Italy 8-Day Self-Drive Tours & Itineraries

Explore 4 self-drive trips designed by local kimkim specialists to get ideas for your trip to Italy.
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Umbrian countryside outside of Spoleto
Self-Drive Italy: Hill Towns of Tuscany & Umbria - 8 Days

The medieval hill towns of Tuscany and Umbria take center stage on this relaxed, 8-day road trip through the Italian countryside. Starting in the ancient city-state of Cortona, you'll set out on day trips to the stunning fortified towns of Montepulciano and Arezzo, discovering a treasure trove of Renaissance art and architecture. Hop over to quieter Umbria for spectacular scenery and more magical hilltop locales, visiting historic fortresses, cathedrals, and cities from your base in beautiful Assisi.

Enjoy a visit to Siena and explore its Medieval buildings
Map of Tuscany Self-Drive Tour - 8 Days
Tuscany Self-Drive Tour - 8 Days

The vineyards of Chianti, the quaint seaside villages of the Cinque Terre, and the iconic Leaning Tower of Pisa await on this colorful eight-day road trip through Tuscany. Start in Florence, where you'll see Michelangelo's world-famous "David" sculpture, then drive to Pisa, where you'll base yourself while day-tripping to Lucca and the Cinque Terre. Continue to picturesque San Gimignano and historic Siena, finishing the trip with a wine tasting amid the vineyards in the Chianti Classico region.

Enjoy a gelato as you stroll through the elegant streets of Noto
Map of Sicily Highlights Self-Drive Tour - 8 Days
Sicily Highlights Self-Drive Tour - 8 Days

Featuring a combination of culture, adventure, and relaxation, this eight-day self-drive tour of Sicily will bring you to the regional capital of Palermo, the Greek temple ruins of Agrigento, and the brilliant Baroque laneways and staircases of Ragusa Ibla, Modica, and Scicli. Marvel at the impressive Norman-Byzantine details of Monreale Cathedral, hike the slopes of Mount Etna and take in the breathtaking scenery in Savoca and Forza D'Agrò.

Italy's capital, Rome, is situated along the Tiber River
Map of Rome, Assisi & Florence - 8 Days
Rome, Assisi & Florence - 8 Days

This scenic eight-day tour through Italy checks off two world-class cities and a UNESCO-listed hill town in the Umbrian countryside. First, stay three nights in Rome to see ancient ruins and the Vatican's many museums (including the Sistine Chapel). Then pick up a car and drive through the rolling olive groves and wineries to get to medieval Assisi, the birthplace of 12th-century St. Francis. Finish the adventure in Florence, where you'll discover elegant gardens and Renaissance masterpieces.

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