Need help planning your trip? Get a custom travel itinerary.
 

The Ultimate Italy Trip

 

 

I’ve been traveling to Italy for almost two decades, and have had used that time to make (and correct) a whole host of mistakes. But what if you’ve got only one shot at la dolce vita?

This is where my Custom Italy Itinerary service comes in. When you book a session with me, I use more than a decade of real-world travel experience to plan a trip you’ll never forget.

Have just a week, but want to see all of Italy’s major cities without stressing out? Go off the beaten path in Puglia or Sicily? Eat life-changing pasta from a nonna in Bologna? Frolic on paradise beaches less than two hours from the vineyards of Tuscany? Did you choose Italy as your honeymoon destination, but couldn’t come up with any details beyond that?

No matter where in Italy you plan to travel or why you plan to go, let me curate experiences you’ll be talking about for years to come.

Whether you visit Italy for business, pleasure or both, a Custom Italy Itinerary equips you with information, inspiration and a comprehensive itinerary—all you’ll need to do is get on the plane!

Book your session now, or continue reading to learn more about how my Custom Itinerary Itinerary service works:

 

One-on-One Consultation

Whether you prefer to video chat via Zoom, Skype or email, we’ll chat until I understand exactly the trip you want to take. You can ask me any questions you have, as well!

Comprehensive Italy Itinerary

Your Custom Italy Itinerary includes detailed, personalized suggestions* for daily accommodation, transport, activities, dining and more. Sample itinerary available upon request.

Ongoing Support and Advice

It’ll only take me 1-2 weeks to get your Italy itinerary put together, but I’m available to assist you right up until departure with questions and even minor** last-minute changes.

 
 
 

Due to the amount of time, energy and love I devote to crafting your custom Italy itinerary, my service is subject to a fee. My 2025 Custom Italy Itinerary fee schedule is below:

 
Weekend
$500
1-2 weeks
$700
3-4 weeks
$1,400
5-8 weeks
$2,800
9+ weeks
On request
 
 

Just need some advice or pep-talk, but not a full Italy itinerary? I offer à la carte Italy Travel Consulting calls! Please send me an email for pricing and availability.

 
 
All prices are in U.S. dollars. Sample itineraries available upon request. Payment is made via PayPal or Zelle in advance of Zoom/Skype/email chat to secure session. If booking window does not open, please email Custom Italy Itinerary request to robert@leaveyourdailyhell.com
*I am not a travel agent and I don’t book hotels or make dinner reservations. I will provide you with all the information you need for your trip, but I don’t want to lock you in!
**Examples of “minor” changes include suggesting a different restaurant one night, or selecting a new hotel for one city on account of changed circumstances
 
 
 
A Custom Italy Itinerary is the best way to make your next trip the best you’ve ever had, but don’t take my word for it. Here’s what my biggest fans are saying!
 
“Robert helped me find calm amid Italy’s chaos, and craft a truly unforgettable trip.”

-Debra, Canada

“We chose Italy as our honeymoon destination, but drew a blank when we tried to plan something. Robert took care of the logistics, so we could focus on our love.”

-Jason & Alana, USA

“I could never have explored hidden gems in southern Italy without Robert’s help!”

-Chris, New Zealand

“Robert’s restaurant recommendations were out of this world, especially in crowded Venice!”

-Richard & Sophie, Singapore

“I hired Robert to plan a trip to Italy for me after I worked with him on my Japan itinerary. Very good decision.”

-Muhammad, UAE

 
 
 
 
 
 
 
 

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