Couple's Getaway: Two Weeks in Southern Italy

What to expect on this itinerary
Fourteen days will give you and your partner ample opportunities to explore the rich heritage of Southern Italy. From the crumbling cliffs of Capri to the rustic charm of Naples’ old city center, every aspect of this itinerary is best paired with your companion and has been custom-tailored to those couples that enjoy a blend of both comfort and excitement during their international travels. As you witness the class of the past and present that is this region, it is best to leave plenty of space on your camera’s digital memory because each stunning view will be replaced by another stunning view.
Customizable Itinerary
Naples – An Introduction to Southern Italy
Italy is a land of story. From myths of Sirens and sea nymphs to the impact of two world wars, one needs to look no further than their immediate surroundings to see evidence of the centuries-worth of history that has taken place here. This adventure will give you the opportunity to write your own verse to a story that goes back millennia.
All of this will feel like nothing but anticipation as your flight glides down out of the clouds to arrive at the Naples International Airport. A private driver will swiftly escort you from the busy hub of the airport to your luxurious hotel in the heart of the city. As you and your partner begin to admire the sights, your open window will ensure that the smells and sounds of this Neapolitan life greet you as well. You will be greeted to the sounds of children as they shout amidst a game of street soccer, the buzz of scooters and fiats as they precariously navigate the traffic around you, and the eventual sound of the ships as they come and go. These next two weeks will be your story, and Naples is the perfect setting.
What's Included:
Naples – Visit the Vibrant Teatro San Carlo
Naples – Witness Life and Loss at Pompeii
Sorrento – Relish the Flavor of the Sorrentine Peninsula
Sorrento – Learn to Make the Perfect Pasta in a Private Course
Capri – Uncover the Hidden Gems of this Mediterranean Paradise
Capri – Enjoy a Private Boat Tour of a Romantic Sea Cave
Capri – Survey the Scene from Monte Solaro
Amalfi – Explore the Past of this Onetime Maritime Empire
Amalfi – Ride the Waves of the Famous Amalfi Coast
Palermo – Discover the Highlights of Sicily’s Colorful Capital
Palermo – Savor a Tour of the Open-Air Markets
Palermo – Tour and Taste Your Way through an Operating Vineyard
Palermo – Depart for Home
Trip Highlights
- Stroll the cobbled streets of Naples in search of the perfect slice of Margarita pizza
- Delight in a tour of the Roman ruins at Pompeii and witness the colossal power and tragic past of Mt. Vesuvius
- Plunge into the decadent history of the Teatro San Carlo on an immersive journey through the venue’s vibrant operations
- Follow the guidance of your instructor on a comprehensive and tasty study of Italy’s ancient love affair with pasta
- Wander the quaint alleyways and pedestrian-friendly boulevards of the resort town of Sorrento
- Dive into the history and culture of the hidden grottos of Capri where crumbling Roman villas emerge out of the bougainvillea, and terraced gardens give way to stunning vistas
- Scale the promontory of Mt. Solaro and survey the surrounding Italian countryside from the best view of Capri
- Indulge in a private boat tour around Capri that provides you with plenty of privacy and a memorable trip to a superb sea cave known as the Blue Grotto
- Enjoy the sun and sand of Italy’s Amalfi Coast where the only thing better than the beaches is the views of the pastel-colored communities that cascade down the steep hillsides
- Indulge in the bountiful produce of farms and vineyards in a visit to Sicily’s colorful, capital city of Palermo
Detailed Description
Southern Italy has long been the destination of choice for travelers from all corners of the globe. Even during the ages of antiquity, Roman emperors found the views and coastal grandeur of this region to be the perfect antidote to the civic stress of running an empire. This 14-day journey through some of the highlights of this region was designed to offer you the same treatment, but with fewer volcanic eruptions. This adventure also offers a handcrafted escape for couples who are seeking a blend of comfort and adventure.
