Traversing Tuscany With Chef Bob Waggoner

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April 28, 2020 (Tue)

Val d'Orcia, Italy
Tuscany, Pienza, Montepuliciano, Siena, Chianciana Terme, Cortona, Florence
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Cost: $5775

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Enjoy a once-in-a-lifetime tour of Tuscany's villages and cities and enjoy the finest Tuscan wine and epicurean offerings under the guidance of one of the most highly acclaimed chefs in the United States and France, Chef Bob Waggoner. 

April 28-May 9, 2020 and May 8-May 19, 2020
11 Nights From $5775 if booked by July 15, 2020*; Based on Double Occupancy
Single Supplement:  An additional $1800

Deposit:  $1000 per person due by July 15, 2019 to secure your space
Limited to 18 people per week


Traverse Tuscan cities, villages and vineyards under the tutelage of Chef Bob. Indulge in a Pecorino cheese tasting and a charcuterie tasting at small, local farms, and stroll through vineyards, and feast on chefs dinners with him, as well as local esteemed chefs. Relax and refuel at your rustic-yet-modern farmhouse in the Val D'Orcia region.

Space for May 8-19, 2020 is limited due to the popularity of this experience, so we've added an additional week, April 28-May 9, 2020. Call Judy at 843.237.9903 or email today.


Day 1
Depart US for Rome, Italy

Day 2 – Rome, Orvieto, Contignano
A private transfer will be waiting for you for travel to your villa. Depart Rome and travel through the rolling hills, olive groves and vineyards of the beautiful Tuscan countryside where a stop will be made to visit the beautiful town of Orvieto. As you stroll along the main street, you will see nice, small shops and taste some of the local produce. Experience a typical Italian lunch in a local trattoria, stroll the picturesque alleyways and see amazing views of the countryside from this lovely village.  Following lunch, continue on to Villa Casa Crete. After time to settle in and rest from your travels, all will gather for a Welcome Wine and Cheese reception. Observing the preparations for your dinner while enjoying the wonderful wines of Tuscany, makes for a truly memorable first evening in beautiful Tuscany!  Buon Appetito! Welcome Wine and Cheese Reception and Welcome Tuscan Chef’s Dinner at the villa. 

Day 3 - Pienza
Wake up to breakfast and the amazing views of the Val d’Orcia region of Tuscany, a UNESCO World Heritage site. Spend the morning on a guided tour in the lovely town of Pienza, known as the “ideal city of Renaissance” and sits amidst gentle, undulating hills and wonderful natural landscapes. The central Piazza Pio II is framed by 15th century buildings like the Pienza Cathedral and Piccolomini Palace. The latter was Pope Pius II’s summer residence and features a roof garden with valley views. To the west is the Pieve di Corsignano a Romanesques church with a circular bell tower which dominates the landscape viewed from afar. This picturesque village enjoys a strategic position standing high atop a hill, dominating all the Orcia Valley with extraordinary views. Pienza is known for its famous pecorino cheese and offers many shops for tasting. There will be time for exploring and shopping on your own in the many fantastic shops and quaint cafes in which to stop for lunch. Join Chef Bob on a visit to the local pecorino cheese shops to select the finest varieties of pecorino cheeses. Upon return to your villa, enjoy a tasting of the varieties of aged pecorino cheeses. Included Dinner with Wine Pairing offering 6 different wines; Osteria La Porta, La Cantina in Monticchiello, Tuscany. 

 Day 4 - Siena

Your day begins with a step into the past that takes you to the city of Siena with its narrow back streets, fortified houses, medieval towers, tiny piazzas, and lesser known churches rich in masterpieces. Walk around the Palio de Campo, where a bare-back horse race has taken place for centuries in the main square, the Campo, while continuing to stroll past the many cafes, bars and shops.  Note the fan-shaped central square where you will view the Palazzo Pubblico, the Gothic town hall, and Torre del Mangia, a slender 14th century tower with sweeping views from its distinctive white crown.   This tour takes you behind the scenes into the neighborhoods (called Contradas) with the church and museum, which give an understanding of the spirit and the fascination of this event. After your tour, you will enjoy a gelato tasting at La Vecchia Latteria or similar. Choose lunch and/or shopping on your own, before meeting your driver to return to your villa.  Savor a glass of wine, while the Tuscan Chef demonstrates the unique “art of pasta making.” Opportunity to observe the “art of pasta making” and Chef’s Dinner with Tuscan Chef and Chef Bob.

