Best of Southern Italy & Sicily Tour

Gorgeous view of the Calabria, Italy coastline

What to expect on this itinerary

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.

Countries Visited

Italy

Places Visited

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

Suggested Duration

14 Days

Customizable Itinerary

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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. Your flight will land at 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 around the 3,000-year-old City of the Dead on a private tour of the Monterozzi necropolis with the oldest dating back to the 7th century BC. 

What's Included:

Transfer
Accommodation
Breakfast
Day 2

Sorrento – Visit Caserta Palace and Naples Archeological Museum

Day 3

Sorrento – Discover Remarkable Pompeii and Herculaneum

Day 4

Sorrento – Traverse the Charm and History of the Amalfi Coast

Day 5

Sorrento – Indulge in the Grandeur and History of Capri

Day 6

Ostuni – Explore Matera and Alberobello en route to Ostuni

Day 7

Ostuni – Delight in the Unique Ambiance of Lecce and Otranto

Day 8

Maratea – Enjoy the Distinctive Seaside Luster of Maratea

Day 9

Taormina – Travel Across the Strait of Messina to Taormina

Day 10

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

Day 11

Taormina – Revel in the Ancient History in and around Siracusa

Day 12

Palermo – Wander Ancient Temples in Agrigento en route to Palermo

Day 13

Palermo – Tour the Fabulous History and Culture of Palermo

Day 14

Palermo – Depart for Home

Trip Highlights

  • Revel in the thrills of a private helicopter ride over the Amalfi Coast to reach the inspiring atmospheric scenery of the island of Capri
  • Discover the authentic flavors of Sicily during a luxurious wine tour, visiting a mixture of family-owned estates along the foothills of Mt. Etna
  • Witness the magnificent collection of ancient artifacts from Roman colonies such as Pompeii in the National Archeological Museum in Naples
  • Wander through millennia of history along the Italian Peninsula during a private tour of the cave-dwellings of Matera
  • Embrace the historic charm and enchanting ambiance of the collective seaside towns of Maratea
  • Delight in the immersive, fairytale atmosphere of Alberobello, which derives from the unique Trulli homes that shape the diverse neighborhoods
  • Bask in views one of the largest ancient Greek theaters in the world during your private walking tour of Syracuse
  • Sample the delectable cuisine of Sicily when indulging in a memorable dinner at a celebrated Michelin-starred restaurant in Palermo
  • Discover gilded embellishments and displays of regal opulence in Caserta Palace that can be found both in the royal apartments and across the luscious gardens
  • Marvel at the gorgeous scenery and chic Baroque architecture of Taormina on a cliff that overlooks the sapphire waters of the Ionian Sea

Detailed Description

Whether discovering the rich history of Rome or the impressive architecture of Syracuse, indulging in the flavors of vineyards that are spread across the foothills of Mt. Etna or wandering along the turquoise waters of the Adriatic Sea in Otranto, your 14-day, highlights tour of Italy and Sicily will reveal the beauty of local heritage and the magnificence of the natural landscape. This exploration through Italy will provide you with an unrivaled journey that takes you from the regal Etruscan tombs of Tarquinia to the ancient Greek Theater of Syracuse. You will take your time to enjoy the majesty of Italy with private tours, luxurious excursions, and unique activities that will shape your memorable journey, spanning coastline, gorges, and an epic and ancient history.

Your highlights tour of Southern Italy and Sicily will begin with your arrival in Rome, where you will stay for one night and discover the marvels of the underground tombs of Tarquinia, finding elaborate artwork and unique burial traditions of the pre-Roman civilization. You will have four nights in a captivating hotel in Sorrento for plenty of opportunities to explore the wondrous scenery and culture around the Bay of Naples from the extravagance of the Caserta Palace to a private driver that transfers you to the various towns of the Amalfi Coast.

