A Luxurious Italian Escape Through Five Iconic Cities
Ready to live your own Italian love story? This 14-night itinerary is tailor-made for couples or duos seeking a once-in-a-lifetime experience through Italy’s most iconic destinations. From fashion-forward Milan to the dramatic cliffs of Amalfi, each stop blends romance, culture, cuisine, and curated luxury.
Photo Credit: Château Monfort
Milan: The Gateway to Glamour (3 Nights)
Your journey begins in Milan, where contemporary flair meets old-world charm. Stay at the elegant Château Monfort, a boutique hotel that feels plucked from a fairytale. Highlights include a private walking tour of the city, followed by a chauffeured excursion to explore the Duomo, La Scala, and the fashion meccas of Via Montenapoleone and Via della Spiga.
Why we love it: Milan offers the perfect mix of high-end shopping and architectural elegance to ease into the Italian rhythm.
Photo Credit: Aparthotel Forte16
Florence: Heart of the Renaissance (4 Nights)
After a scenic train ride, arrive in Florence and check in to Aparthotel Forte 16 for spacious comfort and spa indulgence. Enjoy skip-the-line access to the Accademia Gallery (hello, David!), roll up your sleeves in a hands-on cooking class at MaMa Florence, and venture into the Tuscan countryside for wine tasting and medieval gems like San Gimignano and Siena.
Why we love it: The balance of cultural immersion and culinary delight makes Florence a dream for art lovers and foodies alike.
Photo Credit: Hotel Marmorata
Florence: Heart of the Renaissance (4 Nights)
After a scenic train ride, arrive in Florence and check in to Aparthotel Forte 16 for spacious comfort and spa indulgence. Enjoy skip-the-line access to the Accademia Gallery (hello, David!), roll up your sleeves in a hands-on cooking class at MaMa Florence, and venture into the Tuscan countryside for wine tasting and medieval gems like San Gimignano and Siena.
Why we love it: The balance of cultural immersion and culinary delight makes Florence a dream for art lovers and foodies alike.
Photo Credit: Hotel Luna Convento
Amalfi: Seaside Splendor (3 Nights)
Descend to Amalfi and settle into Hotel Luna Convento, a former monastery that whispers centuries of coastal history. Highlights include a guided tour of Amalfi’s historic center and the charming Paper Mill Museum, plus a full-day adventure to Positano and the Marisa Cuomo Winery, complete with lunch overlooking the vineyards.
Why we love it: Coastal elegance at its finest, with wine, views, and small-town charm.
Photo Credit: Casa Monti Roma
Rome: A Grand Finale (2 Nights)
Descend to Amalfi and settle into Hotel Luna Convento, a former monastery that whispers centuries of coastal history. Highlights include a guided tour of Amalfi’s historic center and the charming Paper Mill Museum, plus a full-day adventure to Positano and the Marisa Cuomo Winery, complete with lunch overlooking the vineyards.
Why we love it: Coastal elegance at its finest, with wine, views, and small-town charm.
Travel Made Effortless
This journey includes private transfers, luxury rail, small-group and private tours, and hand-selected boutique hotels. Every detail has been carefully chosen to give you peace of mind and a sense of effortless indulgence.
Let’s Design Your Italian Masterpiece
Inspired to create your own version of this itinerary? I specialize in tailoring seamless, unforgettable escapes through Italy and beyond.
Click here to start planning your Italian escape today.
Extraordinary Destinations. Seamless Luxury. Unforgettable Moments.
Frequently Asked Questions: Luxury Travel in Italy
What is the best way to experience Italy in luxury?
The best way to experience Italy in luxury is through a custom-crafted itinerary that includes private transfers, boutique accommodations, curated cultural tours, and gourmet experiences. A 14-night journey from Milan to Rome can combine fashion, history, cuisine, and romantic coastline escapes.
How many days do you need for a luxury trip through Italy?
A 14-night itinerary allows ample time to explore Italy's highlights at a relaxed, indulgent pace. This includes multiple nights in Milan, Florence, Ravello, Amalfi, and Rome with private tours and unique experiences in each destination.
What are the most romantic places to visit in Italy for couples?
Top romantic spots in Italy include Ravello’s cliffside gardens, a wine tasting in Tuscany, sunset walks in Florence, and rooftop views in Rome. This luxury itinerary includes them all for the perfect couples' getaway or honeymoon.
What’s included in a luxury Italy itinerary?
A well-designed luxury Italy itinerary includes handpicked boutique hotels, private airport and rail transfers, small-group or private excursions, wine tastings, cultural experiences, and expert planning support.
Is Ravello worth visiting on the Amalfi Coast?
Yes, Ravello is one of the most romantic and serene towns on the Amalfi Coast. It offers dramatic views, lush gardens like Villa Rufolo, and boutique hotels with sea access, making it perfect for couples and special celebrations.
Explore the Blog
Live Your White Lotus Fantasy
White LotusMediterranean Escapes Inspired by the Hit SeriesIf you've ever watched The White Lotus and thought, "I need to be there"—you're not alone. With its sweeping coastal views, dramatic architecture, and utterly indulgent settings, the hit HBO series has done...
Magical Must-See Filming Locations
Magical London: A Self-Guided Harry Potter Walking TourFor fans of the Wizarding World, there’s no better place to start your Harry Potter adventures than in London — the city where magic meets Muggle life at every turn. Whether you’re a first-time visitor or a...
Wanderlust Through Words: Travel Inspired by Beloved Books
Embark on a literary adventure as we uncover the enchanting locations that have inspired some of the world's most beloved stories. From the lush landscapes of Middle-earth to the whimsical woods of the Hundred Acre Wood, discover the magic of these storied...
Unlocking the Priceless Value of a Luxury Travel Advisor
Unlock the world with ease and let us handle the details, so you can focus on the journey ahead. You finally sync up with your significant other and find that elusive window on everyone’s calendar for a much-needed vacation. The excitement builds—but then comes the...
Meet the Vendor Series: Santorini Photographer
Meet the Vendor SeriesWho is Ben Rigas?Capturing Love and Landscapes in Greece: The Story of Ben Rigas When you wander through the stunning vistas of Santorini, it's hard not to be captivated by the magic that only Greece can offer. Among those who capture this...
Discover Amorgos: The Hidden Gem of Luxury Travel
Photo Credit to FreeArtistWelcome to a new chapter in luxury travel—a destination where rugged beauty meets authentic charm. Amorgos, one of Greece's best-kept secrets nestled in the Cyclades, offers a unique escape for those seeking refined tranquility away from the...
Your Next Luxury Cruise Getaway Story
Imagine a journey where luxury meets adventure on the sparkling blue waters of the Adriatic. This exclusive expedition cruise invites discerning travelers to explore Croatia, Montenegro, and Greece aboard an intimate, state-of-the-art vessel. This isn’t just a...
“Best-Kept Secret” Beaches in the Mediterranean
Uncover the serene beauty of the Mediterranean's best-kept secret beaches, where tranquility meets breathtaking landscapes. The Mediterranean is synonymous with crystal-clear waters, sun-drenched coastlines, and iconic destinations like Santorini, the Amalfi Coast,...
Experience Montenegro
Montenegro, often referred to as the "Pearl of the Adriatic," offers a wealth of luxurious experiences that cater to discerning travelers seeking both relaxation and adventure. Here are some standout experiences that showcase the country's unique blend of natural...
Discover Montenegro
Embark on your journey to Montenegro, where stunning landscapes and rich culture await. Let us guide you through this enchanting destination.Nestled in the heart of the Balkans, Montenegro offers a captivating blend of rugged mountains, medieval villages, and a...