Day 5 - A Visit to Agricola Fontanelle, Vineyards, Chianciana Terme, Tuscany

Your relaxing morning begins with a short drive over winding roads that meander through the countryside and offer magnificent vistas at every turn to arrive at Agricola Fontanelle, owned by the Rosati family, known for their attachment to culture of the land and hospitality. The excellent D.O.C.G Chianti wine, exclusively from the owner’s vineyard, is intentionally limited and the choice of looking after small areas of land containing the best characteristics of soil, have awarded the owner with high quality wines that are among the more traditional Tuscan classics, but well-structured and complex; the charcuterie comes from their cured pork meats that come only from Cinta Senese pigs, renowned for its meat, such as prosciutto and salame. Lunch with wine from the Rosati brothers vineyard will be in the Old Town at their specialty shop.  Upon returning to the villa, roll your sleeves up for a unique and fun evening in the kitchen! Pandemonium in the Kitchen! - A Cooking Challenge (a surprise ending!). Italian Chef along with “nuovi amici." 

Day 6 – Podere Il Casale Farm

Today, visit a 300-year-old Tuscan farmhouse located on top of one of the renowned rolling hills of Tuscany with a breathtaking view of the town of Pienza, the medieval village of Monticchiello and Mount Amiata and the Orcia Valley. This organic farm property, Podere Il Casale, is a small farm with animals and a dairy, where you will learn about the making of Pecorino di Pienza cheese and taste the distinctive differences created by the aging process.  They also boast of very fine goat cheeses as well. Enjoy the cheese tastings with wine processed from the grapes in the vineyards on the farm, followed by lunch in their restaurant.  The afternoon will be free to explore at leisure and enjoy the villa. You may choose to join Chef Bob on a visit to the local market to select the finest and freshest ingredients for your optional cooking class. Optional Hands-on Cooking Class. Chef’s Dinner with Chef Bob.​ 

Day 7 – Montepulciano - Cortona

After breakfast, your morning travel begins with a tour of the medieval town of Montepulciano set atop a narrow ridge of volcanic rock that combines Tuscany’s superb countryside with some of the region’s finest wines. Make your way up the steep and winding walkways that lead to the narrow streets, where you will arrive at the Piazza Grande, the heart of Multepulciano and the focus of the city.  Stop in the middle of the square or near the lovely fountain and feel the unique atmosphere offered by the Plaza surrounded by the Duomo, the Palazzo Comunal, the Palazzo Tarugi and the Palazzo Contucci. Historic cantinas right within the walls, which have been dug out underneath the prestigious palazzos, make for a nice stop for a glass of wine.  Visit the famous Thursday market in the old town at the top. The marketeers arrive early with their draped stalls and rows and rows of fresh vegetables, aromatic herb stalls and forays of olives, breads, oils and cheeses that will be touted at every turn.  Experience the market with Chef Bob, as he selects the freshest ingredients for your dining experience.  We continue our walk to Cantina Fattoria della Talosa for a wine tasting of their Vino Nobile di Montepulciano, including lunch in the famous Talosa Cellars, which date back to the 16th century.  The brick passageways contain a series of vaults and niches where the barrels are placed.   Inside the Historic Cellar, there are huge oak barrels where Vino Nobile di Montepulciano is aged. After lunch, we make our way to the town of Cortona, made famous in the movie, “Under the Tuscan Sun”.  In Cortona, there will be time for enjoying a bit of history combined with time for shopping in the many wonderful art galleries and shops. Optional Hands-on Cooking with Chef Bob and Chef’s Dinner with Chef Bob.

