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Travel Tips

Italy – Luxury Travel Redefined

Indulgent. Luscious. Stylish. Ancient. Avant-Garde. Sensuous. Traditional… Only Italy is all of these and more. Imagine some of the most impressive art in the world, a divine food scene, a country with 55 UNESCO world Heritage sites. The largest wine producer in the world, and 2,500 varieties of cheese. Astonishing mountain ranges and 1,500 lakes scattered throughout the country. Now imagine experiencing Italy in luxury. Pure bliss.

Our Italy travel portfolio includes stays in medieval villages, private wine tasting and cooking lessons from an Italian chef in their own kitchen, marketing with a local cook, Roman ruins and confounding mysteries, and the height of elegant shopping and dining. All are tailored to suit your personal interests. Visit Italy, reimagined, the way it should be—in the sort of luxury that raises life to an art.

Bespoke Italy


Rome was called the “Eternal City” by ancient Romans because they believed that no matter what happened in the rest of the world, the city of Rome would remain standing. The Colosseum, Pantheon, Parthenon, Roman Forum, trattorias with renowned cuisine, and a vibrant nightlife are the essence of la dolce vita—the sweet life. There are secret pockets down every lane, filled with wonders. The capital city of the Tuscany region and the heart of Renaissance art, Florence is a must for any traveler to Italy for art, shopping, culture, and the beauty of buttered light.


Situated on 118 small islands, interconnected by 400 bridges, mysterious Venice is a world of its own. This is a compact city that’s easy to explore. Venetian Gothic architecture, wide piazzas, winding canals, the Doge’s Palace, St. Mark’s Square—possibly the best thing you can do in Venice is to explore the canals, sit, relax in a square with wine or coffee, people watch, and simply take your time. Medieval Lucca isn’t heavily visited, although it is many people’s favorite Italian city. There are hidden passages, a botanical garden, a historic library, performers atop the walls, an herbarium, and Puccini opera—visit Puccini’s home for an extraordinary treat.


A hilltop, walled town southwest of Florence, Volterra is a treasure trove of museums, archeological sites, restaurants, shopping, and stunning views of Tuscany. Take your time and ramble through the medieval streets. Another hilltop Tuscan village, Pienza is the perfect place to dine on the local favorite, pecorino cheese, and explore a Renaissance palace. This charming town is a UNESCO World Heritage Site. Small, elegant Reggello is a shady place in the Florentine mountains. The parish church of S. Pietro a Cascia, with Romanesque architecture, was built in the 11th century. Vallombrosa Abbey was founded in 1036, additions were made until the 17th century, and the luxurious Sammezzano Castle is a must. The history of a building on this site dates to Roman times.


Naples, one of the largest cities in Italy, is a historic hotspot, and it was also here that pizza was invented! Explore underground ruins and catacombs from the Greeks and Romans. The home of exceptional opera, Naples Teatro di San Carlo Opera house has been wowing visitors since 1737. There are more than 500 churches within the city limits—dip inside the 1,000 year-old Naples Cathedral. Astounding. And, of course, Naples is a shopper’s dream.


Take a romantic walk through the town made for romance, Minori. Beautiful Bari has the largest port on Italy’s Adriatic coast. An off-the-beaten-path destination, you’ll find fabulous food, castles, churches, and welcoming folks. Lecce, known as “Florence of the South,” is home to astonishing Baroque architecture. Renaissance doors mark the entrance to Martina Franca. This 1,000 year-old town of white-washed buildings sparkles in the sun, has picturesque views, and unique frescoes.


The small town of Matera should be on your Southern Italy bucket list. It is one of the oldest continuously inhabited areas in the world, dating to the Paleolithic period. Ancient neighborhoods, called “sassi,” are a series of caves carved from limestone. Explore the caves and dine in one. An amazing experience.


In the unparalleled grace of the Lakes Region, Bellagio is a stand out. Situated on a piece of land that separates the southern branches of Lake Como, Bellagio has been a star-studded getaway for 2,000 years. Stroll cobblestone lanes, peek into elegant shops and stores, walk past villas and riotous gardens with stunning views, and you’ll understand why this town is known as the “Pearl of Lake Como.” Walk the lakeside promenade in Stresa on Lake Maggiore, and then board a boat for the evocative Borromean Islands. Heaven.


Milan, Italy’s most stylish city, is a combination of urban vibe and romantic charm. The financial hub of the country, Milan has perfect architecture representative of every era. It is also foodie heaven. Shop, go to a trattoria and savor cuisine that comes from the area’s mountains, coasts, lakes, and farms. It is also the original home of panettone and the aperitivo. Go to Chianti and wander through vineyards, castles, olive orchards, and medieval villages. It is a Tuscan dream. Breathtaking Bologna, in Northern Italy, is a maze of plazas, arched colonnades, cafes, medieval towers, and the Fountain of Neptune. This city is made for walking.


