DISCOVER TUSCANY:
A Food and Wine Experience
October 5 - 12, 2024
Join us for an unforgettable journey to discover one of Italy’s most exquisite locations where hospitality, food and wine are a way of life.
La dolce vita, the sweet life, begins with our accommodations - a stunning private villa in Chianti that has been completely updated for the 2024 season!
The ancient building perched on a panoramic hill was originally a lookout tower, dating back to 1,000 AD. Today it is a luxury residence that boasts an array of premium modern amenities and beautiful contemporary furnishings.
Spacious living areas and impeccably appointed en-suite bedrooms ensure maximum comfort. Huge arched windows throughout the villa frame incredible views of the rolling Chianti hills, while elegantly furnished outdoor garden terraces and a panoramic heated swimming pool are the perfect places to unwind and recharge.
Our itinerary for the week will ensure a balance between discovery and relaxation - so you can enrich your mind, body and soul.
Bespoke private experiences will allow us to meet the locals who run boutique wineries, organic farms, and even castles, so we can get an insider’s glimpse of what “Made in Italy” really means.
We will taste the best foods and wines Tuscany has to offer, while visiting the iconic historic towns and venues where these delicacies are produced.
Itinerary
Day 1 - Welcome to Tuscany
We will all depart together from Florence in the afternoon, with private Mercedes vehicles and English-speaking drivers, to go to the villa.
After having some free time to settle in and unpack, the evening will begin with welcome cocktails followed by a delicious gourmet dinner prepared by our private chef.
Day 2 - Wine and Cheese Tasting/Pizza Making
Start the day with a delicious Sunday Brunch.
In the early afternoon, feel free to participate in a relaxing yoga class or enjoy the beautiful heated swimming pool and villa grounds.
Later in the day, a cheese and wine expert will come to the villa to introduce us to an award-winning local producer’s collection of pecorino cheeses and some of the area’s renowned Chianti wines.
Then we’ll roll up our sleeves and join the chef to make our own brick oven pizza for dinner!
Day 3 - Montepulciano, Pienza and Montalcino
We will depart after breakfast to go to the picturesque Val d’Orcia - the beautiful area of southern Tuscany that is recognized as a UNESCO world heritage site.
Our private guide will meet us in Montepulciano, a lovely medieval and Renaissance hill town. We will visit the Church of San Biagio and the historic center, where we’ll discover a fascinating ancient underground wine cellar that dates back to the Etruscans.
Afterward, we’ll go to Pienza, one of Tuscany’s most beautiful hill towns - and another UNESCO World Heritage Site. We’ll also enjoy a guided tasting of the famous local specialty: Pecorino di Pienza cheese so we can compare it to the ones we tried on Sunday.
The next stop will be at a boutique Brunello Winery where we will meet the owners and enjoy a private tour and a wine tasting with light lunch.
We’ll end the day by taking a walk through Montalcino, the charming fortress town that gives its name to Tuscany’s most exclusive wine, Brunello di Montalcino.
When we get back to the villa there will be some time to relax before our chef serves dinner.
Day 4 - Private Cooking Class and Castle Winery Tour
We will depart after breakfast to go to a family-run 15th century olive estate in Chianti where we will experience authentic Tuscan country living while learning to prepare traditional recipes with the charming owner.
This is much more than a cooking class. We will visit the beautiful estate, which includes a private chapel, see the olive groves and taste their extra virgin olive oils, stroll through the organic vegetable garden and farm before putting on our aprons to begin cooking in the impressive historic villa - surrounded by beautiful frescos.
During our hands-on class we will prepare a full 3-course meal, as we sip wine and learn about Tuscan cuisine and the culinary secrets passed down for generations.
After lunch, we will head to a privately-owned Chianti Castle Winery for a cellar tour and tasting. Tuscany boasts many magnificent castles where top quality wines are still produced today, thanks to their ancient cellars which offer excellent conditions for aging.
When we get back to the villa there will be some time to relax and have cocktails by the pool before our chef serves dinner.
Day 5 - Florence - Food and Art
After breakfast, we will depart for Florence - the quintessential Renaissance city.
We will meet our private guide at Florence’s most authentic open air food market, to discover the incredible selection of local specialties and gourmet foods.
This food tour will be a sensory experience, where we can taste, indulge and learn both the history and modus operandi of this centuries old, yet contemporary cuisine.
Later, we will take an introductory walking tour of the historic center and visit the famous Accademia Gallery, home to Michelangelo’s masterpiece, David.
