PERSONAL ITALY ITINERARY HELP
Stop Second-Guessing Your Italy Itinerary
Turn your scattered ideas, saved posts, and overfilled plans into a calm, realistic Italy itinerary that still feels exciting.
In this private 60-minute trip-planning session, I’ll help you decide what belongs, what doesn’t, and how to create a more thoughtful rhythm—so you can stop planning in circles and start looking forward to your trip.
60-minute Google Meet · Advance itinerary review · Written recap · $197 USD
I currently accept three sessions per month so I can give each traveler’s plans personal attention.
Your Italy Trip Should Feel Exciting—Not Exhausting
At first, planning Italy is fun.
Then the tabs multiply. Every town looks unmissable. Every train, hotel change, reservation, and “quick day trip” has to fit somewhere. Before long, the trip you imagined as beautiful and restorative begins to resemble a race you have to manage.
And the hardest part is not finding more information.
It is knowing which advice fits your trip—and having the confidence to leave the rest behind.
That is where I can help.
During your Slow Italy Trip Planning Session, we’ll look at the trip as a whole and shape it around what matters to you: the places you most want to experience, the pace you can genuinely enjoy, and the way you want to feel while you are there.
You will leave with a simpler, saner plan—and a clearer sense that your trip can actually work.
This Session Is for You If…
-
Your Italy itinerary is beginning to feel like a puzzle—or a nightmare.
-
You keep adding destinations because you wonder, “When will I be back?”
-
You want slower days, but you are not sure what to cut.
-
You need help choosing the right home base or deciding how many nights to spend in each place.
-
You want an experienced person to spot unrealistic connections, awkward pacing, or unnecessary hotel changes.
-
You have read plenty of advice but still do not feel confident making the final decisions.
-
You want a trip that reflects you—not a generic list of Italy’s greatest hits.
This session is not designed for travelers who want to visit 15 cities in eight days or want someone else to make every reservation for them. It is for travelers who value thoughtful guidance and want to remain involved in shaping their own trip.
What We’ll Do Together
Before we meet, I’ll review your questionnaire and any itinerary or notes you send. That means we can spend our hour working through the decisions that matter instead of starting from scratch.
During the session, we may:
-
Clarify how you want the trip to feel—restful, connected, inspiring, adventurous, or a blend of several things
-
Review your route and identify where it feels rushed, inefficient, or unrealistic
-
Decide which destinations deserve more time and which ones may be better saved for another trip
-
Choose practical home bases and discuss the right number of nights in each place
-
Think through transportation, arrival days, departure days, and the real cost of changing locations
-
Refine the balance between planned experiences and time to wander
-
Talk through Tuscany and other parts of Italy with firsthand, culturally grounded insight
-
Answer the specific questions keeping you stuck
You do not need to arrive with a polished itinerary. A collection of ideas, possible destinations, and honest questions is enough.
What You’ll Leave With
You will not receive a generic itinerary generated from a template. You will leave with:
-
A clearer and more realistic structure for your trip
-
Confidence about what to keep, change, or remove
-
Recommendations shaped around your interests, pace, and priorities
-
A short written recap of our key decisions, suggestions, and relevant links
-
One follow-up clarification email within seven days
Most importantly, you will know what to do next—without reopening every tab and questioning the entire trip again.
1
Request a Session
Complete the short request form and tell me about your dates, destinations, current plans, and biggest questions.
2
Receive Your Payment and Scheduling Links
I’ll review your request to make sure this session matches the help you need. If it is a good fit, I’ll email you a payment link and a scheduling link so you can choose a time. Your appointment is confirmed once payment is complete.
3
Send Your Plans
Before our call, send your draft itinerary, notes, or list of possible destinations. I’ll review them in advance so we can use our time well.
4
Meet With Katie
We’ll meet privately on Google Meet for 60 minutes and work through your itinerary, priorities, and questions together.
5
Receive Your Recap
Within a few days, I’ll send a short written recap with the main decisions, suggestions, and links we discussed.
Buon viaggio—now with a plan that leaves room to enjoy being there.
How Your Planning Session Works
What’s Included
-
A 60-minute private Google Meet with Katie
-
Advance review of your questionnaire and draft itinerary or planning notes
-
Personalized guidance on route, home bases, pacing, and priorities
-
Time to work through your specific Italy-planning questions
-
A written recap with key decisions, suggestions, and relevant links
-
One clarification email within seven days of the session
Introductory Rate: $197 USD
I currently accept three planning sessions each month so I can review every traveler’s plans personally and give each trip the attention it deserves.
Payment is non-refundable. If you have a scheduling conflict, your session may be rescheduled for another available time.
This is a consultation and itinerary-review service.
I do not book flights, hotels, transportation, restaurants, activities, or tickets on your behalf.
Italy Advice Grounded in Real Experience
I’m Katie Portanova, founder of Truly Italy.
My relationship with Italy began in 2002 and eventually led me to live in Florence for four years. I speak Italian, am married to a Florentine, and have spent years creating intimate Tuscany experiences rooted in local relationships, cultural understanding, and a slower way of traveling.
I know that an itinerary can look perfectly reasonable on a screen and feel completely different once you account for train schedules, driving, check-in times, hills, crowds, and the energy required to keep moving.
I also know that the most memorable moments in Italy rarely come from fitting in one more attraction.
My role is not to tell you there is only one correct way to travel. It is to help you make thoughtful, practical choices based on how Italy actually works—and how you want your time there to feel.
Read more about Katie and Stefano’s story.
What Truly Italy Guests Say About Katie’s Guidance
Frequently Asked Questions
Can you help with destinations outside Tuscany?
Yes. Tuscany is my deepest area of expertise, but I can also help you think through the structure, route, pacing, and practical flow of a broader Italy itinerary. Share your planned destinations in the request form, and I’ll confirm whether the session is a good fit.
Do I need to have a complete itinerary already?
No. You can bring a draft itinerary, a rough list of destinations, or several ideas you are struggling to organize. The more you can tell me about your dates, priorities, and questions beforehand, the more focused our session can be.
Will you book hotels, transportation, restaurants, or activities for me?
No. This is a guidance and itinerary-review service. I will help you make clearer decisions and may share useful suggestions or resources, but you remain responsible for researching availability and making all reservations and purchases.
Can my travel companion join the call?
Yes. A travel companion who is part of the same trip is welcome to join the Google Meet.
What should I send before the session?
Please send any draft itinerary, planning notes, confirmed reservations, or list of destinations you are considering. I’ll also ask about your priorities, travel style, and the decisions you most need help making.
How soon will I receive my recap?
You will receive a short written recap within a few days of the session. It will summarize our main decisions, suggestions, and any helpful links discussed during the call.
What if I have a question after our call?
One brief follow-up email for clarification is included and must be sent within seven days of the session. It is intended to clarify something we discussed rather than review a newly rebuilt itinerary.
What if I need more than a one-hour session?
If your trip requires a complete multi-stop itinerary rather than focused guidance, I may recommend a more extensive planning service after reviewing your request. I will let you know before you book this session if I do not believe 60 minutes will provide the help you need.
Is the session refundable or transferable?
Payment is non-refundable. If you have a scheduling conflict, your session may be rescheduled for another available time.
You Don’t Need More Tabs.
You Need a Trip You Trust.
There will always be another beautiful town, another restaurant recommendation, and another person insisting that something is unmissable.
The goal is not to fit all of Italy into one trip.
The goal is to make the time you have feel meaningful—and to arrive with a plan spacious enough to let Italy surprise you.
If you are ready to stop second-guessing your itinerary, request a Slow Italy Trip Planning Session below.