Ultimate Two-Week Family Vacation to Southern Italy

Stretching far into the Mediterranean, Southern Italy enjoys a unique vantage point at the juncture of three continents at the heart of the Ancient World. Antiquity saw it settled by Greeks and Romans who added their artwork and sophisticated engineering skills to the cities they left behind. Later, the region was invaded and influenced by other European powers, including the Byzantines, Lombards, and Normans who competed with local kingdoms over control of trading privileges and economic dominance. This constantly shifting cocktail of geopolitics, culture, and history contributes greatly to the Southern Italy that awaits you today. From the cuisine to the architecture, everywhere one looks in this region lies evidence of a past that has only recently departed.

Naples was originally a Greek settlement on the protected shores of the Gulf of Naples, which is the bay that shares the city’s name. It boasts a cornucopia of artistic, cultural, and ancient treasures, and its old city center enjoys the status of being a UNESCO World Heritage Site. Not to be outdone by its history, the city also claims to be the birthplace of pizza and offers plenty of opportunities to try some during your stay.

Upon landing at Naples International Airport in the nearby suburb of San Pietro a Patierno, you will be greeted by a friendly guide who will lead you on a tour of the city center. Scooters and fiats will wiz about you as your seasoned driver leads you past the towering housing blocks near the outskirts of town and toward the more modestly sized, but older city center. Buildings that were commissioned by 20th-century dictators will be replaced by buildings that were commissioned by 10th-century kings as you enter the city center of Naples. Soon, your tour will conclude, and you will be returned to your luxurious hotel. As your head hits the pillow for some well-earned rest, your mind will be filled with the adventures that are waiting for you tomorrow and the remainder of your stay in this unique corner of Europe.

Looming out of the sea mist, Mt. Vesuvius lies to the South of the Bay of Naples and boasts commanding views of the surrounding countryside. In 79 AD, this usually peaceful mountain erupted, launching heated rock, lava, and ash miles into the air only to fall back down on the surrounding landscape and its inhabitants. Standing directing in the path of this geologic onslaught lay the Roman communities of Herculaneum and Pompeii, where residents had little time to flee before being buried by pyroclastic debris. Unluckily for them, this formula of volcanic ash and dust usually killed or crushed most of the people of these two cities but also preserved the bodies and ruins. In fact, the preservations remained so intact that travelers can visit the site and observe the architecture and mosaics of the buildings in addition to the outlines of fleeing figures that were caught up in the cascade of lethal volcanic material.

After a tasty meal of expertly poured espresso and an assortment of fresh rolls and pastries, you and your family will be escorted a short distance to this sleeping giant to visit the ruins of these ancient communities. You will be met at Pompeii by an expert guide who will provide you with a private tour, which will be complete with factual details as well as dramatic stories from the disaster. Broad boulevards and sturdy walls will exhibit the engineering skill of this Roman city. Not to miss are the remains of the forum, which is an ancient gathering place that was typical in many ancient cities, and a visit to the Garden of Fugitives where the final moments of some of Pompeii’s inhabitants are remarkably well preserved.

After a day spent exploring the somber ruins of a destroyed city, you may need to rest. Best practices for visiting this bustling port city include grabbing an outdoor seat at a neighborhood cafe to watch the morning commute of Neapolitans as they go about their routine. From the well-dressed businessmen and women who sport the latest Italian fashions to the civic street cleaners, people watching in downtown Naples is a must for visitors who are new to this region.

After a morning of people watching or a visit to the impressive National Archeological Museum, you will feel rejuvenated enough to indulge in a gelato-making course. Since arriving, you will have noticed the occasional shop or vendor that proudly displays tubs of what looks like ice cream, but to mistakenly label it as such invites the ire of proud gelato vendors everywhere. Nearby your conveniently located hotel, you will meet your instructor who will be able to lead students, young and old, on the path from selecting the best ingredients to add the proverbial cherry on top to your hand-crafted, gelato masterpiece. The best part about the course is you get to enjoy your masterpiece at its conclusion. Returning home to your luxurious accommodation, you will already be planning how to treat your family to future creations of this tasty Italian treat.

