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Tuscany Wine & Countryside Small-Group Tours (Max 8 Guests)
Immerse yourself in the heart of Tuscany’s most legendary wine regions with Cooltours’ exclusive small-group journeys. Capped at just 8 participants, our full-day tours combine breathtaking landscapes with elite wine culture—far away from the mass-tourism buses.
Why our Wine & Countryside Tours Stand Out:
Expertly Selected Wineries: Curated by professional wine guides and sommeliers, we bypass generic commercial stops to visit exceptional boutique, organic, family-owned, and historical estates. Each winery is selected by 3rd level Sommelier and wine expert Anna.
Behind-the-Scenes Access: Walk through historic underground cellars, learn about traditional and modern winemaking processes, and explore scenic vineyards overlooking rolling hills.
Educational Wine Tastings & Pairings: Enjoy guided tastings of world-renowned labels—such as Chianti Classico, Brunello di Montalcino, or Vino Nobile di Montepulciano—expertly paired with authentic Tuscan multi-course lunches or artisanal farm-to-table products (local cheeses, cured meats, and extra virgin olive oil).
Iconic Landscapes & Panoramic Drives: Travel in comfort through postcard-perfect vistas, rolling hills, and medieval hilltop villages (like Pienza, San Gimignano, or Montepulciano), with dedicated stops for unforgettable photos.
Hassle-Free Experience: Benefit from convenient front-door pick-up and drop-off from your hotel or apartment, accompanied by a professional English-speaking drivers and specialized wine guides. Plus all the reservations and logistics are curated from the beginning until the end by our CEO.
All included & no hidden costs: Benefit from a complete peace of mind cause at the moment of the booking the price includes from transportation to tastings and lunches along with cards fees and taxation, so you will not be surprised by extra expenses to add on top of what you have booked.
Small Groups - Signature Wine Tours
Chianti Classico Exclusive Wine Tasting Tour 3 Wineries
When: All year
Days: Monday-Saturday
Time: 9-9.30 am till 5-5.30 pm
Pick up: Hotels/apartments/others
Price: from €240 per person
Enjoy our most popular wine tour from Florence: the Chianti Classico wine region
We will visit three selected wineries ranging from family, organic and sustainable to award winning wineries with historical cellars. All surrounded by amazing views and settings.
The selection is hand picked so we don't have a standard list of wineries, we like to customize our tours anytime to meet our clients' needs and to create unique days each time.
In each winery we will visit the cellars, the grounds and we'll learn about some winemaking as part of our culture and tradition.
Wine tastings include several types of wines and extra virgin olive
Lunch will be a mouthwatering 3 courses food and wine pairing session
INCLUSIONS:
Front door pick up & Transportation
3 Cellar visits
3 Wine Tastings
1 Lunch
Scenic Chianti Classico Wine Experience 2 Wineries
When: All year
Days: Monday-Saturday
Time: 9-9.30 am till 5-5.30 pm
Pick up: Hotel/apartment/other
Price: from €220 per person
Enjoy our perfect wine tour from Florence: the Chianti Classico wine region & stunning views
We will visit two selected wineries ranging from family, organic and sustainable to award winning wineries with historical cellars. All surrounded by amazing views and settings.
The selection is hand picked so we don't have a standard list of wineries, we like to customize our tours by listening too our clients.
Wine tastings include several types of wines and extra virgin olive
The tour includes a visit to two different wineries and cellars, with lunch at one winery for a complete food and wine pairing session.
Depending on the order of the itinerary we will visit a quaint town in the morning or after lunch.
INCLUSIONS:
Front door pick up & Transportation
2 Cellar visits
2 Wine Tastings
1 Lunch
Top Brunello di Montalcino Wine Tasting Tour 3 Wineries
When: All year
Days: Monday-Saturday
Time: 8.30-9 am till 5.30-6 pm
Pick up: Hotel/apartment/other
Price: from €235 per person
Indulge in the greatest red wine region of Tuscany: Montalcino and its Brunello wine
An exclusive wine tour to visit 3 selected and unique Brunello wineries and to sample the technical differences from one side to the other of the hilltop of Montalcino
Mainly Brunello along with Rosso di Montalcino, Supertuscans and extra virgin olive oil of course!
We will visit three selected wineries ranging from family, organic and sustainable to award winning wineries with historical cellars. All surrounded by amazing views and settings.
The selection is hand picked so we don't have a standard list of wineries, we like to customize our tours anytime to meet our clients' needs and to create unique days each time.
In each winery we will visit the cellars, the grounds and we'll learn about some winemaking as part of our culture and tradition.
Wine tastings include several types of wines and extra virgin olive
Lunch will be a mouthwatering 3 courses food and wine pairing session
INCLUSIONS:
Front door pick up & Transportation
3 Cellar visits
3 Wine Tastings
1 Lunch
Montepulciano Nobile Wine Tasting Tour
When: All year
Days: Monday-Saturday
Time: 8.30-9 am till 6 pm
Pick up: Hotel/apartment/other
Price: from €240 per person
Always willing to see the rolling hills of southern Tuscany and the Valdorcia but without missing a very well know wine region?
With this tour we can go to 2 wineries and then relax with a stroll in the hilltop town of Montepulciano or we can focus on Nobile wine and visit 3 wineries and time permitting include a stop to the town.
