Two-Week Highlights of Southern Italy Tour

Cathedral of Palermo in Italy

What to expect on this itinerary

Southern Italy offers a genuine contrast to the icy elegance of the North as this is a land that has no time for the inauthentic. This luxurious, 14-day tour of the Bay of Naples, the Amalfi Coast, and Sicily’s capital is handcrafted to reveal what is unique about the South while offering all the sights, sounds, and flavors that have made Italy one of the most sought after destinations in Europe. From the heights of Mount Vesuvius to the depths of the Grotta Azzurra, this adventure will ensure that there is nothing to distract you from the rich heritage and cultural legacy that are waiting for you.

Countries Visited

Italy

Places Visited

Naples, Pompeii, Sorrento, Amalfi, Positano, Capri, Salerno, Palermo

Suggested Duration

14 Days

Customizable Itinerary

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Day 1

Naples – A Neapolitan Welcome

Italy is a land that is steeped in history and tradition, and nowhere is this more evident than in the sunbaked cities of Southern Italy. Hugging the West Coast of the Italian peninsula, Naples has had a front-row seat for the dramatic history that this region has seen as the centuries have passed. Today, Naples represents the third largest metropolitan area in Italy with significant urban sprawl, surrounding the original structures of the city. Situated on the Northern end of the Gulf of Naples, its strategic position has made it a sought after city for merchants, traders, and generals before international travelers discovered its host of culinary treasures. Your private transfer will meet you at Naples International Airport and escort you to your luxurious hotel, which will be located close enough to the port for you to experience the charms of the city but just far enough away to avoid the noise and bustle of incoming cruise ships and freighters.

After you have had a chance to settle into your conveniently located accommodation, you will be met by your helpful guide who will provide you with an introductory tour of Naples, beginning at the church of San Domenico Maggiore. The spirit of Southern Italy will quickly express itself to you through the casual conversation of locals who rarely fail to pause and exchange a few words with their neighbors no matter how busy they are. Carved out of the surrounding neighborhoods, the Piazza del Plebiscito offers some relief from the jumble of narrow alleys and stunning views of the Royal Palace of Naples. As you acquaint yourself with this charming corner of Italy, the history and architectural splendor that surrounds you will leave no doubt in your mind as to why the city center has been a UNESCO World Heritage Site since 1995.

What's Included:

Transfer
Accommodation
Breakfast
Day 2

Naples – Dig Into History at the Museo Archeologico Nazionale

Day 3

Naples – Witness Nature’s Power on a Day Trip to Ruins of Pompeii

Day 4

Naples – Stroll the Old City Center of Naples

Day 5

Sorrento – Stretch Your Legs on the Slopes of Mt. Vesuvius

Day 6

Sorrento – Practice the Passeggiata in Sorrento’s Center

Day 7

Capri – Marvel at the Mediterranean Splendor of Capri

Day 8

Capri – Enjoy a Boat Tour of the Grotta Azzurra

Day 9

Amalfi – Dive Into the Coastal Brilliance of the Sorrentine Peninsula

Day 10

Amalfi – Brave the Waves on a Boat Excursion of Amalfi Coast

Day 11

Amalfi – Meander the Hiking Trails Surrounding Amalfi

Day 12

Palermo – Immerse Yourself in the Dramatic History of Palermo

Day 13

Palermo – Visit the Palatine Chapel and Norman Museum

Day 14

Palermo – A Sicilian Send-Off

Trip Highlights

  • Unearth hidden treasures from Italy’s colorful past in a visit to the Italian National Museum of Archeology
  • Wander the crisscrossing alleys and streets of Naples’ Centro Storico and sample some of the classic Italian cuisine that can be found here
  • Observe the tragic remains of Italy’s volcanic past in a visit to the ancient ruins of Pompeii and the well-preserved relics of the past
  • Experience the pristine views of the Bay of Naples and the Sorrentine Peninsula from the slopes of the imposing Mt. Vesuvius
  • Witness the proud maritime tradition of Sorrento and enjoy an evening stroll, or passeggiata, through the neighborhoods to witness the impressive works of local artisans
  • Discover your sea legs on a ride to the island of Capri and marvel at the stunning seascape that can be found on a tour of the Grotta Azzurra
  • Immerse yourself in an exploration of the rugged mountains and precipitous drops of the Amalfi coastline.
  • Delight in Sicily’s proud history and vibrant culture through a visit to the Palatine Chapel and the Museum of Norman History

Detailed Description

Italy has long been a destination location for travelers hoping to experience the best of Europe. Contrasting the verdant beauty of the North, the rugged, Southern landscapes and sea fairing communities offer much to the traveler who is hoping to catch a glimpse of the Mediterranean past while enjoying the comfort of modern amenities. As August has long been the vacationing month for locals, early Spring and Fall remain the best times to visit these destinations because you can combine the promise of summer warmth with the absence of crowds. Southern Italy has long seduced visitors from all walks of life from queens and emperors to pilgrims and traveling artists.