The first leg of your journey includes an exciting stay in the bustling port community of Naples. From this starting point, you will have plenty of opportunities to explore the dynamic and lively neighborhoods of the city before striking out to enjoy a trip to the nearby community of Pompeii. It is this region that witnessed the stunning eruption of Mt. Vesuvius, which covered Pompeii in ash and left an indelible mark on the geologic and social history of Campania. The second leg of your tour will lead you to the Sorrentine Peninsula, and the Amalfi Coast makes up the Southern end of the Bay of Naples. These rugged mountains afford visitors a plethora of stunning views of mountains that drop precipitously into the azure waters. Much in the same way they have for centuries, Sorrento, Capri, Amalfi, and Positano will all offer you unique glimpses into these distinct societies that persist through today. Finally, Sicily in the South will beckon you with promises of exotic flavors and intimate settings for you and your partner to enjoy.
As summers can be quite warm, timing will be everything on this tour. The busier months tend to be June, July, and August for international as well as domestic travelers, so Spring and early Fall are usually the best times to go for those who desire a quieter setting. This enchanting region is also home to Homer’s infamous Sirens, which were sea creatures that lured sailors into dangerous waters with their beautiful song, but rest assured that uncovering ancient myths and enjoying yourself are your only requirements of this satisfying tour of Southern Italy. Consider learning more about our travelers’ favorite Italy travel experiences 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.
Verified Traveler Reviews
Based on 1041 reviews
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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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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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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Zicasso’s travel professional crafted an unforgettable Sicily trip for our group of seven. After discussing our preferences, she designed a flawless itinerary, incorporating unique experiences that became trip highlights. Her communication was exceptional, with prompt responses to our questions before the trip and daily updates for the next day's activities, including driver and guide details, which were incredibly helpful.
We stayed at superb hotels in Taormina, Agrigento, Palermo, and Cefalù, each with stunning views and private tours. Sicily’s warm, hospitable people stood out compared to other European destinations. At our hotel on Via Leonardo da Vinci in Taormina, the staff greeted us warmly, setting a perfect tone. Other stops included Mount Etna, Erice, Castelbuono, and Savoca. All of these locations were great, but don't miss Castelbuono!
Two standout experiences were private meals with families. Near Erice, a chef and his family welcomed us into their sea-view home, preparing amazing Sicilian meals that felt like dining with family. In Palermo, another home chef and her husband created a similarly memorable evening, with lots of great conversation and stories.
Every driver was professional, friendly, and informative, while our guides — often archaeologists or historians — were engaging and knowledgeable.
Highlights included a welcome dinner in Taormina, a farm cooking class, two wine tours with lunch, a Mount Etna hike, a Valley of the Greek Temples tour, town and village tours, cheese and pastry tastings near Cefalù, and a farewell dinner. The Godfather tour in Savoca was special, with our guide introducing us to a local who played Apollonia’s mother, waving from her balcony.
Our travel professional's meticulous planning and personal touches made this trip extraordinary. Thanks to Zicasso for matching us with the tour company and we highly recommend them for a perfect Sicilian/Italian adventure!
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Zicasso's travel designer did an excellent job planning a three-week trip for us in Naples, the Amalfi Coast, Capri, and several cities in Sicily. We appreciate that she met with us by Zoom on two occasions to tweak the draft itinerary to be sure it was the trip we were looking for. She listened to us and created an itinerary that met all of our needs.
The guides, drivers, and accommodations were excellent. The guides all spoke excellent English, were easy to understand, and obviously well educated and informed about the details of the history, architecture, art, and culture of each site we visited. The experience was educational, in addition to just enjoying the beauty of Southern Italy and Sicily.
We had one potentially disruptive event when a labor strike caused a cancellation of our flight from Naples to Sicily. Her team did an amazing job of creating an alternative, involving going by train to Rome, then catching a plane from Rome to Catania, and our arrival was only a few hours later than the original itinerary. Our word to describe their creative plan is "Brilliant."
Overall it was a great and memorable experience, thanks to the excellent recommendations, planning, and making all of the arrangements for our visit.
We will have no hesitation to recommend her and her team to our friends and family. Thank you for arranging for us to benefit from their incredible services.
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