Luxury Italy Family Vacation

A 16 day trip to Italy 
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From the pleasures of high culture to the joys of adventure, this is an Italian excursion that offers something for all ages. Taste buds will revel in the joys of Bologna, eyes will feast upon the immaculate detail of the Sistine Chapel, and your skin will glory in the soft sun and gentle breeze on the shores of the Med. Be you father or daughter, brother or mother, sister or husband or wife, there is something in Italy just for you.

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Most tours are customized for private travel.

General Information

Aerial view from the tower in Bologna old town center.
Detailed Itinerary

Places Visited 

Milan, Venice, Sardinia, Bologna, Florence, Rome, Pompeii, Vatican City

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Touching Down on the Peninsula

You land this morning in Malpensa Airport, where a personal driver will be waiting to take you into the heart of incredible Milan, right to the door of the Hotel Felice Casati, your elegant accommodations while in Milan. The rooms have all been recently remodeled, and come equipped with all of the finest modern luxuries and amenities, and the hotel is situated within easy access to all of the best sights in Milan.

This afternoon, explore the many attractions of Milan, from the city’s amazing Duomo, a Gothic marvel that is one of the largest churches in Europe, to the boutiques of the world’s greatest designers that line the streets of this world fashion capital. The Galleria Vittorio Emmanuel is one of the most upscale malls on the planet, and more astounding boutiques can be found at the well-known Quadrilatero, where some of the finest streets in fashion collide. Dinner this evening is at one of the city’s fine restaurants, but be sure to save some room afterwards because there's gelato around nearly every corner. 

What's Included: transfer, dinner, accommodation

Day 2: From Magnificent Milan to the City of Canals

This morning, after a delicious and hearty breakfast, set out to uncover the treasures of the streets of Milan with a private local guide will give you the perfect introduction to the history and culture of this majestic metropolis. You can stop by the Zucchi collection of antique hand blocks and learn more about Milan’s well-known Alessi products before touring the museum at the world-famous La Scala, one of the greatest opera houses on the planet. You’ll be amazed by all the exhibits at this fascinating facility, from period costumes to original scores to a noted sculpture collection, and truly awed by the interior of this stupendous structure. 

The afternoon sees you boarding a train across the beautiful landscape of northern Italy to the shores of the Adriatic Sea, where you’ll find the winding waterways of romantic Venice eagerly awaiting your arrival. A private water taxi will be waiting to pick you up at the train station and will escort you to the immaculate Hotel Ala, located less than five minutes from Piazza San Marco, but seemingly miles away from the bustle of traffic near the Grand Canal. You’ll be sure to enjoy the charm of this boutique establishment, and the friendly and attentive staff is sure to see to your every want and need. 

Spend some time this afternoon making your way through the labyrinthine streets of the city, enjoying the scene at the Piazza San Marco, or gazing across the lagoon to the monuments and edifices that are found on the nearby islands. From the expanse of the Rialto Bridge to the climbing campanile near St. Mark’s Basilica, everywhere you look in Venice is sure to catch your eye.

What's Included: breakfast, tour, transfer, accommodation

Day 3: Exploring the Queen of the Adriatic

A short jaunt to Piazza San Marco begins your engaging and informative tour of the Floating City, led by an expert guide who will show you places that others can only dream of. Explore the sumptuous St. Mark’s Basilica, its gilded domes rising gracefully into the air, its gold-laced mosaics brilliant in their vision and execution, and tour the halls of the Doge’s Palace, where Venetian affairs were run for centuries. You’ll also get a number of great shopping and dining recommendations from your tour guide, giving you all the information you need to discover even more secrets of the city.

This afternoon, set out for the islands around the Venetian lagoon, where you can find some of the finest handcrafts in the country, like beautiful glass work from Murano and delicate, gorgeous lace offerings from the artisans in Burano. Return to the main city for dinner at the outstanding Aciugheta restaurant, where the cicheti (Venetian small plates) and wine are as excellent as they are eclectic, and where the ambience exudes the laid-back attitude that suffuses this charming metropolis. 