Whether the culinary charm of Naples to the rural beauty of the Amalfi Coast, there is something for everyone on this 14-day tour of Southern Italy, and you should leave plenty of space on your camera to capture the countless moments that you will undoubtedly encounter. The first leg of your journey will introduce you to the Bay of Naples and the surrounding cultural and geologic history that has been the subject of books, songs, and film for generations. A side jaunt up the slopes of Mt. Vesuvius will then offer a panorama of one of the must-see destinations on this tour.

The second leg of your adventure comprises of visits to the island of Capri and the Amalfi Coast, which is where the rugged mountains plunge into the waters of the Mediterranean and the local villages offer quaint and quality samples of local ingredients and dishes. Boats and cars will be your primary modes of travel, and you will always be steered by the most experienced hands. A trip to Sicily will almost seem like another country as the extravagance of Capri is replaced by the rustic charm of Palermo, which is a city that claims to have been the most conquered of any in Europe.

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

Starting Price

$5,100 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

  • 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 1061 reviews

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 Tour Review: Rome, Florence, Amalfi Coast, Pompeii, Mount Vesuvius, Ancient Sites, Cooking Class, 1 Week

I can confidently say that Zicasso's travel specialist is truly dedicated to providing her clients a luxury experience. From the outset, we had a 20-minute call where she wanted to learn about our dream vacation and get to know us. She was attentive to every request we made and organized our itinerary accordingly. During the trip, she texted us daily to inform us about our drivers and guides for the next day. Additionally, she checked to ensure our trip was progressing smoothly.

Here are some highlights:

Rome: We were greeted at the airport by our agent, who expedited our passage through passport control. The following day, we started our exploration at the Vatican. Our agent had purchased our tickets in advance, allowing us to skip the line. She also planned the remainder of our self-guided tours of the Colosseum, Roman Forum, and other ancient sights. We accomplished so much in just two days!

Florence: We took part in a pasta-making class with a chef who was fantastic! Her husband was also quite charming. Our experience there was truly wonderful. Special thanks to our driver, who was incredibly helpful and informative.

Sorrento (Amalfi Coast): We began with a visit to Pompeii, where our guide, also arranged by our agent, was spectacular! His passion and extensive knowledge made the experience enjoyable. Next, we had a fun blind wine tasting. When we arrived at our amazing hotel, we were greeted with a surprise.

While in Rome, we encountered a minor issue, which our agent resolved quickly. She even went above and beyond by ordering us a bottle of prosecco to celebrate. We also took a car tour of Positano and Ravello, guided by a local from Ravello who was informative, knowledgeable, and delightful. We loved her! Our day ended with a lovely sunset cruise off the coast! Both days had excellent drivers.

This trip was a dream come true for my husband and me. Without a doubt, our agent made it the luxurious experience we desired. I highly recommend her and her team!

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Italy Vacation Review: Venice, Florence, Rome, Sorrento, Murano, Burano, Pisa, Vatican, Colosseum, Pompeii, Capri, Private Tours, Cooking Class, 10 Nights

I apologize for the delay in writing this review, but was very busy the last few months and wanted to dedicate the time it deserved. This review will address my wife and my trip to Italy from September 26, 2025, to October 6, 2025. Please feel free to share all or any portion of this review.

Trip Planning:

As a bucket-list event, I spent a great deal of time doing research, but would not have been able to put together the ideal vacation without the support of Zicasso and the travel company. Upon hearing my general interests, Zicasso provided two groups whom they thought would be able to plan and implement my trip. Both groups interviewed me and my wife about interests and price range, and then prepared an initial itinerary. Both groups would have done a fantastic job by their presentation, but it seemed I was slightly more in tune with the travel company and selected them. This proved to be a very wise choice, as the entire team at the travel company, particularly the travel specialists, were the absolute best and I would recommend their service without reservation. Fully responsive to my many questions before the trip, addressing all potential itinerary changes, and providing invaluable guidance throughout the entire process. Their response to inquiries while in the country was unbelievably prompt and thorough. At our request, the travel specialists made restaurant recommendations and reservations that were spot-on. I can’t say enough good things about these ladies.

