Best of Southern Italy & Sicily Tour

Noto Cathedral, in Sicily, Italy
A 14 day trip to Italy 
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Capture the essence of history, culture, and cuisine during your customizable, highlights tour of Southern Italy and Sicily. Indulge in the alluring splendor of Italian heritage that is featured in colorful towns around the Amalfi Coast and within the elegantly-preserved architecture of Palermo. The majesty of ancient Greek temples at Agrigento reveals the remarkable depths of heritage, which are emphasized by artifacts that are displayed in galleries like the National Archeological Museum of Naples. 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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Most tours are customized for private travel.

General Information

Gorgeous view of the Calabria, Italy coastline
Scenic view of the rocky coastline and cliffs of Capri, Italy
Snow covered Mount Etna with green rolling hills in the foreground in Sicily, Italy
Royal Palace of Caserta in Italy
View of the ancient town of Sassi di Matera in Italy at sunrise
Artwork in a burial room in the old city of Tarquinia, Italy
Colorful alleyway in the town of Maratea, Italy
Belltower of the Trullo Church in Alberobello, Italy
Sunrise in Syracuse, Sicily, Italy
Stigghiola, a typical Palmero street food being seared to perfection
Greek theater in Taormina, Italy with Mount Etna in the background
View of coastline in Lecce, Italy
Detailed Itinerary

Places Visited 

Rome, Tarquinia, Caserta, Naples, Pompeii, Herculaneum, Sorrento, Amalfi, Ostuni, Lecce, Otranto, Matera, Maratea, Taormina, Mt. Etna, Syracuse, Valley of the Temples, Palermo

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Rome – Arrive in the Rome with a Tour of Ancient Tarquinia

The city of Rome remains a powerhouse of history, rising along the banks of the Tiber River. The spectacle of the past lines the medieval cobblestone alleyways and adorns the city skyline with marvelous domes, peaked rooftops, elaborate columns, and the glamorous palaces that are eager to lead visitors into the past. Your flight will land a Fiumicino Airport, where your private transfer will greet you upon your arrival and escort you into the bustling heart of the city center. The trickling water of the Trevi Fountain will embody the grandeur of the Baroque era and marvels of the greater city with images of an opulent Oceanus that is framed by the detailed life of the sea.

After settling into the comforts of your luxurious hotel, your guide will meet you in the lobby and lead you to the magnificent acropolis of Tarquinia, which acted as the capital of the Etruscan settlement over two millennia ago. Authentic and unforgettable history will come to life as your guide immerses you into a private world during a private tour around the 3,000-year-old City of the Dead. The Monterozzi necropolis contains 6,000 graves with the oldest dating back to the 7th century BC. The landscape resembles rolling hills but is actually mounds, beneath which stand Etruscan tombs that are decorated with elegant frescoes and signs of luxurious life. The Tom of The Lionesses was constructed in the 4th century BC and consists of a small room beneath a sloped roof with images of flying birds and jumping dolphins as they surround the lively images of the Etruscan aristocracy.

What’s Included: airport transfer, accommodation

Day 2: Sorrento – Visit Caserta Palace and Naples Archeological Museum

The aroma of fresh espresso will fill the dining room of your hotel in the morning and will be accompanied by the buttery, sweet, and sharp aroma of a sour cherry tart with ricotta cheese. Your guide will meet you in the hotel lobby after breakfast and lead you toward the city of Naples, stopping first to discover the opulent design of the Caserta Royal Palace. The elaborate palatial complex was inspired by Versailles in France with an extravagant aesthetic, adorning 1,200 rooms and a breathtaking garden that was constructed in the 18th century.

Your guide will lead you on a private tour of the serene grounds with the sounds of the fountains that will offer a soothing soundtrack of splashing falls and trickling droplets of water. The impressive landscaping resembles a large park that leads into the foothills of the Briano Mountain. The scent of blossoming orange citrus adds to the soothing luster of the waterways and fountains that are adorned with detailed sculptures. You will find elaborate and intricate images of Venus and Adonis that are reflected in the smooth pool that is surrounded by lions and wild boars and crowned with charismatic nymphs, cupids, and stunning marble.

