Tailor Made Itineraries
Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

8 Day Custom Tour
Dynamic pricing from $2,859
Bask in the splendor of Sicily during this luxurious 8-day getaway. A vacation to Southern Italy and Sicily is a discovery of the beauty, history, and culture of some of the premier regions of the country. Immerse yourself in la Dolce Vita, uncover the landscapes of Southern Italy, venture to the ancient city of Pompeii, venture to the island of Capri, and discover the splendor of the of the Amalfi Coast.

10 Day Custom Tour
Dynamic pricing from $3,575
The trails of Southern Italy lead you through the unforgettable splendors of Roman ruins and volcanic peaks, coastal vistas, and tranquil villages. Overlook cliffs as the stunning rock formations rise out of the Mediterranean Sea. Climb to the top of Mount Vesuvius for a sweeping panorama of the Bay of Naples and then stroll along the ancient streets of Pompeii to witness lava as it sprouts from a conical peak like fireworks on a secluded island near Sicily. Your custom tailored tour lets you experience the history and beauty of Italy’s southern landscapes from the shores of Amalfi to the Sicilian Coast.

14 Day Custom Tour
Dynamic pricing from $5,637
A soulful ambiance with ancient splendor, sun-bleached coastline, and enticing cultural cuisine immerse you in the beauty of land, sea, and heritage during your luxury two-week Southern Italy tour. Explore gripping history from Greek settlements to Arab traders. Savor the culinary prowess at the Crossroads of the Mediterranean. Enjoy the natural beauty that accentuates established cities as you discover the grandeur of Sicily and Puglia at your pace.

14 Day Custom Tour
Dynamic pricing from $5,007
Through the beauty of the cuisine, you will discover endless passion, embrace unfamiliar flavors, and take pleasure in history and gastronomy while exploring Southern Italy. Olive trees captivate with produce ready for harvest and grapevines absorb vibrant minerals, adding depth to sophisticated wines; lemon trees offer fragrant hints of citrus and the coastline erupts with revitalizing aromas of the sea. Celebrate zesty sauces and inspiring seafood, mouthwatering stews and refreshing salads during your customizable Southern Italy itinerary connecting you to the villages, towns, and cities of the region, from Sicily to Puglia.

9 Day Custom Tour
Dynamic pricing from $3,217
Experience Southern Italy and Sicily’s stunning landscapes, historical landmarks, and mouthwatering cuisine with this unforgettable 9-day family vacation. The history and culture of each destination will come to life through private tours and exclusive experiences. Immerse yourself in the beautiful lifestyle of Southern Italy and Sicily, climb Mt. Vesuvius, indulge in a cannoli-making course, and visit the gorgeous island of Capri.

7 Day Custom Tour
Dynamic pricing from $2,501
Discover the breathtaking towns, stunning landscapes, and the delicious cuisine of Southern Italy and Sicily during this amazing week-long vacation crafted especially for seniors. Exclusive experiences and private tours await at every destination as you uncover the history, culture, and ideal lifestyle of the area. Wander through the historic streets of Palermo, venture to the majestic island of Capri, and experience the fascinating city of Pompeii.

7 Day Custom Tour
Dynamic pricing from $2,501
Enchanting cities and captivating landscapes await you on this 7-day trip to Southern Italy and Sicily. Crafted with couples in mind, this exclusive vacation will begin in Rome and continue to Sorrento, Cosenza, and the gorgeous island of Sicily. Private tours and delicious dinners for two will be enjoyed at every destination. Visit the captivating island of Capri, Journey up Mt. Etna, and immerse yourselves in the iconic sites and cuisine with this 7-day tour.

10 Day Custom Tour
Dynamic pricing from $3,575
Experience scenic hikes, exhilarating ziplines, intriguing caves with this immersive 10-day vacation to southern Italy and Sicily. Unique experiences and private day trips are included in this amazing and unforgettable vacation. Zipline in Castelmezzano, climb Mt. Vesuvius to enjoy incredible views of Naples, and venture to the Blue Grotto.

