabaster, Towers and Wine-Creating:  Volterra and San Gimignano

After a delicious breakfast meet your dedicated private guide and driver and travel to Volterra, Tuscany’s most bewitching town. The town dates back over 3000 years, and ever since ancient times its main commercial activity has been the extraction of alabaster, the only translucent mineral existing in nature.


Roam the town at leisure, discover the Etruscan walls, the necropolis and the Fortezza erected by the Medici family. Browse the shops for art, jewelry and household objects made of precious alabaster, and indulge your taste buds with delicious panforte, and other local sweet specialties, at the town’s best café.


Time for fun: set off in the thick, mysterious woods for a real truffle hunt led by an authentic tartufaio, a local truffle hunter. Learn all there is to know about the delectable tubers from your expert guide, master the techniques used for finding and digging them. Led by the tartufaio’s expertise search for precious delicious truffles yourself! You will then indulge in a delicious lunch based on truffle and local dishes.


Then travel on to San Gimignano, UNESCO World Heritage Site. Renowned as “the city of beautiful towers” or "Tuscany's Manhattan" it boasts an exceptional skyline and has been used as a background in many movies. Wander through the maze of quaint cobblestone streets at leisure, admire the graceful tall towers which were once homes. Relax, enjoy the atmosphere, and stop for a creamy break: a tasting of specialty artisan-made gelato at the town’s best gelato shop.


Drive back through the hills and get ready to unveil the secrets of the marvelous realm of wine with an exceptional guide: an expert sommelier. Learn all about world-class wines, understand how blending different kinds of pure wines results in a variety of combinations acidity and aromas, and enjoy the uniquely thrill of a real hands-on experience: create your very own personal wine!


End your day with a mouth-watering Tuscan meal at the hotel restaurant


Sweet dreams at Relais Villa Olmo



DAY 4 – Chianina meats and Renaissance Marvels: Montepulciano and Cortona

After a delicious breakfast bid the Florentine Chianti vineyards farewell; set off with your private guide and driver for a dreamlike journey through the Tuscan hillside, to the discovery of Valdichiana, Montepulciano and marvelous Cortona.


Your first stop will be in the heart of Valdichiana, a broad green valley dotted with medieval villages. The area is renowned for its rich orchards, olive groves and prized Chianina cows, one of the oldest breeds of cattle in the world and the essential ingredient in Tuscan. Here you will visit a charming farmstead and enjoy the delectable flavor of dishes made from the estate’s produce: premium meats, vegetables and fragrant focaccia!


Travel on to visit Montepulciano, surrounded by imposing 15th century walls and world-renowned birthplace of the famous poet "Poliziano". Roam the town on your own, see Medieval remnants and gorgeous noble palaces, and then enjoy a memorable in-depth visit of one of the area’s most ancient historic wineries. Escorted by the winery’s staff explore the cellars and taste the best blends.


End your day with spectacular views of the valley from delightful Cortona. Explore the town center (so picturesque that many parts of “Under the Tuscan sun” were filmed right here!), have fun choosing your favorite haunt among the town’s many restaurants and quaint trattorias, and relish a tasty dinner at your leisure.


Sweet dreams in Cortona


DAY 5 – Cheese, Wine, Views and Michelin-star Cuisine:  Val d’Orcia

After a delicious breakfast meet your dedicated private guide and driver and journey through the countryside to the Val d’Orcia hillside, birthplace of Brunello, one of the world’s most celebrated wines, and countless other tasty delights among which scrumptious cheese.


On the way you’ll marvel at the dreamy landscape of stark rolling hills, marked by winding roads lined with dark cypresses, fortified towns and magnificent vineyards.


Your first stop is delightful Pienza, a Renaissance icon and one of Italy’s most stunning jewel-towns, for some time at leisure to stroll and explore.


Travel on to a state-of-the-art 100% organic podere, i.e. typical farm, that rears livestock and has won a number of awards for its cheese production. Cheese-fans this is your day: pecorino (from ewe's milk), caprino (from goat's milk), ricotta and more are made here, all with
the milk from the estate animals! Touring the grounds admire the stables and fields and enjoy the privilege of getting behind-the-scenes, for an insider’s view on cheese-making. Lunch on traditional specialties based on the farm’s delicious products at the farm’s restaurant.


Continue to a visit to a sensational winery producing Brunello wines. Lear about the production and the characteristics of this world-renowned wines. Discover about the cutting-edge premises and taste their excellent wines.


Crown your day with a magnificent farewell dinner with a view in the Cortona countryside: a delectable Michelin-star gourmet experience you will never forget.


Sweet dreams in Cortona


DAY 6 – Visit and wine tasting in a Castle winery, departure

After a delicious breakfast bid Cortona farewell and set off with your private guide and driver and drive back to Florence. You will stop on the way to a scenic castle winery, to celebrate your Tuscan experience with a visit and wine tasting at the property.


After lunch comfortably relax on board your minivan, and travel back to Florence.






  • accommodation for 5 nights included ( 3 in chianti area at Relais Villa Olmo, 2 in val d'orcia area)
  •  all transportations included
  •  6 lunches and 5 dinners with local products and wines
  • 4 wine tastings based experiences are provided
  • 2 different cooking classes are included
  • several villages are visited, located in different area in the entire Tuscany
  • esclusive experiences are included, such as truffle hunt, visit to etruscan necropolis and more!
  •  licensed guide and driver is provided
  • insurances included

Meeting Point

FLORENCETOWN TOURS & NEWS STAND - Piazza della Repubblica (next to the APPLE STORE under the loggias, corner with Via Pellicceria) - Florence - SEE ON MAP


Please inform us of any food intolerance or allergy in advance.
Please note that Italy's law doesn't permit selling alcoholic beverage to teens under 18 y.o. so clients under this age will be served non-alcoholic beverages.
We suggest good walking shoes (no flip-flops!)
We regret to inform that this tour is not suitable for guests with wheelchairs or with impaired mobility.

Rain Policy

This tour runs rain or shine.

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from 3 250

EUR 3250 (Price based on a party of 2 pax)
EUR 3700 ( price for a single partecipant)

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