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

Day 4: From the Mainland to the Islands

Today, you leave the canals of Venice and venture out into the bosom of the Mediterranean Sea and the ancient island of Sardinia. A private water taxi will take you to the airport, where you’ll board a plane that will take you to Olbia, where a pirvate minivan will be waiting to take you to the Hotel Baja Bianca. This quaint and delightful hotel is set in the heart of the Tavolara-Capo Coda Cavallo Protected Sea-Area, where the wildlife is varied and the scenery awe-inspiring, where the history of the people mix provocatively with the natural environment. Dinner this evening is at the superb hotel restaurant.

What's Included: breakfast, transfers, dinner, accommodation

Day 5: The Charms of Scenic Sardinia

Today is yours to explore the island of Sardinia as you see fit. Cagliari is the island’s capital, and offers a wide array of amazing attractions, like the opulent Royal Palace of Cagliari – a former seat of the House of Savoy – and the neo-Gothic Cagliari City Hall, an intricate, elegant building cast in white and reflecting the rich tradition of the region. The city also boasts a beautiful cemetery, filled with some notable names and stunning statuary, as well as nice views of the city surrounding it. 

Nature lovers are sure to enjoy Sardinia, as there are a number of incredible parks and outdoor areas that are simply longing to be explored. There are beautiful beaches on the north and northeast coast of the island, and a number of large caves that can be accessed at Dorgali, Oliene and Santadi, among others.

What's Included: breakfast, accommodation

Day 6: A Journey Through Time and History

Sardinia is one of the oldest – and longest continually inhabited – spots in Italy, and today is dedicated to exploring this ancient and august past. You can visit Sassari near Porto Torres to visit Mone’dAccoddi, a megalithic structure that is thought to be the oldest building in Italy, or stop by one of the Giant’s Graves, a megalithic gallery grace built in the Bronze Age. For slightly more recent history, there are the remains of the Phoenician and Roman town of Tharros, as well as a well-preserved hot bath of the Forum Traiani in the commune of Fordongianus. There are also a number of excellent edifices from modern history as well, from the Santa Sabina Byzantine Church in Silanus to the impressive statue dedicated to Eleanore of Arborea, one of the island’s favorite heroines and a judge of almost mythical stature.

What's Included: breakfast, accommodation

Day 7: Turning to the World’s Oldest University Town

After two incredible days of relaxation and discovery, you’ll leave the shores of Sardinia, bound for Bologna in the heart of Italy’s culinary heartlands. While in Bologna, you’ll stay in the impeccable Hotel Orologio, surrounded by some of the town’s best sites and filled with a history that seems to come standard here in northern Italy.

This afternoon, spend some time to reconnoiter this scenic village, a UNESCO City of Music, a European capital of culture, and one of the most darling cities in the area. You can walk the campus of the University of Bologna, generally considered to be the oldest university in the world, inspect the wares of the antiques market that fills Piazza Santo Stefano, or gaze upwards at the famed Due Torri, a pair of medieval towers that have have become city landmarks. This evening, enjoy the best Bolognese sauce you’ve ever tasted at one of the city’s many excellent restaurants.

What's Included: breakfast, transfer, accommodation

Day 8: A Visit to Italy’s Famous Automakers 

An experience unlike any other awaits you today, as you set out to discover the places where the finest cars in the world are produced, grand tourers, sporting coupes, and supercars that have come to symbolize wealth, power, speed and class. Visit Maranello and the world-renowned factory of Ferrari, one of the first Italian supercar automakers and one of the most successful racing brands in the world, or stop by Sant’Agata Bolognese to see how they make the famous Lamborghini, from the sharp-edged, angular Countach to the sleek and elegant Murcielago. You can also visit Ducati – makers of some of the best sport motorcycles in the world – or the incredible vintage cars of Stanguellini, before returning to Bologna for a delicious dinner.

