Itinerary #1: Sicily Road Trip & Relaxing Sardinia
Spend three weeks on this self-drive tour of Sicily, including four days in nearby Sardinia, combing two cultural melting pots known for their archaeological treasures and gorgeous beaches, and including a hike on Mount Etna.
|Day 1||Arrive in Palermo||Palermo|
|Day 2||The soul of Palermo||Palermo|
|Day 3||The day of salt and wine: Mozia and Marsala||Trapani|
|Day 4||Ancient history: Segesta, Erice & Trapani||Palermo|
|Day 5||Drive to Agrigento||Agrigento|
|Day 6||Guided tour of Valley of the Temples||Agrigento|
|Day 7||Self-drive from Agrigento to Ragusa||Ragusa|
|Day 8||The Baroque Triangle: Modica, Ragusa & Noto||Ragusa|
|Day 9||Self-drive from Ragusa to Syracuse||Syracuse|
|Day 10||Highlights of Syracuse||Syracuse|
|Day 11||Free day in Syracuse||Syracuse|
|Day 12||Self-drive from Syracuse to Catania||Catania|
|Day 13||The Cyclopes Bay: Acireale Coast||Catania|
|Day 14||Self-drive from Catania to Taormina||Taormina|
|Day 15||Highlights of Taormina||Taormina|
|Day 16||Free day in Taormina||Taormina|
|Day 17||Fly to Cagliari (Sardinia)||Cagliari|
|Day 18-20||Free Time in Cagliari||Cagliari|
|Day 21||Depart Cagliari|
Begin in Palermo, the regional capital of Sicily, with a guided tour of the city's main plazas and 16th-century catacombs before visiting the salt flats and windmills of Mozia, sampling the famous wines of Marsala, and sneaking in beach time in Trapani. Next, drive the scenic coastal route to Agrigento, where a full day of exploring the Valley of the Temples with an expert guide brings the Greek ruins to life. Then, it's on to hilltop Ragusa, with its sloping and tangled alleyways, before hitting the road for the "Baroque Triangle": Modica (with time to visit a famous chocolatier), Ragusa, and Noto.
For week two, make your way to Syracuse, with stops en route to enjoy the beaches. After a guided walking tour of this ancient cultural center, plus free time on nearby Ortygia Island, drive to chaotic, gritty, and mesmerizing Catania (perfect for nightlife). Here, you'll be accompanied by a private guide as you explore enchanting villages along the Acireale Coast. Then head north to hike Mount Etna before arriving at the popular resort of Taormina, where a guided tour (including the well-preserved ancient Greek Theatre) precedes an entire day free for relaxing or for exploring its museums and other sites.
On day 17, fly to Cagliari, in Sardinia, and pick up your rental car before exploring the city's historic center, rich with ancient Roman ruins. Finally, spend three days exploring Sardinia, taking in the seaside archaeological site of Nora and the many beautiful beaches along the stunning Chia Coast. Learn more
Itinerary #2: Venice, Florence, Amalfi Coast & Rome
This 21-day immersive itinerary delivers a deep dive into Italian lifestyle and culture as you explore many of the most quintessential cities, plus the sunny beaches and cliff-hanging resort villages of the Amalfi Coast.
|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 & 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 Tour||Rome|
|Day 20||Free Day in Rome or Ostia||Rome|
|Day 21||Depart Rome|
Start in Rome, then transfer by high-speed train to Venice. Begin with a romantic gondola tour, followed by an evening foodie walking tour. The next day, tour the highlights, like Piazza San Marco and San Marco Basilica, the Grand Canal, and the Doge's Palace. You'll also explore Venice by bicycle, and nearby islands by motorboat, including a glass-making tour in Morano. Follow five days in Venice with five nights in Florence. After visiting Florence's iconic Duomo, Galleria dell'Accademia (displaying Michelangelo's "David"), and the world-famous Uffizi Gallery, spend a day touring the Chianti region of Tuscany.
