Couple's Getaway: Two Weeks in Southern Italy

Mondello beach near Palermo, 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.

Countries Visited

Italy

Places Visited

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

Suggested Duration

14 Days

Customizable Itinerary

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Day 1

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:

Transfer
Accommodation
Day 2

Naples – Visit the Vibrant Teatro San Carlo

Day 3

Naples – Witness Life and Loss at Pompeii

Day 4

Sorrento – Relish the Flavor of the Sorrentine Peninsula

Day 5

Sorrento – Learn to Make the Perfect Pasta in a Private Course

Day 6

Capri – Uncover the Hidden Gems of this Mediterranean Paradise

Day 7

Capri – Enjoy a Private Boat Tour of a Romantic Sea Cave

Day 8

Capri – Survey the Scene from Monte Solaro

Day 9

Amalfi – Explore the Past of this Onetime Maritime Empire

Day 10

Amalfi – Ride the Waves of the Famous Amalfi Coast

Day 11

Palermo – Discover the Highlights of Sicily’s Colorful Capital

Day 12

Palermo – Savor a Tour of the Open-Air Markets

Day 13

Palermo – Tour and Taste Your Way through an Operating Vineyard

Day 14

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

$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 655 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 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 Tour Review: Rome, Bari, Positano, Sorrento, Naples, Amalfi Coast, 2-Week Trip

We had an amazing 2 weeks in Italy, from Rome, to Bari, Positano, Sorrento, and Naples. The planning and execution of our trip through Zicasso’s tour operator was flawless! They worked with me quite a bit in the planning phase to make sure this was going to be our dream trip.

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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 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 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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Customizable Itinerary

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

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