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Highlights of Tuscany

  • Duration8 Nights
  • StylePrivate
  • When to GoApril - October
  • Price GuideFrom $4,170 Per Person
One of Italy’s most famously beautiful regions, Tuscany is a vast area known for its vineyard-covered landscapes, olive trees, sunflowers, medieval hilltop villages, and fine wine. If you’ve dreamed of visiting as so many others have, this is the ideal trip for exploring the highlights and enjoying some unique experiences too. You’ll start in Florence, the cradle of the Renaissance, and then head to charming towns like Cortona, Siena, San Gimignano, and Volterra. There will be many opportunities to discover Tuscany through its flavors, from a cooking class to wine tastings. Enjoy private guided tours, private luxury transfers, and upscale accommodations throughout.

At a Glance

  • Days 1 - 2
    • Florence

    • Days 3 - 5
      • Cortona

      • Days 6 - 9
        • Siena

        • Meet our Expert

          Perian, Travel Specialist


          Italy Specialist

          Hi I’m Perian. I’m originally from Toronto and now live in Milan. I frequently travel around Italy throughout the season in search of new off the beaten track experiences and charming boutique properties for my clients.

          CALL US ON: +1 844 879 7838
          Request a Quote

          What's Included

          • 8 nights in hand-picked 4- and 5-star hotels
          • Expert planning/customizable itinerary
          • Staff support is available 24/7
          • Private Florence walking tour, including Accademia Gallery
          • Winery visit, including a tasting
          • Cooking class in Cortona
          • Private walking tour in Siena
          • Private tour of Gimignano and Volterra
          • Private luxury transfers from start to finish

          Day by Day Itinerary

          • Days 1 - 3:


            The Brunelleschi Duomo in Florence, Italy.View of Dante in Santa Croce square in Florence, Italy.

            Your journey through the Highlights of Tuscany begins upon your arrival to Florence’s airport where your driver will be waiting to welcome you and provide private transfer to your hotel in the city. After checking in, enjoy the rest of the day to yourself. You might want to rest after a long flight or stretch your legs with a stroll along the cobbled streets. It seems there’s something to discover around nearly every corner here, including impressive galleries, art museums, and even churches with incredible works. Or find a seat at one of the many outdoor cafes to enjoy a drink and fantastic people-watching.

            Half-Day Walking Tour, including Accademia Gallery

            You’ll get to know Florence more in-depth on a private half-day walking tour with our local guide. You’ll see many of the city highlights, including Piazza del Duomo, its most iconic square, home to the Florence Cathedral. Visit the 13th-century Santa Croce Church where Italian greats like Michelangelo and Galileo are buried and Piazza della Signoria, another famous square, long a hub of political life. Accademia Gallery is included too. Michelangelo’s David is its crown jewel although there are many masterpieces here, including paintings by Raphael and Botticelli. You’ll have time after your tour to explore on your own, returning to your hotel at leisure.


            • Hotel Brunelleschi in Florence

              Brunelleschi Hotel

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            • Prestige Suite of Portrait Firenze Lungarno Collection

              Portrait Firenze

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          • Days 3 - 5:


            Tuscany rolling hillsCortona town in Tuscany, Italy.

            Wine Tasting at Avignonesi Winery 

            Heading into the Tuscan countryside with your private driver/guide, your ultimate destination is the walled hilltop town of Cortona which was made famous by the novel and film, “Under the Tuscan Sun.” But first, you’ll stop to visit Avignonesi Winery in the Montepulciano wine region for a tasting. It’s best known for Vino Nobile di Montepulciano, made with the Sangiovese grape, but the facility also makes grappa, honey, and olive oil. Once you reach Cortona, you’ll check into your hotel with the remainder of the day all yours. There are elegant squares, palaces, and museums waiting to explore along with plenty of tasty eats to enjoy.

            Cooking Class

            One of the top experiences on your itinerary will be enjoyed today: a cooking class at Baracchi winery. It’s been continuing the tradition of a family who made wine here for over 150 years, including the first Syrah Riserva and the first Cabernet Riserva. Learn how to cook some of the most delicious Tuscan dishes in the chef’s kitchen getting hands-on, learning how to prepare favorite recipes using the region’s abundance of fresh, seasonal ingredients. You’ll discover the secrets of Tuscan cuisine as you help prepare them. The best part is enjoying the results alongside tasty wines produced right here in the winery cellars.

            Day at Leisure

            A full day of leisure is yours, providing the perfect way to savor the little moments like simply wandering the streets, and discovering that perfect family-run trattoria that serves homemade dishes based on recipes handed down through generations. There are plenty of sights to see within the walls of the historic center too. Don’t miss the chance to visit Piazza Garibaldi where you’ll enjoy a panoramic view that stretches from Montepulciano to Val di Chiana. You’ll want to see the 14th-century Palazzo del Popolo and the 13th-century Palazzo Comunale too. If you’re interested in Cortona’s history, be sure to explore the Museum of the Etruscan Civilization.


            • Il Falconiere Hotel in Cortona, Tuscany

              Il Falconiere

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            • External view of Villa di Piazzano in Cortona

              Villa di Piazzano

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          • Days 6 - 9:


            Volterra town in Tuscany, Italy.Windy road near Pienza in Val D'Orcia, Tuscany.

            Guided Siena Walking Tour

            Leaving Cortona with your private driver, you’ll travel to your final destination: Siena. Upon arrival, you’ll check into your hotel and then join a guide for a walking tour. This pretty medieval hilltop town may best be known for Piazza del Campo, the famous fan-shaped square that hosts the Palio di Siena horse race twice each year. It also hosts the 335-foot-high Torre del Mangia bell tower and a 13th-century City Hall. You’ll see it all along with the gothic Siena Cathedral that dates to the 12th century, Gaiai Fountain, and some impressive works of art, including sculptures, paintings, and frescos created by renowned Italian artists.

            Day at Leisure

            There’s plenty to enjoy in Siena so we’ve provided another day of leisure. This town is best enjoyed at a casual pace that will allow you to immerse yourself in its grandeur. Perhaps linger over breakfast and then head to the Torre del Mangia bell tower in Piazza del Campo to climb the 400 steps for a panoramic view. There are multiple museums to explore, with one of the most impressive and one of Italy’s oldest private museums, Museo dell’Opera del Duomo which is located in Sienna Cathedral. It displays the original statues from the cathedral’s façade along with Duccio masterpieces dating to the 14th century.

            Full-Day Private Tour of San Gimignano & Volterra

            On your final full day in Tuscany, your private driver will bring you to San Gimignano, known for its over a dozen medieval towers that have survived for a thousand years, creating a spectacular skyline that can be seen for miles. You’ll visit the tallest of the towers which soars nearly 180 feet to enjoy an awe-inspiring view of the surrounding landscape. Afterward, continue to Volterra where you’ll meet a local guide for a walking tour. The town was one of the Etruscan power centers from the 4th through 6th century BC and features intriguing landmarks, including a 1st-century AD Roman theater.


            Savor your last moments in Tuscany, enjoying breakfast before your private driver meets you at your hotel for transfer to the airport in Florence, with your journey soon coming to an end. There you can head out to explore elsewhere or catch your flight home, taking your memories, and probably many photos with you. There are many fabulous destinations that can easily be reached from here if you’d like our travel experts to create a bespoke itinerary addition. Otherwise, we wish you a safe return trip and hope to see you again on another Unforgettable adventure.


            • Hotel Athena in Siena

              Athena Hotel

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            • Grand Hotel Continental in Siena

              Grand Hotel Continental

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