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 563 reviews

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 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 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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Italy Travel Review: Rome, Ravello, Amalfi Coast, Positano, Sorrento, Naples, Pompeii, Capri, Mount Vesuvius, Cooking Class, Local Cuisine, 20 Days

My husband and I were thrilled with our recent trip to Italy that Zicasso’s travel designer put together. We began by attending a family friend’s wedding, held in Ravello, on the Amalfi Coast. Due to my husband’s mobility issues, we were met by a driver and headed to the Amalfi Coast. The driver was first class and the trip was very comfortable.

After the wedding festivities, we were able to have the most wonderful experiences visiting the towns of Amalfi and Positano, and our base for one week was in beautiful Sorrento. We attended a cooking class and enjoyed eating what we prepared. We had in-depth learning opportunities in Naples and Sorrento. Every guide we had spoke excellent English and was so knowledgeable. We especially enjoyed Pompeii! A super-fun day was had on the small group tour of Capri. The crew was fantastic and very accommodating in consideration of my husband’s mobility issues.

From beginning to end everything went well. The use of a messaging app was great for making sure everyone was on the same page.

The only thing that was a disappointment was the pizza in Naples. It wasn’t the best.

The hotel in Sorrento was phenomenal - it couldn’t have been better. The view of Mt. Vesuvius from our balcony helped create memories we will have forever. The hotel in Rome was also very nice. It was right in the middle of the main attractions.

We are very happy with our experience with this travel company and would not hesitate to recommend it!

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Italy Vacation Review: Venice, Florence, Tuscan Hills, Pompeii, Rome, Amalfi Coast, Sorrento, Capri, Cooking Class, Lemon Farm, Wine Tasting, Olive Oil Tasting, 2 Weeks

We had the pleasure of working with Zicasso’s travel agents to create the perfect Italian adventure. I had quite a few specific requests, from travel logistics to hotel preferences, and they were incredibly patient and collaborative, offering multiple variations of the itinerary until it matched exactly what we envisioned.

Our journey began in Venice, where we were seamlessly picked up by a private driver, transferred to a water taxi, and dropped directly at our hotel. After a wonderful stay, we were taken by private driver to the train station for our ride from Venice to Florence, our one and only train trip, as we opted (based on their smart recommendation) for private transportation for the rest of our travels to avoid potential delays and enjoy added convenience.

From Florence, we were driven into the Tuscan hills, where we experienced magical wine tastings, vineyard tours, olive oil tastings, and unforgettable meals with wine pairings. 

Next, our private driver brought us to Pompeii, where we enjoyed a fascinating tour with our private guide, and then continued on to Rome. In Rome, we loved the private golf cart tour of the city’s major landmarks, as well as a delightful cooking class that was arranged for us; it was a real highlight!

Finally, we traveled by private driver to Sorrento. From there, we had a breathtaking driving tour of the Amalfi Coast, a lemon farm tour, and an amazing day trip to Capri. Every detail was thoughtfully planned and executed.

Summary:

Planning and Itinerary Creation: Zicasso’s consultants made the entire process easy and stress-free. They worked closely with us to perfect the itinerary and were always receptive to changes and feedback.

Hotels: My sister and I requested adjoining rooms and were provided with beautiful family suites throughout the trip. Each hotel was ideally located, comfortable, and well-appointed, with all the amenities we needed.

Transportation: Every transfer was smooth and punctual. The private drivers were professional, friendly, and knowledgeable. (A special shoutout to our driver in Florence/Tuscany – he was the best!)

Communication: Throughout our trip, the travel company’s team was always accessible. Whether we needed to make adjustments or had a question, they handled everything promptly, allowing us to relax and fully enjoy our vacation.

We spent just over two unforgettable weeks in Italy and it was absolutely perfect, all thanks to the hard work, attention to detail, and excellent communication from Zicasso’s travel company! I highly recommend them and would not hesitate to use them again for future adventures.

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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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Customizable Itinerary

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

31,000+ Verified Traveler Reviews