Join us from October 5-12, 2024, for an unforgettable journey to discover one of Italy’s most exquisite locations--Tuscany, where hospitality, food and wine are a way of life. Guests will stay in an exquisite villa where they will be able to enjoy the beautiful countryside and villa amenities while experiencing daily excursions to some of Tuscany's most amazing cities including Florence, Siena, San Gimignano and Montepulciano.
Our itinerary for the week will ensure a balance between discovery and relaxation - so guests can enrich their minds, bodies, and spirits. Bespoke private experiences will allow the group to meet the locals who run boutique wineries, organic farms and centuries-old castles, so guests can get an insider’s glimpse of what “Made in Italy” really means. We will savor the finest foods and wines that Tuscany has to offer, while visiting iconic historic towns and venues where these delicacies are produced.
The exquisite villa has its own personal private chef who will prepare gourmet meals in its state-of-the-art kitchen and teach guests various aspects of Italian cuisine and cooking. The luxuriously renovated villa boasts a heated pool, outdoor dining/lounge areas and spectacular vistas where guests can unwind and relax. In addition, gorgeous interior common spaces, high-end en suite rooms and beautiful dining areas allow guests to mingle or enjoy their privacy.
Dovetail Travel joins forces with its literal and figurative “sister” company located in Italy, New Tuscan Experience, to carefully craft luxury small group tours. To ensure that Dovetail’s trips offer the highest quality guides, chefs, drivers, and accommodations, New Tuscan Experience lends its established treasure trove of professionals to help create incredible itineraries. 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 other 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.
Life has taken Maya and Kathy, two sisters originally from New York, to different parts of the world, but their ability to work together creates a special bond--both between them and between their clients. Come join us on a Dovetail Travel tour where you will feel like a member of the family. 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.
What’s included:
Participants are responsible for:
A personal message from Maya:
I am thrilled to be your group leader for this unforgettable food and wine tour in Italy. Having spent my entire life traveling to Italy thanks to having close family living there, I have developed a deep and abiding love for this beautiful country and consider it my second home.
With a background in teaching and a passion for learning, I have always enjoyed sharing knowledge and experiences with others. My love for travel, entertaining, cooking and wine inspire me to share Italy’s rich history, stunning landscapes, and vibrant culture with others.
Italy is renowned for its incredible cuisine and world-class wines, and I can’t wait to introduce you to the flavors and traditions that make Italian food and wine so special. Throughout our tour, you will have the opportunity to meet local artisans, taste exquisite wines, and savor authentic dishes that reflect the heart and soul of Italy.
But beyond the food and wine, what truly makes Italy magical is its people. Italians are known for their warmth, hospitality, and zest for life. By delving into the Italian culture, you’ll experience firsthand the joy and passion that permeate every aspect of life here.
I am looking forward to creating lasting memories with you as we explore the wonders of Italy together. Get ready for an adventure filled with learning, laughter, and of course, delicious food and wine!
Buon viaggio!
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.
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!
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.
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.
Firenze - Fine 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.
Siena & San Gimignano
Following breakfast at the villa, 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.
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!
Departure Day
We will soak in the views during one more spectacular breakfast before we depart. Then our 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!
