When you drive through Italy, you get to explore towns and landscapes you might otherwise miss and do it at your own pace. Below, you'll find advice for planning the perfect trip, featuring suggestions for a week in Sicily and coastal adventures.
Whether you have a week or more, and regardless of your preferred destinations, we likely have an itinerary for you, such as this week-long drive across Tuscany or this 21-day drive from Milan to Naples.
If you have a week in Sicily, it’s best to focus on one or two regions as opposed to trying to see everything. There's the wine country of the west, the medieval villages of the southeast and the giant Etna volcano in between. The following 7-day itineraries offer some of these attractions, plus incredible food, dramatic coastal views and a history and culture that stretches to time immemorial.
Italy is a country made for slow touring: whether you’re cruising through vineyards and silver-green olive groves that dip to the sea in sun-baked Puglia, negotiating hairpin bends on a cliff-hugging road skirting the dramatic island of Sardinia, or making an epic drive along the coast of Sicily. Wind down the window, breathe in the scent of wild herbs on the breeze, crank up the radio and get ready for five of our all-time favorite coastal road trips.
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.
An island as beautiful and historically rich as Sicily deserves to be experienced at a leisurely pace. This 15-day itinerary features beaches and cathedrals, fishing villages and urban markets, a volcano and ancient archeological sites. Take your time as you circumnavigate this stunning region of Italy.
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.
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.
Wind your way through the hill towns and vineyards of the Tuscan countryside on this weeklong exploration of Italy's most famous wine country. Arrive in Florence and kick things off with a guided walking tour in the birthplace of the Renaissance. Then it's time to hit the road to Siena, San Gimignano, and Montepulciano, where medieval architecture and plenty of wine-tasting experiences await.
Combine historic hill towns, fine wines, and the Tuscan countryside for an Italian eight-day road trip to remember. Get your bearings amid the Renaissance splendor of Florence, then set out into the surrounding landscapes—basing yourself first in Siena and then in Montepulciano. Along the way, you'll experience wine tastings and workshops focused on local Chianti vintages and set off on day trips to hilltop villages like San Gimignano, Monteriggioni, and Cortona.
Wheel your way through northern Italy on this road trip with stops that school-aged children and parents can enjoy, with timing adjustable to your own preferences. You'll start amid the Renaissance influences of Florence, then set out into the Tuscan countryside and Chianti Valley on winding olive- and vineyard-lined roads. From there, head to the coast to wander the beaches of the Italian Riviera and then up to Lake Como to explore its luxurious shores. Wrap up your Italian sojourn on the playful shores of Lake Garda before you return to Florence.
This 10-day itinerary features a perfect mix of culture, history, adventure, and relaxation. Explore ancient Greek and Roman cities, medieval hilltop towns dotted with ornate baroque buildings, and coastal ramparts. Begin in Sicily's regional capital of Palermo and drive your way around the Italian island to end in Catania. You'll visit stunning landscapes, like Trapani's historic salt pans, sip fortified wine in charming Marsala, and dine on fresh seafood in sophisticated Taormina.
Get to the heart of Sicily on this 9-day road trip that explores cities, countryside, and coastlines. Venture into volcanic caves on Mount Etna, relax by the Ionian Sea in elegant Taormina, stroll the labyrinthine old town of Syracuse, and discover the Baroque highlights of the Val di Noto. After walking in the footsteps of the ancient Greeks in the Valley of Temples, your adventure draws to a close in the lively capital of Palermo.
Load the family into the car and hit the road for this trip through lovely Northern Italy, ideal for school-age children and families who want to manage their own budget and schedule. You'll start in fashionable Milan for a culture and history lesson before cruising around the glittering shores and garden villas of Lake Como. Then head to the park-filled shores of Lake Garda, Italy's most family-friendly lake, before heading back to Milan for your departure.
This complete 12-day self-drive tour covers Sicily's best, from cultural stops in baroque-infused cities to the exploration of ancient Greek and Roman temples and archaeological parks. Explore medieval hilltop towns, lively markets, ancient ruins, and old Norman castles. You'll sip fortified wine in Marsala, hike the slopes of active Mount Etna, and relax on Cefalù's inviting golden-sand Lungomare beach.
Enjoy cultural and historical experiences on this 9-day circuit of Sicily beginning in the regional capital of Palermo, a cultural melting pot, and ending in lively Catania. Along the way, you'll visit stunning landscapes, like the limestone cliffs of Scala dei Turchi, roam ancient Greek and Roman ruins at Agrigento and Syracuse, and learn to cook a traditional Sicilian meal in Taormina.
Spend a week exploring the best of Tuscany on this weeklong road trip! You'll begin in Florence, touring the city's historic center with an expert guide before picking up your rental car and venturing into the Tuscan countryside. Stop to see the Leaning Tower of Pisa, then take a full day to experience the pleasures of the Cinque Terre, hiking between quaint villages by the sea. Finish the itinerary in Siena, strolling around the historic center and day-tripping to the Chianti Classico region for a wine tasting.
