Hiring a travel designer is an investment — in your time, experience, and peace of mind. A travel advisor builds a network of trustworthy suppliers and partners so that clients can benefit and travel with ease only thinking about relaxing and enjoying.
But how do you know if the person you’re hiring is the right fit for your trip?
The truth is, not every travel planner works the same way. Some focus on luxury hotels, others on immersive cultural experiences, others on logistics only.
To help you find the right match — and get the most from your investment — here are ten smart questions to ask when you hire a travel designer in Italy.
What’s Your Process for Designing a Trip?
A professional travel designer should have a clear, structured process — from consultation to delivery.
Ask how they start:
- Do they begin with a call or a questionnaire?
- Do they share a proposal before finalizing?
- Will they handle bookings, or just design the itinerary?
Knowing this upfront helps you understand what’s included — and how involved you’ll need to be. When I work with clients, I always start with a Discovery Call to understand travel goals, timeline, and budget. From there, I create a personalized itinerary that fits how you want to experience Italy.
How Do You Personalize Each Itinerary?
Every traveler is different — and so should be every itinerary.
Ask how your designer tailors their recommendations.
- Do they use a standard template or build everything from scratch?
- Do they take the time to ask you questions about your lifestyle, passions, and priorities?
A good answer will mention adapting to your interests, travel pace, and personality.
Example: I tailor itineraries based on whether you’re traveling for food, art, history, or slow exploration — not just based on where you “should go” or where the “must-sees” are.
What’s included in the design fee?
Transparency matters.
You want to know what your investment covers — and what it doesn’t.
Ask:
- Does the fee include hotel or tour bookings?
- Are there extra costs for revisions?
- Is ongoing support included?
My fee for the custom itineraries covers all research, itinerary design, custom mapping, logistics, and travel support before and during your trip. You pay suppliers directly — no hidden markups.
If you’d rather have me design your itinerary as well as book everything for you, I will deliver a full package in which I clearly state what’s included and what not.
How familiar are you with the regions I want to visit?
Italy is incredibly diverse — each region has its own rhythm, cuisine, and travel challenges.
If your designer hasn’t been to the places you’re visiting, you may not get the nuance you need.
Ask where they’ve personally traveled or lived in Italy and which regions they specialize in.
I’m aware that with the huge amount of online content and AI, many plan their trips without knowing a place. This can be possible if they rely on trustworthy sources, but will the trip feel personal?
As someone who’s lived in Rome and traveled extensively across Italy — from Puglia to the Dolomites — I draw on firsthand experience when crafting routes and experiences.
Do you work with local partners or global suppliers?
This question reveals a lot about the authenticity of your trip.
Local connections mean access to smaller, high-quality experiences — private vineyard tastings, artisan workshops, countryside stays.
Ask who your designer partners with and how they vet local providers.
I collaborate with local guides, small family-owned hotels, and regional experts who share my values of responsible, meaningful travel. Being a guest of an authentic workshop, wine cave, or vineyard as opposed to visiting where everything is prepared for the tourist changes the whole experience of a trip.
How do you choose hotels and experiences?
Hotels and experiences set the tone for your entire trip.
Ask what criteria your designer uses — price, sustainability, comfort, or authenticity.
A professional will match your personality and expectations with properties and activities that make sense — not just what looks nice online.
I personally review each hotel I recommend, and every activity I include has been vetted for quality, ethics, and local impact.
Of course, even if I pick rural accommodations such as an agriturismo, I choose those that feature all the necessary facilities for a comfortable stay. But I’m careful to match a place with the travelers’ personality.
This is why I usually design tours for cities and regions I personally know.
What kind of support do you offer during the trip?
Even the best plans can face surprises — delayed trains, weather shifts, or last-minute closures.
Ask if your designer will be available for support during the trip.
Some offer limited help after the itinerary is delivered. Others, like me, stay available to assist with adjustments or recommendations while you travel.
Is the restaurant you wanted to go is closed? Are you leaving earlier than expected and have time for an archaeological site or town visit on the way? During your trip, I’m easy to reach via email and WhatsApp.
It’s the difference between feeling guided and feeling on your own.
How many revisions are included?
Designing the perfect itinerary can take a few tweaks.
Ask how many rounds of edits are included — and whether they’re collaborative.
I typically include one full revision round after presenting your draft itinerary, plus smaller adjustments to fine-tune details.
The goal is to create a plan that feels exactly right, and I won’t stop until you are happy with the result.
What makes you different from a travel agent?
What makes you different from a travel agent?
This is key — because “travel designer” isn’t just a new label for “travel agent.”
A travel designer creates custom experiences based on your goals and personality. A travel agent typically sells pre-packaged trips or focuses on booking logistics.
The difference? Intentional design vs. transactional planning.
As a travel designer, I don’t sell destinations — I craft journeys built around your story. And since I know the areas I include in my itineraries, I can give first-hand advice and informed suggestions.
How do you measure success?
This one’s simple but powerful and not so easy to answer.
Ask how they define a “successful trip.” If they talk about smooth logistics or five-star hotels only — they’re missing the point.
A great designer measures success by how the trip made you feel: connected, inspired, and at ease.
That’s the goal behind every itinerary I create — a trip that feels deeply you. A trip that makes you feel regenerated and changed, rather than ticking off a bucket list.
Bonus tip: Notice how you feel when you talk to them
Hiring a travel designer is personal.
You’re trusting them with your time, your memories, and your budget. You are relying on them to make the most of your leisure time, a moment you need to relax and rejuvenate before getting back to your work routine.
Do you feel understood? Heard? Excited? If yes, that’s your sign you’ve found the right one.
Hiring a travel designer in Italy isn’t just about convenience — it’s about creating a trip that feels intentional, authentic, and effortless.
Asking the right questions helps you find someone who truly understands your needs — and knows Italy well enough to make it all come alive.
If that’s what you’re looking for, I’d love to help you plan your trip.
