Experience Sicily in all its glory by driving around the island in 2 weeks. Highlights of this tour include Palermo, a cultural melting pot with stunning monuments and vibrant local markets and Taormina, the elegant village famous for its Greek theater and the postcard views. You'll also visit Syracuse and Agrigento, with their archaeological masterpieces, and hike Mt. Etna—Europe's most active volcano.
Italy 2-Week Tours & Itineraries
The traditional two-week vacation is just enough time to plan the ideal Italian getaway. You could embark on a food and wine tour that involves pizza making on the Amalfi Coast, wine tasting in Tuscany, and sampling the famous hams of Parma. You could also explore famous cities like Venice, Florence, and Rome, laze on the sun-kissed beaches of the lesser-visited Puglia region, or go on a family adventure that mixes kid-friendly museums with fun walking tours and even gladiator training.
See our itineraries below or read our guide to the best 14-day trips in Italy.
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Discover the sights and delights of Italy on this two-week highlights tour. Explore the floating city of Venice, the Renaissance jewel of Florence, and the Eternal City of Rome. Ride a Vespa through picturesque Tuscany and discover the stunning Amalfi Coast. Soak up the culture, food, and wine while you fall in love with Italy.
If you have two weeks and a thirst for Sicilian sunshine, delicious street food, and fascinating culture, then this is the trip for you. Spend four days exploring Palermo's diverse history, shopping at bustling markets, and relaxing on sunny beaches. Visit Syracuse—home city of mathematician Archimedes—and explore the Old Town of Ortygia, then head to Taormina to hike Mount Etna and catch a performance at the ancient Greek Theater. End your trip with a street food tour and sunny views of the Ionian Sea in Catania.
Spend two weeks living La Dolce Vita on this relaxing getaway trip. Spend 4 days exploring rocky beaches and sprawling summer villas on the Amalfi Coast, then head to Sorrento for beautiful architecture and a cooking class. Go shopping in Naples' glass-roofed Galleria Umberto, then head to Rome to discover Roman ruins, cozy streetside cafes and serene city parks.
From fairytale Trulli homes to rocky sun-soaked beaches, this two-week trip to Puglia is perfect for travelers who want to see authentic Italy. See baroque architecture in Lecce, scrubby pine forests in Gargano National Park, and sunny southern towns of Otranto and Gallipoli. End your trip in the busy port city of Bari where a maze-like old town, deep-fried panzerotto, and 12th-century churches await.
Rome wasn't built in a day, but you can spend fourteen days eating and drinking your way through Italy's top culinary destinations! Go for a gondola ride in Venice, try the decadent tiramisu, and sample the local Cicchetti. Head to Bologna to see 11th-century architecture and try the Parmeggiano, then head to Florence to see Michelangelo's David and Leonardo's top works. Pair a bottle of Tuscan Chianti with a farm-to-table charcuterie board, then head west for four days on the sunny Amalfi Coast. Explore medieval fishing villages and learn to make the perfect Neopolitan pizza before capping your trip off with visits to the Sistine Chapel, Colosseum, and local gelateria in Rome.
Spend two relaxing weeks enjoying art, culture, and food. Shop for treasures at the Quadrilatero della Moda district and join the locals at the Navigli canals for high-energy nightlife in Milan. Spend four days on peaceful Lake Como, touring sleepy fishing harbors and learning to make the perfect pasta dish. Visit serene lakeside estates on Lake Maggiore, then end on Lake Garda for award-winning wine tasting and Tyrolean charm.
Discover why Pisa's famous tower leans so much (and why it's not the only one!), plus much more on this exploration of Tuscany. Start in Florence to see Da Vinci's 'The Annunciation' and other famous Renaissance works in the Uffizi Gallery. Look for treasures in the San Lorenzo market, browse shops on the medieval Ponte Vecchio, and explore history in the medieval cities of Siena and Lucca. End your trip with sweeping ocean views on the Cinque Terre hiking trail.
Spend two weeks exploring the Cinque Terre to your heart's content on this packed itinerary. Start in the medieval village of Manarola where you'll learn traditional cooking from a local, then head up the coast to the beautiful town of Portofino to explore the rugged coast from the water. Continue to Genoa for medieval alleyways and a food tour, then end in Pisa to learn why, exactly, the famous tower leans.
Spend two weeks delving into Italy's historic and cultural sites on this packed itinerary. Ride a gondola down Venice's Grand Canal and see art by Michelangelo and da Vinci in Florence. Explore Tuscany's medieval towns, then continue to the Amalfi Coast for ancient summer villas, limoncello, and seaside terraces. End in Rome to see the Vatican and explore eclectic neighborhoods.
Spend two weeks experiencing Italy's cities and Amalfi Coast in luxury. Start with a private tour of Venice to see ornate palaces and visit a traditional gondola workshop. In Florence, dine on world-class food and wine and go on a hot-air balloon ride above the Tuscan hills. Dive into history with priority access to the Vatican and a private tour of the Colosseum, then soak up the sunshine and ocean views on the gorgeous Amalfi Coast.