What's Included: breakfast, Ferrari factory tour, accommodation

Day 9: The Culinary Treasures of Bologna

In a country known for its incredible food, there is perhaps no city, town, or village with quite the history and tradition as Bologna. It is home to some of the best and best-known Italian dishes, fare that has made the country a premier foodie destination. Perambulate past the stalls and the scrumptious offerings at the medieval-era market before making the acquaintance of a baker and pasta maker at Beccari’s Salsamenteria. After learning about the noteworthy pasta of Bologna – like tagliatelle and tortellini – you’ll stop by a chocolate maker before visiting a fun and casual osteria right on the fringes of the University of Bologna.

What's Included: breakfast, tour, accommodation

Day 10: Tricks of the Trade in an Italian Kitchen

Don your apron, make ready your cooking minds, and step into the kitchen as today is dedicated to giving you an in-depth look at the labor and love that goes into making some of Italian cuisine’s favorite dishes. You’ll watch these skilled cooks painstakingly prepare pasta and their accompanying sauces, hearty and warming Bolognese with wide tagliatelle ribbons, stuffed tortellini resting in cream sauce, and the best lasagna you’ve ever tasted. You’ll learn all the stories and customs of this sacred part of the Italian home, the one room that has the ability to bring everyone together with laughter, love and – of course – some really good food.

Following an afternoon of exploring the city as you see fit, you’ll enjoy one more scrumptious dinner in this truly incomparable town.

What's Included: breakfast, cooking class, lunch, accommodation

Day 11: West to Tuscany’s Famous Capital

Turn to Tuscany, one of the most beautiful regions in all of Italy, to discover the incredible history of this vibrant area. You’ll get the pleasure of a unique and unforgettable pit-stop as you make a brief detour at Modena, the home to the best balsamic vinegar in the world, aged and sweet and inky black, perfect on everything from salads to strawberries. Your final destination today is fascinating Florence, one of the great art cities on the planet and the center of the Italian Renaissance, that great movement that swept the West in the 15th and 16th centuries and help put Italy on the cultural map.

While in Florence, you’ll stay at the fantastic Residenza Casanuova, part of a building designed by a famous 18th-century architect and now one of the best bed-and-breakfasts in Florence. All guests receive a personal welcome from the owners and will stay in one of five delightful rooms, sure to make you feel right at home.

Spend the rest of the afternoon in a precursory exploration of Florence, where you’ll feel the presence of genius on every street corner, from the sonnets of Petrach to the sculptures of Michelangelo to the puissance and influence of the Medici Family. Dinner tonight is in a delicious and traditional Florentine trattoria, where you’ll find sumptuous meat, delectable wines, and delicious desserts.

What's Included: breakfast, transfers, dinner, accommodation

Day 12: Hitting the Highlights of the Birthplace of the Renaissance

You’ll get the full introduction to this magical metropolis as a local expert guide chauffeurs you to and through some of the best spots in Florence, from the teeming Piazza della Signoria to the victorious David of Michelangelo at the Accademia. Begin at Santa Croce, a beautiful Franciscan church with elegant cloisters and the remains of some of the great minds in Italian – and world – history: people like Michelangelo and Machiavelli, Rossini and Galileo. Climb the gentle ridges that surround the city until you arrive at the gorgeous church San Miniato al Monte where you’ll be treated to a breathtaking view. 

The late morning sees you dropped off at the Piazza della Signoria to enjoy a Florentine lunch and some excellent people-watching, after which you’ll set out to enjoy the amazing collection at the Uffizi, one of the best art galleries in Europe and one of the most visited museums on Earth. You’ll see crowning achievements in Renaissance Art, like masterpieces from Botticelli and Titian, as well as artifacts from Roman and Etruscan history and stories about the ruling Medici clan who dominated the city’s politics for generations. 

The evening sees you back at one of Florence’s best restaurants, the captivating Cavolo Nero restaurant, where a delightful courtyard offers the perfect atmosphere to enjoy some of the most consistently excellent food in Florence. 

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

Day 13: All Roads Lead to Rome

Turn south from Florence as you take a first-class train along the coastlands of the Mediterranean, past the fertile fields that have fed the peninsula for centuries, until you reach the splendid streets of resplendent Rome, the capital of Italy and once the centers of the Western world. A private driver will take you from the train station to the incomparable Hotel Canada, a building with a history stretching all the way back to the 19th century and with a charm that knows no bounds. You’ll feel like royalty when you step in to your tastefully decorated and luxuriously appointed room, filled with the best amenities and conveniences.

