Italy 2-Week Self-Drive Tours & Itineraries

Explore 5 self-drive trips designed by local kimkim specialists to get ideas for your trip to Italy.

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Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days

Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You'll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you'll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.

Lie out on the black sand beach of Stromboli Island

Sicily Highlights Self-Drive Tour with Aeolian Islands - 14 Days

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.

Travel by gondola in Venice's iconic canals

Discover Venice, Tuscany & Rome - 14 Days

Travelers with two weeks to spare will love this Italy tour, which offers a mix of guided excursions and free time. The adventure starts in Venice, where you'll glide through charming canals and sail to lesser-known islands before taking a train to Florence. After a few days of Renaissance culture, pick up your car for a Tuscan road trip through wineries, hill towns, and beaches in Cinque Terre. Finish in Rome, where you'll see the classic sites, as well as hip neighborhoods like Trastevere.

Sicily Highlights Self-Drive Tour - 14 Days

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.

There'll be plenty of opportunities on this trip to eat and drink your way through local Italian restaurants

Italian Vineyards, Cuisine & Culture Trip: Tuscany, Umbria & Piedmont - 14 Days

Love food and wine? This 14-day trip is plucked straight from your Italian dreams. Over two weeks, you'll explore the lush, rolling landscapes of Tuscany, Umbria, and Piedmont, visiting vineyards and olive groves for tastings, enjoying lunch at a hazelnut farm, and hunting for the prized white truffle of Alba. In between, you'll tour medieval villages, explore ancient cathedrals, and see both Renaissance and contemporary art.

Other durations: 7 days · 8 days · 9 days · 10 days · 11 days · 12 days · 13 days · 14 days · 15 days · 16 days

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