Trip or Vacation

Traversing Tuscany On Chef-Led Culinary Adventures -- Multiple Departures

Fri, April 23, 2021 (Departure Date)

Cost: From $5975

Through our Expertly Done Travel Series, explore cultures, food, and wine enhanced by the knowledgeable, approachable insights of Premier’s hand-selected expert chefs, such as Chef Bob Waggoner. Enjoy a once-in-a-lifetime tour of Tuscany's villages and cities and enjoy the finest Tuscan wine and epicurean offerings.

Traverse Tuscan cities, villages, and vineyards under the tutelage of the Chef. 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 beautiful farmhouse in the Val D'Oricia region--a UNESCO World Heritage Site.

April 23-May 4, 2021 – This tour will operate with a local Italian chef.

From $5975*; Based on Double Occupancy

Single Supplemen $2000

Deposit: $1000 per person; Limited to 18 passengers

June 2-13, 2021** – An Exclusive Departure with Chef Bob Waggoner

From $5975*; Based on Double Occupancy

Single Supplemen $2000

Deposit: $1000 per person; Limited to 18 passengers

October 1-12, 2021 – This tour will operate with a local Italian chef.

From $5975*; Based on Double Occupancy

Single Supplemen $2000

Deposit: $1000 per person; Limited to 18 passengers


Depart the United States for Rome, Italy

Day 1 – Rome, Orvieto, Contignano

Arrive Rome International Airport in the morning.

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, 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 to Villa Casa Crete. After time to settle in and rest from your travels, all will gather for a Welcome Wine & 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! Wine & Cheese Reception and Welcome Tuscan Chef’s Dinner at the villa.

** This would be a good time to select some wine, spirits or other beverages of choice for your personal use at the villa.

Day 2 – Pienza - Podere Il Casale Farm

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.

After lunch, 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. Upon return to your villa, enjoy a tasting of the varieties of aged pecorino cheeses. Optional Hands-on Cooking with Chef. Chef’s Dinner.

Day 3 – 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, 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 Waggoner.

Day 4, 2020 – At Leisure Pienza

Today, you will have the day at leisure. You can enjoy the property and simply relax, or join Chef in a hands-on cooking class. Chef’s Dinner.

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 a glass of 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 with Chef

Day 6 – Montepulciano

After breakfast, your morning travel begins with a visit to 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 Montepulciano 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 Waggoner, 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. Dinner with Wine Pairing offering 6 different wines; Ristorante Daria in Monticchiello, Tuscany.

Day 7 – Cortona

For your last day in Tuscany, we make our way to the well-known town of Cortona, made famous in the movie, “Under the Tuscan Sun”, for a guided walking tour. This small charming town is in the Valdichiana, or Chiana Valley, in the province of Arezzo in southern Tuscany. The city, enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill about 600 meters (about 1968 feet) above sea level. This dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno. 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. Wine Tasting Experience at the Villa with Sommelier, Klajdi Belaj (Private Sommelier to George Lucas, Producer/Director) and Chef’s Farewell Dinner; “pairing the food with the wines of Tuscany.”

Day 8 – Transfer to Florence

Private Group Transfer to the Brunelleschi Hotel 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. On the way to Florence, there will be a stop in the beautiful town of San Gimignano. Known as the Town of Fine Towers, San Gimignano is famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses, which, with its hilltop setting and encircling walls, form "an unforgettable skyline". The "Historic Centre of San Gimignano" is a UNESCO World Heritage Site. There will be time for shopping, exploring the sites, and lunch on your own before continuing on to your hotel in Florence. Dinner on your own.

Day 9 – 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.

Day 10 – Florence

This morning set out to visit the San Lorenzo Market with Chef Bob Waggoner. 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. Farewell dinner.

Day 11 – Transfer to Florence International Airport for flight to United States.

 *IMPORTANT INFORMATION: Itinerary subject to change. Premier Tours & Travel reserves the right to modify programs and itineraries (including arranged sightseeing, accommodations, dining experiences, aircraft, trains, vessels, and so forth) at any time due to unforeseen circumstances or circumstances beyond Premier Tours & Travel’s control, including force majeures. In the instance our Expert host cancels due to unforeseen circumstances, Premier Tours & Travel has the right to substitute another Expert host, such as a chef, in such an emergency (timing allowed) and/or the tour will continue in its entirety. Every effort is made to operate our itineraries as planned but alterations may need to be made after the final itinerary has been issued. Airfare is not included. Deposit is non-refundable. Wine is included as noted otherwise alcoholic beverages are the responsibility of each adult guest. Please see General Terms & Conditions on our website.

** The June 3-13, 2021 exlusive departure with Chef Bob Waggoner will begin with a 2-night stay in Florence and end with a one-night stay in Rome. Depart Rome to USA on June 13, 2021.

Premier Experiences, Premier Advantages

  • English-speaking Premier Director and local Premier representatives
  • ​Airport meet and greet
  • Private transfers
  • Curated luxury accommodations
  • 10 Breakfasts; 4 Lunches; 8 Dinners
  • Hand-selected cheese, charcuterie, and olive oil tastings, and a private wine tasting with Sommelier Kljadi Belaj
  • Curated tours and experiences, including entrance fees and taxes
  • Internet (where available)
  • 24/7 Premier support


Chef Bob Waggoner Bob received his formal training with Michael Roberts at Trumps in Los Angeles from 1981 to 1983, and later in France at a constellation of Michelin-rated restaurants with chefs Jacques Lameloise, Charles Barrier, Pierre Gagnaire, Gerard Boyer and Mark Meneau. At 23, he took on his first chef position at the private club “Members” in Caracas, Venezuela. Chef Bob Waggoner returned to France at age 24 to become chef of the Hotel de la Poste in Avallon for three years. Then, in 1988 at age 26, in the town of Moneteau in Burgundy, he became the first American chef to own his own restaurant in France, the much acclaimed Le Monte Cristo. He is one of the few Americans to be Knighted with the “l’Odre du Mérite Agricole” from the Government of France. In 1991, Waggoner was offered the opportunity of Chef de Cuisine with Chef Jean-Pierre Silva, the two-star Michelin, at Le Vieux Moulin in Beaune, France. After 11 years in France, he returned to the States in 1993 to cook at the award-winning Turnberry Isle in Florida, before joining The Wild Boar in Nashville, where he earned the restaurant a coveted AAA Five-Diamond Award and the Grand Award from Wine Spectator. He finally found his way to Charleston where he was Executive Chef of Charleston Grill at Charleston Place for a dozen years. Every year, Chef Bob was at the Charleston Grill, it was awarded AAA Four-Diamond and the Mobile Four-Star award, and in 2001-2005 he was nominated four times for The Beard Foundation "Best Chef Southeast" award. Always well regarded as a media-savvy chef, he has won an Emmy for his television show “Off the Menu” with Turner South. He also hosted 2 cooking shows with PBS, U Cook with Chef Bob and Sing for Your Supper with Chef Bob. Currently, he is the owner of “In the Kitchen with Chef Bob Waggoner” where he hosts cooking classes in a relaxed, casual, and sophisticated atmosphere. With his easygoing nature, he can teach anyone the culinary tips and techniques for "how it's done" in the finest restaurants.

More information:


  • Italy
  • Tuscany
  • Florence
  • Pienza
  • Orvieto
  • Montepulciano
  • Cortona
  • Siena
  • Culinary Tour
  • Wine Tour
  • Tuscan Wine

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Premier Tours & Travel, Inc.

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