 Day 8 – Montalcino

For your last day in Tuscany, visit a vineyard near Montalcino and taste the Brunello wines. The town’s fame derives from its production of one of Italy’s finest red wines known as Brunello di Montalcino. Brunello, a diminutive of Bruno ("brown"), is the name that was given locally to what was believed to be an individual grape variety grown in Montalcino, and the name Brunello evolved into the designation of the wine produced with 100% Sangiovese. Today, it is one of Italy's best-known and most expensive wines.  Following your wine tasting experience, there will be time for browsing the shops and strolling the streets of Montalcino, a town whose history dates back to the Etruscan and Roman periods. Wine Tasting Experience at the Villa with Sommelier, Klajdi Belaj (Private Sommelier to George Lucas, Producer/Director) and Chef Bob’s Farewell Dinner; “pairing the food with the wines of Tuscany." Complimentary wines with dinner.

Day 9-  Transfer to Florence

Private Group Transfer to the Brunelleschi Hotel or similar for three nights. The historic location of the Brunelleschi Hotel inside the oldest tower of the city of Florence and the medieval church, will allow you to immerse yourself in enchantment and mystery of Renaissance Florence. Welcome Dinner at a local, typical Italian restaurant; Wines and alcoholic beverages available for purchase.

Day 10 - Florence

Wake up to breakfast and an amazing view of the city of Florence, the birthplace of the Renaissance.  Today, embark on a guided walking tour of Florence’s Renaissance heart, followed by a visit at the Galleria dell’ Accademia to see works by many of the greatest artists of the 14th and 15th centuries to include Michelangelo’s famous sculpture of David. The rest of the afternoon will be free to explore Florence on your own.  Florence is filled with Renaissance riches to include the Duomo and the 14th century Ponte Vecchio, framing delightful views of the Arno River. Dinner on your own  at leisure. 

Day 11 - Florence

This morning, visit the San Lorenzo Market with your guide.  The Market runs along several streets surrounding the Mercato Centrale. File between the hundreds of stalls on either side of the street with vendors selling pottery, clothing, souvenirs and various leather goods.  This is a great place to find gifts to bring back to your friends and family.  After your shopping experience at the outdoor market, you may choose to visit The Centrale Market, which is a two-level food market making up the second half of the San Lorenzo Market. The Mercato Centrale is in a beautiful building designed by Giuseppe Mengoni, a famous architect. Enjoy lunch at one of the many food vendors or wander to find the perfect Osteria to savor local Italian wine and cheeses. Be sure to sample the gelato on your walk about! The rest of the day is free to discover Florence with its many shops at your leisure or choose a dinner venue to enjoy the best Tuscan cuisine in one of the many restaurants available. Dinner on your own at leisure. 

Day 12 – Transfer to Florence International Airport for flight to US 


Casa Crete is a superb and stylish farmhouse with extensive outdoor areas, set in one of Tuscany’s most spectacular locations, immersed in Val d’Orcia’s enchanted countryside. Each and every corner is characterized by rustic, understated elegance and unique country-style furnishings that are enhanced by sophisticated, creative touches such as the ceilings’ wooden beams whitewashed in pastel colors and the antique terracotta floor tiles. The property has a main villa and a charming annex, an ancient barn, and both have been fully renovated and splendidly furnished and decorated.  All bedrooms are ensuite with fully renovated and modern baths. Surrounded by the typical Val d'Orcia clay hillocks, you can enjoy stunning 360° views over the valley and its hill towns. The common areas are spacious and beautifully furnished and decorated in a unique style. You will marvel at the hilltop villages, castles and vineyards and sip the celebrated red wines of Montepulciano, while soaking up the Tuscan countryside.

* PLEASE NOTE:  THE COST OF AIRLINE TICKET IS NOT INCLUDED. We highly recommend purchasing travel insurance. If you decide to purchase travel insurance, we are happy to help you with that. If deemed necessary, this itinerary may be altered at the discretion of Premier Tours & Travel, Inc. Contact Judy at 843.237.9903 or to learn more or to register to join this exclusive tour. 1/4 bottle of wine per person for chef's dinners as noted.

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