Private Luxury Italian Packages

Experience Italy Beyond the Guidebooks. At 58 Stars Travel we book experiences that make you feel Italian. We bring authenticity by curating the best guides who know the most popular sites and the small hole in the wall places that others can only dream about.

Our Most Beloved Italian Destinations

Embark on a journey to the heart of Italy with our specially curated vacations to the country’s most beloved cities. From the ancient streets of Rome to the serene canals of Venice, the vibrant art scene of Florence, and the bustling markets of Milan, Italy’s cities are treasure troves of culture, history, and unparalleled beauty.

Our exclusive, customized travel itineraries are designed to offer you an immersive experience into Italian life, allowing you to explore the iconic landmarks, savor the exquisite cuisine, and engage with the rich traditions that make each city uniquely enchanting.

Whether you’re seeking romance, adventure, or the pure joy of discovery, our vacations promise to fulfill your dreams of an authentic Italian getaway. Let us guide you through Italy’s most popular cities, where every corner tells a story and every moment is a chance to feel Italian at heart.

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Revel in the eternal luxury of Rome, where ancient history and contemporary luxury blend seamlessly, offering an exquisite escape into a world of unparalleled cultural richness and gourmet delights. Wander through its storied streets to uncover exclusive boutiques, Michelin-starred dining, and private tours of the Vatican’s treasures.

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Experience the cradle of the Renaissance in Florence, where art, architecture, and artisanal craftsmanship converge to create a uniquely luxurious voyage through history. Immerse yourself in sumptuous accommodations that offer breathtaking views of the Arno River, and exclusive access to the city’s renowned museums and galleries.

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Indulge in the rustic elegance of Tuscany, with its rolling hills, vineyard-clad landscapes, and villas, offering a serene retreat into Italy’s heartland of gastronomy and fine wine. Enjoy personalized wine tours, gourmet cooking classes, and horseback riding through picturesque countryside, all tailored to your tastes.

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Amalfi Coast

Embrace the epitome of Mediterranean luxury along the Amalfi Coast, where dramatic cliffs meet the azure sea, and chic resorts offer sublime relaxation and breathtaking views. Explore quaint fishing villages, indulge in fresh seafood delicacies, and set sail on private yachts to secluded beaches for an unparalleled experience.

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Discover the diverse beauty of Sicily, an island adorned with ancient ruins, baroque cities, and luxurious seaside resorts, all set against the backdrop of Mount Etna’s majestic presence. Delight in exclusive culinary tours, private archaeological excursions, and stays in exquisite hotels that embody Sicilian elegance.

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Lose yourself in the romantic allure of Venice, where luxurious palazzos, enchanting gondola rides, and lavish celebrations make every moment an unforgettable celebration of life. Experience the city’s legendary art and music scene with VIP access to private galleries and performances in historic venues.

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Step into the world of high fashion and sophistication in Milan, Italy’s cosmopolitan heart, where luxury shopping, avant-garde design, and vibrant nightlife await. Stay in iconic designer hotels, enjoy bespoke shopping experiences, and dine at exclusive rooftop restaurants with panoramic city views.

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Lake Como

Retreat to the tranquil luxury of Lake Como, where glamorous villas and lush gardens line the crystal-clear waters, offering an idyllic escape into Italy’s most picturesque landscapes. Charter a private boat to explore hidden coves, visit historic estates, and relax in spa resorts that offer treatments inspired by the natural beauty of the region.

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Immerse yourself in the understated elegance of Puglia, where luxury meets the untouched beauty of Italy’s southern charm. Here, amidst ancient olive groves and azure coastlines, exclusive resorts and private villas offer a serene escape into a world of exquisite cuisine, rich history, and bespoke experiences, promising an unforgettable retreat into Italy’s hidden gem.

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Experience Authentic Italy


A Day in the Amalfi Countryside

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You’ll be picked up in the morning from your hotel and you’ll be on your way to visit a local farm to discover and taste local flavors! Your local guide focuses on cheese, mozzarella, fior di latte and wine! The best and most local products are in this part of the region! You’ll visit local farms and villages, and have incredible food tasting and wine experiences! You will experience a beautiful countryside, surrounded by beautiful nature, amazing landscapes, and full of local unique flavors! And, you’ll end the day by learning how to make the most amazing limoncello, tasting different versions of this Italian delight.


