Wonders of Sunny Southern Italy & Sicily Itinerary

View of Town in Sorrento, Italy

What to expect on this itinerary

Sun-swept valleys and glistening azure waters warmly greet you on your luxurious, 14-day adventure through Southern Italy. Journey through the soul-stirring Amalfi Coast, delight in the tantalizing natural beauty of the luxurious coastline, and explore candy-colored villages that cling to rugged cliffs and drop dramatically into the Adriatic Sea. Your dynamic two weeks in Italy will lead you to the heartbeat of the Roman civilization while simultaneously dazzling you with awe-inspiring landscapes.

Countries Visited

Italy

Places Visited

Sorrento, Ostuni, Alberobello, Matera, Tropea, Cefalu, Taormina, Amalfi Coast, Capri, Pompeii

Suggested Duration

14 Days

Customizable Itinerary

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Day 1

Sorrento – Stroll through Sorrento’s Iconic Streets

The southern sun will warm your back as you step out of Naples International Airport and into the chauffeured car that waits for you at the curb. Your private driver will whisk you away from the bustling airport and head to your luxurious accommodation in Sorrento. Sorrento sits proudly on steep cliffs that overlook the calm Tyrrhenian Sea. Olive vineyards and lemon groves blanket the rolling hillsides while cobblestone streets braid through the Centro Storico, which is the center of town. Moreover, markets tend to display fresh produce on tables while dried red and orange chili peppers hang above on hooks. You will slip effortlessly into la dolce vita, which is the sweet life, as you stroll through the streets, sampling many of Southern Italy’s finest delicacies.

What's Included:

Transfer
Accommodation
Day 2

Sorrento – Witness the Blue Grotto on the Island of Capri

Day 3

Sorrento – Soar above Mt. Vesuvius on a Helicopter Ride

Day 4

Sorrento – Luxuriate in Villages along the Amalfi Coast

Day 5

Ostuni – Discover the Secrets of Cultivating Olive Oil

Day 6

Ostuni – Explore Trulli Neighborhoods in Alberobello

Day 7

Ostuni – Sail along the Coastline of Polignano a Mare

Day 8

Matera – Tour Matera’s Iconic Sites on a Tuk-Tuk

Day 9

Tropea – Wander along the Beaches of the Tyrrhenian Sea

Day 10

Cefalu – Admire Byzantine Mosaics and Sicilian Sunsets

Day 11

Cefalu – Cruise to the Remote Aeolian Islands

Day 12

Taormina – Attend an Opera in an Ancient Greek Theater

Day 13

Taormina – Hike Past Dried Lava Beds and Dense Forest

Day 14

Taormina – Depart for Home

Trip Highlights

  • Stroll through the heart of Sorrento, sample homemade limoncello, and indulge in freshly baked pizza
  • Cruise to the glamorous island of Capri, where you will walk in the ancient Phoenicians’ footsteps as you explore hilltop villas
  • Venture along the Amalfi Coast in a private car ride, soaking up the stunning views and ambling through picturesque towns
  • Take to the skies on a thrilling helicopter ride that will have you viewing Mt. Vesuvius and the Bay of Naples from high above
  • Meander through the pearly white streets of Ostuni, where you will visit an olive grove and learn how to cultivate traditional olive oil
  • Sail through the pristine waters of the Adriatic Sea and admire the glorious coastline from a unique perspective
  • Immerse yourself in an outdoor opera at a Greek amphitheater in the exclusive resort town of Taormina
  • Trek through magnificent landscapes as you conquer Europe’s largest volcano, Mt. Etna

Detailed Description

The Southern Italian sun sparkles like a million tiny diamonds, merrily reflecting off of the calm blue waters. During your lavish, 14-day excursion, you will travel by air, sea, and land to encounter the most renowned sites in Southern Italy. Your trip will begin when your private driver collects you at Naples International Airport to spend four nights in Sorrento. You will be led by your tour guide and can stroll through Sorrento’s iconic cobblestone streets, where you can pause at local markets to sample the many varieties of flavorful limoncello that are sold by local vendors. You will then set off on a cruise to the famed island of Capri, where you can visit opulent villas and experience the renowned Blue Grotto. The following day, you will step into the ancient ruins of Pompeii, where you will board a private helicopter to fly over Naples Bay and Mt. Vesuvius. Your personal driver will escort you through charming towns that line the Amalfi Coast, and here, you can visit sherbet-hued villages, which cling tightly to steep cliffs that rise from the Tyrrhenian Sea.

