Upon arrival at the airport, you will be transferred to your hotel in Florence, where you’ll spend the next two nights. The birthplace of the Renaissance, Florence is a living museum to some of the world’s greatest artistic treasures, from Michelangelo's David to Botticelli's Birth of Venus. As the regional capital, Florence is also the gateway to the rolling hills of Tuscany.

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Savor your first taste of Tuscan cuisine this evening when you join your fellow travelers for a welcome dinner.

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Note: if you wish to spend more time in Florence, ask your Personal Vacation Manager about the optional hotel extension – which will add one or two nights to your Florence hotel stay.

This morning, we’ll visit Villa Machiavelli, an elegant 15th-century villa set among 600 acres of vineyards and olive groves. When the Medicis returned to power in Florence in 1512, Niccolò Machiavelli was banished from the city and moved into the family’s villa on the outskirts of Florence. It was here where Machiavelli wrote The Prince, arguably the most controversial political novel of all time. We’ll enjoy a cooking class followed by lunch and wine tasting, along with a guided tour of the magnificent villa, designed by Michelangelo for the Machiavelli family.

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After our visit, we’ll return to our hotel, and you’ll have the remainder of the day and evening to explore the Renaissance treasures of Florence at your leisure.

Today, we’ll set out into the Tuscan countryside, beginning with a visit to a family-owned olive oil mill. Tuscan extra virgin olive oil is considered among the best in the world, and many small towns have family-owned mills where the locals take their hand-picked crop of olives for pressing, just as they have for generations. We’ll learn about the production process during our visit and enjoy tastings to compare the flavorful varieties of olive oil made here.  Family-owned butcher shops—or macellerie—are another longstanding Tuscan tradition, and we’ll stop for a sampling of some of the cured meats and other quality products offered here.

Following our visit,we’ll arrive at our hotel in Colle di Val d’Elsa, a medieval town nestled inthe heart of Tuscany that makes an ideal base for our discoveries over the nextfew days.

Begin the day with a guided tour of the picturesque hilltop town of Volterra. Surrounded by ancient walls and perched on a hill overlooking Val di Cecina, Volterra is renowned for sculpting beautiful works of art from alabaster, a craft that dates back to the Etruscans.  We’ll visit a workshop to discover how skilled alabaster artisans—alabastrai—are keeping this proud tradition alive in Volterra. You’ll also have some free time in Volterra to enjoy lunch, do some shopping, or just stroll along the medieval town’s atmospheric stone lanes.

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Then, we’ll enjoy a demonstration of another centuries-old Tuscan artistic tradition, hand-painted ceramics, during a visit to the hilltop town of Certaldo. Inhabited since Etruscan times, this medieval hamlet in the heart of the Val d'Elsa is also the birthplace of Boccaccio, author of the Decameron.

Our Tuscan discoveries continue with a visit to the enchanting town of Cortona. Perched on a hilltop overlooking the Val di Chiana and Lake Trasimeno, Cortona is often called the “pearl of Tuscany,” but many know it better as the setting for Frances Mayes’ heartwarming true story, Under the Tuscan Sun. You’ll have free time to wander through Cortona’s medieval streets and take in the scenic vistas that perfectly capture the relaxed pace of Tuscan life portrayed in Mayes’ bestselling memoir.

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After our visit, we’ll stop in Montepulciano, a medieval hilltop town teeming with elegant Renaissance palazzi inside its ancient walls. Home of one of the most prestigious of all Italian wines, Vino Nobile di Montepulciano, our visit features a private tour and tasting at one of the boutique wineries set amidst the beautiful Tuscan countryside. A light lunch and relaxation time is also included before we return to our hotel.

This morning we’ll visit Siena, a one-time capital that once rivaled Florence that is now considered the best-preserved medieval city in all of Italy. We’ll explore Siena’s magnificent Duomo, a Romanesque-Gothic cathedral whose outside features statues of the heads of 172popes peering down as you enter, and sculptures by Michelangelo and Bernini waiting inside. We’ll also spend time in one of Europe’s most splendid medieval squares, Piazza del Campo, a UNESCO World Heritage Site. This fan-shaped medieval gem is home to Italy’s most famous horse race, the Palio di Siena, a twice-yearly tradition dating back to 1633.

After exploring Siena, we’ll head into the Tuscan countryside for a visit to a local winery, followed by a light lunch featuring farm-fresh local ingredients that are hallmarks of Tuscan cuisine.

After returning to our hotel, you’ll have your final evening at leisure—perhaps to linger over a glass of wine while reflecting on how no other region of Italy embodies the essence of la dolce vita like Tuscany.

After breakfast, we’ll have to say “Arrivederci, Toscana” and transfer to the port in Civitavecchia, where you will board the Celebrity Constellation and begin your transatlantic cruise to Florida.

Ports of call include Alicante and Malaga, Spain; Gibraltar, United Kingdom; Casablanca, Morocco, concluding in Tampa.

Enjoy breakfast onboard, then disembark the Celebrity Constellation and transfer to the airport for your return flight home.‍

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For meals not included in your land programs, all hotels chosen include a restaurant on property where you may relax and enjoy a meal. In addition, your guide is available to make suggestions on nearby dining, shopping or sightseeing.