Travel | Eat | Connect in Italy

Central- Northern Italy

Known for its unique, boot-like shape, Italy is famed around the world for its culture, traditions, food, and endless historical sites to discover. Italians are also known for their boundless zest for life and hand-made pasta – not to mention their unparalleled reputation as romantic and passionate lovers!

What makes Italy truly unique goes beyond the opera and the arts. Every city has its own culture, dialect, food, and traditions, making this a destination packed with endless opportunities for your cultural enrichment and personal connection.

We’ll follow in the footsteps of ancient Romans, live la dolce vita (“the good life”), discover Michelin-starred restaurants and local markets, and learn the secrets of hand-churned gelato. In Napoli, we’ll get inspired by the novel My Brilliant Friend, learn the secrets of Neapolitan pizza, and take in the panoramic views on secret islands.

In Florence, we’ll marvel at art and architecture as we sip fine wines. At the same time, we will also discover Italy’s gastronomic treasures through cooking classes with the locals. In Bologna, we’ll go hunting for truffles. In Trieste – a hidden gem – we’ll discover Vienna by the sea, an intersection between the Mediterranean and European culture.

Join us to discover Italy’s culture, fine art, picturesque towns, and unforgettable food and wine!

There are some places you can’t help but fall in love with at first sight, and Tuscany is surely one of them. The most picturesque region of central Italy, whose capital is Florence, Tuscany contains a dazzling number of the world’s iconic masterworks, as well as some of its most luscious wines, scrumptious foods, and charming landscapes. It’s ridiculously impossible to adequately describe all the pleasures and pride of visiting the area! 

Enjoy fabulous cuisine, colorful cities, gorgeous rolling hills, fabulous vineyards, towering mountains, and ancient historical sites on this 7-day Tuscany itinerary as you travel, eat and connect from Rome to Florence. 



  • Immerse yourself in the local culture, art, history, appetizing cuisine and, of course, wine
  • Experience a model Renaissance town surrounded by Val d’Orcia
  • Discover hilltop towns like Pitigliano and Chianti
  • Unveil the true heart of Tuscany through your palate
  • Find hidden gems: villages, castles, and vineyards
  • Devote two days to the Tuscan capital of Florence which is packed with architectural Renaissance  masterpieces

Day 1: Arrival in Rome

Drive towards Val d’Orcia, a model Renaissance town, and begin your special journey between sweet tastes and marvelous panoramas that you will never forget. Optional:  stop in Orvieto for visit and welcome to Italy lunch in a 500-year-old cellar.


Day 2: Val d’Orcia

Open your day with the glorious scenery of hills covered with vineyards, olive groves, cypress, beech and chestnut trees, ancient medieval houses. Discover the true heart of Tuscany through your palate by participating in a cooking class and visiting a local winery. 

Day 3: Pitigliano

Drive to Pitigliano, perched atop a volcanic rocky outcrop towering over the surrounding countryside, also known as “Little Jerusalem”, visit the old synagogue, meet the locals and hear some fascinating stories. Continue to the enchanting town of San Vincenzo. 


Day 4: Pienza

Begin your morning on a dairy farm for a Pecorino cheese making experience, then drive to Pienza, a spectacular Renaissance town. Continue to Montalcino, known globally as the home of one of the world’s great wines, Brunello di Montalcino. 

Day 5: Panzano

 Drive to Panzano for a visit to Italy’s most famous butcher for the Bistecca Fiorentina and enjoy a cooking demonstration, then head to a Chianti winery for a wine tasting experience, and meet the owners. Leave the area and drive to Florence

Day 6:Florence

Explore Florence’s greatest hits– the seat of Renaissance art, continue to a “walking lunch” market tour, then prepare to be amazed by the Synagogue & Jewish Museum of Florence and its marvelous architecture. End your day in a Michelin star restaurant. 


Day 7: A bit of Florence before departure

Before we end this journey, learn how to make and prepare typical and delicious Gelato by a local master. After this workshop it’s time to say “arrivederci” as you leave Florence by train to Rome to catch your flight back home. 

From Revered vineyards, medieval hilltop towns, and UNESCO-lauded artwork of central Italy to elegant northern cities and coastline, this 12-day tour encapsulates Italy’s inimitable natural and cultural diversity. Start your journey in the central region’s capital, Florence, a city known for its wealth of world-class art and architecture, continue to Tuscan scenery, hilltop towns, vineyards, AND cypress trees, and spend some time stopping off at wineries and vineyards along the winding countryside roads in this area. Head North to Bologna, famous for its beautiful plazas and arched colonnades, also known as a food-lovers paradise! Discover the Italian countryside in the northwest cities of Friuli Venezia Giulia and Trieste before wandering through the maze of alleys and narrow streets of Venice, the magical city over the water. 



