Explore multiple Italian cities, landscapes, and regions while never feeling rushed on this 18-day luxury itinerary. Whisked to each destination by a blend of private drivers and concierge train journeys, you can focus on immersing yourself in an Italian grand tour. Start in Naples to explore the clifftop villages of the Amalfi Coast, then head to Rome for ancient history and buzzing nightlife. Taste your way through Tuscany as you tour Chianti’s lush countryside and discover Florence’s Renaissance splendor, before ending your journey of a lifetime amongst the palaces and canals of Venice.

Highlights

  • Experience lively Naples & the enchanting villages of the Amalfi Coast
  • Follow ancient footsteps at Rome's Colosseum, Forum & Palatine Hill
  • Visit lush vineyards in Tuscany's Chianti region
  • Discover Renaissance art & history in Florence
  • Explore Venetian canals by gondola

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive Rome - Transfer to Sorrento Sorrento
Day 2 Scenic Amalfi Coast Driving Tour Sorrento
Day 3 Free Day in Sorrento Sorrento
Day 4 Sorrento to Rome, Stop in Pompeii Naples
Day 5 Explore Naples Naples
Day 6 Naples to Rome Rome
Day 7 Small-Group Tour of Colosseum & Roman Forum Rome
Day 8 Free Day in Rome Rome
Day 9 Rome to Radda in Chianti Radda-in-Chianti
Day 10 Pienza & Montalcino Radda-in-Chianti
Day 11 Siena & Chianti Radda-in-Chianti
Day 12 Florence City Tour Florence
Day 13 Free Day in Florence Florence
Day 14 Florence to Venice - Evening Gondola Ride Venice
Day 15 Jewels of Venice Venice
Day 16 Free Day in Venice Venice
Day 17 Venice to Rome  Rome
Day 18 Depart Rome  

Detailed Itinerary

Day 1: Arrive Rome - Transfer to Sorrento

Welcome to Sorrento

Welcome to Italy! Upon arrival at the Rome airport, you'll exit customs into the arrivals hall and be privately transferred to the train station where you'll begin your rail journey to Naples—with luggage, check-in, and all other logistics managed by your personal concierge. Upon arrival in Naples, a private transfer takes you to your hotel in beautiful Sorrento. Beloved by Italian and international vacationers for its stunning views, tranquil atmosphere, and terraced lemon groves, Sorrento will serve as your gateway to the Amalfi Coast and home base for the next three nights.

After settling in, take a stroll along the waterfront as you head to the Sorrento's central Piazza Tasso for dinner and drinks.

Day 2: Scenic Amalfi Coast Driving Tour

Positano's steep, colorful houses

Meet your private driver today and venture out for a breathtaking driving tour along the Amalfi Coast, visiting towns like Positano, Amalfi, and Ravello. This stretch of coastline south of Naples is renowned for its exceptional beauty and iconic cliffside fishing villages. Lemon groves and sprawling summer villas cling to the rocky hillsides overlooking sparkling blue waters. 

Your first stop is dashing Positano, where colorful houses tumble down to the sea in a cascade of sunbleached peach, pink, and terracotta. No less photo-worthy are its steep streets and steps, flanked by wisteria-draped hotels, smart restaurants, and fashionable retailers. Visitors have flocked to Positano since the days of the Roman Empire, but today the village is popular for its lush scenery and cobbled streets flanked by bougainvillea flowers. Stop in Piazza dei Mulini and walk through the narrow alleys leading to the waterfront. These streets also lead to the cathedral and are characterized by charming shops selling lemon, shoes, and clothing. 

Continuing along the coast, you can pass through the villages of Praiano, Furore, and Conca dei Marini before reaching the ancient maritime republic of Amalfi, now a UNESCO World Heritage Site. Famous for its white-washed buildings, historic churches, and paper-making industry, Amalfi is a jewel of the Mediterranean coast. Stroll through the town to see the sights and soak up the atmosphere, stopping by La Piazzetta di Sant'Andrea—the town square—to see the Duomo and the Cattedrale di Sant'Andrea.

Further east sits the tranquil oasis of Ravello, perched high above the sea and a perennial favorite of artists, poets, and musicians. Visit the ornate Villa Rufolo for its fascinating cultural history and panoramic views, before returning to Sorrento for the evening—just in time for a leisurely aperitivo before dinner.

Day 3: Free Day in Sorrento

View of  Sorrento from a hotel terrace
Views over Sorrento from a hotel terrace

Today is yours to explore Sorrento at your leisure. Soak in the sunshine in Piazza Tasso, Sorrento's largest and most popular gathering place, or stroll from the piazza down Corso Italia, a busy street lined with shops and boutiques. 

