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.
|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 11-13||Explore Rome||Rome|
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.
|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.
Chat with a local specialist who can help organize your trip.
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.
|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.
|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 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 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.