From the sunny Amalfi Coast to Rome's buzzing nightlife, this incredible 20-day highlights trip through Italy is perfect for travelers who want to see it all. Start in Venice to see the famed Grand Canal, then head to Florence for Tuscan wines and da Vinci's art. Round out your trip with a stay in the small coastal town of Amalfi before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.


  • Explore the floating city on a gondola ride of Venice’s city canals
  • Take a day trip to Capri Island, Ancient Rome’s favorite summer getaway
  • Make—and eat!—a traditional Florentine meal
  • Climb Pisa’s famous leaning tower
  • Go back in time with a tour of the Colosseum and Roman Forum

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome, Travel to Venice Venice
Day 2 Venice Walking Tour Venice
Day 3 Venice Street Food Tour With a Local Guide Venice
Day 4 Murano, Burano & Torcello Excursion Venice
Day 5 Free Day in Venice Venice
Day 6 Venice to Florence, Food Tour Florence
Day 7 Tour of Tuscany & Wine Tasting Florence
Day 8 Tour of Pisa & Leaning Tower Florence
Day 9 Market to Table Cooking Class Florence
Day 10 Free Day in Florence Florence
Day 11 Florence to Amalfi Coast, Positano Sunset Cruise Amalfi
Day 12 Explore Maiori, Evening Pizza-Making Class Amalfi
Day 13 Capri and Anacapri Day Tour Amalfi
Day 14 Free Day on the Amalfi Coast Amalfi
Day 15 Amalfi Coast to Rome, Afternoon Colosseum and Forum Tour Rome
Day 16 Vatican & Classic Tour of Rome Rome
Day 17 Food Tour of Monti Rome
Day 18 Rome Crypts & Catacombs Tour, Afternoon Cooking Class Rome
Day 19 Galleria Borghese, Free Afternoon in Rome Rome
Day 20 Goodbye Italy!  

Detailed Itinerary

Day 1: Arrive in Rome, Travel to Venice

Gondola on the Grand Canal
Gondola on the Grand Canal

Welcome to Italy! Arrive in one of Rome's two international airports, then transfer to the Roma Termini Station for a ride on the high-speed train en route to Venice. Once in the city, a water taxi will transport you to the town center and 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.

Venice is well known for several artistic movements, particularly from the Renaissance period. The city's many musicians, like Antonio Vivaldi and others, played important roles in the shaping of symphonic and operatic music. Numerous artists have called Venice home, and their work continues to draw visitors worldwide. 

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.  

Depending on when you arrive, a great introduction to the city is to take a romantic cruise down Venice's canals on a historic gondola to see stunning architecture and narrow waterways. This is not a guided tour but rather a relaxing cruise that allows you to take in the amazing city from the water. 

In the evening head to the Cannaregio District, site of the former Jewish Ghetto, for a walking food tour. The area is filled with restaurants & shops offering kosher Venetian specialties, a Jewish museum, and several tourist-friendly synagogues. Eat and drink your way through regional specialties as you learn about the Jewish and Kosher influences and sample Cicchetti, creamy risottos, and sweet pastries and local wines. Buon appetito!

Day 2: Venice Walking Tour

Waterfront and Doge's Palace
Waterfront and Doge's Palace

Experience Venice's highlights with a guided walking tour. Start at Piazza San Marco (St. Mark's Square), the heart of the city's cultural and administrative district. Tour 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. 

Adjacent to the palace is the San Marco's Basilica, 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. 

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. 

After the morning's tour, grab lunch at one of the city's many cafes before spending the afternoon exploring.

  • Tour the 18th-century Chiesa di Santa Maria Assunta (also known as I Gesuiti) in the Cannaregio district and the baroque 17th-century Basilica di Santa Maria della Salute, Venice's second most renowned church
  • Ride the elevator to the top of the Campanile di San Marco for a bird’s-eye view of Venice
  • Dive into history at the Correr Civic Museum to see art and artifacts displays from Venice's history as well as the former royals quarters
  • Go shopping at the famous Rialto fish market, located at the heart of Venice. The smell of seafood and sound of vendors vying for shoppers' attention make this colorful and hectic market a must-see for any Venice traveler 

In the evening, rent a bike and go for a relaxed bike ride around the city before finding the best bars and nightlife for a night out.

