With two weeks in Italy, you can see many of the country's top sights in one trip—Rome, Florence, Venice, the Amalfi Coast—or spend your time exploring a particular region in depth, like Tuscany or Sicily. On these four unique itineraries, you'll take a pizza-making class in Naples, road-trip around Sicily, explore the wine-growing region of Chianti, or get a taste of several Italian cities, moving quickly between destinations on the country's network of high-speed trains.

Itinerary #1: Highlights of Italy: Venice, Florence, Rome, Naples

This classic two-week trip plan features Italy's greatest hits: Rome, Venice, Florence, and Naples, plus a trip through Tuscany and an adventure along the Amalfi Coast.

Going for a gondola ride in Venice
Going for a gondola ride in Venice
Day Highlights Overnight
Day 1-3 Explore Venice Venice
Day 4-6 Florence, Pisa, & Tuscany by Vespa  Florence
Day 7-8 Amalfi Coast, Positano, & Ravello Amalfi
Day 9 Mt. Vesuvius & Pompei Naples
Day 10 Naples Naples
Day 11-13 Explore Rome Rome
Day 14 Depart  


Kick off the trip in
Venice, where you'll spend the first three days and nights exploring the Floating City and the nearby islands of Murano and Burano. On the last evening, you'll take a gondola ride through Venice's famous canals. On day four, catch the high-speed train to Florence and enjoy a guided walking tour of the historic center. Side-trip to the Tuscan towns of Lucca and Pisa, then see Chianti wine region on a Vespa tour.

On the second week, you'll begin with a train ride to Naples, gateway to the Amalfi Coast. Relax in the seaside village of Amalfi, making excursions to the towns of Positano and Ravello. On day nine, you'll hike to Mount Vesuvius and see the ruins of Pompeii on a guided tour. The end of the trip is devoted to urban sightseeing in Naples and then Rome, where you'll have a guided tour of the Vatican Museums and the key monuments of the Eternal City, savoring leisurely meals in Trastevere and world-class gelato on an evening passeggiata (stroll). Learn more 

Find out more about the ideal amount of time to spend in Italy here.

Itinerary #2: Explore Tuscany 

On this two-week itinerary, you'll enjoy Tuscany at a leisurely pace, visiting Florence, Siena, Lucca, and Pisa before hiking the Cinque Terre hiking trail in the nearby region of Liguria.

One of Tuscany's many hilltop villages
One of Tuscany's many hilltop villages
Day Highlights Overnight
Day 1 Welcome to Florence!  Florence
Day 2 Uffizi Gallery Tour Florence
Day 3 Truffle Hunting Tour Florence
Day 4 Tour of Pisa & Leaning Tower Florence
Day 5 Free Day in Florence Florence
Day 6 Florence to Siena Siena
Day 7 Montepulciano and Pienza Tour Siena
Day 8 Brunello di Montalcino Winery Tour Siena
Day 9 Free Day in Siena Siena
Day 10 Siena to Lucca, City Tour Lucca
Day 11 Pasta Making Class in Lucca Lucca
Day 12 Cinque Terre Hiking Day Trip Lucca
Day 13 Free Day in Lucca Lucca
Day 14 Goodbye Italy!  


On this itinerary, you'll base yourself in three places—Florence, Siena, and Lucca—with side trips to a number of Tuscan villages. Begin in Florence, where after seeing Palazzo Vecchio and the Uffizi Gallery, you'll go on a truffle-hunting tour in the countryside outside the city. Detour to Pisa and it's famous Leaning Tower and take some time for shopping and relaxing in Florence before moving onto Siena. The city's historic center, a UNESCO World Heritage Site, is one of Italy's most popular attractions. Day-trip to the medieval towns of Montepulciano and Pienza on day seven, then spend a full day learning about Tuscan wine on a full-day tour of Montalcino and its family-run wineries.

In the second half of the trip, highlights include a tour and pasta-making class in the medieval city of Lucca, plus an excursion into the Italian region of Liguria for a full day of hiking the Cinque Terre. This dramatic stretch of coastline takes you through five villages, all part of Cinque Terre National Park. Unwind in Lucca on the last day, with free time for shopping, sightseeing, and sitting in outdoor cafés. Learn more

Interested in cycling in Tuscany? This six-day itinerary is just the ticket.

Itinerary #3: Food & Wine in Italy: Venice, Bologna, Florence, Rome, & More

This indulgent two-week tour around Italy is custom-made for foodies and wine lovers. Taste Chianti in Tuscany, feast on thin-crust pizza in Naples, share tiramisu in Venice, and stroll around Rome with gelato: it's all part of the adventure.