A Day in Capri

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You will be transported to Capri for a wonderful private boat trip that takes you around the island. You’ll have your own skipper who will bring you to famous caves, swimming spots, snorkeling, and of course the famous Blue Grotto. After exploring the island’s enchanting waters, enjoy a leisurely lunch at a secluded beachside restaurant, where you’ll savor the finest local cuisine with breathtaking views of the Mediterranean. The day ends with a stroll through Capri’s charming streets, visiting boutique shops and enjoying a gelato as the sun sets over the sea, perfectly encapsulating the island’s magical allure.


The Tuscan Hills Come Alive

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You’ll explore the unique and stunning Tuscan hills, where you’ll visit beautiful little towns like Montalcino, Cortona, Pienza, San Gimignano, and more. Sip and savor Tuscan wines, the divine Chiantis of the region, and our favorite Brunello of Montalcino. Tuscany delivers the sips, the scents, and the scenery. As you wander through ancient vineyards and historic estates, you’ll learn the centuries-old secrets of winemaking that make this region a haven for connoisseurs. And as the day draws to a close, find yourself dining al fresco at a rustic farmhouse, indulging in a feast of local specialties prepared with the freshest ingredients, all while the rolling hills of Tuscany unfold in a panoramic spectacle before you.


A Day on Lake Como

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Embark on a luxurious journey to Lake Como, where the serenity of crystal-clear waters meets the splendor of the Italian Alps. Your day begins with a private boat tour, gliding past elegant villas and lush gardens that dot the shoreline, each telling a story of opulence and charm. The skipper will navigate to secluded spots known only to locals, where you can swim in the lake’s refreshing embrace or simply bask in the sun’s warmth. For lunch, dock at a lakeside restaurant accessible only by boat, offering exclusive dishes that blend traditional Italian flavors with modern culinary artistry. As the afternoon unfolds, visit the historic towns of Bellagio or Varenna, with their cobblestone streets and vibrant floral displays, perfect for an leisurely exploration.

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Discover the timeless allure of Greece, where ancient ruins whisper tales of gods and heroes, and azure seas embrace sun-drenched shores. From the Acropolis standing majestically over Athens to the idyllic islands of Santorini and Mykonos, Greece offers a captivating blend of history, culture, and unparalleled natural beauty. Embark on a journey where every moment is a postcard come to life, promising an unforgettable escape into the heart of the Mediterranean’s most cherished gems.

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Experience the enchantment of Paris, a city where the romance of the Seine River intertwines with the elegance of its boulevards and the timeless beauty of landmarks like the Eiffel Tower and Notre-Dame. Indulge in the world-renowned cuisine, explore art-filled museums, and wander through historic neighborhoods that inspire love and creativity at every turn. Paris isn’t just a destination; it’s a backdrop for unforgettable moments and the beginning of your own French love story.

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Venture into the vibrant heart of Spain, a country rich with the legacy of kings and conquerors, where flamenco rhythms ignite the soul, and the architecture is as diverse as the landscapes. From the sun-soaked beaches of the Costa del Sol to the historic streets of Barcelona and Madrid, Spain offers a feast for the senses. Savor the flavors of tapas, indulge in the art of siesta, and immerse yourself in a culture where tradition and modernity dance together under the Iberian sun, promising an adventure filled with warmth, passion, and unforgettable experiences.

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Italian Vacations: FAQ

Absolutely, tours in Italy offer unparalleled opportunities to experience the country’s rich history, stunning architecture, and world-renowned cuisine through the eyes of local experts. They provide unique insights and access to hidden gems that might otherwise be missed, making them a valuable addition to any Italian vacation.

The best way to vacation in Italy is by blending planned experiences, like guided tours and museum visits, with spontaneous adventures, allowing for leisurely exploration of its charming streets, local markets, and breathtaking landscapes. Embracing both the iconic sights and the everyday Italian lifestyle will give you a deeply enriching and authentic experience of Italy’s diverse regions.