8 Day Custom Tour
Dynamic pricing from $2,859
During this immersive 8-day vacation, you will discover the rich history, lively culture, and delicious cuisine of the area. Picturesque towns and stunning landscapes can be found throughout southern Italy and Sicily. Exclusive tours and private tastings will be enjoyed at every destination as you indulge in la dolce vita during this unforgettable vacation.

21 Day Custom Tour
Dynamic pricing from $7,513
Relish your introduction to the must-see beaches, the majestic history, and incredible cuisine during your custom-tailored tour of Southern Italy and Sicily. Savor your time in the white sands that lead to clear turquoise waters in Calabria, and then learn about the complexity of flavor in traditional Pugliese olive oil. Explore the enchanting ambiance of cave-dwellings in Basilicata, and then traverse the fuming craters of an active volcano in Sicily. The endless marvels of Southern Italy hold captivating layers that showcase both elegance and rustic charm, ancient Greek aesthetic and preserved Roman customs intertwined with the vibrancy of contemporary life.

11 Day Custom Tour
Dynamic pricing from $3,933
All roads lead to Rome, but your unique path begins in the fascinating heart of Sicily. Historic structures shimmer an aged gold. Emerald grapevines carpet the landscape beneath the shadow of Mount Etna’s peak. Ancient Greek temples speckle the landscape, overlooking olive orchards and orange groves. Cave dwellings honeycomb the walls of a ravine, and conical homes create a fairytale ambiance in the rolling hills of the southern Italian scenery. The radiance of Italy’s south bursts with life and culture, history and charm, ensuring your custom tailored Southern Italy and Sicily tour overflows with all the wonders in between.

14 Day Custom Tour
Dynamic pricing from $5,007
Capture the essence of history, culture, and cuisine during your customizable, 14-day highlights tour of Southern Italy and Sicily. Indulge in the alluring splendor of heritage featured in colorful towns around the Amalfi Coast and within the elegantly-preserved architecture of Palermo. From walking the excavated streets of Pompeii to strolling beneath luxurious, Baroque adornments in Lecce, your Southern Italy and Sicily tour embraces grandeur and immerses you in unrivaled beauty.
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More About Southern Italy & Sicily Tours
Crystal-clear waters, golden shorelines, and ancient history are revealed when visiting Southern Italy. Greek temples rise above open plains. The cuisine speaks to the familiar flavors of local and seasonal ingredients steeped in la cucina povera. Colorful fishing villages become elegant getaways for the historical elites eager to bask in the exceptional views. Ancient Roman ruins, dramatic castles, surprising caves, and corners of untouched culture reflect the endless majesty you can discover with our Southern Italy Travel Guide to help plan your perfect trip.
The best time to visit southern Italy is typically March through May, spring, and September through November, fall.
The promise of breathtaking scenery that unveils glistening waters, charming coastal coves, and historic towns nestled into rugged hills can capture your imagination during the best time to visit. Visitors flock to the country’s Meridione region to relax in the warm weather and wander through the diverse, quaint settings that provide adventures down medieval lanes or visions of ancient temples.
Dive into a world of color and historical treasures as you find yourself lost in southern Italy's beauty and culture during stunning times for this region.
Embrace the beauty of nature and culture that abounds at every turn with our top seven things to do in southern Italy.
City treasures, breathtaking beach escapes, and historical wonders await. From ancient Greek temples to stunning volcanic peaks, prolific vineyards to mouthwatering cuisine, the heritage of southern Italy reveals timeless customs and genuine charm.
Enjoy the many active adventures and captivating experiences, or simply sit and savor the culture and cuisine of a beloved part of Italy that can immerse you in luxury or unravel rustic wonder.
From the rumbling of Europe’s most active volcano to the golden shores that feed into three different seas, Sicily is a cultural marvel at the crossroads of Mediterranean heritage. Explore the delights of inviting local cuisine and embrace stunning views sweeping over Roman ruins and glowing coastline to a snowcapped volcanic peak. Whether visiting the largest Greek temples in Italy or embracing lavish Baroque architecture, Sicily is a breathtaking collection of beauty and charm. Our Sicily Travel Guide has plenty of information about what you can do during your trip, when to visit, and more.
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