If you have 10 days to spend in Italy, this tour blends two world-class cities and a road trip through the countryside for a well-rounded adventure. Start in Rome to see the Vatican and learn about the height of the Roman Empire with local guides. Then pick up a rental car and make your way to the hilly Umbria region for medieval towns, like UNESCO-listed Assisi, plus wineries and olive groves. Finish in Florence for Renaissance culture and a cooking class, where you'll learn recipes to take home.
Explore the back roads and small villages that characterize the countrysides of both Italy and Greece on this three-week road trip. You'll visit well-known highlights, like Florence, charming Tuscan hill towns, and the first Olympic site in Olympia, as well as some places a bit off the beaten path: Romeo and Juliet's Verona, the medieval villages of the Peloponnese, the wineries of Nemea, and more. With full control of the daily driving schedule, you'll have time to plan for spontaneous stops for coffee, for shopping at roadside markets, and for late-afternoon beach breaks.
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.
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 Mount Etna.
Experience Italy from north to south in all its glory with this diverse 10-day itinerary that combines the freedom of a road trip with touches of luxury. Tour Milan's magnificent Gothic Duomo, sample Piedmont cuisine in Turin, visit the wine country of the Langhe, and soak up the Renaissance atmosphere of Florence. Your journey ends in vibrant Naples, where you'll step back in time with a tour of ancient Pompeii.
This sophisticated 10-day trip is ideal for travelers looking to experience art, culture, food, and wine—all things that make Tuscany one of Italy's most sought-after regions. Start in Florence, the birthplace of Renaissance art and architecture, to experience the city's rich history and walkable center. Then begin a self-guided road trip around Tuscany, visiting UNESCO-listed monuments, picturesque hill towns, and notable vineyards, including a memorable sit-down lunch and wine pairing in Montepulciano.
This 12-day trip through Italy is perfect for travelers who want to see the highlights. Starting in Venice, you'll walk along the bridges and ride a gondola through the famed Grand Canal. Then hop on a train to Florence to see world-class cathedrals and Renaissance masterpieces. From here, pick up your car and start a self-drive adventure, exploring the stunning region of Tuscany (and its wineries) before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.
Hit the road for a nine-day self-drive adventure through Tuscany! Start in Florence, exploring the historic center and learning to make pasta in a cooking class. Then pick up a rental car and drive to Pisa, where you'll see the famed Leaning Tower and sleep in lodgings in the countryside. Continue to the villages of the Cinque Terre, take a day trip to medieval Lucca, and finish the itinerary in picturesque Siena. You'll enjoy a wine tasting in the Chianti Classico region before heading back to Florence.
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.
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.
Enjoy this 11-day self-drive itinerary around the Italian island where you'll begin in Palermo and end your stay in Catania. Along the way, stop to explore medieval hilltop towns and baroque cities, wander amid ancient Greek and Roman ruins, hike active Mount Etna, and choose from a number of stunning beaches along the coast. Catch a sunset over the Trapani salt ponds, sample fortified wine in charming Marsala, and learn to cook a 4-course Sicilian meal in Taormina.
This 13-day grand tour of the Sicilian island perfectly blends culture and history with adventure. Start in the regional capital of Palermo and wander the historic centers of Trapani and Erice before spending a little time on the Aegadi Islands. Visit the impressive Valley of the Temples and sprawling mosaics of Villa Romana del Casale, discover ornate baroque architecture in Noto, Modica, and Scicli, and lose yourself in the maze of narrow streets and underground passageways of Syracuse's Ortygia Island.
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.
Discover Sicily's historic and scenic highlights with this seven-day self-drive itinerary. Starting in the regional capital of Palermo, you'll spend time discovering the Norman-Byzantine Monreale Cathedral before cutting across the island to explore the Greek temple ruins of Agrigento. Cap off the trip with four nights in Catania, the perfect access point to the Sicilian-Baroque cities of Ragusa Ibla, Modica, and Scicli, as well as the historic Syracuse and the elegant seaside town of Taormina.
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.
Enjoy culture, history, adventure, and relaxation on this 15-day Sicily highlights tour, starting and ending in Palermo. Discover the monuments and markets of the regional capital, visit ancient Greek and Roman ruins in Syracuse, wander the narrow and winding streets of Ragusa Ibla, and swim in the inviting Tyrrhenian Sea off of Cefalù. You'll explore the medieval core of Erice, visit historic palazzi in Menfi, marvel at the expansive mosaics in Villa Romana del Casale, and hike Mount Etna.