Take the afternoon to get your bearings in this bustling city bursting with life. Enjoy a cappuccino or one of the many street treats that are offered at Roman cafes before taking an early dinner at the sensational Antica Trattoria Tritone, a restaurant that, like the city, is filled to bursting with history and tradition, as well as being home to an excellent wine list, delicious food, and a truly unbeatable ambience, where you can almost hear the tinkling from the renowned Trevi Fountain.

This evening, your private guide will show you the monuments of Rome in a way that most people have never witnessed: bathed in the light of a southern Italian moon. Make your way from the Piazza Venezia to the Michelangelo-designed Piazza del Campidoglio, home of a beautiful terrace that overlooks the Roman Forum and the striking Palazza Senatorio, the former building that houses the Roman Senate during the Middle Ages and on through the Renaissance. Wind past some of the city’s great attractions, like the enthralling Colosseum and the immaculate Piazza San Pietro, before ending your night at the Trevi Fountain, one of the most endearing attractions in the city. 

What's Included: breakfast, transfer, tour, accommodation

Day 14: A Guided Tour of Unforgettable Pompeii

Continue south today into the transfixing Campania region as you prepare yourself for a trip unlike any other: a trip back in time, far into the annals of history, when a sleepy Roman town called Pompeii was submerged in the ash and detritus of forbidding Mt. Vesuvius. An expert guide will show you the best sites of this inspiring city, like the House of the Faun and the Garden of the Fugitives, as well as regale with you stories of the city’s flourishing days, its destruction, and its unbelievable rediscovery.

After a delicious lunch in the area, the afternoon sees you back in Rome, where you’ll have plenty of time to do some more exploring before a delicious dinner at one of the metropolis’s best eating establishments.

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

Day 15: The West’s Greatest Empire and the World’s Smallest Country

Your final day in Italy is spent at two of the country’s most amazing destinations, as today takes you deep into the glories of Rome, to the incredible stretch of the Circus Maximus, the soaring reaches of the Colosseum, and the divine gifts of human creativity that fill the halls of the enormous Vatican Museums. Begin in the morning with an excursion to the Roman Forum, where you can see the remains of the old Senate building and behold the grandeur of the Basilica of Constantine, the largest building that could and can be found at the Forum. Marvel at Michelangelo’s incredible carving of Moses – meant to adorn to tomb of Pope Julius II – at the Basilica of St. Peter in Chains before making your way along a scenic route in what was once the city center, winding along the Circus Maximus and between the renowned Aventino and Palatino Hills.

After a delicious and filling lunch, you’ll make your way to the domains of the Holy See, where you’ll encounter some of the most incredible instances of the human spirit known to man, crowning achievements from the Renaissance and throughout the history of Christianity. Begin at the miles of galleries of the Vatican Museum where you’re sure to enjoy the Raphael Room and the impressive Gallery of Maps, and end in the world’s most famous chapel, casting your eyes to the sky to take in the sensation ceiling of the Sistine Chapel. Following this incredible adventure into the world of art, you’ll visit the cavernous Basilica of St. Peter, where you can admire the art, check out the reliquary below the main level, or simply sit in awe and reverence of this incredible shrine, this remarkable structure that is one of the holiest sites in Christendom.

Your final dinner in Italy is at the bustling Piazza Navonna at Tre Scalini, where you’ll find a wide-ranging and delicious menu, a superb wine list, and an ambience that only be characterized as prototypically Roman. It’s sure to be a meal that provides the perfect end to an amazing and unforgettable vacation. 

What's Included: breakfast, dinner, accommodation

Day 16: Saying Goodbye to Enchanting Italy

This afternoon, you’ll be taken from the hotel to the airport outside of Rome in plenty of time to board the flight that will take you home. From the marvels of Milan to the glories of Rome, from fascinating Florence to brilliant Bologna to the undeniable allure of Venice, this is sure to be a vacation that you talk about for years to come.

What's Included: breakfast, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.