Italy 16-Day Tours & Itineraries

Explore 12 trips designed by local kimkim specialists to get ideas for your trip to Italy.
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Rome's Pantheon at sunrise
Map of Venice, Florence, Amalfi Coast & Rome - 16 Days
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
Map of Sicily Highlights Self-Drive Tour with Aeolian Islands - 16 Days
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.

View of the Cinque Terre
Map of Florence, Cinque Terre, Rome, & Amalfi Coast - 16 Days
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. 

Rustic cafe tables in Sorrento
Map of Relaxed Amalfi Coast, Naples & Rome - 16 Days
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.

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Map of Naples, Amalfi Coast, & Sicily - 16 Days
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.

Rome, Amalfi Coast, & Sicily - 16 Days
Map of Rome, Amalfi Coast, & Sicily - 16 Days
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 Mt. Etna, and more.

Discover Taormina's ancient Greek theater and admire views of Mount Etna
Map of Sicily Highlights Self-Drive Tour - 16 Days
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.

Verona skyline
Map of Rome, Florence, Verona, & Venice - 16 Days
Rome, Florence, Verona, & Venice - 16 Days

Your trip to Rome and Florence starts with guided tours through Rome's historical core, Vatican City, and the Roman Forum, with walks through the Colosseum and to the top of Palatine Hill. Head to Florence to experience its historic squares, cathedrals, and museums. End your trip in Verona, visiting the infamous romantic of Shakespeare's love story and the floating city of Venice.

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Map of Puglia & Sicily Highlights - 16 Days
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.

Enjoying a meal with friends
Map of Italy Food & Wine Immersion: Treviso, Verona, Perugia, Urbino - 16 Days
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.

Siena's main square
Map of Discover Venice, Tuscany, & Rome - 16 Days
Discover Venice, Tuscany, & Rome - 16 Days

From the canals of Venice to Rome's buzzing nightlife, this incredible trip through the highlights of Italy is perfect for travelers who want to see it all, making your way across the country with a mix of trains and rental car. Start in Venice to see the famed Grand Canal, then head to Florence for its famed cathedrals and da Vinci's art. From here, start the self-drive portion of your trip exploring the stunning region of Tuscany to its fullest before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.

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Map of Rome & Sicily Highlights - 16 Days
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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