Unforgettable Travel Company

Highlights of Tuscany

  • Duration8 Nights
  • StylePrivate Tour
  • When to GoApr - Oct
  • Price GuideFrom $4,485 Per Person
Tuscany is one of Italy’s most popular regions to visit. It covers a vast area, with vineyard- and olive tree-covered landscapes, medieval hilltop villages, and a wealth of historic treasures. This 9-day, 8-night trip begins and ends in magnificent Florence where you’ll see the iconic statue of David and countless other renowned works by the Italian masters. Visit a Montepulciano winery, take a cooking class led by a talented Tuscan chef, explore magnificent medieval hilltop towns, and enjoy multiple locally led walking tours to discover iconic historical landmarks. In between, you can be sure there will be plenty of mouthwatering Tuscany dishes and fine wines to enjoy too.

At a Glance

  • Days 1 - 2
    • Florence

      • Private transfer from Florence Airport to hotel
      • Private half-day walking tour of historic Florence
      • Entrance to Accademia Gallery - home to the Statue of David
  • Days 3 - 5
    • Cortona

      • Private transfer from Florence to Cortona in rural Tuscany
      • Visit Avignonesi Winery with tour & tasting
      • II Falconiere Cooking Class, hosted at Baracchi Winery
      • Day at leisure to enjoy Cortona
  • Days 6 - 9
    • Siena

      • Private transfer from Cortona to Siena
      • Private walking tour of Siena
      • Day at leisure to explore Siena
      • Full-Day Private Tour of San Gimignano & Volterra
      • Private transfer from Siena to Florence Airport
  • Meet Our Expert

    Perian 257 246


    Italy Specialist

    From the snowy peaks of the Dolomites to the sun-kissed coasts of Puglia, my European journey has been nothing short of diverse and immersive. Now based in the chic ambience of Milan, this deep connection with Italy and Malta ensures that I bring unmatched authenticity to every travel itinerary I curate.

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

    What's Included

    • 9 nights in 4 or 5-star accommodation
    • Daily breakfast at all hotels
    • Private arrival and departure airport transfers, including VIP fast track immigration on arrival
    • All mentioned airport transfers and road transport on a private basis in Air Conditioned minivans
    • All mentioned tours and sightseeing on a private basis with private driver and English-speaking local guides
    • Entrance fees for any mentioned sightseeing, permits, local taxes, etc
    • 24/7 support from our dedicated staff
    • Flexible, personalized itinerary based on your interests

    What's not Included

    • International flights from your country of origin
    • Tips or gratuities to guides, drivers, hotel staff
    • Any meals, tours, or activities other than those specifically mentioned in itinerary
    • Incidental local expenses - souvenirs, laundry, taxis, etc
    • Visas for Italy. Your consultant will advise of any required visas and how to obtain them.
    • Travel insurance - we strongly recommend you purchase travel insurance as soon as you have booked your trip.

    Day by Day Itinerary

    • DAY 1

      Florence: Arrival into Florence

      D3Florence 2 1Florence ceiling 500x333 1

      Being your journey through the highlights of Tuscany in the cradle of the Renaissance. Upon your arrival at Florence’s airport, you’ll be met by our driver for a private transfer to your hotel in the city. The rest of the day is yours to rest and refresh, perhaps beating any jet lag by taking a walk through the cobbled streets with fresco-filled churches, grand 15th– and 16th-century palaces, and world-renowned art museums with works by masters like Botticelli and Michelangelo. If you need a pick-me-up, you’ll find plenty of cafes for sipping an espresso, including options for people watching with a Duomo view. Or, head to the terrace at Borgo San Jacopo restaurant which offers an especially romantic view of the city’s oldest bridge, Ponte Vecchio.

      Accommodation Options:

      • Brunelleschi Hotel main

        Brunelleschi Hotel

        Read More
      • Portrait Firenze

        Portrait Firenze

        Read More
    • DAY 2

      Florence: Half-Day Walking Tour, including Accademia Gallery

      David 500 x 333Florence Street 500 x 333

      Our local guide will meet you at your hotel this morning for a walking tour of Florence that includes a guided visit to the Accademia Gallery. Start at Santa Croce Church, built in the late 13th-century and most notable as the burial place for Italian greats, including Michelangelo and Galileo. Continue from here to Piazza del Duomo which houses the famous Florence Duomo and Piazza Della Signoria, the main square in Florence and the center of political life since the 14th-century which is overlooked by Palazzo Vecchio. In Accademia Gallery, you’ll see Michelangelo’s David, which was moved here in 1873. His St Matthew and Prisoners sculptures can also be viewed along with paintings by Raphael, Botticelli, and more. One of the newer sections is the Museum of Musical Instruments which displaces one-of-a-kind masterpieces by Bartolomeo Cristofori, the inventor of the piano. At the tour’s conclusion, return to your hotel at leisure.

    • DAY 3

      Cortona: Private Transfer from Florence via Avignonesi Winery

      Cortona 1 500x333 1Cortona street 500x333 1

      Say farewell to Florence with your private driver providing transfer to the walled hilltop town of Cortona, made famous by the book and subsequent film, “Under the Tuscan Sun.” It’s about a 90-minute drive, but along the way, there will be a stop made to visit Avignonesi Winery in the world-famous Montepulciano region for a tasting. It’s renowned for its Vino Nobile di Montepulciano, made from the Sangiovese grape, but it also produces grappa, honey, and olive oil. After reaching Cortona and getting settled into your hotel, enjoy the rest of the day at leisure. Enjoy the impressive view of the valley below or wander through the streets with some 3,000 years of history to discover, including beautiful squares, palaces, and intriguing museums.