Eating pizza in the streets of Naples
Eating pizza in the streets of Naples
Day Highlights Overnight
Day 1 Arrive in Rome, Travel to Venice Venice
Day 2 Venice Street Food Tour With a Local Guide Venice
Day 3 Discover Bologna, Food Tour Bologna
Day 4 Day Trip to Parma: Ham and Parmesan Tasting Bologna
Day 5 Bologna to Florence Florence
Day 6 Tour of Tuscany & Wine Tasting Florence
Day 7 Free Day in Florence Florence
Day 8 Welcome to the Amalfi Coast! Maiori
Day 9 Wine Tasting, Marisa Cuomo Vineyard Maiori
Day 10 Free Day on the Amalfi Coast Maiori
Day 11 Pizza Making Class Maiori
Day 12 Amalfi Coast to Rome, Evening Rome Excursion Rome
Day 13 Trastevere Food & Wine Tour Rome
Day 14 Goodbye Italy!  


You'll enjoy a mix of cultural sightseeing, eating, and drinking when you begin this trip plan in Venice. Between museum stops and gondola rides, you'll sample traditional tiramisu and other local specialties on a street food tour. Stop in the bustling Rialto Market to pick up some cheese and wine for a DIY picnic.

The following day, catch the train to Bologna. After checking out the 11th-century University of Bologna, one of the city's main attractions, you'll do another walking food tour with a local guide, stopping into pasta shops and bakeries to try artisanal tortellini, mortadella, and a variety of cheeses. Side-trip to Parma to try the region's traditional ham before moving onto Florence. Here, you'll be led around by a guide to the city's best off-the-beaten-path gelato and coffee shops, truffles, fresh-pressed Tuscan olive oil, handmade chocolate focaccia, and locally produced wine.

The following day, you'll venture into the Chianti wine region to visit family-run wineries. It's a good basis of comparison for the second part of the trip, when you'll travel to the Amalfi Coast and taste wines made there. Take a pizza-making class in Naples and finish up in Rome with a food and wine tour in Trastevere, one of the Eternal City's most charming neighborhoods. Learn more

Read this article about Italy's best culinary experiences for more information. 

Itinerary #4: Spectacular Self-Drive Tour Around Sicily

Enjoy the luxury of time on this two-week road trip around Sicily. Instead of zipping between major cities and sights, you'll take your time exploring country roads and traditional villages in between stops in Palermo and Taormina—and you'll side-trip to smaller islands via hydrofoil.

The crystal-blue waters of Zingaro Nature Reserve
The crystal-blue waters of Zingaro Nature Reserve
Day Highlights Overnight
Day 1 Arrive in Palermo Palermo
Day 2 Palermo and Monreale Palermo
Day 3 Scopello and the Zingaro Natural Reserve Trapani
Day 4 Levanzo and the Egadi islands Trapani
Day 5 Trapani Trapani
Day 6 The Salt Road Sciacca
Day 7 Agrigento and Piazza Armerina Agrigento
Day 8 Villa Romana del Casale Modica
Day 9 The Sicilian Baroque Syracuse
Day 10 Syracuse Syracuse
Day 11 Riviera dei Ciclopi Taormina
Day 12 Mt. Etna Tour Taormina
Day 13 Cefalù and Palermo Palermo
Day 14 Goodbye Italy!  


Begin the trip in Palermo, where you'll have some time for sightseeing before day-tripping to Monreale and its extraordinary cathedral, considered the greatest example of Norman architecture in the world. Pick up your rental car on day three and drive to the seaside village of Scopello, gateway to the Zingaro Nature Reserve, famous for its crystal-blue water. After hiking and swimming, you'll move on to the Trapani region for a three-night stay in a wine resort. From Trapani, take a hydrofoil to Levanzo, the smallest of the Egadi islands, returning at the end of the day for wine and a leisurely meal at the resort.

On week two, drive along the coast to Agrigento for a guided tour of the archaeological site Valley of the Temples, then stay overnight at a farmhouse. You'll tour Villa Romana del Casale and a pair of baroque Sicilian towns on your way to Syracuse, where the itinerary includes a guided visit to the Neapolis Archaeological Park with its famous Greek theatre. Wrap up the trip with a hike to the summit of Mount Etna and a visit to the picturesque fishing village of Cefalù before returning to Palermo to catch a flight home. Learn more

Short on time? Try these ideas for one-week road trips around Sicily.

More Unique Italy Itineraries

Find more two-week Italy itineraries here, then read more about how kimkim trips work in Italy.