Naples, Pompeii, Sorrento, Amalfi, Positano, Capri, Palermo, Sicily
Dates are flexible and customizable for private departures.
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...
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.
Naples – Visit the Vibrant Teatro San Carlo
After a night of fitful rest, any sign of jet lag will be washed away with a cup of the famous Neapolitan espresso, which is a tasty treat that can be found in abundance on every block and the fuel upon which the city functions. A short morning stroll around the iconic city center will reveal that you are in the heart of the old city, and many famous and worthwhile destinations are within a few short blocks of your luxurious hotel. The hotel staff will be happy to offer suggestions for what to see and do in your downtime, but today, you will be met at your hotel by a knowledgeable guide who will escort you to the picturesque steps of the Teatro di San Carlo for a private tour of this 18th-century landmark.
The theatre itself is the oldest continuously active opera house in the world, and upon entry, you will see why it had a difficulty shutting its doors. Resplendent Foyers help to create an atmosphere that is fit for a king, and the balustrades and royal boxes of the main hall will take your breath away. Opening day for the Teatro San Carlo was in 1737, and since then, it has survived fires and Allied bombings and continues to provide audiences with fits of laughter or tears at the exquisite performances that are shown here. After your tour concludes, you will be free to indulge in an intimate dinner at a nearby restaurant or inquire about show times to catch a performance.
Naples – Witness Life and Loss at Pompeii
After arriving in Naples, you will have noticed the imposing mountain to the South, and after enjoying a typical Neapolitan breakfast of coffee and pastry, you will be met by your guide who will accompany you on the short drive South to the slopes of this conspicuous prominence. On August 24th, 79 AD, Mt. Vesuvius erupted, launching volcanic gas, rock, and ash miles into the sky and into the adjacent country. Lying just at the base of this active volcano, the Roman communities of Herculaneum and Pompeii never had a chance as liquefied mud, burning debris, and pyroclastic flows buried, smothered, and otherwise crushed most of the local inhabitants. An unexpected consequence of the volcanic material involved in this natural disaster was the quality of preservation that it ensured for the cities and people that it buried. Today, you can visit both sites and see intact examples of Roman ruins, including the mosaics that decorated the walls and the more somber reminders of the human cost through plaster molds of human figures.
As you stroll along the excavated roads that were once strewn with molten rock and rubble, you will have an exciting glimpse of how ancient Romans lived. You can take special note of how these ancient communities practiced roadbuilding strategies that engineers still use today in the technique that is used to divert rainfall laterally to the side of the road by raising its center. The molds of the volcano’s victims will cause you to hold your partner a little tighter as you both consider life’s fleeting nature and are inspired to completely enjoy each day. When satisfied with your day trip to this breathtaking neighborhood, your driver will be waiting to provide you a comfortable and convenient return to your elegant accommodation.
Sorrento – Relish the Flavor of the Sorrentine Peninsula
On your final morning in Naples, the sun will bring with it the sounds of a city that is coming to life. Once again, an open window is the best method of ensuring your unobstructed view of the excitement as it unfolds. Through it, you will be able to hear the sounds of the street cleaner below, the echoing sounds of freighters as they arrive and depart the busy port, and the charming hum of commuters and locals as they navigate their way on a busy commute. Your hotel will tempt you to stay for another delicious breakfast with both healthy and tasty options but now is not the time to look back because you will have a car that will be waiting to escort you out of Naples in search of a more rural landscape. Your destination will be Sorrento, which is a cliffside community that is perched on the Southern end of the Bay of Naples, and it is a popular spot for those who are searching for comfort, adventure, and romance.
Sorrento most likely began as a Greek colony but was developed considerably by the Romans after the conquest of the lower peninsula in the 4th and 5th centuries B.C. Since then, it has changed hands often across the centuries but through it all has maintained its status as a destination location for those who are wishing to find shelter from Italian summers. Nowadays, it is also the port of departure for those who are wishing to visit the nearby island of Capri. Landlubbers beware: this region was also the mythical home to the sirens, which were the band of water creatures that lured countless sailors to their doom with sweet, intoxicating songs. Your driver will effortlessly navigate the narrowing streets and alleys of this town before leaving you at your conveniently located quarters near the city center.