Then head to Pisa to climb the famous Leaning Tower and learn the art of Tuscan cooking before departing by train to Naples for the Amalfi Coast and a sunset boat tour to Positano. Spend four days on the Amalfi Coast, where highlights include a hike to Castello di San Nicola, a pizza-making class, and a hydrofoil ride to the isle of Capri for swimming in the iconic Grotta Azzurra ("Blue Grotto"). Finally, you'll head to Rome, with four days to dive into Roman Empire history with a tour of the Colosseum and other ancient sites. The next day, you'll visit the Vatican and its Sistine Chapel and St. Peter's Basilica.
You'll also explore off-the-beaten-track venues, savor a food tour of the eclectic Monti neighborhood, and head underground to explore the 2nd-century Roman Catacombs. Finally, you'll take a guided tour of Villa Borghese gardens and the Galleria Borghese, one of the world's premier art museums. Learn more
Chat with a local specialist who can help organize your trip.
Itinerary #3: Crossing Northern Italy
This comprehensive three-week experiential itinerary spans Northern Italy from Venice to Milan, including Lakes Garda, Como, Maggiore, and Orta. It combines hiking, swimming, kayaking, and Cinque Terre trekking with plenty of time for more relaxed sightseeing and culinary adventures.
|Day 1||Arrive in Venice, Self-Guided City Tour of Venice||Venice|
|Day 2||Guided Walking Tour & Private Gondola Ride||Venice|
|Day 3||Merano Mountains and Hiking; Trauttmansdorff Castle||Merano|
|Day 4||Natural Swimming Bath Gargazon; Explore Merano||Merano|
|Day 5||Stelvio National Park Drive and Hike (or Skiing)||Merano|
|Day 6||Visit Garda Lake||Peschiera del Garda|
|Day 7||Panoramic Cableway of Mount Baldo; Hiking, Mountain Biking, and/or Paragliding||Peschiera del Garda|
|Day 8||Desenzano & Sirmione Walking and Boat Tour||Peschiera del Garda|
|Day 9||Bergamo; then free afternoon relaxing on the Lake||Lake Como|
|Day 10||Kayak Tour from Bellagio||Lake Como|
|Day 11||Free Day in Lake Como||Lake Como|
|Day 12||Discovering Lago Maggiore||Stresa|
|Day 13||Knowing the Borromean Islands||Stresa|
|Day 14||Private Tour around Lake Orta and its Mounts||Stresa|
|Day 15||Cinque Terre Trekking & Train Card, Hiking Monterosso to Vernazza||Cinque Terre|
|Day 16||Cinque Terre Trekking & Train Card, Bathe in the Ligurian Sea, Boat Trip||Cinque Terre|
|Day 17||Cinque Terre Trekking & Train Card, Pesto Cooking Class||Cinque Terre|
|Day 18||Cinque Terre Trekking & Train Card, Wine Route and Tasting Experience||Cinque Terre|
|Day 19||Free Day in Cinque Terre||Cinque Terre|
|Day 20||Cinque Terre to Milan, Best of Milan Walking Tour||Milan|
|Day 21||Depart Milan|
For two days in Venice, you'll cover the major attractions and cross plenty of iconic bridges spanning the Grand Canal. There's exploration of lesser-known districts, such as Cannaregio, plus a classic ride in a Venetian gondola. Then head to the Merano to hike the Sarentino Alps and/or Stelvio National Park, bathe in the natural swimming pool at Gargazon, and explore Trauttmansdorff Castle. Next comes lakeside Peschiera del Garda, with three days dedicated to such activities as sailing and windsurfing on Lake Garda, a panoramic cableway ride to the top of Monte Baldo, and a scenic boat ride to Sirmione.
After free time to further explore Lake Garda, head to Lake Como for a kayak tour, then to Lake Maggiore for your choice of activity. Dedicate another day to exploring the three Borromean Islands in the middle of Lake Maggiore, getting between them by ferry. End your second week with a private guided boat cruise around Lake Orta, including hiking to the heights of the Sacro Monte di Orta religious complex. Your final week spends four days trekking in the Cinque Terre coastal region. After the fifth day at leisure in Cinque Terre, hop aboard a high-speed train for Milan, where you'll see Leonardo da Vinci's "The Last Supper." Learn more
More Great 3-Week Italy Itineraries
Looking for more inspiration for your trip to Italy? Check out these other 3-week Italy itineraries, with trekking trips, cultural adventures, and best-of trips to hit the highlights.