You will continue to the remarkable city of Naples, where the aroma of the sea drifts in from the harbor and fades beneath the ubiquitous scent of fresh Margherita pizza. The National Archeological Museum of Naples has overtaken the former 17th-century cavalry barracks and displays ancient treasures that date back to Ancient Egypt, showcasing the secrets of Pompeii. Your guide will lead you through the fabulous collections and will offer historical and artistic context to the captivating artifacts, including the giant Farnese Hercules that stands 10.5 feet tall. The dramatic image of the legendary hero was crafted in the 3rd century BC with impeccable detail, blending both the man and the myth with the pelt of the Nemean lion that is draped over a gigantic club.

What’s Included: accommodation, tour, breakfast

Day 3: Sorrento – Discover Remarkable Pompeii and Herculaneum

The soothing aroma of orange and lemon citrus will drift through the streets of Sorrento in the morning, overtaking the fragrant sea breeze. Fishers will return to shore and anchor their colorful boats in the marina before bringing their fresh catch of the day to market. You will travel around the Bay of Naples to reach the captivating and excavated city of Pompeii, which was buried under nearly 20 feet of pumice and ash after the eruption of Mount Vesuvius in 79 AD.

The peak of the active volcano continues to loom over the city in the distance and is visible from the top row of the Large Theater. The stadium seating could hold up to 5,000 spectators and remains in use during the summer for shows that are connected to the Son et Lumière festival. Your guide will introduce you to the fabulous history that can be unveiled in the preserved daily lives of the Roman city at the that is embodied in the Stabian Baths. A colonnaded palestra surrounds a swimming pool and leads to the visible stoves that were used for heating water. You will find air-ducts on the floor and walls where the pools were heated.

In Herculaneum, you will find the preservation of the city in the magma that entombed the buildings, protecting vases, furniture, and the integrity of villas in a town that was once populated by upwards of 6,000 people. The scent of rich soil remains prevalent amid the ruins that rise against the backdrop of the wading sea. The Sacello degli Augustali acted as a shrine and connected to the Cult of Augustus. A marvelous fresco retains its vibrant color, depicting the hero Hercules on Olympus with Juno and Minerva in addition to an image of Hercules as he fights an Etruscan deity.

What’s Included: accommodation, tour, breakfast

Day 4: Sorrento – Traverse the Charm and History of the Amalfi Coast

The buttery aroma of sfogliatelle will overtake the dining room of your hotel in the morning, drifting from the delicate, flaky pastries with a shell shape that is stuffed with citrus cream. You will venture out of the charming, seaside setting of Sorrento for a day of exploring the fabulous history and gorgeous scenery of the legendary Amalfi Coast with your private driver. The 25-mile roadway hugs the shoreline and overlooks the sapphire splendor of the Tyrrhenian Sea. The aromas of lemon groves will roil over the fragrant sea breeze as you reach the town of Amalfi. The enchanting ambiance derives from the former prestige of the maritime powerhouse before its naval defeat by Pisa in the 12th century.

The luxuries of the past shimmer in the main piazza where small cafes set out tables and chairs in view of the 62 steps that lead to the cathedral’s antique portico. Majolica tiles adorn the façade of the 13th-century bell tower and soar above the elegant bronze doors. The magnificent doors were designed in Syria in the 11th century during the height of trade between the Republic of Amalfi and the Byzantine Empire. In the afternoon, you will return to Sorrento for a private cooking class that will offer secret insight into the pleasures of making traditional Margherita pizza. You will indulge in delicious flavors of local wine as your private chef introduces you to the fresh, seasonal ingredients that are used to craft the savory sauce before sampling the creamy texture and milky flavor of buffalo mozzarella, which will deliciously top your fresh dough.

What’s Included: accommodation, tour, breakfast

Day 5: Sorrento – Indulge in the Grandeur and History of Capri

In the morning, you will have a private transfer to the Naples Airport for a scenic helicopter flight over the Tyrrhenian Sea that will have you land on the legendary island of Capri, which is known for its beauty that has enchanted the likes of Roman emperors and Hollywood starlets alike. The bordering cliffs of the island reach upwards of 200 feet above sea level and offer dramatic views beneath the looming summit of Mount Solaro at 1,929 feet above sea level. The helicopter ride will take you soaring through the sky and will provide elaborate panoramas of the picturesque villages, and iconic Faraglioni sea stacks rise from the blue-green water.

