What $44,995 in Italy Actually Looks Like
Not all jet-set travel looks the same.
Fall 2025: 11 days, four regions, and one thoughtfully designed flow across Italy’s mainland and islands. Boutique hotels. Insider access. Clifftop lunches. Vineyard hikes.
And yes. From $44,995* per person.
This post breaks down what’s included, what makes it work, and how I design private versions tailored to your preferences, pace, and purpose.
The Itinerary at a Glance
- Duration: 11 days
- Destinations: Rome, Sardinia, Puglia, Sicily
- Style: Boutique properties, curated experiences, seamless private air transfers
- Guests: Capped at 13 travelers, by design
This journey blends iconic cities with lesser-known escapes. It’s a rare example of high-end Italy that isn’t overdone.

Rome:
- Lunch at the birthplace of fettuccine Alfredo
- Private entry to Villa Farnesina’s Renaissance frescoes

Sardinia:
- Jeep safari along the rugged coast
- Farmhouse lunch overlooking the sea
- Visit prehistoric Nuraghe ruins

Puglia:
- Olive oil tasting and cooking class in a masseria
- Explore Alberobello’s iconic trulli
- Design Your Day: choose from cheese tasting, a countryside hike, or a visit to Ostuni

Sicily:
- Vineyard hike + Nero d'Avola tasting
- Modica chocolate workshop
- Farewell dinner in baroque Ragusa
I design tailored versions of trips like this for travelers who want something quieter, slower, or more personal.
Italy by private jet. Or at your pace.
*Pricing current as of July 2025. Subject to change.
Design My Trip
Inspired to plan a journey with meaning?
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