Your adventure will continue to Ostuni, which is the pearly-white town that is perched prominently on tall mountains that overlook the Adriatic Sea. You can meander through the white-washed lanes that lead you to grand cathedrals or emulate la dolce vita in quiet piazzas that invite you to enjoy an afternoon aperitif. You will then venture through the emerald Valle d’Itria to explore the various towns that pepper the rolling countryside. You will come across the ancient cone-shaped stone huts that are known as trullis in the town of Alberobello, which has recently become a cherished Unesco World Heritage Site. The following day, you will visit the beautiful seaside town of Polignano a Mare, where a private guide will lead you on an intriguing tour through the city center. Afterward, you can dip your toes into the blue waters as you sail along the coast and soak up the coastal splendor from a new perspective.

As you journey toward Sicily, you will visit a couple of enchanting towns along the way. Matera, which is one of the oldest inhabited cities in the world, sits in the rugged region of Basilicata. You will be provided with the opportunity to tour the mystifying sites by tuk-tuk, riding through the winding streets and marveling at ancient cave dwellings. Afterward, you will luxuriate in Tropea, which is a picturesque resort town that boasts sandy beaches. Next, you will continue to Sicily, where worlds merge and you may find yourself fortunate enough to be immersed this unique culture. Here, Arab domes intertwine effortlessly with Byzantine art and Norman palace walls. In Cefalu, you will hike up large cliffs that buffer the sea, which is where you will discover the ruins of one of these Norman castles. The following day, you indulge in a relaxing cruise to the alluring Aeolian Islands, where you can splash in the warm waters and taste delicious local wines. You will then venture to the Ionian Sea on the opposite side of Sicily. In Taormina, you can attend an opera in an ancient Greek theater, which can be followed by an exhilarating trek up the boisterous Mt. Etna. On your final day, your private driver will escort you to Catania Fontanarossa Airport for your flight home.

Starting Price

$9,100 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

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.

4.9

Verified Traveler Reviews

Based on 658 reviews

Italy Birthday Travel Review: Amalfi Coast, Rome, Pompeii, Mount Vesuvius, Capri, Ischia, Sorrento, Minori, Cooking Class, Winery, 10 Nights

Our trip to the Amalfi Coast, arranged by Zicasso's travel specialist, could not have been more perfect! All our travel ran so smoothly. It was so nice not to worry about arranging pick-up and transportation. We were even met right as we got off the plane in Rome! All the drivers and guides were excellent, sharing helpful tips that ensured we used our time wisely to see the most interesting sites.

The hotels were all wonderful, with perfect locations, beautiful and spacious rooms, and breathtaking views. Our food journey was inspiring, with lots of fish, buffalo mozzarella cheese, pasta, and even a wonderful cooking class at an organic farm for my birthday! A team member made sure all our restaurant reservations were secured and even tipped us off to a transit strike in Italy so we could arrive early at the airport.

The travel specialist's suggestion that we visit a winery on Mount Vesuvius and visit Pompeii was excellent, so fascinating! The travel specialist and her team also arranged boat rides for us in Capri and in Sorrento to Ischia, which were extra-special. Our Sorrento boat captain even brought a delicious chocolate cake to celebrate my birthday!

Thank you so much for arranging such a special birthday trip and for making our travel so effortless, a truly relaxing retreat!

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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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Italy Tour Review: Sorrento, Pompeii, Capri, Amalfi Coast, 2 Weeks

We had a beautiful week in Sorrento, with days in Pompeii, Capri, and the Amalfi Coast. Zicasso’s travel specialist planned the trip exactly as we discussed and we loved every minute!

The one thing that was a bit challenging was that all of our excursions were booked under my middle name, which I do not use, and we had to explain several times to the trip operators.

The hotel was lovely, our room was perfect, and the pool was excellent. Unfortunately, there was a very long ramp required to walk up and down every time we left the hotel, and even though all of the rest of the hotel was excellent, we would have preferred a little less of a distance from the lobby to the street. These items were not at all a big deal, but we are learning what sorts of things to be sure to discuss when planning the next trip.

The travel company was very responsive throughout the trip and communicated with us regularly, which we appreciated!! Overall, I highly recommend this trip and can't wait for the next one!

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Italy Trip Review: Sorrento, Positano, Amalfi, Ravello, Pompeii, Herculaneum, Naples, 5 Days

Zicasso’s travel company helped us plan and execute a vacation to the Amalfi Coast. The travel specialists suggested sites and arranged hotels, ground transport, and guides. It was all accomplished flawlessly; we had a perfectly paced itinerary.

Not only were the drivers well experienced with the incredible labyrinth of roads along the coast and in Sorrento and Positano, where we stayed, but they were also great sources of local colorhighly experienced with the incredible labyrinth of roads along the coast and in Sorrento and Positano, where we stayed, but they were also great sources of local color and conversation, and, above all, they conversation, and, above all, showed their love for the country and region.

We had several guides who were spot-on, including an archaeology graduate for Pompeii and Herculaneum, and an incredible historian on a walking tour of Naples.