While on Capri, the island will be yours to discover at your preferred pace. You can stroll up the ancient 500 steps that were craved by the Phoenicians, visit the town of Anacapri to view the majolica-tiled floor of the church that depict the story of Adam and Eve, or wander along the cobbled lanes of Capri Town between the boutique shops and restaurants that fill with the aromas of fresh espresso. Villa San Michele hosts a private collection of a wealthy doctor, displaying Roman, Egyptian, and Etruscan antiques beside 20th-century masterpieces. The tranquil gardens will remind you of an antique palace with elaborate views, which are framed by pergolas that are draped in vines and illustrious marble statues.

What’s Included: accommodation, tour, breakfast

Day 6: Ostuni – Explore Matera and Alberobello en route to Ostuni

You will venture by private transfer to the fascinating city of Matera in the morning, where you will uncover the hidden jewel of the Basilicata region. Your guide will greet you upon your arrival in the city and will introduce you to the splendor of a city that has not been inhabited for more than 7,000 years. The preserved, medieval architecture crowns the plateau of the gorge and shines with golden hues from the local, quarried stone. You will traverse the remarkable sassi for which the city has become famous, and you will follow your guide through the cave-dwellings that were used by locals as recently as the 1960s.

Beneath the foundations of the elegant Duomo, you will discover the rows of former dwellings that overlook the rugged pockmarked walls of the cliffs that lead to the Sasso Caveoso neighborhood. Many locals have returned to the caves, turning the rustic interior into lavish restaurants or chic hotels, but a museum also offers a glimpse into the life of the caves with a replica of a home that depicts a single room with a bed, table, and kitchen that often held entire families.

You will continue to the region of Puglia and the fairytale structures of Alberobello known as Trulli. White cylindrical homes support conical rooftops that resemble the homes of ferries as they shimmer in the sunlight, they are responsible for the storybook ambiance of Puglia. The design dates back to the 18th century and provides a unique aesthetic to the landscape with the charismatic roofs that rise above the cobbled lanes amid the waving palm trees. The sporadic hoots of terracotta whistles ring out from ceramic shops, and locals linger in neighborhood bars, sipping wine, snacking on almond cookies, and enjoying their time as the day passes.

What’s Included: transfer, accommodation, tour, breakfast

Day 7: Ostuni – Delight in the Unique Ambiance of Lecce and Otranto

At breakfast, the enticing aroma of a short-crust pastry, which is known as pasticciotti stuffed with custard, will fill the dining room and will be accompanied by the decadent scent of frothy cappuccino. Your guide will meet you in the hotel lobby and will be eager to introduce you to the magnificent history of the Salentine peninsula, beginning in Lecce. The Baroque architecture will capture your imagination as a distinct characteristic of the Southern city that is embodied in the decorative gargoyles, columns, and gremlins that peer down on you from the surrounding structures. Cafes set out chairs and tables along the walkways throughout the city center where locals can enjoy long lunches of purpu alla pignata, which is braised octopus that is seasoned with garlic, oil, tomato, parsley, and chili pepper.

The 2nd-century Roman amphitheater hides in the city center and is surrounded by apartments where locals dangle their laundry on clotheslines outside of their windows. You will explore the beauty of the city that is symbolized in the Basilica di Santa Croce and where the Baroque design boasts an allegorical feast for the eyes with detailed statues of sheep, dodos, cherubs, and beasts. You will continue to the seaside town of Otranto, where the calm turquoise water of the Adriatic Sea laps against colorful fishing boats and the whitewashed walkways of the marina.

Restaurants will fill with the aromas of olive oil and grilled calamari that has been drizzled with lemon juice. You can take your time, strolling along the stone walkways around the defensive walls of the Aragonese castle or admiring the rose window of the majestic cathedral. The fascinating architecture of the religious center contains 700 square feet of mosaics, featuring the Tree of Life with branches that spread across the majority of the artwork around signs of the Zodiac, images of a game of chess, and references to Scandinavian, Greek, and Persian mythology.