Other recommended activities include:

  • Go shopping at the colorful Via San Renato street market, a weekly open-air market selling everything from clothes to household items to fresh produce and delicious cheeses.
  • Get lunch in Marina Grande Beach, Sorrento's fishing village that's famous for its seafood restaurants and volcanic sandy beach (the perfect place to relax after a delicious meal).
  • Tour the nearby coastal city of Salerno and the ancient Greek city of Paestum (the site contains some of the world's best-preserved Greek temples). 
  • Enjoy a private sommelier-guided wine tour of two prestigious estates in Campania’s rugged Apennine Mountains.

As the sun sets, head to the Puolo neighborhood for dinner. Its crescent beach and waterfront promenade make it a perennial favorite with locals.

Day 4: Sorrento to Naples, Stop in Pompeii

One of Pompeii's vivid frescoes

This morning starts with a stop at the ruins of Pompeii, a bustling seaside city that was buried underneath 13-20 ft (4 to 6 m) of ash and volcanic debris after the 79 CE eruption of Mount Vesuvius. The ash, which killed many of the city's residents, acted as an archaeological time capsule by preserving many original buildings and features completely intact. 

The city was lost for 1,500 years following Mount Vesuvius' eruption before its accidental rediscovery in 1599 CE. Your guided 2-hour walking tour of Pompeii's ancient streets will show off preserved villas, shops, public buildings, and plazas, giving you an insider's look into life 2,000 years ago. 

After the tour, you'll continue to Naples, a bustling port city renowned for its art, architecture, and religious frescoes. Settle into your accommodation before venturing out for some sightseeing:

  • Visit the Naples Archaeological Museum to see Roman, Greek, and Renaissance-era ruins, including artifacts from nearby Pompeii.
  • Tour the Castel dell'Ovo, a seaside castle located on the former island of Megaride.
  • See the 16th-century Museo Cappella Sansevero, which houses thousands of veiled sculptures.
  • Go underground to explore the network of tunnels and passageways built under the city streets.
  • Get outside and see the dormant Solfatara volcano, located a half-hour drive west of Naples.

In the evening, go for a stroll along the Caracciolo e Lungomare di Napoli, a waterfront promenade, then head to the Quartieri Spagnoli, a lively commercial hub, for dinner at a trattoria. On the way, stop at the Toledo Metro station, the Stazione della Metropolitana dell'Arte, to see beautiful mosaic inlays.

Day 5: Explore Naples

Cliffside buildings on the Amalfi Coast
Naples' bustling downtown

Today is devoted to exploring the best of Naples on foot. From your hotel, head out on a guided tour to see the city's elegant historic and cultural center. 

Start with the Piazza del Plebiscito, the main square, to see the Basilica di San Francesco, built as a tribute to the emperor, and the 17th-century Royal Palace, which houses a museum and two theaters. View the Teatro di San Carlo, one of the Royal Palace's theaters, then head across the plaza to see the beautiful Galleria Umberto, a massive 19th-century glass-roofed shopping mall.  

From here, walk next door to the 13th-century Castel Nuovo, located across the street from the Naples port. Make a stop at a cafe to enjoy a caffè Napoletano, then continue your walk along the historic Via Toledo, the city's main shopping street. 

Stop here for lunch to sample the famous local seafood. Try the montanare—small fried pizzas served with tomato sauce, cheese, ricotta, and anchovies—and the Neapolitan cuoppo, a cone of assorted fried seafood. Finish your meal with a glass of local white wine and while enjoying some people watching on the piazza. 

Day 6: Naples to Rome

Rome's Tiber River

After a relaxing breakfast, it's time to bid Naples farewell. This morning you'll catch a high-speed train back to Rome, where you get settled into your hotel before heading out on foot to explore your new surroundings. 

According to legend, Rome was founded by brothers Romulus and Remus in 753 BCE, atop what is now Palatine Hill. The long-time center of the powerful Roman Empire, Rome boasts nearly 3,000 years of architecture, history, and culture. These days, Italy's capital is considered one of Europe's top cities thanks to its ancient monuments, incredible art masterpieces, and cosmopolitan vibe. It's a center for fashion, with a buzzing food culture and a growing nightlife scene. 

Visitors and locals wanting to soak in the sunshine flock to the beautiful Giardino degli Aranci, the city's vibrant orange tree gardens on Aventine Hill, or relax in the lush greenery of the Villa Borghese Gardens. For dinner, head to the Trastevere neighborhood for some of the city's best trattorias.