      Accommodation Options:

      • Relais Il Falconiere 3 Small 300x200 1

        Relais Il Falconiere & Spa

        Read More
    • DAY 4

      Cortona: Cooking Class

      Italy pasta making 1Italy cooking class 500x333 1

      A highlight of your time in Tuscany, today you’ll step into the kitchen of a talented chef as part of the II Falconiere Cooking Class, hosted at Baracchi Winery. A fully immersive experience, it’s one of the best ways to get to know the delicious Tuscan fare, making exquisite recipes that are typical of the area using fresh seasonal ingredients. The secrets of why this food is so renowned will be revealed as you help prepare two dishes with a tasting during your lesson included. It will be combined with wines that were produced here in the cellars of Baracchi Winery, which has been following the tradition of a family who has cultivated the vines and produced the wines since 1860. That includes the first Syrah Riserva, the first Cabernet Riserva, and unique wines such as the first sparkling wine produced from Sangiovese.

    • DAY 5

      Cortona: Day at Leisure

      Cortona 2 500x333 1Vineyards Cortona

      Enjoy a day of leisure, perhaps exploring Cortona’s historical center that’s still surrounded by well-preserved walls. Highlights include the Piazza Della Repubblica which holds the 14th-century Palazzo del Popolo and the imposing Palazzo Comunale that dates back to the 13th-century. From Piazza Garibaldi, you can take in a breathtaking panoramic view that stretches from Val di Chiana to Montepulciano. The best way to learn about the origins of the town is to visit MAEC, the Museum of the Etruscan civilization with its fascinating, eclectic collection. It includes a famously unusual 5th-century BC chandelier, the largest of its kind ever found, with dolphins and waves surrounding a gorgon’s head. The elegant décor and 17th-century frescoes alone make it worth the visit, but there are Roman statuettes and many artifacts, like bronze figures, weapons, paintings, and much more.

    • DAY 6

      Siena: Private Transfer from Cortona & Guided Siena Walking Tour

      Siena 1Siena flags 500x333 1

      Heading to the final destination this morning, a private transfer will bring you to Siena, the classic medieval hilltop town best known for Piazza del Campo, the vast, fan-shaped piazza that hosts the Il Palio horse race. After checking into your hotel, you’ll meet your local guide for a walking tour of the city, including the famous square. It’s not only the site of the globally famous horse race but it hosts the 13th-century City Hall and the nearly 335-foot-high Torre del Mangia bell tower. You’ll see Gaia Fountain and Sansedoni nearby as well as the exterior of Siena’s gothic cathedral that dates to the 12th-century and the Battistero. Both feature remarkable sculptures, frescoes, and paintings created by some of the Italian greats.

      Accommodation Options:

      • Hotel Athena main

        Hotel Athena, Siena

        Read More
      • Grand Hotel Continental main

        Grand Hotel Continental

        Read More
    • DAY 7

      Siena: Day at Leisure

      Siena 1 1Siena town hall 500x333 1

      Enjoy the city of Siena at your leisure today. It’s easy to get lost among its medieval grandeur, best done by slowing down your pace to take in the enchanting atmosphere. By climbing Torre del Mangia you’ll enjoy an awe-inspiring vista from one of Italy’s tallest secular towers. There are more than 400 steps to get to the top, but the 360-degree view that awaits is a reward that makes it well worth the effort. Afterward, we recommend sampling what’s said to be the best gelato in Italy (and the world) at an authentic gelateria, La Vecchia Latteria. The Museo dell’Opera del Duomo is one of Italy’s oldest private museums, housed on the south side of the cathedral. It features the original statues from the cathedral façade and one of the early 14th-century masterpieces by Buoninsegna.

    • DAY 8

      Siena: Full-Day Private Tour of San Gimignano & Volterra

      D4San Gimignano ItalyVolterra 500x333 1

      Enjoy a scenic drive to San Gimignano, the City of Beautiful Towers. The hilltop town is famous for its 14 surviving medieval towers that create a stunning skyline visible from the surrounding Tuscan countryside, sometimes referred to as “The Manhattan of Tuscany.” The towers date from the 11th to 13th centuries, with Torre Grossa the tallest at nearly 180 feet. From here you can take in a jaw-dropping view of the landscape below. Continue your journey to picturesque hilltop Volterra, one of a dozen Etruscan power centers between the 4th and 6th centuries BC. You’ll meet a local guide here for a walking tour that includes a stroll through Piazza Dei Priori and a close-up look at the medieval walls, gates, a 1st-century Roman theater, and renaissance-style palaces.

    • DAY 9

      Siena: Departure

      Florence ItalyTuscany country road

      Enjoy your last morning in Siena, fueling up with breakfast before your driver picks you up for a private transfer back to the airport in Florence. If you’d like to spend more time here or combine this trip with another, reach out to our expert travel staff who will be happy to help you make it happen. Otherwise, we wish you a safe trip back home and hope to host you on another memorable adventure in the future.

    Let’s make this itinerary yours.

    Speak to our experienced Destinations Experts about designing this itinerary around your budget and needs

    Other trips you may be interested in