Day 3: Venice Street Food Tour With a Local Guide

Tiramisu, a layered coffee cake
Tiramisu, a layered coffee cake

Eat and drink your way through Venice's culinary delights on this 2.5-hour street food tour. Explore buzzing piazzas, visit medieval churches, and go shopping in the bustling Rialto Market.

Stroll around the Campo Santa Margherita to see 14th- and 15th-century buildings, take a boat ride on the Grand Canal (if you've already checked it out, there's enough to see here to make another visit worth it), and visit the Italian-Gothic Basilica dei Frari, a 13th-century church which houses many notable medieval works of art, including "Madonna and Child with Saints," and the "Assumption".

Later in the day, explore the eclectic San Polo neighborhood and stop by a trendy restaurant for drinks and Venitian specialties like tramenzzini (little sandwiches), and desserts like buranelli and tiramisu, and enjoy dinner out on the town.

Day 4: Murano, Burano & Torcello Excursion

Glassmaker on Murano
Glassmaker on Murano

Head out for a tour of Venice's three famous neighbors—the islands of Murano, Burano, and Torcello. Begin your boat and walking tour aboard a motorboat en route to Murano, passing the island of San Giorgio Maggiore, the tip of Sant'Elena and the Lido. Tour Murano, which is famous for its colorful glass-making. Visit a glass blower to learn about the process and marvel at the intricate pieces, including elaborate chandeliers. 

From here continue to Burano, a picture-perfect island known for its colorful houses and elegant lacework. You'll have time to explore the island before the short boat trip to nearby Torcello to see the ancient cathedral with its fine mosaic inlays, followed by a visit to the Church of Santa Fosca. 

After spending a full day enjoying the sights and sounds of the unique islands, return to Venice by boat in time for a relaxed evening in a neighborhood restaurant.

Day 5: Free Day in Venice

Homes in the former Jewish Ghetto
Homes in the former Jewish Ghetto

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

Day 6: Venice to Florence, Food Tour

Ponte Vecchio bridge
Ponte Vecchio bridge

After breakfast head to the train station to catch a train to Florence. Florence is 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, including the iconic Duomo, a terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's 'David' sculpture. 

Spend the day exploring the top sites, located in the medieval city center. Popular highlights include the sprawling 15th-century Pitti Palace and the world-famous Uffizi Gallery, which houses works by artists like Michelangelo and Leonardo de Vinci. As a center for art, Florence has hosted many of European history's most notable figures, including Botticelli, Donatello, Dante, Boccaccio, and Niccolò Machiavelli. 

In the afternoon indulge yourself on the decadence of Tuscany's culinary delights. A guided walking tour of the city led by a local is the perfect way to discover the region's history and find the best off-the-beaten-path gelato and coffee shops. 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 with a glass of chilled prosecco or Chianti wine.

Day 7: Tour of Tuscany & Wine Tasting

Siena Cathedral and medieval Old Town
Siena Cathedral and medieval Old Town

In the morning head to the Tuscan countryside to explore the Chianti Region. Your first stop is the medieval village of San Gimignano, a UNESCO World Heritage Site located an hour away from Florence which is famous for its Vernaccia wine and award-winning gelaterias. Explore the beautiful squares, palaces, and churches of the city before grabbing a coffee in an open-air cafe. 

Continue to the Chianti Classico wine region to visit a typical Tuscan winery. The unique characteristics of the local climate have made the region unfavorable to most crops but ideal for growing wine grapes. Alternating fields of olive orchards and vineyards characterize this idyllic landscape.

The Chianti wine, made primarily of Sangiovese grapes, is the local staple. Tour the cellars and vineyards, then enjoy a wine tasting accompanied by a delicious Tuscan lunch of pasta, cured meats, cheeses, and local desserts. 

In the afternoon visit nearby Siena, located a scenic hourlong drive away, to see the magnificent Cathedral, Torre del Mangia, and Town Hall, site of the famous Palio horse race. Finish the day with a visit to the medieval fortress of Monteriggioni before returning to Florence for the night.