What’s Included: accommodation, tour, breakfast

Day 8: Maratea – Enjoy the Distinctive Seaside Luster of Maratea

You will arrive by private transfer to the collected villages that create the greater town of Maratea, which is scattered across the tranquil, rugged coastline of Basilicata and overlooks the sapphire waters of the Tyrrhenian Sea. The luscious vegetation will fill the air with the aromas of blossoming flowers and sea spray with tiered gardens that accentuate the soft-spoken beauty of art nouveau architecture. The statue of Christ the Redeemer crowns the dramatic summit of Monte San Biagio at 2,044 feet above sea level. You can venture into the Grotto delle Meraviglie, which is the Cave of Wonders, to view the impressive highway of caverns that are decorated with dripping stalactites and soaring stalagmites that have formed naturally over time.

The heart of town offers panoramic views over the coastline and a stunning view of homes that date back to the 13th century and that line the two main piazzas and narrow winding lanes. Small shops display authentic artisan foods and specialty crafts among the famous 44 churches that are hidden among the hilltops. After exploring the town at your own pace, you can relax in a photogenic piazza and revel in the outstanding colors of sunset as the sun sweeps across the horizon.

What’s Included: transfer, accommodation, tour, breakfast

Day 9: Taormina – Travel Across the Strait of Messina to Taormina

You will arrive in Taormina by private transfer and settle into the comforts of your luxury hotel in the chic and elegant resort town that overlooks the Ionian Sea. Your guide will meet you at your hotel and lead you on a marvelous private tour of the town’s fascinating history that will take you through the charming cafes, aromatic gelateria, and past the funicular, before reaching the exceptional Greek Theater. The ancient landmark was first constructed in the 2nd century BC with a diameter that reaches over 357 feet long.

The top row will provide you with a gorgeous panoramic view of the coastline to the interior island landscape with the captivating peak of Mount Etna that rises in the distance at 10,991 feet above sea level. A narrow strip of sand connects the shoreline to the nature preserve of Isola Bella, where the placid water shines various shades of green and blue. Locals swim in the warm, clear sea where you can dip your toes in and enjoy the refreshing Mediterranean temperature.

What’s Included: transfer, accommodation, tour, breakfast

Day 10: Taormina – Embrace the Powerful Allure and Beauty of Mt. Etna

You can indulge in the scent of fresh cannoli in the morning that will be displayed in the tranquil ambiance of your hotel dining room and accompanied by the decadent aroma of frothy cappuccino that has been sprinkled with chocolate. After breakfast, your guide will meet you in Taormina and escort you to the foothills of Mt. Etna for an exceptional wine tour that will have you visiting a variety of wineries that thrive in the volcanic mineral-rich soil. The lush rows of vines sprawl across the landscape in view of the barren craters of the upper peaks, reaching up to 10,991 feet above sea level. The luscious woodlands juxtapose the altitude, power, and the beauty of the volcanic slopes. You will begin your wine tour at a family-owned estate, where the aroma of arid soil blends with the sweet scent of the plumping grapes.

The greater, protected area of Parco dell’Etna encompasses 228 square miles that are decorated with lunar desert and infertile, black lava fields, soaring beech trees, and the delicate vineyards that produce wines that are protected by the DOC status, Denominazione di Origine Controllate. After a private tour of the grounds and a visit to the cellar where rows of stacked oak barrels hid from the Sicilian heat, your guide will pour you a sample of a red wine that has been made primarily of Nero d’Avola and Frappato grapes. The scent of dark raspberries and tar will drift upwards from the glass, leading to a lingering sweet cherry flavor.

What’s Included: accommodation, tour, breakfast

Day 11: Taormina – Revel in the Ancient History in and around Siracusa

The combination of ancient and contemporary history will captivate you as the aromas of citrus orchards from the outskirts of town blend with fragrant espresso that emanates from the cafe tables in the impressive piazzas. The sunlight washes over the medieval lanes, causing a honey hue to shine across the city that leads to the sparkling sapphire waters of the Ionian Sea. Your guide will lead you on a private tour of the remarkable city with foundations that date back to the 8th century BC. You will reach the ruins of the Greek Theater inside the archeological park, where ancient engineers used the natural gradient of the hillside to build one of the largest remaining Greek amphitheaters in the world, which is capable of holding up to 16,000 spectators.

