Custom Italy Travel Beyond the Obvious

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Exclusive, Customized Italy Travel Experiences

We meticulously craft your tailor-made Italy trip around comfort, service, and an authentic experience with the utmost attention to detail.

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Our Italy Travel Services

We offer three levels of Italy trip planning services;
Gold, Platinum, and Diamond.

Gold

Our Gold Italy planning service is for the traveler who has booked hotels, needs help with the rest.

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Platinum

Our Platinum Italy travel planning service is for the traveler looking for VIP level tours and treatment.

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Diamond

Our Diamond Italy travel planning service is for groups of 6 or more looking for either level of service.

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More About Our Services

The App Our Travelers Use on the Road

Click below for a more in-depth look at the app our travelers use on the road.

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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..."

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Italy Travel Expert Madeline Jhawar

Italy Travel Expert Madeline Jhawar

As soon as you work as a tour leader in Italy, everyone wants advice. So I’d been planning trips to Italy for friends and family since about the mid-1990′s, and until August of 2008 I wasn’t charging for them. But when I started spending time getting to know my travelers in order to make good recommendations, I realized that it was much more time-consuming compared to doing it for friends I already knew well.

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Recent Articles

5 Reasons to visit the town of Monza

5 Reasons to visit the town of Monza

March 05, 2026

Only 10 minutes by train from Milan, and on the way to Lake Como, the bustling small town of Monza is a great escape from the big city. I lived in Monza as an exchange student in high school and…

What to do in Italy on Sundays

What to do in Italy on Sundays

March 01, 2026

When we create custom itineraries at Italy Beyond the Obvious, we always include the day of the week – not just the date – during the planning process. The main reason for this is that Sundays (and sometimes Mondays) require a…

Amalfi Coast Towns: where to stay

Amalfi Coast Towns: where to stay

February 19, 2026

If you drove along Italy’s Amalfi Coast from the city of Sorrento to the city of Salerno, it would take at least a couple of hours, one-way, with no traffic. During that drive, you’d pass the iconic Amalfi Coast towns…

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Italy Advice & Tips In Your Inbox

Italy Advice & Tips In Your Inbox

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The Travel Expert Network

Check out the Travel Expert Network where you’ll find Certified Travel Experts™ like us ready to plan custom bucket trips for you all over the world!

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Office Locations

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+1 773 621-3024
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Milan
+39 320 028 6827
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Rome
+39 331 222 2349
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