Sorrento – Learn to Make the Perfect Pasta in a Private Course
After your successful arrival on the Sorrentine Peninsula, you will have a chance to delight in the most mouthwatering of Italian food groups: pasta. Italy is known throughout the world over as being the birthplace of pasta, and since your arrival, you will have no doubt noticed the ubiquitous types and varieties of ways that it can appear. From Tagliolini to Pappardelle, the types of pastas that are produced in Italy will be enough to make your head spin, but luckily, you will have a guide to explore the pinnacle of Italian cooking.
After a leisurely morning of enjoying your traveling companion while you explore the famous artisanal shops of Sorrento, you will be met at your hotel by your local expert in all things pasta who will lead you the short distance to the kitchen. Here, in the kitchen, you will be trained in the intricacies of selecting and making pasta. Be prepared to roll up your sleeves and get to work as Italian cooking is best done with good company and good wine. By the end, you and your partner will be well versed in pasta making and will be able to sample the fruits of your labor. Your instructor will happily answer any question that you have and recommend new dishes and ways to spice up old ones.
Capri – Uncover the Hidden Gems of this Mediterranean Paradise
Any hint of the wine the night before will be washed away with a shot of espresso and a bracing stroll along the waterfront, where the winds off of the Gulf of Naples will cause you to hold your partner just a little tighter. This morning is your final morning in Sorrento, and you will be provided with a private transfer to the enchanting island of Capri, which is just off the Western point of the peninsula. Like the mountains of the mainland, Capri juts violently out of the azure Tyrrhenian Sea and displays its sheer cliffs and craggy peaks. The island has been included in recorded history since ancient times when it was treated as a resort for rich and famous Romans. The influence of antiquity is evident everywhere with crumbling villas and romantic gardens that offer opportunities for quiet reflection and enjoyment.
After your arrival at the main marina, a short stroll will lead you to your accommodation in the heart of the old city center. From here, many of the top attractions are well within walking distance, and the island itself is only 4 miles long and 2 miles wide. Once you are settled in, you can amble your way past the charming cafes and fancy boutiques or escape to the Giardini di Augusto or Augustus’s gardens, which is a veritable oasis of botanical beauty uphill from your accommodation. From these terraced gardens, it is possible to spy various species of geraniums, dahlias, and other species of blossoming flowers and is the perfect place to relax after your uphill climb.
Capri – Enjoy a Private Boat Tour of a Romantic Sea Cave
One of the best times to explore Capri is in the early morning before the gamut of mainlanders arrives. While folks are still slumbering, a quick stroll down the main cobbled boulevard or up a side street will make you feel as if you are the only one in the city and as if you are walking in the footsteps of the Roman emperors who used to visit here. At your hotel, a steaming breakfast awaits your arrival, and you can sample tasty treats steeped in Italian culinary tradition. It might be a good idea to take some provisions for the road because today you will be heading down to the marina for a private excursion to the most famous site on the island.
The Grotta Azzurra or Blue Grotto is a partially submerged sea cave that is situated on Capri’s Northern side. This natural formation of land and sea has captivated visitors since antiquity with its magical combination of light, water, and rock. You will be forced to duck your head as a rowboat takes you into the narrow entrance of the cave, but the gorgeous view inside will distract you from any thought of claustrophobia. Light from outside arrives through an aperture and reflects off the sandy bottom of the cave, causing the seawater above to glow blue. The sound of the waves and vocally gifted rowers will add to your ambiance of this site, ensuring that your depart with plenty of snapshots and vivid memories.