Beautiful settings, family wineries but with an elegant and modern touch as well.
Lunch will be an explosion of tastes for every palate.
INCLUSIONS:
Front door pick up & Transportation
3 Cellar visits
3 Wine Tastings
1 Lunch
Montepulciano & Montalcino Combo Wine Tasting Tour 3 Wineries
When: All year
Days: Monday-Saturday
Time: 8.30-9 am till 6 pm
Pick up: Hotel/apartment/other
Price: from €290 per person
The combo wine tour in Montepulciano and Montalcino was a Cooltours' idea a few years ago and our wine lovers clients love it!
We will visit 3 wineries in total and together with you, we will decide how many in each region.
Red wines and a lunch to live a day like a true Tuscan.
INCLUSIONS:
Transportation and Front door pick up
3 Cellar visits
3 Wine Tastings
1 Lunch
Unique Picturesque Tuscany Tours
Tuscany Rolling Hills
When: All year
Days: Monday-Saturday
Time: 9-9.30 am till 5-5.30 pm
Pick up: Hotel/apartment
Price: from €235 per person
Indulge in one of the most beautiful landscapes of Italy: the rolling hills of Valdorcia
An exclusive sightseeing tour to visit two of the most breath-taking towns of Tuscany, Montepulciano and Pienza.
Savour the local food in a feast of farm to table meal and cheeses
Chianti Highlights Tours
When: All year
Days: Monday-Saturday
Time: 9-9.30 am till 5-5.30 pm
Pick up: Hotel/apartment
Price: from €200
Explore the Chianti area like nobody did before: a unique customized sightseeing tour to visit the small hamlets of the region from where to soak in the dramatic views and landscape only Chianti has.
Include one winery visit and tasting or a winery for food and wine pairing.... otherwise we'll take you to a local trattoria for an authentic Tuscan meal.
Private Tours: Authentic Tuscany Experiences
Winemaker for a day
When: All year (Subjected to availability)
Days: Monday-Saturday
Time: 8.30-9 am till 6 pm
Pick up: Hotel/apartment/other
Price: on request
Tour type:
Private
Family Style Cooking Class
When: All year (Subjected to availability)
Days: Monday-Saturday
Time: 8.30-9 am till 6 pm
Pick up: Hotel/apartment/other
Price: on request
Tour type:
Private
Truffle Hunting
When: All year (Subjected to availability)
Days: Monday-Saturday
Time: 8.30-9 am till 6 pm
Pick up: Hotel/apartment/other
Price: on request
Tour type:
Private
Bike tours and...more
When: March-October (Subjected to availability)
Days: Monday-Saturday
Time: 8.30-9 am till 6 pm
Pick up: Hotel/apartment/other
Price: on request
Tour type:
Private
My Wonders of Tuscany
Siena & San Gimignano
When: All year
Days: Monday-Saturday
Time: 8.30-9 am till 6 pm
Pick up: Hotel/apartment/other
Price: on request
Tour type:
Private
Small group
PRICE ON REQUEST
Lucca & Pisa
When: All year
Days: Monday-Saturday
Time: 8.30-9 am till 6 pm
Pick up: Hotel/apartment/other
Price: on request
Tour type:
Private
Small group
PRICE ON REQUEST
Florence Private Tour + Accademia Tickets
Private Guided Walking Tour and Accademia Skip-the-line Tickets
Meeting point at your front door where our certified guide will meet to start the walking tour through the charming streets of Florence.
Depending on the pick up location, on your main interests, the tour is tailored made and it can include other museums along with the Accademia.
We can provide skip-the-line tickets with advanced reservations.
Shore Excursions from Livorno
Private tours from Livorno port
Away from the crowds or the big buses, choose an authentic tour to visit the coastal area like Bolgheri, Castagneto Carducci or take an upscale Supertuscan wine tour to sample the top end wines from the coast.
Another great option is to visit Volterra and San Gimignano with the possibility to add a wine tasting in between the two towns.
Cooltours® is a registered trademark leader for wine tours, wine vacations and sightseeing tours in Tuscany since 18 years!
Tours and activities are planned by CEO Anna also the front woman of the majority of the tours as driver-guide, tour leader and LEVEL 3 sommelier.
*We also provide a high selected team of wine guides, English speaking drivers, city guides, selected accommodations and restaurants.
ANNA'S MISSIONS:
Wine tasting tours to visit boutique wineries, sustainable, family style, award winning where you will taste selected high quality wines and farm to table products including extra virgin olive oil and more. As part of each experience food & wine paring is included.
Scenic Tuscany tours to explore postcard-perfect tuscan locations, famous hilltop towns, off the beaten path villages with sightseeing tours all over Tuscany.
Our tour types include:
small group tours limited to 8 passengers in order to keep the intimacy of a semiprivate tour
private full day tours in Tuscany and beyond
customized private weekly packages (upon request)
customized 3-4 days exclusive private wine vacations (upon request)
****DUE TO SOME TECHNICAL ISSUES WITH THE ENQUIRY FORM WE KINDLY ASK YOU TO EMAIL US DIRECTLY FOR ANY INFO
Book your customized private tour OR joinable tour
with award winner driver guide:
Best Private Driver Guide Operator 2016 -2023
Excellence in Service in Tuscany 20234
Best Driving Operator 2024
Private Operator 2024
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