Plan your dream trip to Italy – without the overwhelm.
Your Italy trip deserves more than a copy-and-paste itinerary.
Whether you’ve spent hours researching or simply don’t know where to start, I’ll help you cut through the noise and create a plan that fits your travel style and interests.
With my custom Italy travel planning service, I’ll design a personalized itinerary that blends iconic sights with authentic, local experiences – so you can simply show up, relax, and enjoy la dolce vita.
Personalized Italy travel planning
Two ways to plan your trip with Maddy’s Avenue – tailored to your needs and travel style.
Trip Planning Session
$149 USD
For travelers who just need expert clarity.
Maybe you’ve started planning, but your route feels rushed, or you’re not sure which towns to skip (or swap). Over Zoom, we'll review your plans, fine-tune your itinerary, and answer your Italy travel questions.
- 30-minute Zoom consultation
- Pre-call questionnaire to maximize our time
- Tailored advice on routes, timing, hotels, restaurants, tours
- Follow-up email summary with notes and booking links
- Does not include bookings or live support
Custom Itinerary Design
From $749 USD
For travelers who want a perfectly curated Italy trip.
Tell me your dates, interests, and budget, and I’ll craft your dream Italy itinerary from scratch. Each day is mapped out with hotels, tours, and restaurants – all organized in a beautiful, easy-to-follow format.
- Custom day-by-day itinerary (7–14 days typical)
- Detailed hotel, restaurant, and activity recommendations
- Direct booking links (you handle the reservations yourself)
- Private Google Map with all stops pinned
- Does not include bookings or live support
How it works
Trip Planning Session
- STEP 1: Complete your payment
- STEP 2: Book your time + complete the questionnaire
You’ll receive a link to schedule your Zoom call and fill out a short pre-call questionnaire so I can prepare for our chat. - STEP 3: Meet on Zoom
We’ll review your plans, fine-tune your route, and answer your Italy travel questions – from timing to trains to tours. - STEP 4: Get your notes
You’ll receive a follow-up email summarizing the itinerary tweaks and recommendations we discussed. - Does not include bookings or live support
Custom Itinerary Design
- STEP 1: Complete your payment
- STEP 2: Complete your questionnaire
Share your dates, interests, budget, and travel style so I can design your dream Italy itinerary around you. - STEP 3: Review the rough plan
You’ll receive a preliminary outline via email for feedback and approval before I create your final itinerary. - STEP 4: Receive your final itinerary
Within 14 business days, you’ll receive your complete, easy-to-follow Italy itinerary. - Does not include bookings or live support
Why Work With Maddy?
I’ve been travel blogging for over a decade, and millions of travelers have used my guides to plan unforgettable trips around the world!
After exploring Italy from top to bottom – from the Dolomites to the Amalfi Coast to Puglia, and Verona to Siena to Rome – I know what’s truly worth your time (and what isn’t).
I usually spend a few months in Italy each year, researching new places, revisiting old favorites, and keeping my recommendations up to date.
Now, I’m bringing that experience to you personally – so you can skip the stress and travel Italy more like a local.
I can’t wait to help plan your dream trip to Italy!
Book your Italy Trip Planning Session ($149) or request your Custom Itinerary Design (from $749) now.
What Travelers Are Saying
Ready to Plan Your Dream Trip?
Let’s make it effortless, authentic, and unforgettable.
I take on a limited number of clients each month to ensure every itinerary gets my full attention. I can't wait to curate the Italy trip you're dreaming of – click below to get started!