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Day 8: Tour of Pisa & Leaning Tower

The perfect place to enjoy a gelato
The perfect place to enjoy a gelato

Head to Pisa today, located an hour and a half away on the coast, to see the famous Leaning Tower of Pisa (tickets included) at the Piazza dei Miracoli. 

Begin the tour with a walk around Pisa's medieval walls, as well as a tour of the Cathedral to see the Romanesque masterpieces. See the 12th-century Baptistery and Monumental Cemetery, then continue to see the tower. Admire the exterior, then head inside to climb the steps to the bell tower to take in the views. 

The tour concludes with a stop to see a typical Tuscan wine shop with a tasting of regional wines, followed by some souvenir shopping and a visit to the local Gelateria for a cone of creamy gelato. Return to Florence in time for dinner. 

Day 9: Market to Table Cooking Class

Cicchetti, a traditional Venetian snack
Cicchetti, a traditional Venetian snack

Start your day with a quiet morning in the city. Enjoy people watching with a glass of espresso in a sun-filled piazza, shop for gifts and antiques at the neighborhood flea market, or go for a quiet walk away from the crowds.

In the afternoon try your hand at Florentine cuisine during a 5.5-hour cooking class. Together with your expert chef, begin the culinary adventure at the central market, where you'll purchase local ingredients for your lunch. Head to the cooking school and learn to make Tuscan favorites, including bruschetta, homemade pasta, and dessert.

Afterward, enjoy the fruits of your labor accompanied by a couple of glasses of local Chianti. This class is limited to 25 people to keep the experience as intimate as possible.

Day 10: Free Day in Florence

Leather sandals at San Lorenzo
Leather sandals at San Lorenzo

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 11: Florence to Amalfi Coast, Positano Sunset Cruise

View of Positano from the water
View of Positano from the water

After breakfast at a sunny open-air cafe head to the train station to take the train to Naples, then transfer to your hotel on the Amalfi Coast. This stretch of coastline south of Naples is renowned for its exceptional beauty and iconic medieval cliffside fishing villages. Lemon groves and sprawling summer villas cling to the steep cliffs that lead to sparkling blue water. 

In the afternoon head onto the water with a sunset boat tour to Positano from Amalfi. With its steep houses tumbling down to the sea, old-timey hotels draped in flowering vines and restaurant terraces Positano is an obvious favorite with travelers looking for a getaway. Soak in the views of the coast and the Ionian Sea from the boat as you enjoy a glass of Prosecco and some light aperitifs. Swim or snorkel in the clear blue waters, or simply enjoy the view. 

Disembark in Positano for a romantic dinner with ocean views. Enjoy a pasta dinner with fresh seafood, paired with a glass of fruity Falanghina. Return to Amalfi for the night.

Day 12: Explore Maiori, Evening Pizza-Making Class

Beach in Maiori
Beach in Maiori

Spend the day exploring Maiori, a small town on the coast famous for its colorful houses. In previous years Maiori was a major port thoroughfare, housing the Admiralty, customs checkpoint, and arsenals. These days it welcomes visitors eager for the turquoise blue sea and Mediterranean climate. In the evening go for a short walking tour of the city to see the main sights: 

  • Hike up to the Castello di San Nicola,  a 15th-century fortress which offers great views of the coast
  • See the 13th-century Church of Santa Maria a Mare
  • Enjoy the peaceful serenity, coastal views, and several thousand varieties of plants in the terraced gardens of the Giardino Esotico Beniamino Cimini
  • View the marble halls and Renaissance art of the Mezzocapo Palace
  • Visit the Santa Maria de Olearia, an ancient abbey built into the cliffside, famous for its 10th-century frescoes

In the evening, learn to make the ultimate Italian food—the humble pizza. From its simple beginnings as street food to its worldwide popularity, pizza has gained fame and popularity—and for a good reason. 

Start with handmade dough, local ingredients, and traditional techniques, then finish with a traditional wood oven to get the perfect crust. At the end of the lesson, enjoy the fruits of your labor along with an appetizer and a glass of Limoncello for dessert.

Afterward, head to the beach for a late evening walk along the water.