You will have a scenic helicopter transfer to Capri island and enjoy a tremendous private tour through the impressive history of Pompeii and Herculaneum, featuring remarkable mosaics and the preservation of daily Roman life. Two nights in the charming Pugliese town of Ostuni will take you across the peninsula toward the Adriatic Sea, delving into the rugged cave-dwellings of Matera, the Baroque architecture of Lecce, the seaside heritage of Otranto, and the fabulous fairytale images of Trulli homes in Alberobello.

Your tour will return you to the Western shores of Italy with a night in Maratea, which is a collection of resort towns that overlooks the Tyrrhenian Sea and is known for its stunning views and 44 churches. Three nights in Taormina will introduce you to the pleasures of Sicily with private tours that will take you deep into traditions that date back to the Phoenicians and Magna Grecia. You will taste a range of fabulous wines that have been produced on family-owned estates at Mt. Etna in addition to finding the remains of ancient Greek architecture that accentuate the Baroque designs of Syracuse. The end of your Southern Italy and Sicily vacation will culminate in vivacious Palermo where you can indulge in the sensational flavors of a Michelin-starred restaurant and the exquisite culture of markets, Norman and Arab architecture, and elegant squares.

Consider learning more about our travelers’ favorite Italy travel activities by reading their Italy travel reviews.

Starting Price

$6,300 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

Verified Traveler Reviews

Based on 677 reviews

Sicily Vacation Review: Syracuse, Noto, Ragusa, Modica, Ortigia, 1 Week

We had a fabulous time in Sicily. It was our first visit and Zicasso’s travel company planned an excellent itinerary, with great recommendations on the cities and towns to visit that felt like a truly local experience. (Other agents focus on the big cities of Palermo and Taormina, but the travel company recommended we spend more time in Syracuse/Noto, Ragusa, and Modica.)

We loved our primary driver and the boutique hotels they selected for us. Communication and documents were all easy to follow.

The only piece we wish might have been curated a little more was the recommended dining options. There were too many and not necessarily great restaurants.

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Italy Trip Review: Taormina, Agrigento, Palermo, 8 Nights

Our Zicasso travel specialist did a fantastic job planning our family vacation for five adults.

Each hotel was top-notch. At the villa in Taormina, the rooms were luxurious, with unbelievable views of the bay and Mount Etna from private verandas. The staff were gracious and the restaurant's breakfast buffet delicious. Lunch and dinner were top-notch. The hotel in Agrigento was modern and the grounds were exceptional. It was close to the Valley of the Temples, with amazing views of the ruins from each room and the beautiful infinity pool. The hotel in Palermo was old-fashioned luxury with up-to-date facilities and close to the old town.

Our tour guides and drivers were excellent.

My only regret is that we only had 10 days to explore Sicily as there was so much more to see!

Our agent did a yeoman's job helping us plan this trip.

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Italy Tour Review: Rome, Amalfi Coast, Taormina, Sicily, Sorrento, Capri, Mount Etna, Pizza-Making Class, Boat Ride, Wine, Local Cuisine, 9-Night Trip

We were absolutely thrilled with our first trip to Italy! This was a journey we had dreamed about for many years and we decided to make it happen as a special way to celebrate our anniversary this year.

The planning process with Zicasso was seamless, easy, and incredibly efficient. We were amazed by all of the thoughtfully planned activities, tours, and transfers throughout our trip. We visited Rome, the Amalfi Coast, and Taormina, Sicily—each destination offering something unique and unforgettable.

For this trip, we wanted a balance of adventure and relaxation, along with a few specific requests, and the team went above and beyond to make it happen. They truly bent over backwards to incorporate everything we envisioned and exceeded our expectations in every way.

We highly recommend traveling with Zicasso! They connected us with outstanding partners who truly elevated our experience and made our trip unforgettable. We honestly wouldn’t have changed a thing.

From the bottom of our hearts, Grazie mille!