Transportation and travel between locations:

Although not involved in the flights, the travel specialists provided great guidance concerning flights, trip insurance, and other logistics.

One key point that I fully expressed was that I did not want to flounder at the various transportation points and did not want to lug luggage in foreign areas on the way to and from lodging. The team took this to heart and provided me with either an escort or driver to and from every terminal. Everyone providing this task was friendly and provided information that made the travel much easier. Particularly valuable were our escorts, who adeptly negotiated our entrance and exit from Venice, and provided great insights into this historic city.

Venice:

Our hotel in Venice seemed to be right in the middle of everything, which allowed us to explore, and we have never had so much fun getting lost. At night, we opened our windows and fell off to sleep listening to nearby music; it was idyllic. The staff was professional and friendly. Breakfast was the best of all the hotels we stayed at in Italy.

The first full day in Venice, the travel company leveraged “skip the line” so we could make the very most of our time and is essential to any planning. Both guides were great and really good company. One guide’s knowledge of the Doge Palace really brought it to life for us. Another guide had a real insider’s view of Burano, as this was her family’s island. As private tours, we could go at our own pace, which we really liked. Probably the least enjoyable tour was the glass factory in Murano. We got the impression most of the tour beyond the initial exhibition was an attempt to sell their products. My wife succumbed and purchased a pair of earrings that broke the first time she wore them. Really disappointing, and I would advise you to spend more time in Burano.

Florence:

As with all the trains, the travel was very comfortable and we enjoyed watching the scenery. Our lodging in Florence was right on the Santa Maria square, superb for people watching. The staff was fine, nothing more. The hotel was near the world’s oldest pharmacy, famous as the world's oldest perfumery. Although there is a line to enter, it goes quickly and is historical, to say nothing of buying a scent more than 400 years old. I strongly recommend you go.

While knowledgeable, our tour guide for the Accademia and Uffizi Galleries was a little too technical for us, leaving us with the feeling that we were taking an art history class.

Dinner was based on the travel specialist's recommendation and it was delicious. A strong recommendation.

Day trip to Pisa:

The travel arrangements were perfect. The purpose of the trip was to take the obligatory picture holding up the tower—hokey, but we loved it.

The private cooking class with our instructor was a lot of fun. The view of the city from her window at sunset was beautiful. My wife and our instructor fell into a real rhythm cooking, and she was kind enough not to scoff at my ham-handed attempts. Her directions were simple enough for me to follow, theoretically. She followed up her lesson with an email containing detailed recipes. We have purchased all necessary utensils and are planning a pasta-making party soon. This was a fun change of pace.

Rome:

Our bed-and-breakfast in Rome was our least favorite lodging. Entry into the building was confusing and, as a B&B, the desk was not manned all the time, which made it difficult to secure a taxi early in the morning (we had to walk to a nearby hotel) or get assistance after 8pm or before 6am. When we came in, we attempted to coordinate laundry service with the person working the front desk, followed his instructions, but when we returned the next day, our dirty clothes were still where we were told to leave them. The initial response from the on-duty staff, who I believe was the owner, was that the individual was no longer an employee. Ultimately, the hotel comped and completed our laundry, which was nice. We would have preferred different lodging.

Our first afternoon, we took a four-hour golf cart tour, which was our favorite tour of the entire trip. Adding an extra hour to the traditional length and having only my wife and me allowed us to do everything we wanted to do. Our driver took us everywhere. He would drop us at the top of the Spanish Steps and meet us at the bottom, and would conveniently bring us closest to all other locations. I can’t believe how much we did in four hours. Our driver brought all these iconic sites to life with his marvelous insight and provided a great insider view of these monuments. This is a must-do for all first-time visitors to Rome. The only thing we were not able to do, due to no fault of our driver, was the Aventine Keyhole. When we got there in the afternoon, the line was 45 minutes and not a wise use of our time. If this is a strong interest, he recommends going early in the morning.

