Take your time this morning and enjoy a leisurely breakfast at the hotel before departing for our first winery visit to Azienda Agricola Brancatelli in the tiny town of Riotorto, just two miles from the sea. Here we will be welcomed by the chef-turned-winemaker, Giuseppe, and his partner, Catherine, who will guide us on a private tour of the gorgeous property. Giuseppe will then cook for us a traditional Tuscan feast paired, of course, with Brancatelli wines.

From here we will drive on to the stunning hilltop village of Pienza, situated between Montalcino and Montepulciano. Conceived and constructed to be the ideal city of the Renaissance, the layout and architecture embody the era’s emphasis on beauty and harmony with nature. The sweeping views from the town’s elevated perch will take your breath away. Pienza is a marvel of picture-postcard perfection, and you will have time to meander the charming streets, shop, and enjoy an afternoon spritz at a sunny cafe.

In the evening, we will return to Casa Newton for a wood-fired dinner together under the villa’s loggia, where we will share yet more thoughtfully chosen wines from the region.

Meals: Breakfast; Lunch at Azienda Agricola Brancatelli; Multi-course dinner with wine pairings
Activity: Winery tour and tasting; daytrip to Pienza
Accommodation: Luxury hotel in the Tuscan countryside

Enjoy a slow start and breakfast at the hotel. We will then travel together to Tenuta Corte Pavone. Merely approaching this winery is an experience—crossing through tall, wrought iron gates, driving a lane lined with towering cypress, arriving at a picturesque estate with views of Montalcino. Here we will be given a private tour and tasting of their world-class wines.

After our time at the estate, we will take a scenic drive to Montepulciano, an enchanting Renaissance village atop a hill that offers the iconic Tuscan imagery that makes this region the stuff of movies and memories. You will be free to explore, have lunch on your own, and enjoy a glass of the namesake red on a sunny terrace, taking in the rolling hills of vineyards and olive groves that surround the village. 

We will have some time back at Casa Newton to refresh before heading to our extraordinary dinner. Together we will experience the first Michelin-starred meal of our trip with Chef Marcelli who weaves traditional local specialities with modern, global influences into something deliciously all his own. Paired with local wines, this is a meal you will not soon forget.

Meals: Breakfast; Multi-course dinner with wine pairings
Activity: Winery tour and tasting; daytrip to Montepulciano
Accommodation: Luxury hotel in the Tuscan countryside

After breakfast this morning, we will depart Casa Newton as we journey on to Rome. On our way, we will visit the Pileum Winery, in the heart of the hills of the Piglio region, about fifty miles from the center of Rome. This winery was established by four families who banded together and bundled their land and resources to focus on producing superior wine from two indigenous grape varieties, Passerina and Ceserese del Piglio. We will be given a private tour and enjoy a lunch and tasting of their unique wines.  

Then, Rome. One of the most iconic and historic cities on earth. Our home for the night that we are here is the Palazzo Roma, a boutique hotel on the Via del Corso, resplendent with Renaissance flourishes and contemporary luxury. After settling in, you have the option of joining us and our local guide for a walking tour of some of Rome’s most unmissable landmarks. 

This evening, you can venture out for dinner on your own. Rome, of course, offers abundant dining options, from walk-in casual to three-star Michelin. We are very happy to offer recommendations for some of our favorites. Buon appetito!

Meals: Breakfast; Lunch at winery with tasting
Activity: Winery tour and tasting; Walking tour of Rome
Accommodation: Five-star luxury hotel in the heart of Rome

This morning is yours to enjoy the final few hours in Rome. If you like, join us for a guided tour of the Vatican museum, or sip a cappuccino in a piazza and people-watch. 

Midday, we will transfer to the airport for our short flight to Sicily. After a brief drive we will arrive on the island of Ortigia in Siricusa, our home for the next four nights. This walkable, picturesque island pulses with Sicilian charm, from the pebbled beach to the balcony-lined lanes. Settled by the ancient Greeks, ruins are sprinkled among the honey-hued shops and cafes. We will stay at the Maniace Boutique Hotel overlooking the sea. The hotel, a six-minute walk from the Temple of Apollo, blends luxury with the amalgam of Sicilian culture, drawing influence from the civilizations that marked the region. 

You will have a few hours to relax and refresh after our day of travel before an incredible dinner together highlighting Sicilian specialities and regional wines.

Meals: Breakfast; Multi-course dinner with wine pairings
Activity: Optional tour of Vatican museum; Flight to Sicily
Accommodation: Luxury seaside boutique hotel

Enjoy breakfast at the hotel before beginning our exploration of Sicily. We will drive first to the beautiful town of Ragusa, where we will experience one of our favorite lunches of our journey at a restaurant where contemporary insight is applied to traditional and local cuisine. The views from this venue are as spectacular as their food, wine, and service. 

After our leisurely meal, we will travel to the heart of Sicily’s most prestigious wine region, Cerasuolo di Vittoria, to the COS winery. This organic winery was one of the first western wineries to use amphora, large clay vessels that predate barrels, in their aging process. While adhering to the traditions of the region, COS is producing some of the most respected natural wines in the world; we will have a private tour and tasting and discover for ourselves exactly why. 

From here we will drive to Noto, a golden-hued city known for its Baroque architecture, having been completely rebuilt after being leveled by an earthquake in 1693. You will have free time to wander, or join us if you like for an aperitivo before a fabulous dinner together with free-flowing Sicilian wine.

Meals: Breakfast; Lunch; Multi-course dinner with wine pairings
Activity: Winery tour and tasting
Accommodation: Luxury seaside boutique hotel

This day is yours! Explore Ortigia and the larger city of Siricusa. There is much to see—from the 5th-century Greek theater to extraordinary examples of medieval and Baroque architecture. This is a wonderful opportunity to shop for gifts, lose yourself, and relax with no pressure to be anywhere but where you are. If you desire, join us for a guided food-focused walking tour, which is the perfect way to lunch and learn some local history at the same time.

Dinner will be up to you—the ideal date night! As always, we can offer tested recommendations to ensure a wonderful experience. 

Meals: Breakfast
Activity: Food walking tour
Accommodation: Luxury seaside boutique hotel

Take your time this morning, enjoying the hotel’s breakfast. Mid-morning we will take a beautiful drive up Sicily’s Mount Etna to the village of Milo. Eight-hundred meters above sea level, Milo offers panoramic views of the eastern coast of Sicily. Here we will have lunch in a cozy, traditional tavern serving classic Sicilian food.  

Following lunch we will visit a historic cellar on the northern side of Mt Etna, where we will tour and taste some of the stunning wines influenced by the volcanic soils of the mountain. 

Back in Ortigia, we will gather in the evening for a superb dinner with wine pairings at a multiple-award-winning, one Michelin-starred restaurant steps away from our hotel.

For some, this will be the celebratory end of our unforgettable journey together; others will choose to travel on with us for an additional four magical nights in Positano. 

Meals: Breakfast; Lunch; Multi-course dinner with wine pairings
Activity: Winery tour and tasting
Accommodation: Luxury seaside boutique hotel

You will depart by private transfer for the Catania (CTA) airport. However, if you wish to extend your time in Italy, we are very happy to offer suggestions to make the most of your stay!