This Italy tour makes the most of a weeklong adventure by combining three legendary destinations. Start with the ancient monuments in Rome, including a guided tour of the Colosseum and Roman Forum. Then pick up your rental car for a gorgeous road trip through the Umbrian countryside, where you'll taste wine and olive oil straight from the source. After exploring the medieval hill town of Assisi, drive north to Florence to absorb the city's Renaissance art and architecture, followed by aperitivos at sunset.
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.
Discover the highlights of Sicily with this 10-day loop of the island, featuring three nights on two of the Aeolian Islands as well as time spent in Palermo, the regional capital, and historic Syracuse. You'll witness Stromboli's spectacular pyrotechnic display of red and orange lava, take a passeggiata along Cefalù's seaside promenade, and enjoy traditional Sicilian fare in a rustic trattoria in Syracuse's historic core. Explore historic Norman castles, ancient Greek temples, and Roman amphitheaters, and enjoy the impressive baroque architecture of lively Catania.
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.
Explore Sicily's highlights, including four days on three of the Aeolian Islands, on this 15-day itinerary. Starting from Catania, you'll head to Milazzo and on to Lipari, Vulcano, and Stromboli to relax in mud baths and on black sand beaches, and to hike the Stromboli volcano. Visit Palermo, the regional capital before checking out the Greek and Roman ruins of Agrigento and Syracuse and ending the trip with a cooking class in the elegant seaside town of Taormina.
Travel by boat, train, and rental car on this exciting 15-day tour of Italy. It all starts in Venice, where you'll glide through charming canals and visit nearby islands. Next is the walkable city of Florence for incredible art and culture (and, yes, pasta). Pick up your rental car from here and explore Tuscan hill towns, Mediterranean beaches, and vineyards in Chianti before heading south. Drop your car in Rome and spend the last few days touring the Eternal City's ancient sites and famous fountains on foot.
This 12-day grand tour of Sicily is a perfect mix of culture and adventure and includes four nights on the Aeolian Islands. Beginning and ending in Catania, you'll discover historic ruins on Lipari, soak in a mud bath on Vulcano, and go on a sunset hike of Stromboli before picking up your rental car in Milazzo. Tour Palermo, the regional capital, wander amid the impressive Greek temples in Agrigento, and enjoy a passeggiata along Syracuse's seaside promenade in Ortygia.
Experience Sicily's coastal cities, Sicilian-baroque towns, and the remote Aeolian Islands with this 9-day circuit from Catania. Start in Milazzo and discover the ruins of Lipari and the black-sand beaches of Stromboli before picking up your rental and driving to elegant Taormina. Learn to prepare traditional Sicilian fare in a cooking class in Taormina, navigate narrow and winding lanes and alleys in Syracuse's historic Ortygia, and take in the embellished architecture of charming Noto.
This 13-day trip explores Italy's three famous cities with plenty of guided excursions. Kick off in Venice to stroll across romantic bridges and glide along charming canals. From here, take a train to Florence, where you'll see its famous Renaissance masterpieces and learn how to make pasta. Then it's time to pick up a rental car for the ultimate Tuscan road trip with stops in Pisa, Siena, and Cinque Terre, before finishing in Rome for three days of sightseeing in the Eternal City.
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.
Travelers wishing to combine Italy's cities and a bit of the stunning countryside will love this nine-day tour. It starts in Rome, where you'll spend three days exploring the ancient sights with a private guide and on your own. Then pick up a car and drive through Umbrian vineyards and olive groves to get to Assisi—a UNESCO-listed town oozing with history. Continue to Florence and spend the last few days walking between Renaissance gems and hilly viewpoints for an adventure to remember.
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.
Perfectly blending culture and history with adventure, this 13-day tour starts in the regional capital of Palermo and takes you to three of the Aeolian Islands. You'll pick up your rental car and check out the popular Lungomare beach in Cefalù, discover the impressive Norman-Byzantine Monreale Cathedral, and wander amid the ridgetop temples in Agrigento. From there, you'll explore the tightly woven network of narrow and winding alleys in Ortygia, hike Mount Etna, Europe's largest volcano, and end your trip in Catania, Sicily's next largest city.
Enjoy this 11-day itinerary from Catania to explore the Aeolian Islands before picking up your rental car and continuing to circle Sicily. Starting with the regional capital of Palermo, you'll dive into its colorful history and impressive architecture on a city tour, then discover the ridgetop temples of Agrigento and the Greek and Roman ruins of Syracuse, capping off the trip with a hike up Mount Etna.
Dramatic mountain scenery, quaint stone villages, and lakeside vistas await on this 12-day self-drive adventure through northern Italy. Starting in Milan, you'll explore the city and zip over to Switzerland via the scenic Bernina Express before grabbing the keys to a rental car. Start the ignition and journey north to admire the serene beauty of Lake Como and Lake Garda with boat trips and lakefront dining, then tour the picturesque Prosecco Valley and end in Venice with a classic gondola ride.
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.
