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Private & Semiprivate Tuscan Wine Tours with Wine Guides 

Chianti Classico - Brunello di Montalcino - Nobile di Montepulciano 

Authentic Sightseeing Full Day Tuscany Tours 

Valdorcia - Siena - San Gimignano - Chianti - Lucca & Pisa - Arezzo & Cortona

Customized Itineraries in Tuscany and Italy

Our small group tours are known as custom semiprivate tours because


Our private tours are known as the best value tours because

My Signature Wine Tours

Chianti Classico "Black Rooster" Wine Tasting Tours


When: All year

Days: Monday-Saturday

Time: 9-9.30 am till 5-5.30 pm

Pick up: Hotel/apartment/other

Price: from €200 

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 by listening too our clients.

Tastings include several type of wines and extra virgin olive

Lunch will be a mouthwatering 3 courses food and wine pairing session 

Top Brunello di Montalcino Wine Tasting Tours


When: All year

Days: Monday-Saturday

Time: 8.30-9 am till 5.30-6 pm

Pick up: Hotel/apartment/other

Price: from €200 


Indulge in the greatest red wine region of Tuscany: Montalcino

An exclusive wine tour to visit 3 Brunello wineries and sample the differences from one side to the other of the hilltop 

Mainly Brunello along with Rosso di Montalcino, Supertuscans and extra virgin olive oil of course!

Lunch ranges from a family style setting with home made farm to table products to unique settings, in any case we'll surprise you and we'll make this tour an unforgettable experience.

Montepulciano Wine Tasting Tours


When: All year

Days: Monday-Saturday

Time: 8.30-9 am till 6 pm

Pick up: Hotel/apartment/other

Price:  from €200 

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.

Montepulciano & Montalcino Wine Tasting Tours 

When: All year

Days: Monday-Saturday

Time: 8.30-9 am till 6 pm

Pick up: Hotel/apartment/other

Price: from €250           

The combo wine tour in Montepulciano and Montalcino was a Cooltours' idea a few years ago and we found out that our wine lovers clients love it!

We will visit 3 wineries in total and together with you, we can decide how many in each region.

Red wines and a lunch to live a day like a true Tuscan.

My Unique 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 €19

Tour type: 



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 €195 

Tour type: 



My Private Tuscany Experiences

Family Style Cooking Class


When: All year

Days: Monday-Saturday

Time: 8.30-9 am till 6 pm

Pick up: Hotel/apartment/other

Price:  on request

Tour type:

Truffle Hunting 


When: All year

Days: Monday-Saturday

Time: 8.30-9 am till 6 pm

Pick up: Hotel/apartment/other

Price: on request          

Tour type:

Bike tours and...more


When: All year

Days: Monday-Saturday

Time: 8.30-9 am till 6 pm

Pick up: Hotel/apartment/other

Price: on request          

Tour type:

Winemaker for a day


When: All year

Days: Monday-Saturday

Time: 8.30-9 am till 6 pm

Pick up: Hotel/apartment/other

Price:  on request

Tour type:

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:

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:

Guided City Tours 

Private Walking tours and Skip the line tickets

Are you interested in a guided walking tour of Florence, Siena, Lucca, or any other city?

Over the last 15 years we selected the best guides to take you on a half day or full day tour in several cities

From an easy stroll to indepth details.... It's up to you because the tour is only private and customized for our clients

Shore Excursions from Livorno

Private driving services from Livorno port

Pick up at the dock in Livorno as soon as you will desembark and after visiting Tuscany together we will drive you back to your cruiseship 

What can you visit after you will dock in Livorno....? 

Tuscan Wine Tours

Full day wine tours with your wine expert to visit the best tuscan wine regions and authentic wineries for unique wine tastings.

These can be run as private wine tours or semiprivate wine tours. 

Your wine guide suggests the following top wines regions: 

Top Chianti Classico & Scenic Chianti Classico

Sublime Brunello & Superior Brunello

Finest Nobile di Montepulciano 

Whitish Vernaccia di San Gimignano 

Tuscan Private Somm

Tuscany Tours 

Full day sightseeing tours with a guided driving service to explore breathtaking landscapes and hilltop towns of Tuscany.

These can be run as private Tuscany Tours or Shared Tuscany Tours.

Your driver guide suggests you some Tuscany hot spots:

Chianti Highlights

Authentic Tuscany

Tuscany Jewel Towns

Tuscany off the beaten paths 

Cooltours® is a registered trademark leader for wine tours, wine vacations and sightseeing tours in Tuscany since 13 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:


****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