Itinerary #1: Discover Venice, Florence & Rome
This classic itinerary takes travelers to Italy's top cities and wine-producing regions. Tour Venetian palaces, see the Colosseum, wander through medieval Tuscan towns, ride a gondola on Venice's Grand Canal, and taste wines in Chianti.
|Day 1||Arrive in Rome, Travel to Venice||Venice|
|Day 2||Venice Walking Tour||Venice|
|Day 3||Venice to Florence, Food Tour||Florence|
|Day 4||Tour of Tuscany & Wine Tasting||Florence|
|Day 5||Florence to Rome, Colosseum & Forum Tour||Rome|
|Day 6||Vatican & Classic Tour of Rome||Rome|
|Day 7||Free Day in Rome||Rome|
|Day 8||Goodbye Italy!|
Venice, Florence, Rome: that's the order you'll follow, from north to south, in this mini grand tour of Italy. Begin in the Floating City, kicking off your trip in grand style with a gondola ride down Venice's famous canals. In the evening, wander through the Cannaregio District, site of the former Jewish Ghetto, for a walking food tour. You'll go on a walking tour of the city's cultural highlights on day two, and on day three, catch the train to Florence, where you'll embark on a guided walking tour of the city with a local guide. Highlights of the medieval city center include the 15th-century Pitti Palace and the world-famous Uffizi Gallery; the guide will also point the way to off-the-beaten-path gelato shops and charming sidewalk cafés where you'll relax with a coffee or a glass of prosecco.
The following day, leave the city for the vineyards and olive groves of Chianti. You'll tour the historic village of San Gimignano, a UNESCO World Heritage Site, before visiting a Tuscan winery for a tasting and an al fresco lunch with wine pairings. Spend the afternoon sightseeing in Siena and pay a visit to the medieval fortress of Monteriggioni before returning to Florence for the night. All roads lead to Rome at the end of this trip. You'll spend the last few days seeing the Colosseum, the Pantheon, the Forum, the Vatican, and other key cultural and historic sites on guided and self-guided tours, with plenty of time built in for shopping and relaxing in outdoor cafés. At night, dine at a traditional trattoria in Trastevere and raise a glass to the perfect eight-day trip. Learn more
Brush up on your knowledge of Venice with this ultimate guide to the Floating City.
Itinerary #2: Discover Milan and the Italian Lakes
This northern Italian itinerary mixes cultural sightseeing and shopping in Milan with a visit to Lake Como's quiet beaches, historic wineries, and charming villages.
|Day 1||Arrive in Milan||Milan|
|Day 2||Full Day Milan Tour||Milan|
|Day 3||Milan to Lake Como||Como|
|Day 4||Bellagio Walking Tour||Como|
|Day 5||Free Day in Como||Como|
|Day 6||Lake Como to Lake Garda||Peschiera del Garda|
|Day 7||Dolomites Day Tour||Peschiera del Garda|
|Day 8||Goodbye Italy!|
The trip begins in Milan. Take it easy on day one with some self-guided sightseeing in the historic center: walk to the striking Gothic Duomo and La Scala Opera House, take a coffee and shopping break at Galleria Vittorio Emmanuele. After dark, go for dinner and a walk along the Navigli at Porta Genova, Milan's ancient network of canals and passages. On day two, you'll take a guided tour of the city, partly on a bus and partly on foot: a major highlight is the chance to see one of the world's most famous paintings, Leonardo da Vinci's "The Last Supper," housed inside the Santa Maria della Grazie monastery.
You'll spend the next three days on and around Lake Como. Take a walking tour of historic Como, catch a ride on the funicular railway, stroll along the waterfront, and enjoy a sunset cruise before a four-course dinner with wine pairings back on dry land. Then venture by boat to the lakeside town of Bellagio and continue on foot to the village of Aureggio. Top sights include the neoclassical Villa Melzi and the lovely botanical gardens that surround it. Optional activities on the third day include rock-climbing on the cliffs around Lake Como, renting a kayak for an afternoon on the water, and wine tasting at the lake's oldest winery, Cantine Sorsasso.
At the end of the tour, you'll move onto Lake Garda and the stylish lakeside villages of Sirmione and Desenzano, filled with appealing cafés and restaurants. On the last full day, head into the Dolomite Mountains for a cable car ride, a traditional Tyrolean lunch, and a scenic drive through the Fassa Valley into the Ega Valley and Lake Carezza. The startlingly blue lake is the perfect final photo op. Learn more
See this guide to Italian lakes, including Lake Como, for more information and travel tips.
Itinerary #3: Best of Sicily
Spend a leisurely week exploring Palermo, Taormina, and the largest active volcano in Europe. On this itinerary, highlights include a visit to the 12th-century Norman Cattedrale, a visit to an ancient Greek theater, and an eight-hour trip to the summit of Mt. Etna.
|Day 1||Arrive in Palermo, Evening Guided Tour||Palermo|
|Day 2||Palermo Segway Tour & Cooking Class||Palermo|
|Day 3||Free Day in Palermo||Palermo|
|Day 4||Palermo to Taormina||Taormina|
|Day 5||Mount Etna Tour||Taormina|
|Day 6||Taormina to Catania, Self-Guided Exploration||Catania|
|Day 7||Walking Food Tour of Catania||Catania|
|Day 8||Goodbye Italy!|
Begin your trip in the capital city of Palermo, where you'll sleep for the first three nights. On the first day, explore the historic center on a guided tour, including the 9th-century Palazzo dei Normanni, the oldest royal residence in Europe, and the Cassaro, Palermo's oldest street. Spot the massive Ficus tree in Piazza Marina and go on an informal street food tour and tasting, stopping to try locally made wines and snacks along the way. It'll prepare you for the next day's four-hour Sicilian cooking class, which follows a guided Segway tour of the city's top landmarks.
