A luxury Italy itinerary

The luxury travelers I work with aren’t necessarily looking for VIP treatment. Rather, they are down-to-earth and well-traveled, but they want their luxury Italy itinerary to be about service and comfort while getting to know the locals as much as possible. Recently a client hired me to plan an 18 day luxury trip for him and his wife and their three teenage boys, with no limits on budget:

“We want an unforgettable family trip to Italy. Comfort and service is key, and we need lots of hands-on activities for the kids. Oh, and views.”

See below for details on what they did, and contact me if you’d like me to create a similar trip for your small group!

The Amalfi Coast

Their Sorrento hotel has amazing views and a nice pool so everyone can relax and get over jet-lag. They’ll also visit Pompeii, spend a day swimming off a boat around the island of Capri, and eat pizza.


In Rome one of the highlights will be the views from the terrace of their hotel, and their private guided tours will be fabulous, but I predict that the highlight for their three teenage boys will be the morning they spend at Gladiator School.


They’ll spend a week in Tuscany, living on a farm and experiencing life with the locals. They’ll taste locally made olive oil and goat cheese, have a Tuscan chef come and cook for them, and trick the kids into learning some history by visiting the incredible small towns of the beautiful Val D’Orcia countryside. One morning, at the crack of dawn, they will get up for a private sunrise balloon ride over Tuscany.


On their way from Tuscany to Venice, they’ll stop at Ferrari and do two concurrent one-hour self-drive tours: mom drives one, dad drives one, kids in the back!


They’ve got a couple of suites booked at one of Venice’s top hotels and will see the city’s main sights like St Mark’s Basilica and the Doge’s Palace on a VIP private tour. They’ll arrive in Venice about sunset, and this will be their view from dinner on their first evening in this magical city:


From Venice, they’ll head a couple hours north into the mountains and relax in a five-star hotel with incredible views of the Dolomites. By day they’ll hike with a private guide, do an easy half day bike ride with a cookie factory en route, and go on a tandem paraglide over gorgeous green valleys backed by famous peaks.

Then they’ve got first class seats booked on the spectacular train ride from Bolzano to Innsbruck Austria before heading home.

Client Testimonials

"We had a wonderful trip! We did so many amazing things and experienced many wonderful places yet never felt like..."

"We thank you so much for all you gave us, guided us to, arranged for, and detailed for us. Not..."

"We are in love with Venice and the Dolomites. The ski adventure was amazing and beyond anything we could have..."

"Absolutely everything that you planned went off without a hitch. Every tour, every restaurant, every train and activity came through..."

"Thank you again from all three of us for your help in planning such a delightful trip. I know that..."

"Madeline carefully planned a fabulous, personalized 19 day itinerary (Lake Garda, Dolomites, N/S Tuscany, Rome) that enabled us to be..."

Read More Client Testimonials

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