 

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Day 7: Small-Group Tour of Colosseum & Roman Forum

Rome's Ancient Colosseum

Today you'll dive into the history of the Roman Empire with a guided walking tour of the Colosseum, the world's largest amphitheater. Learn about the lives of some of ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperor Augustus, Nero, and the Flavian Emperors who built the Colosseum. 

Continue to the Roman Forum, where you'll see excavations dating back 2,000 years, revealing the ruins of temples, squares, religious sites, and other buildings. These were the venues for public speeches, processions, elections, and, of course, gladiator matches. Historians and archaeologists refer to the Roman Forum as one of the most celebrated places in world history, and you'll see why as you explore the grounds.

Cut through the Roman Forum along Via Sacra, where you'll pass by the Temples of Vesta, Antonino, and Faustina. The Basilica Julia and Aemilia, a public meeting house that was commissioned by Julius Caesar, is also here.

Your tour of ancient Rome ends 131 feet (40 meters) above the city at Palatine Hill. From here you'll have incredible city views, with the Forum on one side, Circus Maximus on the other, and the Vatican in the distance. In between, the River Tiber snakes through Rome's historic neighborhoods.

In the evening, you'll have free time to continue exploring Rome. Grab dinner in one of the city's other neighborhoods, such as bohemian Monti, and enjoy the quiet hum of city life as the day comes to a close.

 

Day 8: Free Day in Rome

Sunlit street in Trastevere
A sunlit street in Trastevere

Today is a free day to explore the city. Select from the following suggestions to make the most of your time in Rome

  • Visit the Museo Nazionale di Castel Sant'Angelo history museum.
  • Tour the Renaissance Villa Farnesina in the Trastevere district.
  • See art in the Palazzo Colonna and Palazzo Doria Pamphilj.
  • Go for a stroll in the buzzing Monti neighborhood, an eclectic area in the city center full of hip wine bars and trendy boutiques.
  • Head out of the city for a day at the Ostia beach for miles of sand and warm sea.
  • Spend an afternoon at the Musei Capitolini, the oldest and one of the best museums in Italy.
  • Walk through the ornate rooms of the Galleria Borghese and explore the splendid frescoes, stories, and masterful techniques behind the world's most beautiful art museums.

In the evening head to the Trastevere neighborhood for dinner at an osteria or a trattoria, followed by drinks at a trendy wine bar.

Day 9: Rome to Radda in Chianti

Vineyards near Radda in Chianti

After a leisurely breakfast, you’ll bid farewell to the Eternal City and head to the Tuscan countryside via private transfer. After a scenic 3-hour drive through stunning scenery, the peaceful town of Radda in Chianti welcomes you. Check in to your hotel and enjoy some downtime to settle in and unpack.
 
The commune of Radda in Chianti dates back to the 9th century, and the town's medieval stone fortifications and narrow streets serve as a reminder of a time when the city was the main defensive and financial capital of the Chianti region. In the countryside outside the town, endless fields of vineyards supply the wine grapes for the region's famed Chianti wine. 
 
The remainder of the day is free. Rent a bike to explore the city's hilly streets, or head out of town to spend the afternoon cruising around winding country lanes through the peaceful Tuscan landscape.

Day 10: Pienza & Montalcino

Explore the scenic Tuscan countryside

Venture out for a day trip to the medieval towns of Montalcino and Pienza, which date back to the Etruscan era. Your local guide will accompany you through the architectural and cultural highlights of the Val d'Orcia region, considered one of Tuscany's prettiest areas. 
 
Start your day in the tiny village of Pienza, which stands atop a high hill above the Orcia Valley. The charming town is known as the "ideal city of the Renaissance" and was designed by Enea Silvio Piccolomini, who later became Pope Pius II. Piccolomini used his money and influence to transform his birthplace village, then known as Corsignano, into his ideal Utopian Renaissance city. The harmonious composition of the city includes the Cathedral, the Papal or Piccolomini Palace, the Town Hall, and the central square which sits between the buildings. The Cattedrale dell'Assunta features unique paintings and an octagonal bell tower, and Palazzo Piccolomini is famous for its hanging gardens and was the shooting location for Franco Zeffirelli's film "Romeo and Juliet." 
 
Pienza is also famous for its Pecorino cheese, and you'll get a chance to visit a Pecorino facility to learn the secrets of the best cheese and try the local products. The caseificio, or cheese dairy, is located on a large swath of peaceful countryside with sheep grazing quietly between olive groves and vineyards. 
 
