luxury trip to Italy

A Luxury Italy Itinerary

The luxury travelers we work with aren’t necessarily looking for over-the-top VIP treatment. Rather, these down-to-earth and well-traveled clients want their luxury Italy itinerary to be about service and comfort while getting to know the locals as much as possible. Recently, we were hired to plan an 18-day luxury trip for a family with 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 us if you’d like me to create a similar trip for your small group!

planning a luxury italy trip

The Amalfi Coast

We chose a Sorrento hotel with amazing views and a nice pool so everyone could relax and get over jet lag. They also visited Pompeii with a private guide, spent a day swimming off a private boat around the island of Capri, and feasted on pizza that they made during a pizza class.

Rome hotel view luxury trip


In Rome, one of the highlights was the views from the terrace of their hotel, and their private guided tours of the Colosseum and Vatican Museums. The highlight for their three teenage boys was the morning they spent at the Gladiator School learning how to battle like an ancient Roman.

how to plan a luxury italy trip


They spent a week in Tuscany, living in a villa on a farm estate and experiencing life with the locals. They tasted locally made olive oil and goat cheese, had a Tuscan chef come and cook for them, and tricked 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 got up for a private sunrise balloon ride over Tuscany.

ferrari luxury italy vacation


On their way from Tuscany to Venice, they stopped at the Ferrari Museum and then got behind the wheel for two concurrent one-hour self-drive road tests: mom drove one, dad drove one, and the kids rode in the back!

luxury dinner in venice


We booked a couple of suites at one of Venice’s top hotels and they saw the city’s main sights like St. Mark’s Basilica and the Doge’s Palace on a VIP private tour. They arrived in Venice at around sunset, and we booked them a table with a view for dinner on their first evening in this magical city.

dolomites trip luxury italy


From Venice, they headed a couple of hours north into the mountains and relaxed in a five-star hotel with incredible views of the Dolomites. By day, they hiked with a private guide, did an easy half-day bike ride with a stop at a cookie factory en route, and went on a tandem paraglide over gorgeous green valleys backed by famous peaks.

They finished their adventure with 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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