The hotels were wonderful, with experience and professionalism throughout.

The drive along the coast to Amalfi and Ravello was spectacular!

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Italy Vacation Review: Sorrento, Rome, Capri, Amalfi Coast, Positano, Ravello, Schiazzano, Pompeii, Vatican, Colosseum, Forum, Boat Ride, Limoncello Tasting, Pizza Making, 1 Week

We had an incredible time in Italy! Thank you to Zicasso’s travel company! You thoughtfully planned our time in Sorrento and Rome to ensure we had the best experiences, while allowing for some free time to explore.

Our day-trip boat ride around Capri was beyond perfect. The boat captain and guide were very professional and truly charming. He gave us options on how to take in the sights and provided great commentary about the history and culture of the island. We selected to go to Marina Piccola for lunch, which was a great experience. The view from the restaurant was enchanting and the food was delicious. The grottos, Faraglioni rocks, and swimming in the Mediterranean were experiences of a lifetime.

We spent a day driving along the Amalfi Coast. We had a great driver on the mountainous winding roads. We visited charming Positano and beautiful Ravello. Our driver had great advice about where to visit and what to see. We enjoyed an amazing lunch, with a beautiful view, in Ravello.

On day three we enjoyed free time on the beach in the morning. Then we headed out for our limoncello experience! And it was a wonderful experience. The people we met in Schiazzano were very special. We loved the goal of the family businesses to keep and honor their traditions. Our pickup was prompt and we were served a drink at their general store. It is very touching that they began the tour in their church and shared the pride in their community. Then we were off up the hill, along narrow streets to the lemon groves. We learned about farming lemons from two enthusiastic young farmers, we smelled the lemon zest, and they served us fresh lemonade. Then we all got an exciting tuk-tuk ride up and down the very narrow streets to the hilltop farm, where we tasted olive oils, had a cheese-making demonstration, and tasted all the phases of cheese. Then we tasted the limoncello! We really enjoyed the spectacular view. Last, but certainly not least, we enjoyed making our own pizza using tomato sauce that was prepared by grandma that morning using freshly picked tomatoes. We tossed our pizza dough and used fresh mozzarella. The wood-fired oven cooked the pizzas perfectly. We enjoyed eating every bite. When we were planning our trip, I asked for limoncello tasting, but this experience was so much more!

We also had a wonderful time in Pompeii and at the Vatican, Colosseum, and Forum in Rome. All the history is so fascinating. There were many tourists in Pompeii and Rome, and all of our guides were terrific, energetic, and skilled at navigating the crowds.

All of the private transfers, train travel, and hotels were perfect. Thank you for your help and expertise with planning this once-in-a-lifetime trip!

We hope to travel to Italy in the future and would love to work with this travel company again to help us plan that next trip.

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Italy Trip Review: Naples, Amalfi Coast, Sorrento, Capri, Positano, Rome, Boat Ride, Cooking Class, Wine Tasting, Colosseum, 12 Days

I recently completed an incredible 12-day vacation in Italy, arranged by Zicasso’s travel company, and it was one of the best vacations I have ever had. From the initial planning with the travel specialist and her team to the seamless execution on the ground, everything exceeded my expectations for a luxury custom trip.

We started in Italy, where we were immediately met at the airport by a hostess who got us through all the lines in record time and into a Mercedes Sprinter van that took us to Naples. Naples offered us a really vibrant, authentic Italian feel, and the incredible food that the travel specialist recommended from the movie "Eat Pray Love" was the best pizza I’ve ever eaten in my life. I don’t think I can eat pizza in the United States anymore. The private drivers and guides made this whole trip stress-free.

Our next incredible experience was the dream-like Amalfi, Sorrento, and the Isle of Capri. The hotel in Positano was beautiful. We were enchanted with all the colorful cliffs, the boutique shopping, and the stunning view from our balcony room. Sorrento was my favorite city of all. It was very relaxed, with lemon groves everywhere and beautiful sunsets, and our hotel had balconies that opened up on the Mediterranean. The highlight of our trip was the island of Capri. The boat ride was just fantastic and we started at the top of the mountain and did the chairlift so we had a whole view of the city.

The highlights of the trip for me were the boat ride along the Amalfi Coast, the cooking class and wine experience at the female venture, and the wine by Mount Vesuvius.

Our last two nights were back in Rome and it was kind of hard to go from the low-key vibes of Sorrento to the action-packed atmosphere of Rome, but the hotel the travel specialist picked was just perfect. It was 10 minutes from the Spanish Steps and she arranged a tour of the underground Colosseum. I learned so much about everything in that area. All the guides, the drivers, everything was magical. I would highly recommend this travel specialist and the travel company.

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Customizable Itinerary

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

32,000+ Verified Traveler Reviews