Day 13: Capri and Anacapri Day Tour

Views from the Via Krupp
Views from the Via Krupp

Spend the day enjoying the sunshine, summer villas, and clear blue waters of Capri Island, known locally as the Pearl of the Mediterranean. Capri sits on the south side of the Gulf of Naples and is a popular destination. Ancient Romans used the island for summer villas for the Empire's rich and famous, while the Greeks called Capri the 'Isle of Sirens.' 

In the morning head out for a scenic drive along the Sorrentine coast to the Sorrento port, where you'll catch a hydrofoil to Capri. From here go for a guided walking tour of the island's main attractions. See the main harbors (Marina Grande and Marina Piccola), walk along the Belvedere of Tragara (a villa-lined promenade with panoramic views), and explore the ruins of ancient Roman villas. 

Head up the hill to see Anacapri, the Piazzetta, and Augustus' Garden, as well as the best views of the Faraglioni Rocks. 

In the afternoon return to the water to explore the Grotta Azzurra, a naturally hollowed sea cave, and soak in the sunshine on the beach.

Day 14: Free Day on the Amalfi Coast

Lemons, a staple of the Amalfi Coast
Lemons, a staple of the Amalfi Coast

Today is a free day to explore the area and enjoy the pace of life on the coast. Go for a walk on the Lemon Path in Minori, see the illuminated sea cave Grotta dello Smeraldo, or head out for a full day tour of the resort island of Capri. See the local ceramics manufacturing process in Vietri, or go for a half-day hike on the Path of the Gods

Other suggestions include: 

  • Visit the beautiful Villa Cimbrone and Terrace of Infinity in Ravello 
  • Soak in the sunshine on Gravitella Beach in Vettica Maggiore, Lannio Beach in Centra, or Arienzo Beach in Positano
  • Try your hand at windsurfing in Praiano
  • Check out Praiano's nightlife at the Africana and Music on the Rocks nightclubs 
  • Rent a kayak and explore emerald green grottos, tiny hidden beaches, and impressive sea caves 
  • Enjoy a quiet day in the serene town of Atrani, far away from the hustle and bustle of the larger villages 
  • Explore the Fiordo di Furore, Italy's only fjord
  • Visit the Cloister of San Francesco in Sorrento, an oasis of tranquility that's located steps away from the town's historic Sant'Antonino piazza 
  • Enjoy nature in the Ferriere Valley Nature Reserve, famous for its postcard-perfect fishing villages and striking countryside crisscrossed with hiking trails

For dinner head to Ristorante Pizzeria Giardiniello for the best Italian pizza paired with a glass of the perfect local wine.

Day 15: Amalfi Coast to Rome, Afternoon Colosseum and Forum Tour

The ancient Roman Colosseum
The ancient Roman Colosseum

After a relaxing breakfast, it's time to say goodbye to the Amalfi Coast. Catch a high-speed train back to Rome, then check in to your hotel. 

According to legend, Rome was founded by brothers Romulus and Remus in 753 B.C.E. atop Rome's 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 buzzing food culture and has 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

In the afternoon, dive into the history of the Roman Empire with a walking tour of the Colosseum, the world's largest amphitheater (tickets included). Walking through the ancient amphitheater is like taking a trip back in time to the days of the Roman Empire. Learn about some of ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian Emperors who built the Colosseum. 

From here, continue to the Roman Forum and Palatine Hill. Walk along the ancient Roman street Via Sacra to see the Temples of Vesta, Antonino, and Faustina. See the ancient Basilica Julia and Aemilia and experience the grandeur of the Roman Empire.

Day 16: Vatican & Classic Tour of Rome

St. Peter's Square and the Vatican
St. Peter's Square and the Vatican

Today you will visit the Vatican City museums and Sistine Chapel, as well as other top sights for an exclusive 6-hour tour of the city's incredible art and history. Start at the Vatican, where you'll visit the Pio Clementio Museum, Gallery of the Candelabra, Gallery of Tapestries, and Gallery of the Geographical Maps

Continue to see the magnificent Raphael Rooms, ending in the breathtaking Sistine Chapel and St. Peter's Basilica. Experience the magic of Renaissance art as you learn about the secret details and untold stories of the masterpieces. 