Burano, an island in the Venetian lagoon, is known for lace making. Verona, famous as the setting for “Romeo and Juliet,” dates from prehistoric times. Head to Centro Storico, the heart of town, and go to Juliet’s house. Now, imagine the heady scent of lemon blossoms, sipping limoncello on a sunny terrace, views of the Bay of Naples, a day trip to Pompeii or Capri, and you have just fantasized about visiting Sorrento. Many consider it to be one of the most beautiful of Italian villages, and it’s a good base to explore Positano. The province of Perugia, the capital of Umbria in Central Italy, is known as the City of Chocolate. While here, indulge, then consider a hot air balloon ride over the green heart of Italy. Astonishing!


Siena is considered to be Italy’s loveliest medieval village. In the Tuscan region, feel time slip away and become immersed in the atmosphere of the Middle Ages. The town’s grand cathedral was built in the 1200’s, the town square is a UNESCO Heritage Site, and there is fabulous art around every corner. Sicily, just 100 miles northeast of Tunisia, is spicy and exotic. First inhabited 10,000 years ago, and one of the largest islands in the Mediterranean, it is situated at the crossroads of history. A melting pot for numerous ethnic groups, enjoy the tastes, sights, and sounds as you wander through marketplaces. Then head to the beach, relax in a lido bar, or hike in the hills. All is a wonder.

Modes of Luxury Travel

You can choose one mode of transportation for your entire travels in Italy, or you can mix-and-match them. These include luxury small, guided vacations; chauffeur-driven autos, giving you ease, style, and privacy; a rental car for complete freedom of the road and spontaneous diversions; and guided private vacations for friends and family.

Surprisingly Beautiful, and Diverse, Lodgings

Photo: © Hotel Ai Reali

Your Italy travel experience will likely cover the country’s story, from thousands of years ago to the present. Each destination in Italy has a unique personality, shaped by the land and its history. Your accommodations should be worthy of travel, rightly considered. Your choices include, but are not limited to, the heart of Rome iconic hotels; sublime spa resorts; opulent lakeside inns; spacious country retreats; landmark seaview hotels; stylish Baroque hotels; and classic hotels with gardens that go on forever.

A Sampling of Exceptional Custom Add-ons Throughout Italy

  • Roman Golf Cart Photography Experience
  • VIP Vatican Museum Tour with Secret Room
  • Basilicas and Saints Tour in Christian Rome
  • Uffizi Art Gallery Tour
  • Regional Cooking Class in Chianti
  • Walking Tour of Naples Historic Center
  • Guided Tour of Amazing Pompeii
  • Visit a Buffalo Farm where Mozzarella Cheese is Made
  • A Look into Amalfi’s Wonders
  • Spend the Afternoon with a Minori Ceramic Artisan
  • Explore a Lemon Grove near Sleepy Minori and Indulge in a Zesty Lemon Tasting
  • Spend a Day Exploring the Breathtaking and Idyllic Island of Capri
  • Secrets of Traditional Cooking Demonstration, with Lunch, in Ostuni
  • Underground Olive Mill Museum in Gallipoli for Techniques in Making Olive Oil
  • Tastings of Manduria’s Famous Primitivo Wines, Made from Indigenous Grapes
  • Discover the Magic, and Immense Expanse, of the Castellana Caves
  • Walking Tour with Local Guide of Medieval Altamura with Bread Tasting at Charming Bakery
  • Private Como Lake Boat Ride
  • Milan Walking Tour, including The Last Supper
  • Fashion and Design District Tour in Milan
  • Private Tasting Tour of Northern Italy’s Best
  • Authentic Verona Family Dinner
  • Lake Garda Excursion
  • Walking Tour of Sicily with Local Guide and Insight into Palermo’s Anti-mafia Movement
  • Sample a Local Sicilian Farm’s Tasty Olives, Award-winning Oil, and Fresh Breads
  • Chocolate Tasting, Cheese Making, and Almond Cultivation on Rural Farms in Sicily
  • UNESCO World Heritage Tour of the Valley of the Temples
  • Sorrento Street Food Tasting
  • Leaning Tower of Pisa Tour
  • Venetian Dining Experience with Local Host
  • Murano & Burano Islands Boat Tour for Lace and Blown Glass
  • Join a Local Farmer and His Dog, Trained to Truffle Hunt, in the Glorious Hills of Alba
  • Full Day Prosecco Wine Tasting

Surrender to Italy’s vivid personality, humor, cuisine, and hospitality. This is the time to discover the opulent side of Italy that you’ve been dreaming about.

When you’re ready to experience the sumptuous side of Italy that reflects your personal wishes, let your Destination Expert know.