The travel specialists arranged tickets for the Papal general audience on Wednesday. Rising at sunrise was worth it to get the seats as close as we were able to secure. Most online sites suggest getting there an hour and a half before the start time, but I think that is much too late. I recommend you get there three to four hours ahead to get the best seats. The best seats are on the end near where the Pope drives by, ideally near an infant, and His Holiness will stop to personally bless these children. Facing the stage, the right side filled up quicker than the left side, so go directly to the left side of the audience. Being so close to the first American-born Pope was a memory I will never forget. His Holiness blesses all items in the audience's possession, so load up on rosary beads; they will make great Baptism and Communion gifts.

The afternoon was our first group tour at the Vatican Museums. It might be that we were spoiled with the previous private tours, but linking up with the group was chaotic and the quality of the tour was contingent on those in our group. Fortunately, all our groups were good, considerate, and friendly people. The main value was skipping the line for entrance. As with the Doge Palace, our guide was a little too academic and didn't really manage time well, potentially a victim of being in a group, but I would have rather spent more time in the Sistine Chapel and the Basilica. Taxis were extremely hard to get back to the hotel and I would arrange a ride if I were to do it again.

The Thursday tour of the Colosseum and Forum was also a group tour, but led by a guide who brought this ancient land to life. An archaeologist by trade, our guide seemed to know everything and also took a great picture.

The end of a very long but enjoyable day was another group tour of the catacombs and Santa Maria Maggiore. While the catacombs were the main attraction, the after-hours and behind-the-scenes access to Santa Maria Maggiore was an unexpected gem. Going through a second Holy Door, viewing the magnificent nighttime skyline from the roof, seeing the location of a relic from the baby Jesus’ manger, and being struck by the modesty of Bernini’s and Pope Francis’s tombs were all highlights. Unfortunately, taxis were again hard to come by.

Sorrento:

We took a train from Rome to Naples. While there was a national strike, it did not prove more than an inconvenience, no worse than New York City on a regular day. Our driver from Naples told us this simply provided us with a genuine Italian experience. I wish I could remember this driver’s name because he was the best of a very good group of drivers during this trip. En route to Sorrento, we stopped for a tour and meal at a winery and a private skip-the-line tour of Pompeii. We were so impressed with the quality of the winery that we made a large purchase of wines and olive oils that, thankfully, included free shipping.

During our drive to Sorrento, our driver took us through his hometown, which we really enjoyed. Going through the town, he pointed out the birthplace of Bruce Springsteen’s mother. Little did he know, we were from New Jersey and are HUGE Springsteen fans.

Our hotel in Sorrento was a nice place, close to the center of town. I would have preferred a hotel with a view of the coast.

On Saturday, we took a private tour up the coast. This was the most comfortable car I have ever ridden in, with heated and cooled seats, and a convenient icebox. The driver made clear he was at our disposal. The scenery was marvelous and it was a thrill to dip our toes in the Med. Our driver hooked us up with a restaurant on a cliff overlooking the water—beautiful and scrumptious.

Our last day was supposed to be the Gozzo tour of Capri, but was canceled due to weather. We refunded the canceled boat tour, but ate the driver and ferry fees. In hindsight, knowing this day was largely contingent on weather, I would have liked to have a contingency plan and would advise the travel company to plan this in the future.

Based on how smoothly things went, we will be contacting Zicasso to arrange a trip to Iceland and Ireland next fall, and hope they can refer a team as talented as this travel company.

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Italy Tour Review: Amalfi Coast, Sorrento, Positano, Path of the Gods, Cooking Class, Hike, 1 Week

The travel company did a fantastic job planning our Italian vacation to the Amalfi and Sorrento coasts. The hotel in Positano was breathtaking. The excursions that Zicasso's travel designer recommended were fantastic. The cooking class in the hills overlooking the coast was amazing. Our travel plans changed due to airline difficulties and she was incredibly helpful in making adjustments on the fly to ensure our trip went as smoothly as possible.

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Italy Tour Review: Sorrento, Florence, Rome, Pompeii, Winery, Private Tours and Guides, 13 Nights

Zicasso’s travel specialist was a fantastic travel advisor. This tour operator helped us plan our perfect Italian vacation by listening to our desires, from wanting boutique hotels with a view to private tours. They secured transportation from Sorrento to Florence to Rome.

Our driver to the winery was exceptional. He went above and beyond to find a quaint restaurant that served my favorite meal: white-truffle pasta. We also had an amazing guide in Pompeii. He was very informative and even surprised us with his beautiful singing voice in the amphitheater inside Pompeii. This trip was magical. We could not have asked for a better organized, non-stress trip.

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Customizable Itinerary

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

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