Hiring a private tour guide in Italy can greatly enhance your experience, offering personalized insights into the country’s rich history, culture, and local secrets. A private guide can tailor the tour to your interests, help you navigate the language barrier, and provide access to experiences that aren’t available to the general public, making it a worthwhile investment for those seeking a deeper understanding and enjoyment of their Italian adventure.

While many Italians in tourist areas speak English, having a translator or learning basic Italian phrases can enrich your vacation, facilitating smoother interactions and a deeper connection with the local culture. For a more immersive experience or in less touristy areas, a translator or a translation app can be invaluable in ensuring clear communication and enhancing your overall experience.

The ideal length for a vacation in Italy varies depending on your interests and the regions you wish to explore, but a period of 10 to 14 days is recommended to truly experience the diversity of the country. This timeframe allows for a leisurely exploration of Italy’s major cities, such as Rome, Florence, and Venice, along with time to discover the charm of smaller towns and the breathtaking countryside, ensuring a well-rounded and fulfilling Italian adventure.

The best places to vacation in Italy include the historic cities of Rome, Florence, and Venice, where art, culture, and history come alive. The picturesque Amalfi Coast and the stunning landscapes of Tuscany offer breathtaking scenery and exquisite cuisine. For those seeking a blend of beaches, ancient ruins, and vibrant local life, Sicily and Sardinia are unmatched. Each destination offers its own unique charm, promising an unforgettable experience tailored to every traveler’s desires.

Absolutely, a food tour in Italy is highly recommended as it offers a delicious pathway to understanding the country’s rich cultural heritage and regional diversities. Guided by local experts, you’ll explore authentic flavors, learn the stories behind traditional dishes, and discover hidden culinary gems that you might not find on your own. It’s a perfect way to immerse yourself in the Italian way of life and savor the true essence of its varied gastronomy.

Yes, using public transportation in Italy is a practical and efficient way to explore cities and many regions. Italy’s extensive network of trains, buses, and metro systems in larger cities offers a cost-effective and convenient option for getting around, allowing you to experience the country like a local. It’s especially recommended for visiting major urban centers where parking can be difficult and traffic heavy. Plus, it provides a unique opportunity to immerse yourself in the Italian way of life.

Renting a car in Italy can be a great option if you plan to explore the countryside or visit regions less accessible by public transport, such as Tuscany, the Amalfi Coast, or Sicily. It offers flexibility to travel at your own pace and discover off-the-beaten-path gems. However, be mindful of driving in cities where traffic can be challenging and parking scarce. For city visits, public transportation and walking might be more convenient, and for those preferring not to navigate the streets themselves, hiring a driver or using a private car service can offer a stress-free alternative.

Your Journey, Our Assurance: Worry-Free Travel

Choosing to plan your luxury family vacation through 58 Stars Travel Agency means having a partner to help oversee your trip – even when things don’t go according to plan.

When you choose to book your own travel arrangements, the responsibility for every aspect of your trip – from flights and accommodations to activities and contingencies for unforeseen events like adverse weather, flight cancellations, or missed connections – falls squarely on your shoulders. But when you entrust us with planning your journey, this burden is lifted. With us as your dedicated point of contact throughout your vacation, you gain the advantage of having a single source of support and expertise.

When it comes to booking your flights, we have established direct connections with airlines, enabling us to effortlessly manage any adjustments or enhancements to your travel plans. Our established relationships and access to airline resources make it possible for us to resolve issues swiftly and efficiently.

We possess intimate knowledge of the resorts, airlines, and the intricate details of your trip, allowing us to offer expert advice on every aspect of your travel experience. Our personal connections with suppliers and partners at your destination ensure that you receive the finest treatment and the most enriching experiences.

In the lead-up to your trip, we liaise with suppliers to verify that all arrangements are in order and to preemptively address any potential issues. We provide you with a comprehensive list of emergency contacts, all of whom we have personally vetted, so you can have confidence in the quality of service you’ll receive. Rest assured, we select these partners based on our trusted relationships, not just anonymous online reviews.

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