On day four, travel to picturesque Taormina, a resort town on the Ionian Sea. On a guided walking tour of the city, you'll see the famed ancient theater and the Vicolo Stretto, known as the narrowest street in town. The following day, you'll head straight for the largest active volcano in Europe, Mt. Etna. An eight-hour tour includes a cable car ride, a Jeep ride, and hiking to the summit, where you'll feel the heat of lava beneath your feet. Finish up the trip in Catania, a town that's been greatly affected by the volcano's eruptions over time: make sure to see the Fontana dell’ Elefante, a fountain made from lava rock in the historic center. Learn more
Have another week to spare? Check out this 15-day road trip around Sicily.
Itinerary #4: Cycling Through Sardinia
Hit the road on a bicycle to see everything that the Mediterranean island of Sardinia has to offer. This eight-day itinerary includes cycling along the gorgeous coastline of Alghero toward Bosa, riding into the Gennargentu Mountains, and stopping for locally produced wine and traditional dishes along the way.
|Day 1||Arrival in Alghero and Warm-up Ride||Alghero|
|Day 2||Monteleone Loop Tour||Alghero|
|Day 3||Alghero to Santu Lussurgiu||Santu Lussurgiu|
|Day 4||Santu Lussurgiu to Aritzo||Aritzo|
|Day 5||Gennargentu Loop Tour||Aritzo|
|Day 6||Aritzo to Muravera||Muravera|
|Day 7||Muravera to Cagliari||Cagliari|
|Day 8||Departure from Cagliari-Elmas Airport|
Welcome to Italy's second-largest island. On your arrival, sip a glass of locally made Torbato wine—but don't overdo it. The first day of the trip features a 22-mile warm-up ride in the countryside outside Alghero, which gives you a good idea of what the rest of the trip is going to be like. The following day, you'll bike uphill to Putifigari toward the village of Villanova Monteleone. You'll be rewarded with the thrilling downhill ride along the winding road known as the Scala Piccada, offering fantastic views over the bay below. On the third day, continue along the rugged coastline to Bosa, with its beautiful medieval castle, continuing through vineyards and forests to the longest climb of the day: La Madonnina. The ride is challenging, but the panoramic views make it worthwhile, as does the feast you'll enjoy at night in the village of Santu Lussurgiu.
The journey continues downhill through the Tirso Valley, uphill to the village of Samugheo, across the vineyards of the Mandrolisai Region, and through the chestnut forest of Aritzo. The next day offers the trip's greatest challenge: the ride into the Gennargentu Mountains. Take a well-deserved coffee break in the mountain village of Fonni before coasting downhill to the shores of Lake Gusana. At the end of the tour, you'll pass through the Flumendosa River Valley and the Ogliastra Region, known for its pristine rivers and limestone cliffs. From Muravera, you'll ride along a coastal road overlooking the island of Serpentara and the emerald water that surrounds it. Finish in Cagliari for a seafood meal at a family-run restaurant in the old town. Learn more
For a similar itinerary involving boats as well as bicycles, consider this week-long trip plan.
Itinerary #5: Food & Wine in Italy
Taste-test traditional Parmeggiano Reggiano cheese and local prosciutto in Bologna. Sip Chianti at Tuscan vineyards. Learn how to make a thin-crust pizza in Rome. You can do it all—and much more—on this eight-day itinerary.
|Day 1||Arrive in Rome, Travel to Bologna||Bologna|
|Day 2||Day Trip to Parma: Ham and Parmesan Tasting||Bologna|
|Day 3||Free Day in Bologna||Bologna|
|Day 4||Bologna to Florence||Florence|
|Day 5||Tour of Tuscany & Wine Tasting||Florence|
|Day 6||Florence to Rome, Full-Day Rome Excursion||Rome|
|Day 7||Pizza Making Class in Rome||Rome|
|Day 8||Goodbye Italy!|
This foodie adventure begins in Bologna. Have an espresso and do some sightseeing—historic and cultural landmarks include Piazza Maggiore, 14th-century Basilica di San Petronio, the 11th-century University of Bologna with its Anatomical Theater, and the Pinacoteca Nazionale di Bologna (the National Art Gallery)—before breaking for lunch and a walking food tour. You'll stop into bakeries, pasta shops, and marketplaces to see local specialties being made. And, of course, to try artisanal tortellini, cheese, and salami. On day two, you'll get even more up close and personal with the process behind Italian delicacies on a trip to Parma in the Emilia-Romagna region. On a city food tour, you'll visit the local production facilities of Parma ham and Parmigiano Reggiano cheese, try traditional balsamic vinegar, and shop for edible souvenirs.
After a free day in Bologna for more sightseeing and snacking, you'll take the train to Florence for art, architecture, and, of course, more touring of city markets to try local specialties like truffle panini, fresh-pressed Tuscan olive oil, and handmade chocolate focaccia. The following day, side-trip to San Gimignano on your way to the wineries of Chianti for a guided tasting and lunch with wine pairings. Swing by Siena—make sure to get a coffee or a gelato, at the very least—before returning to Florence. The tour ends in Rome, where you'll head off on an after-dark city tour on the first night, sample Roman dishes and delicacies that have been passed down through generations, and learn how to make the perfect thin-crust pizza at a cooking class led by a professional chef. Learn more
If you're interested in spending a few more days in Tuscany, this five-day trip plan is a good place to start.