Join us from May 3-10, 2025, 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 a beautiful villa where they will enjoy the gorgeous countryside and luxurious villa amenities while experiencing daily excursions to some of Tuscany's most amazing cities including Florence, Siena and San Gimignano.. 

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, where 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 villa has its own personal private chef who will prepare gourmet meals and teach guests various aspects of Italian cuisine and cooking. The beautiful villa boasts a heated pool, outdoor dining/lounge areas and spectacular vistas where guests can unwind and relax. In addition, gorgeous interior common spaces, 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 14 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: 

• Accommodations: Week-long accommodations in a luxurious 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 and 7 dinners are included
• Wine and beverages: Served during meals prepared at the villa and at winery tours
• Tours + Activities: Organized group tours and activities specified in the travel itinerary

Participants are responsible for: 

• International airfare and transportation outside of tour itinerary
• Travel insurance: Required for all participants
• Airport transfers
• Excess baggage charges
• Passport, visa and global entry fees
• Custom "add-on" excursions or deviations from the trip itinerary
• Personal expenses such as snacks, additional gratuities and communication costs
• Select meals not listed in itinerary
• Alcohol outside of group meals and wine tours
• International airport departure tax, if applicable

A personal message from Maya:

I am thrilled to be your group leader for this unforgettable Tuscan food and wine tour. My ties to Italy date back to my childhood. I grew up experiencing Italian life during extended visits with my sister and her family who call Tuscany home.  My love for travel, entertaining, cooking and wine inspire me to share Italy's rich history, stunning landscapes, and vibrant culture with others. 

I am looking forward to creating lasting memories with you as we explore the wonders of Italy together through these immersive experiences. Get ready for an adventure filled with learning, laughter, fun and of course, delicious food and wine!

Buon viaggio!

Welcome to Tuscany

We will meet in the center of Florence to enjoy a welcome lunch before departing together 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 cocktails followed by a delicious dinner prepared by our private chef.

Inclusions: Prosecco Lunch, Cocktail Hour, and Dinner

Relaxing day at the villa - yoga, brunch, wine & cheese tasting

Begin the day with a relaxing yoga class or take some time to unwind by the pool and explore the villa grounds.

Afterward we’ll indulge in a delicious Sunday Brunch.

In the afternoon, we will enjoy a wine and cheese tasting at the villa to discover an award-winning local producer’s collection of pecorino cheeses and sample some excellent Tuscan wines. (Wine coach tasting and we provide the cheese)

Before dinner, our chef will let us participate in making our own tiramisù for dessert. Then we’ll enjoy socializing with some cocktails on the panoramic patio followed by dinner at the villa.

Inclusions: Light Early AM Breakfast, Hearty Brunch, Pecorino Cheese Tasting with wine pairings, Cocktail Hour, Chef Dinner

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 at your leisure.

Back at the villa we will unwind with a festive Aperitivo/Happy Hour introducing the famous Aperol Spritz followed by a Pizza Night prepared by our pizza chef.

Inclusions: Breakfast, Aperitivo/Happy Hour, Pizza Dinner Night

Enjoy an easy morning at the villa and a yoga class for those interested. 

We’ll depart by midday to visit Greve in Chianti, a charming local Chianti hill town  close to our villa, where you will be able to stroll, shop and get lunch at your leisure.

Then, we’ll head to a family-run 15th century olive estate 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 oil, 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 private hands-on class, we will prepare a full 3-course dinner, as we sip wine and learn about Tuscan cuisine and the culinary secrets passed down for generations.

Inclusions: Breakfast and 3-Course Dinner with Wine Cooking Experience.

After breakfast, we will depart for Tuscany’s capital, Florence - the quintessential Renaissance city.

We will meet our private guide for 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 free time  to have lunch, shop and explore the city independently before meeting up to return to the villa. 

In the evening, we will gather for another gourmet chef dinner at the villa. Tonight, those interested can sample Italy's famous Limoncello and Grappa with dessert.

Inclusions: Breakfast and Chef Dinner with Wine--followed by dessert with Limoncello and Grappa.

Depart the villa in the morning to go to 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. You’ll have time to explore and shop independently, and can have lunch at your leisure.

Then we will head to a stunning Castle Winery where the scenery and history create a magical atmosphere. We will enjoy a private tour and tasting in the historic cellars.

Back at the villa, we will start with a cocktail party followed by dinner which will be a special Barbecue Night featuring the famous Bistecca Fiorentina, Florence’s signature steak.

Inclusions: Breakfast, Cocktail Party, "Steak Night" featuring a selection of meats and the famous Bistecca Fiorentina with wine. 

It’s Your Choice! 

This final day offers our guests the option of returning to Florence to shop and explore independently, OR, for those who prefer a more low-key local experience, you can opt to discover some of the other charming Chianti hill towns near the villa and enjoy visiting a local winery. 

There will be two morning departures at 10:00 am:

One to Florence, with drop-off will in the historic center and pick-up in the late afternoon, to allow guests to explore the city’s treasures at their leisure.

The other vehicle will stop at the villa owner’s highly rated winery, where you will be introduced to a selection of their wines from different areas of Tuscany. 

Then you will proceed to visit a few of the most famous Chianti hill towns (Castellina and Radda). You will be able to explore independently and get a feel for the charming atmosphere of these medieval villages where the past and present blend to offer hospitality and history in a quintessential setting. Enjoy lunch at your leisure. 

When everyone gets back to the villa, there will be some time to relax.

Then we’ll meet for cocktails before our chef serves our farewell dinner.

Inclusions: Breakfast, Aperitivo and Dinner

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!