Capri – Survey the Scene from Monte Solaro
On your final day in Capri, you will be able to enjoy a leisurely wake up in the comfort of your luxurious hotel room. Do not be afraid to hit the snooze button before finally drawing the curtains to let in a bit of that Mediterranean sunshine. The vistas of Capri are only improved by the sun’s rays, and with the early light that drenches the whitewashed buildings, you will have one of the best viewing platforms on the island. Since you arrived, you have seen countless visitors as they descend from the mountain, wearing grins and sunburns and speaking of a beautiful vista. Today, you can embark on your own quest for such beauty on a stroll up to the sister village that is called Anacapri. Here you will reach the embarkation point for Mt. Solaro, which is the highest point on the island.
Leaving your cares behind, your ascent of Mt. Solaro will afford you plenty of opportunities to stretch your legs while also enjoying a refreshment from the numerous cafes and snack bars that you pass. As you amble along, flowered terraces will distract your eyes with colorful and scented scenery, crumbling villas built by long-dead Romans will distract your imagination, and either the climb or the vistas will take your breath away. You can either hike or take the chairlift to the summit, where it is possible to trace your Italian journey from the distant shores of Naples to the slopes of Mt. Vesuvius and the Sorrentine peninsula. A downhill stroll or ride in one of Capri’s convertible cabs will return you comfortably back at your hotel, where your hosts will be happy to suggest family-friendly eateries nearby for your well-earned appetite.
Amalfi – Explore the Past of this Onetime Maritime Empire
Your final morning on Capri will begin with a hearty breakfast at your hotel as you leisurely prepare for your departure. The smell of freshly baked goods and coffee will lure you down from the comfort of your room before you board your transfer back to the mainland. Once back on dry land, a private driver will convey you the remaining minutes through the luscious landscape of the Sorrentine peninsula to your destination of the Amalfi Coast. As you make your way across the spine of mountains that form the backbone of the peninsula, you will be provided with the opportunity to enjoy the rural beauty of the landscape. Elegant villas dot the countryside, and the quaint communities of Ravello or Positano will offer short examples of the precarious position of these communities where the land falls away into the blue below.
Your destination today will be the iconic village of Amalfi for which this famous coast is named. The Amalfi Coast extends West from the Italian city of Salerno and is a popular tourist destination. In 1997, this region was identified as a UNESCO World Heritage Site and is characterized by rugged mountains that descend precipitously into the crystal-clear water of the Tyrrhenian Sea. The town of Amalfi enjoys only a shadow of the splendor that it once did. Once a major player among other Italian city-states such as Genoa and Pisa, an earthquake and tsunami in 1343 caused the lower portion of the town to simply slide into the sea, taking with it much of the prosperity that was long enjoyed by its denizens. Rest and relaxation are now the commodities that will be enjoyed here, and today, you will find plenty of both during your stay in this immaculate setting.
Amalfi – Ride the Waves of the Famous Amalfi Coast
Only the distant cry of a gull or the puttering of an ancient Fiat down the narrow street will be the only thing to interrupt an otherwise tranquil wake up to your final day in Amalfi. Whatever dream you were enjoying will pale in comparison to the charming bliss that you will find yourself in as you enjoy the pedestrian-friendly streets and stunning vistas that can be found only a short walk from your front door. Today will be devoted to providing you with vivid memories that you and your partner can enjoy for years to come. After your leisurely wake up, you can enjoy the breathtaking beaches or find a local bar to explore before you make your way to the marina to catch a ride in the afternoon.
A pilot who is well versed in the mischief of Amalfi tides will pick you up, and you will enjoy catered comfort on a gentle boat tour of the coast as seen from the waves. Beyond wealthy playboys on their yachts, few are afforded the pleasure to enjoy such handcrafted luxury, and like the butter on your breakfast, you and your partner will melt at the stunning views of the villages of Positano, Ravello, and Praiano in addition to the series of watchtowers that were used to signal threats from Saracens marauders and pirates. A private dinner awaits you on a temporary stay in the seaside village of Positano, featuring much of what is best of the local culinary scene before you again board your sea craft for your comfortable return journey.
