Highlights
- Explore history in Rome with tours of the Colosseum, Vatican, and Sistine Chapel
- Cruise around the fabled island of Capri and see the Blue Grotto
- Take a day trip along the Amalfi Coast to explore three famous towns
- Savor olive oil and Chianti wines in the Tuscan countryside
- Float through Venice in a gondola after a walking tour of the city's top sights
Brief Itinerary
Day | Highlights | Overnight |
---|---|---|
Day 1 | Arrive in Rome, Free Time in the Italian Capital | Rome |
Day 2 | Discover the Vatican & Sistine Chapel, Rome Afternoon Food Tour | Rome |
Day 3 | Explore the Colosseum & Roman Forum, Villa d'Este Tour in Tivoli | Rome |
Day 4 | Train to Naples, Transfer to Sorrento via Pompeii | Sorrento |
Day 5 | Boat Tour to Capri & the Amalfi Coast | Sorrento |
Day 6 | Day Trip Along the Amalfi Coast: Ravello, Amalfi & Positano | Sorrento |
Day 7 | Transfer to Naples, Train to Florence, Explore Renaissance Gems | Florence |
Day 8 | Full-Day Olive & Wine Tasting in the Tuscan Countryside | Florence |
Day 9 | Train to Venice, Free Time in the Floating City | Venice |
Day 10 | Venice Walking Tour & Gondola Ride, Cicchetti & Wine Tour | Venice |
Day 11 | Depart Venice |
Detailed Itinerary
Day 1: Arrive in Rome, Free Time in the Italian Capital
Ciao, and welcome to Rome—the Eternal City! The capital of Italy is filled with incredible bucket-list sights, ancient monuments to gaze at, and delicious pizza and pasta. On arrival at the airport, a private driver will meet you and take you to your accommodation in the center of Rome. Drop your bags and refresh, then head out onto the cobblestone streets to explore at your pace.
This afternoon is all yours to enjoy beautiful Rome. You could hop on a tour boat to explore the city banks from the Tiber River. Or wander the ornate rooms of the Galleria Borghese, viewing the splendid frescoes at one of the world's most beautiful art museums. After, take a peaceful stroll around the Villa Borghese gardens, enjoying its beauty and calm far from the chaos of the city. Then, enjoy the sunshine in the orange groves of the Giardino degli Aranci on the city's Aventine Hill before finding a local trattoria for a soul-warming bowl of pasta.
Day 2: Discover the Vatican & Sistine Chapel, Rome Afternoon Food Tour
This morning you'll explore the world's smallest sovereign state: Vatican City. Join a local guide for a three-hour immersive tour of the Vatican City's museums and the Sistine Chapel. The Vatican is rich in history and art, housing some of the most important Renaissance masterpieces in the world. During the small-group tour, you'll visit the Pio Clementio Museum, Gallery of the Candelabra, Gallery of Tapestries, Gallery of the Geographical Maps, and Raphael Rooms before seeing Michelangelo's masterpiece—the Sistine Chapel—and St. Peter's Basilica.
Day 3: Explore the Colosseum & Roman Forum, Villa d'Este Tour in Tivoli
Step back in time this morning—about 2,000 years—to discover the glories of the Roman Empire. A private guide will lead you first to the Amphitheatrum Flavium, better known as the Colosseum. They'll share stories about the spectacular highlights of Imperial Rome and how the ancient Romans used to live as you stroll through the most historic parts of the city, visiting monuments including the Roman Forum and Trevi Fountain.
This afternoon, you can take an optional day trip to Tivoli, where you'll explore the magnificent Villa d'Este. A private driver and guide will lead the way, helping you explore this symbol of the Italian Renaissance and architectural gem. The estate is now UNESCO-listed, and you'll understand why as you wander the ornate gardens, winding past fountains and sculptures of the Baroque and Renaissance periods. After, you'll return to Rome.
Day 4: Train to Naples, Transfer to Sorrento via Pompeii
Swap the streets of the capital for the coastal Sorrentine Peninsula today. Board a 70-minute high-speed train south to Naples, where a private driver will be waiting to transfer you to your accommodation in Sorrento, about a 45-minute drive away. En route, make a special stop at the archaeological site of Pompeii. Once a thriving and sophisticated Roman city, Pompeii was buried under a thick layer of ash after the eruption of Mount Vesuvius in 79 CE and lost for 1,500 years. A stroll along these ancient streets reveals preserved villas, shops, and plazas.
Once in Sorrento, drop your bags, grab a towel, and set off on a beach-hopping adventure. The beaches along Sorrento's southern coast are some of the most beautiful in Italy. Find the city's main beaches around the Marina Grande and Marina Piccola ports, or organize a car to take you a short drive away to lesser-known stretches of sand. After a quiet and relaxing afternoon sunbathing and swimming in crystal clear waters, head to Piazza Tasso, Sorrento's largest and most popular gathering place, for an evening gelato and spot of people-watching before dinner.
Chat with a local specialist who can help organize your trip.
