Italy 16-Day Tours & Itineraries

Explore 12 trips designed by local kimkim specialists to get ideas for your trip to Italy.

With 16 days to spare in Italy, you have the perfect opportunity to explore diverse regions and soak in the local culture and flavors. If you're food-and-wine-motivated, you might consider a trip such as this food-and-wine immersion itinerary, where you'll visit Treviso, Verona, Perugia, and Urbino. Prefer to explore Italy's expansive coastline? Something like this coastal itinerary might be a fun option, taking you to Cinque Terre's rugged shores and the shimmering Amalfi Coast. Meanwhile, if you're an adventurer looking to discover Sicily by car, you might enjoy a route similar to this Sicilian highlights drive that includes Palermo's Monreale Cathedral, ancient Greek and Roman ruins, and Mount Etna.

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Florence, Cinque Terre, Rome, & Amalfi Coast - 16 Days

This 16-day itinerary travels through all the highlights Italy has to offer. Start off in Florence, strolling along cobblestone streets and across the famed Ponte Vecchio before venturing to the coast and exploring the colorful villages of the Cinque Terre. From here, head south to Rome to discover the Eternal City, delving into the history of the Colosseum and admiring the breathtaking Sistine Chapel. Finish up with some beach time and relaxation along the Amalfi Coast.

Venice, Florence, Amalfi Coast & Rome - 16 Days

Spend sixteen days visiting Italy's incredible cities and explore the sunny Amalfi Coast on this getaway trip. Visit ornate palaces and art galleries in Venice and Florence, go wine tasting in Tuscany, and slow down to a quieter pace of life on the Amalfi Coast. Spend the last four days in the capital city of Rome where ancient ruins and a buzzing nightlife meet for a modern vibe.

Watch Stromboli's routine eruption on an evening tour of the volcano

Sicily Highlights Self-Drive Tour with Aeolian Islands - 16 Days

Experience the highlights of Sicily on this in-depth tour. Beginning and ending in Catania, you'll cover the Italian island as well as spend some time exploring the impressive Aeolian Islands. You'll visit ancient Greek, Roman, and Norman ruins, medieval fortressed towns dotted with ornate baroque buildings and stunning beaches. 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.

Discover Taormina's ancient Greek theater and admire views of Mount Etna

Sicily Highlights Self-Drive Tour - 16 Days

Explore the highlights of Sicily as you circumnavigate the Italian island starting and ending in the regional capital of Palermo, a cultural melting pot with stunning monuments and vibrant markets. Along the way, you will explore ancient Greek, Roman, and Norman ruins, medieval fortressed towns dotted with ornate baroque buildings and stunning beaches. You'll trek coastal trails in the beautiful Zingaro Nature Reserve, sip fortified wine in charming Marsala, and dine on fresh seafood in sophisticated Taormina.

Garden of the villa San Michelle in Anacapri, island of Capri

Relaxed Amalfi Coast, Naples & Rome - 16 Days

Get away from it all on this comprehensive 16-day trip to the Amalfi Coast and Italy's capital city. Soak in the sunshine and explore small fishing villages on the Amalfi Coast. Visit ancient summer villas on Capri and go wine-tasting on the cliffs along the sea. End your trip in Rome, where the world-famous Vatican, bohemian neighborhood food tours, and a buzzing nightlight await.

With your rental car, you'll have the freedom to explore wineries in Tuscany

Discover Venice, Tuscany & Rome - 16 Days

This 16-day tour of Italy combines classic highlights and lesser-known surprises. Start in Venice, where you'll relax on a gondola and visit islands on the Adriatic. Then train to Florence to walk among Renaissance art and discover your pasta-making skills. From here, drive through Tuscany, stopping at medieval hill towns, Mediterranean beaches, and wineries. Finish in Rome to see the big hitters, followed by dinners in Monti and Trastevere—two neighborhoods filled with trendy locals.

Spend three nights in Verona, a UNESCO-listed city

Rome, Florence, Verona & Venice - 16 Days

This 16-day trip to Italy travels from Rome to Venice via high-speed train, with stops along the way. Land in Rome to see ancient sights and the Vatican museums before heading to Florence for Renaissance masterpieces and pasta-making. Then train to Verona—home of Shakespeare's famous balcony—and finish in Venice, where you'll explore the canals and Piazza San Marco. You'll also take scenic day trips to hike on the Mediterranean, taste wine in Valpolicella, and visit a glassblower near Venice.

Visit the Noto Cathedral in Noto, Sicily

Rome, Amalfi Coast & Sicily - 16 Days

This 16-day adventure includes visits to some of the most incredible locales in Italy. This includes everywhere, from the capital of Rome to the Amalfi Coast to the island of Sicily. On top of the beautiful sights, you'll also enjoy unforgettable activities like museum visits, a street-food tour of Palermo, hiking up Mount Etna, and more.

Naples, Amalfi Coast, & Sicily - 16 Days

Get ready for the trip of a lifetime as you abscond to southern Italy for 16 unforgettable days. The grand tour begins with a bit of history on a tour of the Pompeii ruins before you sail off to the ancient Roman playground of Capri Island. The last portion of the trip is a comprehensive tour around the island of Sicily as you enjoy street food in Palermo, visit Greek ruins in Agrigento, and ascend Mount Etna volcano.

Italy Food & Wine Immersion: Treviso, Verona, Perugia, Urbino - 16 Days

Prepare for a full food and wine experience in 16 days on this trip to Veneto, Marche, and Umbria regions. Admire the art and architecture in Treviso as you sample an Italian prosecco. Continue to Verona for Valpolicella wine tasting, then make your way to Marche for the rolling hills and rustic hill towns of Tuscany. Cross the mountains into Umbria to end your trip in the regional capital of Perugia, where you’ll explore ancient ruins, browse Renaissance art, and spend your final day learning to cook the local cuisine.

Puglia & Sicily Highlights - 16 Days

This packed 16-day adventure combines the culturally rich region of Sicily with one of Italy's less-heralded gems: Puglia. First, you're off to the heel of Italy's boot, home to ancient and unique cities like Matera and Alberobello. Then you'll jet to Sicily, where you'll hop in a rental car and drive across the island, stopping at ancient Greek and Roman ruins along the way.

Rome & Sicily Highlights - 16 Days

Lose yourself in the sights and sounds of Italy's capital before venturing south to the historic island of Sicily. This packed 16-day itinerary begins in Rome, where you'll visit the emblematic city sights. Then you'll jet south to Palermo and embark on a road trip around Sicily to discover its rich culture, cuisine, and history.

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