Palermo – Discover the Highlights of Sicily’s Colorful Capital
You will want to stretch out time on your final morning in Amalfi, but the promise of an exotic land to the south as your next destination will be plenty of motivation to depart willingly. Your charming driver will meet you at your hotel for a quick trip back to Naples airport, which will be followed by a direct flight to Sicily. Today will be the longest travel day of your journey, but you can rest assured because soon you will be enjoying an experience that is tailored to your travel style.
Upon your arrival in Palermo, which is the capital city of Sicily, you will have plenty of time to get settled and rest before any effort is made to explore the vibrant districts of the city center. Notable features include the Palermo Cathedral, which is where you can see examples of varying architectural styles that date back to before the 18th century. The Palazzo dei Normanni features examples of stained glass and mosaics from the period of Norman influence in Sicily and is only a short stroll from your comfortable hotel. These sights and much more all await you once you have refreshed yourself from your journey. Once you have had your fill of the city, you can delight in a deliciously recommended dinner or spend the evening however you see fit.
Palermo – Savor a Tour of the Open-Air Markets
A close examination of this city’s languages, architecture, and artwork reveals plenty of evidence to support its claim as one of Europe’s most conquered cities. After a tranquil morning in the calm elegance of your luxurious hotel, you will be met by your expert guide who will be steeped in the lore of this fascinating landscape. You will be escorted to the beginning of your tour, which will be at one of the main open-air markets that offers provisions to much of the local populace. The Vucciria, Ballaró, and Capo markets are where sellers impress buyers with their colorful selections of fruit, fish, and vegetables. As your tour unfolds, you will be greeted by a chorus of sights and sounds. Prawns, urchins, scallops, and crab will crowd the tables of one vendor before being replaced by the lettuce, artichoke, cheeses, and fruit of another.
These markets remain one of the few constants in a city where change seems to be the norm. Through all the wars, the conquests, the kingdoms, these markets have continuously delivered quality produce from the nearby vineyards and shoals to the people of Palermo. At the conclusion of your tour, you will have the option to sample treats from your bulging baskets or take up your guide’s offer to provide excellent local suggestions for delicious restaurants and eateries.
Palermo – Tour and Taste Your Way through an Operating Vineyard
The fertile landscape around Palermo has long been relied upon to produce various agricultural commodities such as olives, grapes, pistachios, and oranges. Likewise, since Sicily is known for its fermented beverages, including varietals of wine and liqueurs such as limoncello and Amaro Averna, and on your final day in Sicily, you will experience this proud heritage by enjoying a tour of a nearby winery in addition to the tasty product that it serves. Marsala wine, in particular, is a local favorite, and a private car will pick you up in the morning for the short trek out of Palermo to the vineyards of the countryside.
As the developed urban sprawl is replaced by rolling hills and stunning views of the sea, you and your partner will be able to see a side of Italy that is missed by most. As you swish the Nero d’Avola in your glass, you can let the aroma wash over you before sipping the savory beverage, which may remind you why some things are better left unchanged after centuries of cultivation. With each flight of wines comes a new opportunity to appreciate the passions and production of this fertile region, and any questions that you may have will be readily answered by your gracious hosts. Once your tour has concluded, your private transfer will arrive and whisk you back to Palermo, where you can rest easy knowing that you have enjoyed some of the best of Italian wines.
Palermo – Depart for Home
Your final day in Sicily will not start too soon as you enjoy the final moments of the handcrafted hospitality that you have enjoyed since your arrival in Palermo. From Naples to Palermo, you and your partner have tasted and toured your way through some of the country's richest landscapes with the sunburns and snapshots to prove it. After a delicious breakfast from your accommodating hotel staff, your private transfer will greet you outside to escort you to the Palermo International Airport, where you will catch your departing flight.
- 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
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.
$3,845 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.
- 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.
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