Day 5: Boat Tour to Capri & the Amalfi Coast
Set sail on a full-day boat tour exploring the Bay of Naples and the Amalfi Coast, with a special visit to the island of Capri and its famous Blue Grotto. You'll see the ruins of a Roman villa near Bagni della Regina Giovanna as you make your way toward Capri, then circle the island by boat to take in the breathtaking views of landmarks such as the towering Faraglioni rocks, the Natural Arch, the famous Villa Curzio Malaparte, and the Punta Carena Lighthouse.
You'll have the chance to stop for a swim or snorkel, or simply relax on board with complimentary snacks and drinks, including a limoncello tasting. This special day out also includes free time on Capri, so you'll have three to five hours to explore as you wish before the return cruise to Sorrento.
Day 6: Day Trip Along the Amalfi Coast: Ravello, Amalfi & Positano
The Amalfi Coast is renowned for its lush landscapes, lemon groves, terraced vineyards, warm hospitality, and fresh seafood—and today, you'll explore the best of the region with a full-day tour. A private driver and guide will take you to three of the coast's most iconic towns: Ravello, Amalfi, and Positano. Start with a 90-minute drive from Sorrento to Ravello along winding coastal roads. Located at the top of the Dragone Valley, Ravello enjoys endless views, and you can wander the rural clifftop village and visit the famous Villa Rufolo and Villa Cimbrone.
Afterward, wind down the hill to Amalfi, a town famous for its lemons and limoncello. Here you can shop for local products, visit the historic Cathedral of Amalfi, and enjoy a zesty pasta for lunch. Then, you'll curve along the coast back to Positano, the jewel of the Amalfi Coast. This colorful village cascades down the hillside in dramatic fashion, ending at a pebble beach where vibrant umbrellas look straight from a movie scene. Wander down the narrow alleyways and staircases and go for a swim at the beach before returning to Sorrento.
Day 7: Transfer to Naples, Train to Florence, Explore Renaissance Gems
Wave goodbye to Sorrento this morning when a private driver collects you for the 45-minute transfer to Naples. From here, you'll board a three-hour high-speed direct train to Florence. On arrival, a private driver will transfer you to your accommodation in the "Jewel of the Renaissance" and the capital of Tuscany. This historic city is filled with architectural beauties, such as the Duomo and is home to world-famous art by Michelangelo and da Vinci, so drop your bags at the hotel and set out to discover this open-air museum.
This afternoon is yours to explore the sights of Florence. You could start at the Duomo, the third-largest church in the world, then grab a quick lunch at the Mercato Centrale. After, wander through the nearby Piazza della Republica and Piazza della Signoria, where you'll find replicas of famous statues, including Michelangelo's "David." Then, enter the Uffizi Galleries, one of the world's great art museums with amazing Italian Renaissance art, including the "Birth of Venus" by Botticelli. End your day crossing the Ponte Vecchio bridge, then climb up to Piazzale Michelangelo for sunset views.
Day 8: Full-Day Olive & Wine Tasting in the Tuscan Countryside
Venture into the Tuscan countryside today with a private driver and guide who will lead you on a special gourmet tour through the rolling Chianti Hills. Your first stop will reveal the secrets of Tuscany's olive oil production. This region is famous worldwide for its high-quality extra virgin olive oil, and you'll visit a mill on an ancient estate to sample the liquid gold. Then, you'll get acquainted with how Tuscans keep the long-lasting traditions of winemaking alive.
Meet a sommelier to hear stories about Chianti wines and the varieties—sangiovese, canaiolo, and more—grown here. Over the course of the day, you'll visit three wineries, tasting different expressions of Chianti wines, enjoying a hearty traditional lunch, and stopping at a beautiful local village to explore the stone streets. With a full heart and full stomach, you'll return to the city in the afternoon.
Day 9: Train to Venice, Free Time in the Floating City
It's time to shoot over to Venice, Italy's famous floating city. Head to the train station in Florence and board a comfortable high-speed train. The direct route to Venice takes about 2.5 hours and you'll pop up within the island city. From here, a private water taxi will take you to your hotel, cruising along atmospheric Venetian canals and past impressive buildings and bridges. Check in and refresh ahead of this free time to explore this afternoon.
Day 10: Venice Walking Tour & Gondola Ride, Cicchetti & Wine Tour
Discover Venice with a three-hour private walking tour and gondola ride this morning. Start on food with your local guide, who will lead you over bridges, through alleys, and along canals to discover marble palaces, rich arcades, and domes all built on a network of islands in the lagoon. Learn about the city, its canal streets, and traditional neighborhoods as you cross the famous Rialto Bridge, take pictures of the incredible Grand Canal, and enter the renowned Piazza San Marco, where you'll see the grand San Marco Basilica and its iconic bell tower.
Afterward, board a gondola and glide down a handful of canals with a singing gondolier as your captain for a postcard-perfect end to your Venetian morning. In the afternoon, discover the Venetian art of cicchetti, a local style of appetizer or snack found at traditional wine bars. A private guide will lead you to the places where real Venetians go to drink and mingle. At each stop, you'll sample regional wines and Prosecco served alongside various cicchetti.
Day 11: Depart Venice
It's your final morning in Italy. If you have time, take one last stroll along the canals before you take a private water taxi directly to the airport for your departing flight home or onward. Safe travels!More Great Italy Itineraries
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