Italy: Countryside, Canals, and 'Cucina' in Tuscany and the North

Get your heart pumping with a combination of incredible experiences, stunning sights, and invigorating activity as you hike, cycle, and tour your way through some of the most beautiful spots in Italy. From sprawling countryside to the bustle of elegant cities, to farmsteads and vineyards, canals and city markets, this tour is for the passionate traveler, who wishes to dive into all Italy has to offer. Fill your glass with experiences that go beyond standard tourism, whether it’s creating your own Venetian mask, spending a day as a medieval pilgrim, or exploring a famous cathedral long after it shut its doors to the public. Drink deeply of Italy, and you’ll savor the flavor forever.

Days 1/2


Your journey begins as you board your overnight flight to Florence. Upon arrival, you will be met by your guide and transferred to your hotel in the Tuscan countryside. Enjoy a welcome cocktail with your fellow travelers and dinner at the hotel. BORGO CORTEFREDA. (Meals Aloft, D)


Day 3


This morning, see Tuscany as it was meant to be experienced, whipping through the fresh air along the Ville di Corsano, with color-changing fields of grain and towering thatches of bright sunflowers sprawling to the horizon on either side of you. Over five hours, you’ll cycle from Chianti to Siena, spotting rustic farmhouses and medieval villages nestled in the landscape. Stop for a picnic lunch and, finally, arrive among the lush vineyards of Montalcino. First, visit the Paradiso di Frassina, which has been inhabited since at least 1,000 AD. Explore the vineyard and cellars, followed by a wine tasting as you relax among the grapevines and wide-open, hilly countryside to the sounds of Mozart playing throughout, part of a scientific study on music and wine. Afterwards, head to Casato Prime Donne, which is the only winery in Italy with all female staff. Meet Donatella Cinelli Colombini, the owner of the winery, and enjoy a tasting of her award-winning Brunello. BORGO CORTEFREDA. (B,L,D)


Day 4


Enjoy a hearty breakfast at the hotel before you set out this morning on a guided hike through the vineyards of Brolio. End your exploration at the castle, where you’ll see the cellars and enjoy a tasting. Stop for lunch in a restaurant tucked into the surrounding foothills before departing for Siena, once a powerful medieval city-state. The buildings and artwork here are testament to a glorious past. See the hill-top cathedral and its treasures, including masterpieces by Michelangelo and Donatello, and Italy’s largest gothic palace, which now serves as town hall. Return to your hotel in the afternoon and enjoy the rest of your day at leisure. BORGO CORTEFREDA. (B,L,D)


Day 5


Take a private coach to Florence this morning, where you’ll enjoy a guided tour of the city that started the Renaissance. Spend time exploring the famous Duomo, the Piazza Signoria, the SIgnoria Palace and Ponte Vecchio. Visit Loretta Caponi Atelier, where the renowned Loretta Caponi once created beautiful garments in silk, linen, cotton, and lace – a tradition now carried on by her daughter, Lucia. Sit down for lunch in the central market, surrounded by stalls selling a variety of delicious food, some of which is packaged to take home. You’ll find a dazzling variety of Italian specialties here, including truffle dishes, gelato, pizza, handmade pasta, cured meats and cheeses, and more. Spend your afternoon at leisure exploring the market or the city around you. BORGO CORTEFREDA. (B,L,D)


Day 6


Spend today following in the footsteps of the pilgrims, on a hike along the Via Francigenia (or Via Romea), a pilgrimage trail that once ran from Canterbury, England to Rome. For centuries, the faithful made this journey on foot or with a mule or horse, to visit the capital of their faith. Become a pilgrim for a day, eating the food they would have eaten on the trail, and receiving at the end a special pass with stamps showing your journey and a roadbook. Tonight, sit down for a final dinner in Chianti with your fellow travelers at one of the osterias near your hotel. BORGO CORTEFREDA. (B,L,D)


Day 7


Depart for Parma, and visit the Museum of Parmigiano Regganio and Peasant Civilization. This museum is built into a 19th century farmhouse, and will walk you through the process of making this famous cheese. Once your appetite is thoroughly whetted, travel to the nearby village of Guastalla, where you’ll indulge in a cooking lesson taught by Cristina Boschi, the niece of the Countess Casanova. While you learn to make pasta, you will also learn about this place and the people who lived here. Emilia Romagna is the main region in Italy where Pasta is still home-made on a daily basis. Enjoy the fruits of your labor and explore the farmhouse, meeting the friendly livestock. In the afternoon, journey to Venice, where you’ll transfer by a private water taxi to your hotel. HOTEL PALAZZO GIOVANELLI.  (B,L)


Day 8


Start the day with a visit to a mask artisan’s laboratory. Meet an artisan and learn how the famous Venetian carnival masks are created and decorated, as well as about the significance of the masks, the four types of design, and the history behind the tradition. Best of all, you’ll get hands-on experience with the chance to decorate your own mask, drawing inspiration from the galleries of masks located in the workshop. Continue your authentic Venetian experience with a visit to a squero, or boatyard, which is home to some of Venice’s 400 handmade and active gondola. Venture out on a Bacaro tour of Venice, enjoying cicchetti and tapas with excellent local wine. This evening, you’ll be allowed into St. Mark’s Basilica after closing time, nearly alone in one of the most magnificent churches in the world. The custodian will unlock doors for you that tourists do not usually see behind, including the crypt where St. Mark himself is interred. Walk along the aisles and see the church’s beautiful mosaics, with all 43,000 square feet lit up, glimmering and sparkling in the dark. HOTEL PALAZZO GIOVANELLI.  (B,L,D)


Day 9


Explore the Tessitura Bevilacqua, an 18th century textile workshop in the quiet hours of the morning. Next, visit the Mocenigo Palace, a museum dedicated to the many industries of Venice, with a costume exhibit, an exhibition dedicated to the tradition and creation of perfumes, and paintings and furniture from the 18th century. Indulge in the romance of the city on a guided tour in the footsteps of none other than Giacomo Casanova. It is the perfect atmosphere to prepare you for an evening aperitif at the breathtaking Sky Bar of Hotel Hilton Molino Stucky, where you’ll admire the city from above. HOTEL PALAZZO GIOVANELLI.  (B,L,D)


Day 10


It’s time to say arrivederci as you fly back home, full of memories of a most unique experience. (B, Meals Aloft)



Indulge in a longer adventure with this post-extension to Padua, Valpolicella, and Lake Como. Tour the city of Padua with its historical university, noble palaces, and elegant churches. Hike through the vineyards of Valpolicella, alongside small villages and Romanesque monuments. Taste more wine and olive oil and luxuriate in views of the stunning Lake Como along a backdrop of majestic mountain ranges. This is true Italian indulgence of every flavor and the perfect finishing note for a full-bodied journey to Tuscany and the North.




  • All ground transfers and excursions in private deluxe air-conditioned motor coach.
  • Continental breakfast daily, a welcome dinner and a farewell dinner and other meals as per itinerary. (B=Breakfast; L=Lunch; D=Dinner)
  • Superior accommodations throughout as indicated or similar.
  • All museum and attraction entry fees indicated on itinerary.
  • Whispers.
  • Porterage for baggage handling.
  • Complimentary baggage tags and passport wallet.
  • Complimentary emergency evacuation insurance.

Prices starting at $5,495. For further booking, date, and pricing info please contact info@classicescapes.

Does not include international or domestic flights. Prices are based on 10 or more travelers, and are subject to change.