After the tour, there will be some free time to explore the city before meeting up to return to the villa.
Once we are back in the countryside, we will unwind with a poolside Wine Sampling followed by a Pasta Tasting Menu prepared by our private chef.
Day 6 - Siena & San Gimignano
After breakfast, we’ll depart for Siena to meet our private guide and discover the interesting history of this famous and unique Tuscan city.
Not only will we visit the well-known historical landmarks and architectural sites, like the impressive cathedral, but we will also learn about one of the most important things that distinguishes Siena from all the other cities in Italy: its Palio, the world-famous horse race.
After the tour, there will be some free time for lunch and shopping.
Then, we will all meet to continue our journey and visit San Gimignano, one of Tuscany’s most charming and well-known hill towns.
We will stroll the quaint narrow streets - and go off the main path, to discover the more authentic qualities of this popular village. And, we will of course, stop to get a gelato at the award-winning Dondoli gelateria.
Back at the villa, we will enjoy a special Tuscan Barbecue Night featuring the famous Bistecca Fiorentina, Florence’s signature steak.
Day 7 - It’s Your Choice!
This final day offers guests the option of returning to Florence or staying at the villa to relax.
There will be a mid-morning departure for those who would like to go to Florence to tour independently. Drop-off in the historic center and pick-up in the late afternoon will allow guests to explore the city’s treasures at their own pace.
Lunch will be available at the villa for those who would like to spend the day at home.
Guests who would prefer a structured activity (in the countryside or in Florence) can select from a list of add-on options at an additional cost.
Our farewell dinner will feature a special gourmet menu to celebrate the week!
Day 8 - Departure Day
Check out time is 10:00 AM.
The drivers will take us back to the center of Florence where guests can make arrangements to stay additional nights or go to the airport for their departure flights home.
Arrivederci!
Meet your Host
Maya Djurasovic
I can't wait to share my love of Tuscany and its rich history, culture, food and wine with you! Italy is like a second home to me because I have had the privilege of spending frequent and sometimes extended visits with my sister and her family who call Italy home.
Italy is known for its beautiful landscapes, majestic architecture and breathtaking artwork. But, in my mind, the most impressive and heartwarming thing about Italy is its people.
Each visit is an escape from the stress of everyday life. Spending time in Italy allows me to slip into a world where life's simple pleasures evoke a sense of comfort and discovery.
Come join me as I introduce you to this insider's experience. Meet my family and learn what life is like from the locals as you forge new relationships with fellow travelers who share your interest in Italy’s amazing food and wine. I hope you come join the adventure. We have so much to share and explore!
Meet Your Team
Dovetail Travel and New Tuscan Experience –
Creating Strong Bonds Through Extraordinary Tours
Dovetail Travel joins forces with its literal and figurative “sister” company, New Tuscan Experience to carefully craft luxury small group tours. This partnership ensures that Dovetail’s trips offer the highest quality guides, chefs, drivers and accommodations.
This amazing food and wine tour has been carefully curated to make the experience special for both solo travelers and groups of friends who are interested in fostering a bond with like-minded travelers looking to broaden their culinary horizons.
Our small-group adventures accommodate a maximum of 12 travelers, guaranteeing an intimate and unforgettable journey where you get to know us personally.
Meticulous planning ensures that we consistently surpass expectations.
Let us help you create extraordinary memories as you make new connections with people and forge lasting bonds through travel, food, wine and new friendship.
Have any questions?
What’s included:
- Accommodations: Week-long accommodations in a luxury Tuscan Villa located in the heart of Chianti
- Transportation: Transportation for all excursions and roundtrip transfers between Florence and our villa
- Trip Host: A Dovetail Travel host accompanies the group throughout the journey
- Select Meals: Daily breakfasts, 6 lunches and 7 dinners are included
- Tours + Activities: Organized group tours and activities specified in the travel itinerary
- Guide Gratuities: Guide gratuities included for organized tours and activities
Participants are responsible for:
- International Airfare
- Travel Insurance
- Airport Transfers
- Alcohol outside of group meals and wine tours
- Select meals not listed in itinerary
- Excess baggage charges
- Excursions or deviations from the trip itinerary
- Personal expenses such as snacks, additional gratuities and communication
- Costs associated with obtaining passports and visas
- International airport departure tax, if applicable
10936 N Port Washington Road
Suite #372
Mequon, Wisconsin 53092, USA
Tel: +1 262-291-1577
