A Perfect Family Getaway to Italy s Coastlines & History

A 8 day trip to Italy

On your family getaway vacation to Italy, your kids wake up with a view of coastal cliffs and the looming summit of historic Mount Vesuvius in the distance. You sneak pieces of fresh mozzarella bufala when rolling out your pizza dough during a family cooking lesson. The ancient city of Pompeii expands before your very eyes, and you have never seen your kids so excited to learn about history. Travel from stunning coastal towns to breathtaking Renaissance cities, each embracing the entire family in wonderment on your handcrafted tour of Italy.

General Information

Detailed Itinerary

Places Visited 

Naples, Positano, Amalfi, Sorrento, Capri, Pompeii, Florence, Lucca, Siena

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Neapolitan Welcome

Naples is a city of intrigue and wonder nestled against the cobalt water of the Bay of Naples. Regal history dates beyond the Spanish Kingdom and the Kingdom of Sicily, to ancient Greeks. One of our Italy tour operators will arrange for a private transfer to meet you at the airport. You will then be escorted through the third largest city in Italy. Palaces and castles decorate the cityscape, most notably at the edge of homes leading to the rich volcanic hills. The city is the birthplace of pizza, giving rise to the indulgent aroma of freshly baked crust and melted cheese that the entire family finds enticing.

Citrus groves grow hardily outside of the cobblestone streets of Naples. The breeze carries the zesty aroma over the cobblestone lanes, offering a unique scent. The oldest street houses a historic market of freshly caught seafood and decadent homemade food brought to the market for sale. Your private transfer whisks you around the Bay, past the looming summit of Mount Vesuvius, and settles your family into a luxurious hotel in the charming seaside city of Sorrento.

What s Included: transfer, dinner, accommodation

Day 2: Family Time and Coastline

Wake up with a marvelous view out to the water, noticing the continued appearance of historic Mount Vesuvius in the distance. The water laps at the shoreline. The sunlight washes over the quiet city. At breakfast, you find the refreshing scent of fresh espresso accompanying the sweet taste of brioche baked earlier that morning.

After your meal, your guide meets you in the hotel taking you through the mountains. Pockets of greenery grow out of the craggy, marbled mountainside before the roadway opens to the famous Amalfi Coast. The kids stare out the window at the view of the azure water. The road hugs the cliff until you reach Positano, an enchanting seaside town cascading down the hillside touching the glimmering Mediterranean. The kids comment on how they feel like they ve stepped into a photograph. Houses glow terracotta and pink. Wisteria drapes down facades and touch the climbing steps. On the beach, you notice vacationers picnicking with a pizza, savoring the view.

The golden dome of Chiesa di Santa Maria Assunta catches the sunlight. Soon your private boat meets the family at the marina. The kids are excited to step onto a real boat and sail along the sapphire water. The salty and sweet aroma of the sea enchants you. The kids start to talk like pirates, turning the boat ride into an unforgettable cruise to the town of Amalfi.

What s Included: breakfast, dinner, tour, accommodation

Day 3: Antique Island

In the morning, you look out over the rugged coastline of Sorrento and find part of the town built atop the cliff overlooking the gentle water. The mountains in the background roll into the sky. Following breakfast, the family makes its way to the ferry on the Amalfi Coast that carries you to the historic island of Capri. The kids are delighted to be on a boat once more, watching the coastline fade into the distance. Capri is known for its fabled beauty and Roman history, creating a contemporary cosmopolitanism. Cool cafes open their doors to let in the sea breeze. Roman ruins hug the rugged seascape.

When you arrive at the Marina Grande, you find an enchanting funicular ready to take you and other ferry passengers up the hill to Capri Town. The kids marvel at the funicular, another unique form of transportation they never imagined. The sunlight in the midmorning washes over the entire island. The Mediterranean brushes up against the pebbled beach. The highest peak on the island is Monte Solaro, and it reaches a height of 1,932 feet above sea level. You journey to the top on an easy chairlift, allowing you to take in the tranquil scenery, and letting the kids ride another fun form of transportation offering an exceptional view of the entire Bay of Naples and the Amalfi Coast.

What s Included: breakfast, tour, accommodation

Day 4: When History Comes Alive

After breakfast, your private transfer meets you at the hotel, once again leading you around the Bay of Naples. The kids point at the towering peak of Mount Vesuvius rising 4,302 feet above sea level. People walk up a trail winding around the outer edges of the volcano before dipping into the crater for a view of slight volcanic activity. You reach Pompeii, the infamous city frozen in time from the eruption of Mount Vesuvius in AD 79.

Outside of the historic site, lemon trees grow like wildflowers, adding a citrus smell to the air. The greenery of the groves fades behind the historic walls separating the modern world from antiquity. The kids are filled with expectation unsure what will come next, but certain of something incredible. The walkway opens up to the archeological site at the Forum, the principal square of any Roman town. Columns continue to decorate the skyline of the plaza that once supported enclosing colonnades.