Spend two weeks visiting Italy's top cities and world-famous winemaking regions. See ornate palaces and colorful bohemian islands in Venice, tour the Uffizi Gallery to see da Vinci's work in Florence, and climb the leaning tower in Pisa. Spend a day touring vineyards and small farms in Tuscany, then make—and eat!—the perfect pasta dish. Round out your trip in Rome for a visit of the Sistine Chapel and buzzing neighborhood wine bar.
Over 15 days you'll experience the highlights of Italy. In the capital Rome, you'll visit landmarks like the Colosseum and historic institutions like the Vatican. You'll then enjoy the pebble beaches and sun-kissed coast of Amalfi before venturing far south to Sicily, where a road trip will take you from Palermo to Mount Etna.
Featuring two weeks of cycling through beautiful and diverse landscapes in northern Italy, you'll also pedal along the Slovenian and Croatian coastline. Begin your journey in Bolzano, the gateway to the Dolomites, and work your way south to Peschiera before turning east to Venice and following the Adriatic Sea around the Gulf of Trieste, where you'll end along the Istrian coast in Croatia's Poreč. Discover romantic Verona, marvel at architectural masterpieces in Vicenza, and soak weary muscles in thermal waters in Padua.
Combine the historical splendor of Italy with its natural charm in this 14-day tour, highlighting the ancient cities of Venice, Pisa, Florence, and Rome with sunset gondola rides, regional dishes in local neighborhoods, and guided walking tours, plus visits to many museums, art galleries, and monuments. Enjoy tasting wine in the picturesque hills of Tuscany, plus guided tours of Siena, Vatican City, and the Roman Forum. Swap lively city centers for outdoor experiences in Lake Como and Cinque Terre, like boat tours, day hikes, and traversing the seaside in search of colorful villages.
If spending two weeks traveling with the family through Italy's top cities and historic sites sounds perfect, then this packed itinerary is for you. Start in Venice to see ornate palaces and ride a gondola on city canals, then continue to Florence for amazing food, kid-friendly museums, and the rolling Tuscan landscape. End in Rome where the kids can follow Percy Jackson's adventures through Ancient Roman ruins.
Spend two weeks delving into Sicily's historic and cultural highlights on this complete itinerary. Discover remote island settlements on Stromboli, meander and climb the narrow laneways and staircases in Modica, Ragusa Ibla, and Scicli, and dine on fresh seafood in sophisticated Taormina. You'll begin and end in lively Catania and spend four nights on the Aeolian Islands before picking up your rental car and touring the Italian island from Palermo to Taormina, with Cefalù, Agrigento, and Syracuse in between.
One of Italy's biggest attractions has always been its food, and you can sample plenty of it over the course of these two weeks. You'll relax by the seaside, walk through former Roman cities, and hike over mountains as you make your way to various tasting and art experiences to satisfy all of your sense.
The city of Alba is best known for its white truffles, sometimes referred to as the "diamonds of Alba" for how prized they are. Sample these truffles and other delights of Northwest Italy on this two-week trip which takes you from the shores of Portofino into the wine- and truffle-rich of the Piedmont. Continue to the medieval streets of Turin, up into the Alps, and back down to the shores of Lake Maggiore before you depart.
You can do a lot with the traditional two-week vacation. Case in point, it's enough time to jaunt to southern Italy and tour beautiful locales like Naples, Pompeii, the Amalfi Coast, and the island of Capri. You'll even have time to road trip around the island of Sicily, enjoying incredible street food and touring ancient Greek ruins as you do.
There's no need to choose between water or mountains on this two-week trip. You'll visit both the lakes and peaks of northern Italy and Switzerland, scouting out real estate that ranges from luxurious villas on the shores of Lake Como to Alpine hiking huts over the course of your trip.
This two-week holiday combines anthropology and history with a road-trip adventure in two of Italy's most unique regions. First, you'll tour Puglia, Italy's "heel of the boot," which is home to beautiful beaches and ancient cities. Then you'll fly to Sicily for a road trip from the cultural melting pot of Palermo to ancient Greek and Roman ruins—plus enjoy a jaunt to Mt. Etna.
Follow this two-week circuit around Sicily for unique cultural experiences, hiking adventures, and coastal relaxation. Begin on the northern shore in cultural-melting-pot, Palermo before heading to Trapani and the Aegadi Islands in the west. Wander amid Roman ruins and extensive mosaics in Agrigento, get lost in the baroque cities of Modica, Ragusa Ibla, and Scicli and their medieval centers, wind through crypts and catacombs in historic Ortygia, and relax along the Ionian Sea enjoying fresh-caught seafood in Taormina.
In two weeks you'll not only immerse yourself in the splendor of historic Rome, but you'll also embark on an unforgettable road trip around the cultural melting pot that is Sicily. In the former, you'll tour famous sights like the Colosseum and Vatican plus take part in a local cooking class. In the latter, you'll drive around the island at your leisure, stopping at historic and beautiful cities like Syracuse, Agrigento, and Taormina.