After lunch, continue to another unique experience—a visit to the Paradiso di Frassina, an ancient medieval farm that dates back to the 11th century. The farm sits just north of the village of Montalcino and is famous for its unique methods of producing the famed Brunello of Montalcino wine. Stroll through the vineyards and enjoy the sounds of Mozart's music that's played through strategically located speakers. The music is not just for the visitors' amazement—it's played for the grapevines, through a complex research project chronicling the beneficial effects of musical frequencies on vines. 
 
Tour the wine cellars and learn about the process of wine-making, then finish the visit with a wine tasting for an incredible multi-sensory experience. At the end of the tour, you'll be transferred back to your hotel in Radda in Chianti for the evening.

Day 11: Siena & Chianti

Siena's perfectly preserved medieval squares

Today you'll discover a different part of Tuscany, as your private driver guides you through the sights of Siena and the Chianti region. 

Start the morning in the medieval hilltop city of Siena, where you can see the magnificent Cathedral and Town Hall on the Piazza del Campo, the famous trapezoidal square where the famous Palio horse race takes place twice a year. Visit the Gothic Cathedral of Santa Maria Assunta, an impressive building filled with treasures by Pisano, Donatello, and Michelangelo as well as frescoes by Pinturicchio, learn about archaeology and history at the Complesso Museale Santa Maria della Scala (the National Archaeological Museum of Siena), or just wander through the perfectly preserved medieval streets and squares soaking up the atmosphere and history. 

After a memorable lunch at one of Siena's characteristic Tuscan trattorias, you'll continue with your driver to the Chianti Classico wine region to visit a typical Tuscan winery. This winery blends centuries-old knowledge with a modern approach to create environmentally-friendly wine cultivation. As part of the project, weeding and chemical topdressing have been eliminated from the growing process and the waste that's produced by the company is recycled into organic fertilizer. 

Enjoy learning about the winery and the unique characteristics of the local climate that have made the region unfavorable to most crops but ideal for growing wine grapes. The Chianti wine, made primarily of Sangiovese grapes, is a local staple. Tour the cellars and vineyards, then enjoy a wine tasting accompanied by some snacks before being driven back to Radda in Chianti in time for dinner.

Day 12: Florence City Tour

Florence's Famous Ponte Vecchio Bridge
Florence's famous Ponte Vecchio Bridge

Leave the countryside behind this morning as you transfer to Florence, Tuscany's regional capital and its most populous city. Long considered a cultural capital and the "Jewel of the Renaissance," Florence is home to many masterpieces of Renaissance art and architecture.

Spend today exploring the city's top sites, starting with a guided half-day walking tour. Stops include the iconic Duomo, with its terracotta-tiled dome, the Galleria dell'Accademia, which displays Michelangelo's statue of David, and the San Lorenzo Church, the former parish church of the powerful Medici family. 

In the afternoon, indulge yourself with the decadence of Tuscany's culinary delights. Discover the region's history and the best off-the-beaten-path gelato and coffee shops, and sample wares from city markets to find the best of the best. Try truffle panini, fresh-pressed Tuscan olive oil, and handmade chocolate focaccia, finished off with a glass of chilled prosecco or Chianti wine.

Day 13: Free Day in Florence

Leather sandals at San Lorenzo Market.
Leather sandals at San Lorenzo Market

Today is a free day to explore some of Florence's other notable attractions and highlights. Recommendations for the day include:

  • Spend some time learning about Florence's history in the Basilica di Santa Croce history museum.
  • Explore science and art at the Museo dell'Opera del Duomo (history and art museum) and the Museo Galileo Institute and Museum of the History of Science. 
  • Visit the Chiesa e Museo di Orsanmichele, which served as the granary for the Sisters of San Michele in previous years.
  • Shop for hidden treasures and your lunch special in the San Lorenzo market.
  • Head to the south bank of the Arno River to the Piazzale Michelangelo viewpoint for panoramic views of the city.
  • Stroll through the peaceful and relaxing greenery of the Boboli Gardens.

Head to La Terrazza Continentale next to the Ponte Vecchio bridge for a pre-dinner cocktail on the terrace while you enjoy the sunset, then make your way to the Sant'Ambrogio neighborhood for dinner accompanied by a glass of Tuscan wine.

Day 14: Florence to Venice - Evening Gondola Ride

Evening Gondola ride
An evening gondola ride in Venice

Spend your last morning in Florence at your leisure, with a relaxed stroll after breakfast or some last-minute shopping. In the early afternoon, you'll say goodbye to Tuscany and journey north by high-speed train to Venice. Upon arrival at the Venice railway station, you will be met by your driver for a transfer to your hotel.