Like sedimentary rocks that were deposited in layers across geologic history, the history of Naples lies in layers across the city, and today, you will dive into the subterranean history of Naples’ darker days. In the social strife of the mid-19th century, King Ferdinand commissioned workers to construct escape tunnels from his residence at the royal palace. This construction overlapped with existing aqueducts that provided water to the city, and efforts were eventually abandoned, leaving cavernous chambers under the feet of unsuspecting locals. During the extensive Allied bombing campaigns of World War II, these same chambers were later used as air-raid shelters by noncombatants. Named the Bourbon Tunnels, these chambers persist today as excellent examples of how historical periods often overlap, and visitors can witness evidence of how one king’s escape tunnel turned into a shelter during the war and eventually a dump before later excavation.

A short stroll from your hotel is all that is required to reach the entrance to these tunnels, and a guide will be waiting to satisfy any question you have. The still air will cause your pulse to quicken, and the rusting cars and bicycles will remind you of a bygone era. As you amble your way through the cisterns and chambers, your mind will reel at the idea that local families used these same chambers for shelter from falling explosives. Just when the beading sweat will seem too much, fresh air will greet your lungs as you once again return to ground level to enjoy the Mediterranean breeze as it drifts off the bay.

Especially in the summertime, having the windows open in your hotel room is a must. Not only due to warmer weather but to access the ambient atmosphere that highlights the colorful Italian characters. From the open windows, you can participate in many customs that are inherent to this part of the world. It is the open window that allows curious grandmothers to carry out their unofficial roles of neighborhood watch, and it will also allow you to chat about a recent football match or complain about the price of bread. In this region, the open window is the threshold to the world beyond, and as a visitor, you will not be able to get enough of it. It is your window that will act as a natural alarm clock as you awake to your final day in Naples. Perhaps, it will be the passing flutter of anxious pigeons in search of a new roost, the singing of a street sweeper as he belts out his best Pavarotti impression, or the distant sounds of the port that will help you shed those dream-like images from the night before.

When you are ready, you will meet your private transfer in the lobby of your hotel for your next stop on this tour of Southern Italy. Perched on a lateral peninsula of mountains that extend into the Mediterranean Sea, Sorrento gained status as a resort town and departure point for those who are visiting the isle of Capri. A favorite aperitif in Italian cuisine is also produced locally, and you will have plenty of time to enjoy the limoncello at any number of tasty restaurants and cafes that dot the town. Likewise, as an artifact from antiquity, Sorrento claims to be the location of the Sirens, which are those fabled sea creatures that lured sailors to their doom with their beautiful songs. The rocky mainland and islands of this region greatly resemble the home of these creatures as described in Greek mythology, so be sure to plug your ears upon hearing any mystical and enchanting tunes during your excursions.

Sorrento is perched along the Bay of Naples and has enjoyed a close relationship with the sea that extends beyond the source of mythical creatures. The main port of Sorrento was once a bustling fishing center where countless vessels plied the waves for the day’s catch. Tourism has replaced fishing as a major economic boom for the city, and hydrofoils depart daily, ferrying locals and visitors to destinations like Naples, Positano, Amalfi, and Capri.

After the smooth notes of a tasty espresso to help stir you from your comfortable accommodation in the heart of the town, you will have some time to stroll through the crisscrossing alleys and streets of this rural community. The pastel-colored buildings clash beautifully with the greenery of the surrounding countryside of the Sorrentine peninsula, and a stiff breeze will lift any remnant of sleepiness that was not already addressed by your earlier coffee. You will need your wits about you today because your family will enjoy an excursion on the waves during a private tour of the coast. Meeting you at the marina, an expert pilot, whose skill at the helm is surpassed only by his knowledge of local maritime history, will escort you past the breakers and out to the Bay. Only from this perspective can you admire the beauty and grandeur of the shore and the unique villages that are perched along the coast. After you have gotten your fill of the sea today, you will be returned to your luxurious accommodation for the remainder of the evening.