  •  Visit villas, Italian gardens, and UNESCO heritage sites
  •  Meet artists and enjoy local hospitality
  •  Participate in countryside adventures and experiences (many to choose from) 
  •  Discover some of Italy’s best red wines and the diversity of the regions’ cuisines
  •  Explore a mysterious region and enjoy the stunning landscape of the Adriatic seaside
  •  Be amazed by Venetian narrow streets and canals

Day 1: Arrival in Florence 

Arrival in Florence, Cradle of the Renaissance, central to culture and trade during the Middle Ages, the birthplace of Dante Alighieri, of the Renaissance – with the Medicis, Michelangelo, and Da Vinci.    Discover Florence with a local who will choose only the best, authentic experiences for you. 

Day 2: Florence 

Walk around the city center, stop at the must-sees, and enjoy some bites of traditional food and drinks along the way. Participate in an afternoon wine tour and unveil the beauty of Florence after sunset. 

Day 3: Florence- Chianti

Visit Medici Villas and Gardens or meet a local artist at work in an artisan lab, continue to Chianti, a territory, with stunning landscapes made of history, lifestyle, culture, warm hospitality, fantastic wine, and good food!

Day 4: Chianti-Tuscan Countryside

Today’s adventures will be in the Tuscan countryside, where you will immerse in nature! You can choose between a bike Tour, walking or trekking, or a Hot air balloon flight- all to observe the Chianti landscape with its hilltop towns, castles, valleys, famous vineyards, olive groves, and woodlands.

Day 5: More of Chianti and Tuscan Countryside

Today we will enjoy more of the Chianti and Tuscan countryside, as we visit the town of Siena, often referred to as an open-air museum celebrating Gothic architecture, and marvel in the vibrant streets populated with artisanal boutiques, sweet-smelling patisseries (pastry shops) and tempting restaurants.

Day 6: Bologna

Begin your day with a Truffle hunting experience, then head to Bologna – a destination with plenty to offer. Discover this marvelous city, home to some of the most delicious and fundamental products of Italy, and participate in the real Italian aperitivo,   a guided tasting featuring some of the best wines and local delicacies.

Day 7: Friuli Venezia Giulia Countryside

Travel to Friuli Venezia Giulia – Tucked far in the northeastern-most part of Italy, this mysterious region touches the borders of Austria and Slovenia. Enjoy its stunning landscape and gentle hills going from the Adriatic seaside right up to the beginning of the Alps. 

Day 8: Trieste

Departure to Trieste, a hidden gem off the beaten track, a tiny Vienna by the sea where the Mediterranean culture fuses with continental Europe. Choose between horseriding in the forest, hiking, a Vespa tour, or a helicopter ride. At the end of the day relax at luxury resort Porto Piccolo. 

Day 9: Explore Trieste

A full day to explore Triete’s natural resources, choose between sailing or beach time.

Hike in the Karst Plateau overlooking the gulf of Trieste, and visit a natural winery- Zidarich. 

In the evening hop across the border into Slovenia for a delicious dinner at Hisa Spakapanova. 

Day 10: Welcome to Venice 

Arrive in Venice, and explore the city with a local, in a completely customized experience, showing you the hidden gems, such as the precious local bookstores (even one with a boat inside), historic bars and cafes with traditional classics or a focus on biodynamic foods and wines, the spots with the best views, and historically important locations, and much more… 

Day 11: Venice

Open your day with a gondola. Ride back In time, enjoy a walking tour of Venice as you’ve never seen before and marvel at amazing panoramic views. Stroll down the narrow alleys of Venice and encounter enchanting squares, receive that local touch with the professional guide as you see the main highlights of this beautiful city. Continue to experience the magic of Venice from a different perspective by learning how to row in one of Venice’s typical rowing boats. 

Day 12: A day of optional activities 

So much to see and do around the city of Venice, and many activities to choose from (Visit Palazzo Ducale, Underground Venice, The Way of Marco Polo, Glassblowing in Venice, Instagram Portrait Session in Venice). We will then have a special farewell dinner. 

Day 13Departure from Venice Airport