Afterward, continue into a city for a tour of the city's most notable landmarks. Cross Piazza della Repubblica to see the Fountain of the Nyands, then continue to see the Trevi Fountain, La Colonna di Marco Aurelio, and the Palazzo di Montecitorio, which was designed by Bernini.

Admire the exterior of the Pantheon and head inside for a look at the ancient Roman temple, then head to Palazzo Madama—the Senate seat—ending at Piazza Navona.

End your evening with a stroll to the neighborhood piazza for gelato and some people watching.

Day 17: Food Tour of Monti

Small cafe in the city center
Small cafe in the city center

In the morning head to the Colle Aventino, one of Rome's famous seven hills. Stroll through the Roseto Comunale, the rose garden which sits on the site of a former Jewish cemetery and the Orange Tree Park overlook (Parco Savello), then find the famous keyhole which gives visitors a direct view of the Vatican. Grab a cappuccino and lunch from one of the adjacent cafes. 

In the afternoon, go on a food tour to explore the eclectic (and less crowded) Monti neighborhood in the historical city center. Together with your guide, stroll through the cobblestone streets, making stops at small cafes to sample a variety of wood-fired pizzas, small plates, and alcoholic drinks. This tour is a great way to learn about Rome's history and local stories as you eat and drink your way through the neighborhood.

Day 18: Rome Crypts & Catacombs Tour, Afternoon Cooking Class

Catacombe di San Pancrazio
Catacombe di San Pancrazio

Head underground today to explore the hidden world beneath your feet. Meet with your guide, then descend to the shadowy tunnels of the 2nd-century Roman Catacombs, a former refuge for early Christians who sought a safe site to practice their forbidden faith and honor the dead. 

After, cross the neighborhood to see the Basilica San Clemente, a 14th-century church whose resident cleric was nearly driven mad by the mysterious sound of running water. On this tour, the guide will point out the sites of the 5th-century church, the 4th-century temple, and the 1st-century street and aqueduct located underneath the basilica. 

Find a local cafe for lunch, then in the afternoon meet up with a professional chef for a several-hour cooking class. Learn how to prepare a 4-course meal, how to hand-make pasta, and how to pair the perfect wine with dinner. Enjoy listening to the local legends and stories while you prepare your food, then sit down to enjoy your dinner, paired—of course!—with a bottle of local wine.

Day 19: Galleria Borghese, Free Afternoon in Rome

Walking path in Borghese Gardens
Walking path in Borghese Gardens

Today is a free day to explore the city. Head to Galleria Borghese, one of the world's premier art museums, for a self-guided visit to see works by extraordinary artists Bernini, Caravaggio, Canova, and Rafaello. The gallery's highlights include sculptures and paintings from Cardinal Scipione Borghese’s collection (1579 - 1633). 

Admire Caravaggio's most important paintings, including "Boy with Basket of Fruit", and see Bernini and Canova's sculpture collection, boasting works such as "Apollo and Daphne" and "David". Rafaello's "Entombment of Christ" is also a must-see. 

Walk through the ornate rooms and explore the splendid frescoes, stories, and masterful techniques behind the masterpieces. End the tour with a peaceful stroll around the Villa Borghese gardens, enjoying its beauty and calm far from the chaos of the city. Please note that although this is a self-guided tour, a guided option is also available. 

Other suggested activities include:

  • Visit the Museo Nazionale di Castel Sant'Angelo history museum 
  • Tour the Renaissance Villa Farnesina  in the Trastevere district
  • 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 
  • Visit the historic and fascinating neighborhood of Testaccio to see the giant Monte Testaccio, an ancient pile of discarded olive oil jars from the 2nd century CE
  • Spend an afternoon at the Musei Capitolini, the oldest and one of the best museums in Italy

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

Day 20: Goodbye Italy!

Little details of life in Rome
Little details of life in Rome

Time to say goodbye to the country of love! After one last cappuccino over breakfast, head to the airport for your connecting flight home. Safe travels!


Map of Venice, Florence, Amalfi Coast & Rome - 20 Days
Map of Venice, Florence, Amalfi Coast & Rome - 20 Days