How I Designed a €300,000 Dream Trip Through Italy for my clients
When most people think of luxury travel, they imagine five-star hotels and over-the-top amenities. But my clients? They want more. No cookie-cutter travel agent packages, no tourist traps.
The Travelers: High Expectations, Hidden Gems, and Foodie Adventures
The group—three couples in their 60s—were highly successful professionals: lawyers, doctors, and business executives. They’d already checked off the big cities like Rome and Venice. This time, they wanted something different: a mix of luxury and countryside charm, with a focus on food, wine, and authentic local culture.
When most people think of luxury travel, they imagine five-star hotels and over-the-top amenities. But my clients? They want more. No cookie-cutter travel agent packages, no tourist traps. They crave authentic, bespoke, and unforgettable experiences with a touch of luxury. That’s where our travel design service comes in.
Recently, one of my American clients gave me carte blanche to plan a month-long dream trip through Italy for six friends. Their budget? €300,000. Their only request? “Show us the hidden beauty of Italy, beyond the obvious.”
They had access to a 24/7 private driver and a dedicated concierge service, ensuring that every moment of the journey was seamless and stress-free. Here’s how we pulled it off.
October: The Perfect Month to Explore Italy
October is one of the best months to travel in Europe. The crowds have thinned, the weather is still pleasant, and the autumn colors are breathtaking. We decided to start in the north and work our way south, creating a perfectly paced journey that blended relaxation and adventure.
Stop 1: Portofino—Seaside Charm and Jet Lag Recovery
Accommodation: Belmond Hotel Splendido, Sea View Suites (2 nights)
Portofino was the perfect spot for jet lag recovery and a gentle introduction to the trip. The Belmond offers stunning sea views and a laid-back luxury vibe. The group spent two days exploring the harbor, enjoying fresh seafood, and soaking up the seaside charm. We also arranged a scenic walk to the San Fruttuoso Monastery, followed by a private boat transfer that brought them back to Portofino in style.
Stop 2: Lake Como—Luxury and La Dolce Vita
Accommodation: Mandarin Oriental, Lake Como (4 nights)
Next, we whisked them off to Lake Como for four days of pure indulgence. They cruised around the lake on a private limousine boat, visiting iconic spots like Villa d’Este, Bellagio, and Cernobbio. Every moment was designed for relaxation, from long lakeside lunches to private villa tours.
Stop 3: Tuscany—Wine, Truffles, and Timeless Villages
Accommodation: Private Villa at Castiglion del Bosco (1 week)
Tuscany was where the magic truly happened. The goal here? Full immersion into the region’s culinary and cultural treasures:
Spa days and cooking classes at the villa
Private wine tastings at renowned vineyards
Cultural tours of Florence, Siena, and Pienza
Truffle hunting with expert guides and truffle dogs, followed by a private chef preparing their fresh truffle feast
Tuscany captured everything they wanted: authentic experiences with just the right touch of luxury.
puglia
Stop 4: Puglia—The Soul of Southern Italy
Accommodation: Luxury Villa Outside Lecce (1 week)
An 8-hour drive from Tuscany to Puglia might sound long, but we broke it up with a VIP tour of Pompeii, giving them a chance to explore ancient ruins and stretch their legs before continuing south.
Their villa, nestled in the middle of an olive grove, came with daily cleaning and a private chef. It served as the perfect base for discovering Puglia’s rich culture and hidden treasures.
Activities included:
Cooking and pottery classes
Golf and olive oil tastings
Private tours of Lecce
Visits to Gallipoli, Otranto, Ostuni, Locorotondo, and Alberobello
Final Stop: Rome—A Grand Finale
Even though they’d been to Rome before, they couldn’t resist returning. This time, it was about enjoying the city’s energy at a more relaxed pace. The highlight? A VIP tour of the Vatican, offering exclusive access and insights into one of the world’s most iconic sites.
A Trip to Remember
This wasn’t just another luxury vacation. It was a journey designed to highlight the best of Italy—authentic, immersive, and deeply personal. It wasn’t about ticking boxes on a travel itinerary; it was about creating experiences they’d never forget.
What’s Your Dream Trip?
If you could design your ultimate dream trip, where would you go? Are you more about hidden gems or all-out luxury? Hit reply and let me know—I’d love to hear your travel style!
Cheers to the art of travel design,
Justine