The vistas of Sorrento are only enhanced by the sun’s rays, and with the early light drenching the whitewashed buildings, you will make your way down the steep streets to the port for your departure from the Italian mainland. Since you have arrived, you will have seen countless visitors as they clamber off ferries, wearing grins and sunburns in addition to speaking of a beautiful grotto to the West. Today, a ferry will carry you to the tranquil atmosphere and eclectic geology of Capri, which is a dot of green in a sea of blue where emperors and celebrities alike have escaped the heat and crowds for centuries. After settling into your luxurious hotel in the city that shares the island’s name, you will have a chance to see for yourself if this locale deserves the reputation that it boasts. Nowhere will your view be better than from the nearby summit of Mt. Solaro.

Like natives who were curious about new visitors, the history of Capri will peek out at you from every corner and crevice of this enchanting landscape. Leaving your luggage behind, your ascent of Mt. Solaro will afford plenty of opportunities to wear out your kids while also providing a refreshment from the numerous cafes and snack bars that you will pass. As you amble along, flowered terraces will distract your eyes with colorful and scented scenery, and crumbling villas that were built by long-dead Romans will distract your imagination. For those with tired legs, relief will come in the form of Anacapri’s Seggiovia del Monte Solaro chairlift to carry you the final few minutes to the summit of the island’s highest peak. From there, it is possible to trace your journey so far 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 to your hotel where your hosts will be happy to suggest family-friendly eateries nearby for your delectable evening meal.

An early morning wakeup will ensure that you get to experience the quiet of the island before the ferries arrive from the neighboring Amalfi coast. You can stroll down to the harbor to see the fishing boats as they cast off or visit the Gardens of Augusts to survey the botanical legacy of Roman emperors. As the cafes begin to open their doors, you will have the opportunity to stop by for a tasty sip of coffee or warm milk to keep the family satisfied. Later in the day, a skiff will be waiting for you down by the dock for a private tour of the island and visit to the famous Blue Grotto, which is a landmark site for families who are visiting Capri.

The 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 escorts you into the narrow entrance of the cave. The view inside will distract you from any thought of claustrophobia, and light from outside arrives through an aperture and reflects off the sandy bottom of the cave, which causes the seawater above to glow blue. The sound of the waves and vocally gifted rowers will add to the ambiance of this site, ensuring your departure with plenty of snapshots and vivid memories.

Your final day on Capri will start 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 from the comfort of your room before you board your transfer back to the mainland. Once back on dry land, you will have a private driver to escort you the remaining distance through the luscious landscape of the Sorrentine peninsula to your destination on the Southern side of the mountains. It is this trip that will remind you of the many villages and towns that provide such an abundance of distinct flavors and features. Whether Positano, Praiano, or Ravello, each of these rural communities boasts an entirely unique history despite being so close together. Finally, your driver will leave you at your luxury accommodations that are perched along the azure of the Mediterranean.

Your destination will be the 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 enjoyed as the Duchy of Amalfi, which is a major maritime powerhouse of the Middle Ages. An earthquake and tsunami in 1343 caused the lower portion of the town to slide into the sea, taking with it much of the prosperity that was long enjoyed by its denizens. Rest and relaxation are now to commodities to be enjoyed here today, and you will find plenty of both during your stay in this idyllic setting.

A short drive from your comfortable hotel will lead your family to the entrance of the Sentiero Degli Dei or Walk of the Gods, which is a twisting tour of the mountains that you have been observing since your arrival. The Walk of the Gods is a three-hour trek that takes you through winding terraces, luscious olive orchards, and deep valleys all of which provide a contrast of green to the rolling azure of the waves below.

Comfortable shoes will be a smart choice for today’s outing. Although well maintained, the packed trail will involve significant ups and downs along rocky ridges and rugged hillsides, and if the exercise does not get you excited, the drops will. Some sections of the trail are perched right above the abyss. Packing a snack or two is not unwise, but afterward, the local olive and cheese varieties will provide a perfect reward for your efforts. In the case that you need to replenish your supplies, markets and delis in communities such as Praiano and Fontanella will offer an abundance of refreshments to the weary traveler.

