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Highlights of Italy

  • Duration8 Nights
  • StylePrivate
  • When to GoMarch - October
  • Price GuideFrom $4,420 Per Person
This exciting itinerary will bring you to three of Italy’s top cities for the perfect way to make the most of limited time. Over nine days and eight nights, you’ll discover ancient Rome, including the iconic Roman Colosseum, Vatican City and its many exceptional museums, a world of incredible works of art in Florence, two of Tuscany’s most stunning medieval hilltop towns, and the dreamy waterways of Venice. Throughout your trip, you’ll stay in four- and five-star hotels that have been hand-selected to ensure your comfort, enjoy 24/7 support from our dedicated staff, and embark on numerous tours led by expert local guides.

At a Glance

  • Days 1 - 3
    • Rome

    • Days 4 - 6
      • Florence

      • Days 7 - 9
        • Venice

        • 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: +1 844 381 5808
          Request a Quote

          What's Included

          • Accommodation in hand-picked 4- and 5-star hotels
          • Personalized trip planning in advance
          • Private transfers as noted on the itinerary
          • Private half-day Ancient Rome tour
          • Private half-day Vatican City & Museums tour
          • Private half-day Florence and the Accademia Gallery tour
          • Private full-day San Gimignano and Siena hilltop towns tour
          • Half Day Tour of Doge's Palace, St. Mark's Cathedral & Glass Showroom

          Day by Day Itinerary

          • Days 1 - 3:


            Colosseum arches in RomeVatican architectures, Italy.

            Welcome to Italy! Upon your arrival at the airport in Rome, you’ll be met by our driver who will provide a private transfer to your hotel. Once you’ve checked in, enjoy the remainder of the day at leisure. It’s a perfect time to rest after a long flight or head out and stretch your legs as the fresh air is great for easing jet lag. It’s fun just to stroll the narrow streets and alleyways with something to discover around every corner with endless historical landmarks, hops, and enticing outdoor cafes where you can sip a glass of wine and enjoy some people-watching.

            Half-Day Ancient Rome Tour

            Get to know ancient Rome by meeting our local guide for a half-day tour. You’ll head to the city’s most famous symbol, the Roman Colosseum which was used for over 500 years from the 1st century through 532 AD. Holding more than 50,000 spectators, it was a venue for everything from theatrical demonstrations and gladiatorial competitions to some vicious battles between man and beast. After exploring, you’ll head to the Roman Forum nearby which served as the religious and political center of the Roman Empire. It includes some of ancient Rome’s oldest structures, with important government buildings, shops, open-air markets, and more.

            Half-Day Vatican City & Museums Tour 

            Joining your knowledgeable guide, you’ll explore the Vatican museums which display works from the vast Catholic Church collection that’s been amassed over centuries. It includes a number of the world’s most renowned Roman sculptures and some of the most important works of Renaissance art. Explore the Gallery of Geographical Maps and the Gallery of Tapestries, and visit St. Peter’s Basilica and the Sistine Chapel where you’ll marvel at Michelangelo’s fresco on the ceiling. The rest of the day is yours, a great time to shop for souvenirs or simply explore the streets near your hotel.


            • Rose Garden Palace Hotel in Rome, Italy.

              Rose Garden Palace

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            • Hotel de la Ville in Rome, Italy.

              Rocco Forte de la Ville

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          • Days 4 - 6:


            Hand details on the DavidView of San Gimignano town in Tuscany, Italy.

            Heading to your next destination today, you’ll take a private transfer to the train station, with tickets in hand for the high-speed train to Florence. Another driver will meet you there, providing a transfer to your hotel in the city. With the remainder of the day at leisure, you might want to enjoy a preview of the city. Mercato Centrale is a great place to shop with stalls selling produce and a wealth of other items or take in a magnificent view of the city from 300 feet above by climbing “Giotto’s Campanile,” the bell tower of the Duomo, Florence’s cathedral.

            Half-Day Walking Tour of Florence and the Accademia Gallery

            Start your day with a walking tour through the city, visiting many of the must-see landmarks, including Florence Cathedral, constructed between 1296 and 1436, Palazzo Vecchio, and Santa Croce Church which serves as a burial place for multiple Italian greats like Michelangelo and Galileo. Your tour’s highlight is Accademia Gallery. Your guide will bring you to the most important works which include Michelangelo’s original statue of David with its remarkable life-like details, along with paintings by Allessando Allori, Andrea del Sarto, Raphael, Botticelli, Pontormo, and more. You can explore on your own at the end of the tour, returning to your hotel at leisure.

            Full-Day San Gimignano & Siena

            Leaving Florence for the Tuscan countryside, enjoy a day trip to the medieval hilltop towns of San Gimignano and Siena. As you approach San Gimignano, its spectacular skyline with 11th-century towers comes into view. After your visit you’ll head to a farmhouse nearby to enjoy a typical local meal and then enjoy the second part of your tour, meeting a local guide in Siena. Discover the world-famous Piazza del Campo that hosts the renowned biannual II Palio horse race as well as being a popular gathering spot for locals. It hosts the 13th-century City Hall and a 335-foot-high bell tower.


            • Hotel L'Orologio in Santa Maria Novella Square in Florence, Italy.

              Hotel L'Orologio

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            • Savoy Hotel in Florence, Italy.

              Rocco Forte Hotel Savoy

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          • Days 7 - 9:


            Grand Canal View in Venice, Italy.Carnival Mask in Venice, Italy.

            This morning you’ll travel to Venice, taking a private transfer to the train station in Florence for a ride on the highspeed train. Upon arrival in Venice you’ll enjoy an afternoon at leisure. Venice is known for it’s stunning canals, bridges, and architecture, which have earned it the nickname “The Floating City”. Stroll through the historic center to admire palaces, churches, and piazzas. Visit the iconic St. Mark’s Basilica and take a gondola ride along the Grand Canal. For lunch, indulge in seafood risotto or cicchetti, and try Venice’s famous Bellini cocktail. Explore museums and galleries or simply wander the streets. Take a romantic stroll through the city at night and admire the canals’ lights and reflections.

            Half Day Tour of Doge’s Palace, St. Mark’s Cathedral & Glass Showroom

            An in-depth half-day tour explores many of the highlights of Venice, including St. Mark’s Square where it all begins. You’ll meet our guide at the square to begin your walking tour that includes the remarkable landmarks here like St. Mark’s Cathedral. As there can be no narration inside, before entering your guide will tell you all about the basilica’s history and then you’ll get to explore the beautiful interior. There will be time to visit the glass showrooms as well where you can browse or purchase authentic Venetian glassware. Visit Doge’s Palace, a fine example of gothic-style architecture with an ornate façade, climb the golden staircase and cross the Bridge of Sighs that links the palace to a historic prison on the other side of the canal.


            With the ninth day here, it will soon be time to depart the Floating City. You’ll want to get your bags packed and ready as you’ll take a private transfer from your hotel upon checkout to Venice’s airport. We hope having explored Rome, Florence, and Venice, you’ll have many memories and photos o take with you. If you aren’t ready to go home just yet, reach out to our travel experts who will be happy to create a bespoke addition to your itinerary.


            • Sina Palazzo Sant'Angelo in Venice, Italy.

              Hotel Palazzo Sant'Angelo

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            • Ca' Sagredo Hotel in Venice, Italy.

              Ca' Sagredo

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