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.

Pricing and more →

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

What To Pack for Italy

What To Pack for Italy

July 23, 2025

The most common questions we get from clients about to leave for Italy have to do with packing conundrums. From comfortable shoes to reliable adaptors, packing details seem to take up a lot of bandwidth in the final days before…

Jet Lag Tips

Jet Lag Tips

July 16, 2025

The majority of our Italy travel planning clients are based in North America, which is a 6 – 9 hour time difference from Italy, depending on where you travel from. So it makes sense that they request jet lag tips…

Eat Like an Italian: A Daily Schedule

Eat Like an Italian: A Daily Schedule

July 09, 2025

When we create personalized Italy itineraries for our travelers at Italy Beyond the Obvious, food usually plays a key role. We offer recommendations on where to eat, of course, but also what to eat, when to eat, and what to…

Read Our Italy Articles

Italy Advice & Tips In Your Inbox

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

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

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Start Dreaming About Your Next Italy Trip

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