As you meander your way through this Mediterranean landscape, you will have little time to worry about anything else. Spectacular panoramas of the surrounding area will help you to keep your bearings and explain why this trail is called the Walk of the Gods. Impressive yachts in the distance will be the only interruption to the blue that stretches to the horizon in almost every direction, and you will feel refreshingly alone after the bustle of Sorrento and Capri. In the afternoon, the path will deliver you back to Positano, where a private transfer will await to convey you back to Amalfi for a well-earned rest.

One of the top reasons that travelers come to this unique corner of Italy is the beaches. As you enjoy a leisurely wake up in the plush comfort of your hotel, you may rest assured that the sights, sounds, and smells of the rolling waves and soft sand are only minutes away from your luxurious resort. After walking with the gods yesterday, you may be interested in napping with the nymphs, and this coastline boasts an impressive array of beaches that are large and small, which allows visitors to find a quiet corner to doze. Some of the best beaches to visit include the Baia di leranto, Spiaggia di Fornillo, and the Marina de Praia.

No matter where you end up, you can depend on the water, waves, and sand to provide a little something for everyone on this day of rest and relaxation. In the summertime, the water provides an ample supply of relief from the heat for those that enjoy floating on the waves or fighting through them. Most of the cities possess public beaches, and for a small fee, you can rent umbrellas and chairs to enjoy the view of passing clouds or yachts. Also, if supplies run low, a market or vendor is usually a short walk away to provide local treats and provisions for your whole family. In the afternoon, your family can make their way back into the narrow alleys and streets of Amalfi for a night of delicious food and drink from any of the local eateries and restaurants.

Surrounded by mountain peaks, it will take some time for the daylight to filter down into the narrow streets and neighborhoods of Amalfi, and you can take advantage of this by enjoying a leisurely morning at your hotel. With the arrival of your final moments in Amalfi, you will want to stretch them out as long as possible to catch any last memories and snapshots before your private transfer arrives to escort you back to Naples. At the Neapolitan airport, you will catch a short, domestic flight for the final leg of your tour of Southern Italy. Sicily is the largest island in the Mediterranean and the region of Italy that is the closest to Africa. Such distinctions have made it a strategic point for both political conquests and commercial interests, and its culture and history exhibit all the traits that would be expected of such a dynamic position.

A car will be waiting for your arrival at Falcone Borsellino Airport in Sicily’s capital of Palermo. An effortless drive into town will lead you through the bustling streets of the old city center where you will have a chance to get settled in before traversing the streets of the new city. Due to its many cultural influences, the city center of Palermo boasts an impressive array of iconic sites, artistic achievements, culinary centers. You can stop by the Palermo Cathedral to 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 will be waiting for you once you have refreshed yourself from the journey and are ready to explore all that this colorful port city has to offer.

A short stroll around the iconic center of this cosmopolitan city will quickly reveal why it claims to be the most conquered city in all of Europe. Nowhere is this more evident than in the busy plazas and squares of Palermo and the open-air markets that occupy them. After a long rest, your knowledgeable guide will meet you at your hotel and escort you to a few open-air markets. A trip to Palermo is not complete without a visit to the Vucciria, Ballaro, and Capo open-air markets. This is where sellers impress buyers with their colorful selections of fruit, fish, and vegetables along with their vocals as they belt out their specials to anyone who will listen. As you walk, 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. As you walk, your guide will happily explain how to beat even the toughest vendor in bargaining before venturing on to the next market. With your bags bulging with treats, your guide will escort you back to your hotel where you can enjoy your recent purchases or venture into the Sicilian dusk to see what restaurants provide the tastiest menus.

This morning, you will be able to hear the distant sounds of the port echo off the stone steps and walls of the city that you have learned to love. Wet ground and a leaf of lettuce may be all that remains from your visit to the open-air market. After a delicious breakfast from your accommodating hotel staff, your private transfer will greet you and escort you to the Palermo International Airport, where you will catch your departing flight, which will be a satisfying culmination to your thorough tour of the beauty and character of Southern Italy.