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Italy Luxury Travel Review: Amalfi Coast, Puglia, Sicily, History, Local Cuisine, Bike Tour, Cooking Class, 2 Weeks
"We recently had an amazing trip in southern Italy, organized by a Zicasso tour company that I can't recommend enough!"

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Italy Trip Review: Amalfi Coast, Herculaneum, Vatican, Capri, Pompeii, Naples, Sorrento, Pantheon, Boat Ride, Street Food Tour, History, Culture, Local Cuisine, 10 Days

We had a fantastic time and Zicasso's tour operator did an excellent job organizing every detail of our trip. Drivers and guides were always punctual, and the itinerary was perfectly balanced—full days, without ever feeling rushed.

Some real highlights for us were Herculaneum, the Pantheon, the Vatican, and our unforgettable Capri boat tour. Our guide brought Pompeii's history to life in a way that made it feel like stepping back in time and the Naples street food tour was delicious and nostalgic—her pizza fritta instantly took me back to the calzones I grew up with in Niles, Ohio. Our driver was with us for several days and made every transfer feel effortless.

There was a small hiccup at the very end with a trip planner, but it was minor compared to the overall quality of the trip. The organization, communication, and attention to detail throughout made this a truly memorable experience and we wouldn’t hesitate to book with this tour agency again. We had a fantastic time and the tour company did an excellent job organizing every detail of our trip.

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Italy Tour Review: Venice, Florence, San Gimignano, Siena, Rome, Vatican, Amalfi Coast, Capri, Sorrento, Positano, Doge's Palace, Colosseum, Palatine Hill, Boat Ride, 12 Days

This was possibly the best trip of my life!

Once I arrived in Venice and put myself in the hands of Zicasso’s tour company, I was supremely well taken care of.

I left my passport on the plane, so I was held up in the airport for probably two hours. This was the first time I used the emergency number (or the chat app). The communication was answered immediately and we were able to let my first guide know I was being held up. I thought the first person who helped me was just someone to get me to the hotel, but she was also a guide in the sense that she described many of the things we saw on the way to the hotel. A very pleasant and gracious guide who made sure also that I was prepared for where to be the next day. It was a very great first experience of the tour company’s service.

Throughout this adventure, the guides were outstanding, the hotels were located practically on top of the interesting sites (especially in Rome) and very pleasant to be in.

Also, I continued to use the emergency number or the chat app multiple times. They were very responsive, very pleasant, and perfectly helpful each time. I don't know if I was high-maintenance compared to other clients the tour company has had, but though I felt like it in my mind, I was treated completely graciously each time.

I loved every destination and I loved having a structured tour, combined with a good portion of free time to explore on my own. Perfect.

I was very well guided on each travel day, being met by drivers to drop me off and to pick me up, and the train travel was very fun.

I think there was only one guide who I thought was just going through the motions, but all the other guides were the height of professionalism. I loved being met by our guides at Doge's Palace, which was absolutely outstanding. Walking around old Florence was great fun! The drive out to San Gimignano and Siena was well-planned and well-guided! In Rome, the guide who took us to the Colosseum and Palatine Hill was outstanding, and it was a great outing. (I had also already pretty much visited all the sights since my hotel was practically in the middle of it all.)

The trip to the Vatican was a whole other story. Unfortunately, I forget that guide's name. This guide was also excellent—entertaining, informative, approachable, and professional. The trip to the Amalfi Coast was a long train ride, followed by a very long car ride, but it was worth it. What a beautiful setting! My trip to Capri was absolutely fulfilling and I was a little sad to say goodbye to the guide—we connected with him so well. The next day was our boat tour from Sorrento to Amalfi and Positano. I absolutely enjoyed being guided by our guides! On the way back after that beautiful excursion, we were just cruising along the water, 1970s music playing, wind rushing by and I had a peak moment of happiness. Truly.

This trip was as if the tour company had read my mind and provided even more than I had imagined. I come away deeply grateful.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

31,000+ Verified Traveler Reviews