Venice in northern Italy is famous for both industry and tourism. With nicknames like "Queen of the Adriatic," "City of Water," and "The Floating City," it's clear that the city's myriad canals are its main draw. Stretching across 117 small islands in the marshy Venetian Lagoon along the Adriatic Sea, the city has long been a commercial and cultural hub thanks to its strategic placement. Silk, grains, spices, and art were traded through the Middle Ages, making Venice very wealthy. The city is also famous for its many beautiful historic attractions, such as the Piazza San Marco and San Marco Basilica, the Grand Canal, and the ornate Doge's Palace. The Lido de Venezia is a popular luxury destination that attracts actors, critics, and other cinema industry celebrities.

There's something to be said for the classics. When in Rome, do as the Romans do, and when in Venice, take a gondola tour of its romantic canals. This is the classic ride—a leisurely 30-minute jaunt along Venice's waterways under the power and guidance of a professional gondolier. It may be a popular tourist activity, but gondolas have been used as transport in the "City of Water "for well over 1,000 years. This elegant and romantic mode of transport will leave you perfectly content as you leisurely glide on the surface of the water, under Rialto Bridge, and past iconic landmarks like Rialto Square

After your 30 minutes on the water, you'll hop off the boat and can continue to enjoy Venice on foot however you choose.

For an evening on the town, head to the Cannaregio District, the site of the former Jewish Ghetto. The area is filled with great restaurants, bars, & shops offering kosher Venetian specialties, a Jewish museum, and several tourist-friendly synagogues. Eat and drink your way through regional specialties as you celebrate your first night in Venice. Buon appetito!

Day 15: Jewels of Venice

Venice's central St. Mark's Square
Venice's central St. Mark's Square

This morning is at your leisure—enjoy a relaxed breakfast, shop for local treasures and souvenirs, or do some exploring on your own. 

In the afternoon, you'll take a stroll through some of Venice's highlights with a local guide. Start at Piazza San Marco (St. Mark's Square), the heart of the city's cultural and administrative district, then tour the Palazzo Ducale (Doge's Palace), a Venetian Gothic palace built as the primary residence for the Doge of Venice in 1340. The palace stands on Piazza San Marco, and its resplendent interior decor and priceless works of art make it a must-see for history and architecture buffs. 

The palace is also connected to the next-door prison by the infamous Bridge of Sighs, which has joined the two buildings since the 16th century. The bridge features a small window onto Venice's harbor and earned its grisly name from the prisoners' sighing as they got one last glimpse of the city on their way to execution. While most visitors gather outside the bridge to look in, you'll get the best sense of history from inside the bridge, looking out from the same window as the doomed medieval prisoners. 

Adjacent to the palace is the Basilica San Marco, originally the Doge's personal chapel. The building is one of the best surviving examples of Italo-Byzantine architecture and features a stunning collection of Byzantine art, gold mosaics, and exquisite marble floors. Your tour includes a visit inside, where you'll be able to see for yourself the incredible art and architecture that the basilica holds. 

Day 16: Free Day in Venice

Homes in the former Jewish Ghetto
Homes in Venice's former Jewish Ghetto

Today is a free day to explore Venice. Make the most of your time in the city with some of the following suggestions: 

  • Discover art at the Ca' Pesaro Galleria Internazionale d'Arte Moderna, Peggy Guggenheim Collection Modern Art Museum, and La Biennale di Venezia Art Museum.
  • Explore San Giorgio Maggiore, one of Venice's smaller islands that stands separate from the main canals.
  • See an opera show at the Teatro La Fenice.
  • Haggle for produce at the busy Mestre market, held every Wednesday and Friday.
  • Go shopping for luxury items on Le Mercerie and Salizada San Moisè.
  • Browse textiles, craft shops, unique boutiques, and galleries in the bohemian San Samuele district.
  • Rent a kayak and explore Venice from the water.

For lunch, grab food on the go and find a spot by a canal to sit down. Depending on how hungry you are, look out for pizza al volo (a full pizza to takeaway), or a slice of your favorite known as pizza al taglio. Around the Rialto Market are restaurants and bacari bars serving good food all day long. At dinnertime, go for cichetti, small plates of Venetian tapas, and order the fresh seafood dishes.

Day 17: Venice to Rome 

Rome's Spanish Steps

This morning you'll depart Venice in style, with a private boat whisking you to the Venice Santa Lucia station where you'll board a train for Rome. Upon arrival, you'll be met by your private driver and taken to your hotel to check in and relax. Your final afternoon in Italy is free to savor at your own pace. 

Day 18: Depart Rome

Main train station in Rome
Farewell Rome!

Time to say goodbye to Rome—for now! After one last Roman breakfast, you'll transfer to the airport for your flight home. Arrividerci!