Your guide will provide historical and architectural context along the stages as you step over a setting that once staged new works of Sophocles and Euripides. In the heart of the city, you will find the 17th-century Duomo that was built on the foundations of a 5th-century BC Greek temple. An elaborate statue of Mary crowns the rooftop as a welcoming sign to Greek sailors who are returning from the sea.

What’s Included: accommodation, tour, breakfast

Day 12: Palermo – Wander Ancient Temples in Agrigento en route to Palermo

In the morning, your private transfer will meet you in your hotel lobby and escort you out of Taormina on a scenic drive through the beautiful landscape of Sicily, venturing to the magnificent, excavated Greek site known as the Valley of the Temples. The stunning ruins rise from the landscape beside the blossoming Garden of Kolymethra. The scent of blossoming myrtles and white poplar trees blends with the sweet aroma of lemon citrus and the fragrant Saracen olive trees. The archeological site dates back to the 6th century BC with the prestige of the former city that is captured in the elegance and powerful design of the standing Temple of Concordia. You will follow your guide across the grounds on a private tour that will introduce you to the marvels of Greek history in Sicily.

Walking along the grounds of the archeological park will also take you to the remains of the Temple of Hercules, which is where a collection of tall Doric columns with wide capitals captures the elegant design of a structure that was dedicated to the classical hero. After discovering the grandeur of the ruins, you will continue with your private driver to Sicily’s vibrant capital city of Palermo for dinner at a celebrated Michelin-starred restaurant that is known for combining the spirit of Italian cooking with dramatic refinement. The aroma of local, fresh ingredients will fill the dining area as you indulge in dishes like risotto with wild fennel or sliced beef steak with a sea urchin emulsion.  

What’s Included: transfer, accommodation, tour, breakfast

Day 13: Palermo – Tour the Fabulous History and Culture of Palermo

The ambiance of Palermo in the morning embodies a feisty and flamboyant nature that derives from the boisterous merchants that line the cobbled lanes during the daily La Vucciria market. Above the sounds of fishmongers who call to one another with jeers of another’s fresh catch, you will hear the sounds of high heels as they clop against the stone street. You will also be greeted by the aromas of herbs, oranges, and pomegranates before your guide shows you the dynamic life of Palermo on a private tour that will take you through the marketplace around Piazza San Domenico and into the majesty of the 9th-century Normal Palace. The architecture combines Arab and Norman aesthetic with embellishments of 17th-century arcades and rounded arches that encircle the courtyard.

Regal mosaics that depict hunting scenes sweep across the walls of the Sala di Ruggiero before you reach the impressive opulence of the Cappella Palatina. The natural light will pour through the windows, causing the Byzantine mosaics that were crafted between the 12th and 14th centuries to shimmer beneath the textured, Arabic ceiling. A royal throne stands on the marble platform with views of the artwork that depict themes from the Old and New Testaments. The sophisticated galleries of The Museo Archeologico Regionale overtake a former Renaissance monastery and house some of the islands’ most remarkable artifacts from Magna Grecia and ancient Rome, including the amazing Bronze Ram of Syracuse, which is a nearly three-foot-tall statue of a ram that was crafted in the 3rd-century BC.   

What’s Included: accommodation, tour, breakfast

Day 14: Palermo – Depart for Home

The decadent aroma of dark-roast espresso will spill through the doors of Palermo’s trendy cafes in the morning and will be accompanied by the scent of setteveli, which is a seductive pastry that is made with seven alternating layers of chocolate, hazelnut, and creamy ganache. The vibrancy of the city will return with the various markets as they set up around the hidden streets to reveal centuries of tradition that is found in the unpretentious cuisine on display in their dishes such as a spongy pizza that is topped with tomato sauce, onions, and caciocavallo cheese, which is known as sfincione. Your private transfer will greet you at your hotel after breakfast and escort you to Palermo Falcone Borsellino Airport for your flight home.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.