At the north end of the square, an almost 10-foot tall base connotes where the Temple of Jupiter once stood. You can easily imagine vendors selling food and wool, with the entire square erupting in energy outside of the shrines of the temple. In the amphitheater, the kids have fun venturing up and down the staircases of the sloping Teatro Grande, which could hold up to 5,000 people. From the top row, you could look down on the performance with a background of Pompeii leading to the site of Mount Vesuvius.

What s Included: breakfast, lunch, dinner, transfer, tour, accommodation

Day 5: A Family of Art

Today, you will wake up in the heart of Florence where the Renaissance comes to life. Stone buildings line cobblestone streets. The gates of the medieval city continue to encircle the city s northern edge. From the lobby, you can see the tip of the famous dome of the Florence Cathedral. After breakfast, you venture into the streets to take in the timeless treasures around the city, including numerous castles, of which the kids are eager to visit.

The Uffizi Gallery was designed for Cosimo I de Medici in the 16th century to house the judiciary offices. When you reach the narrow piazza in front of the museum, the kids stop to look at the numerous statues set under the shadows of the museum pillars. After a few minutes the statues move, the kids squeak with delight, and you continue into the museum. Your private guide leads you up the lavish steps and along the polished marble floors. The interior is enigmatic of opulence, from gold tinted leaves decorating the crown molding, to the spacious windows letting in an abundance of natural light into the hallways.

Your guide creates a game for the kids, encouraging them to look for certain things in the artwork, whether a particular date of a piece or a character type found in a painting. The kids happily accept the challenge, giving you the opportunity to appreciate the masterwork all around, including the Birth of Venus by Botticelli. The painting is 5.6 feet by 15 feet and represents the beginnings of the Roman Goddess of Love emerging from a seashell. You notice the graceful sweeping water calming in the painting s background. Each character has movement and elegance surrounded by the wild. The kids continue their game, and you bask in the view.

What s Included: breakfast, lunch, tour, accommodation

Day 6: Active Walls

The splendor of the morning continues to catch your eye. A subtle mist lingers below the hills, giving the sunlight a specific glow. The moisture quickly dissipates leaving a layer of dew across the foliage. After breakfast, the family journeys to Lucca, a historic town known for its powerful, protective walls. Romans built the first walls around the city in the 2nd century AD, which were later fortified, completed in the 17th century. Chestnut trees shade the pathways encircling the ramparts. Parks emitting tremendous greenery now decorate above and below the walls. Locals stroll around the parks encircling the ancient city center.

The family hops onto bicycles for a leisurely tour of Lucca and the walls, enjoying the nutty aroma of the trees and the rich stone that remains a sign of the city s historic strength. Cafes open out to charming piazzas. Locals linger in the shade and sip frothy cappuccinos. Pfanner Palace draws the kids attention, dating back to the 17th century. The Baroque garden is the only one of its kind inside the city walls. The kids run around the vast space imitating the 18th century statues capturing Greek gods. A zesty citrus aroma arises from the potted lemon trees. You ascend the outdoor staircase to find the main reception gallery of the palace decorated with bright frescoes.

What s Included: breakfast, tour, accommodation

Day 7: Into the Hills

After breakfast, the family makes their way to the mesmeric town of Siena, set across the Tuscan hillside. The kids are continuously amazed by the age of the towns in Italy, finding it to be more of a storybook than real life. Redbrick lanes lead you around and into the city center, cascading up and down the knoll. Gothic architecture turns the entire cityscape into an open-air museum, brimming with coarse walls on the oldest buildings and smooth facades from the Renaissance. In the Cathedral, you find a black and white marbled edifice dating back to the 13th century.

The gargoyles protruding out of the exterior towers captivate the kids. Once inside, you find a vaulted a roof decorated with blue and gold stars, imitating the vast night sky. The marble floor is decorated with 56 panels of various sizes, representing different scenes from the Old Testament. The amount of unique artistry decorating the cathedral is almost overwhelming. The kids linger around the floor panels wondering how the images were made. The entire city presents a similar feeling, conjuring thoughts of medieval and Renaissance times.

What s Included: breakfast, lunch, dinner, tour, accommodation

Day 8: Beyond the Tuscan Sun

In the morning, you can step out into the city for one last look at some of the gifts of the Italian Renaissance. The Arno River trickles underneath the Old Bridge. The Cathedral dome is the largest unsupported brick dome in the world and was constructed in the 15th century. The city center always feels energetic, erupting from an artistically rich past.

After breakfast, your private transfer meets you at the hotel and escorts you to the Peretola Airport for your flight home. The family has come together to discover the endless majesty of Italy, stemming from a rich heritage that continues into the future.

What s Included: breakfast, transfer

For additional itinerary options, browse the tours to Italy section on orient.



orient recommends the following guidelines for customized Italy tour packages, excluding international flights:

  • 5-star: USD $450 - $1,000+ per person per day
  • 4-star: Minimum USD $350 per person per day
  • 3-star: Minimum USD $300 per person per day

The customized package will include hotels, airport transfers and other transportation within Italy, guided tours or activities, unique experiences, trip planning, and 24X7 support during your trip.

Please inquire for a custom quote. The price is customized based on final hotel choices, travel dates, and other custom preferences.