ITALY TRIP PLANNING SERVICES —
Built Around You, Not an Italy Map
Professional Italy Trip Planning Services • Fee-Only & Milan-Based
and planned personally – for your specific Italy, not a template.
You're not here because you don't know how to plan a trip.
— you're here because this trip matters too much to get wrong.
For most people reading this, there’s something attached to this trip. An anniversary, a milestone birthday, a long-postponed dream. That’s exactly why it matters too much to get wrong.
The hours you spend planning Italy aren’t spent daydreaming. They’re spent on the visible decisions — where to stay, how to move, what to see. The invisible ones are what self-planned trips get wrong.
The details that derail are rarely the obvious ones. The pacing that exhausts. The routing that looks logical on a map and breaks down on the ground. The ZTL zone nobody mentioned. The second Florence station nobody told you about.
And for many travellers, Italy planning quietly becomes a second job. The tabs, the shortlists, the itineraries that are almost right but never quite — until the research stops returning useful answers.
That’s where I come in. As a professional Italy travel advisor based in Milan, offering Italy trip planning services personally, with no reason to recommend anything other than the right thing for your specific Italy.
100+
Trips Planned for Families and Couples
Fee-only
No commission, ever
In House
No Middlemen
Milan
Based in Italy
Where your Italy trip takes shape
Five things I handle
— so you don't have to think about them.
Every Italy trip planning service below is handled by me directly — not outsourced, not templated, not passed to a third party. Available as part of the Essential or Signature plan.
Italy Travel Consultation
Every trip starts with a conversation. Before anything is planned, I listen — the dates, the feeling you’re after, the shape of your perfect Italian day. Then I bring what the research won’t show you: what’s actually possible, what’s seasonal, what the route needs to work.
Accommodation & Italy Travel Advice
Where you stay changes everything. Not just the room — the surroundings, the neighbourhood, the feeling you wake up to. I don’t send you a list to scroll through.
For each location on your itinerary, I send you three properties, each carefully chosen for your trip, your occasion, and the Italy you’re trying to experience. Not options to compare. A shortlist where every property already belongs.
I handle ZTL access, direct availability, and cancellation terms, and whether the property actually matches the feeling you described in our first conversation, not just the budget and the star rating.
Logistics & Italy Transportation Planning
Italy doesn’t move the same way everywhere. What works for the cities doesn’t work for the countryside. What works for the countryside doesn’t work for the coast, the islands, or the mountains.
I plan each leg of your trip around the terrain – high-speed rail where it makes sense, a rental car where the landscape demands it, private transfers where neither does. Every movement is chosen for where you’re actually going, not defaulted to whatever’s easiest to book.
If you drive, every ZTL zone on your route is mapped before you leave home.
Tailored Italy Tours & Activities
Italy has no shortage of experiences to book. What it has a shortage of is the right ones — the ones that require a relationship, a referral, or someone who already knows the right person in the right region.
I draw on a network built across all 20 Italian regions – private guides, producers, artisans, and access that exists outside the standard trail. You arrive expected, welcomed, and already known.
I handle every communication, every briefing, every confirmation.
Gastronomic Experiences
Food in Italy is never just food. Every table tells you something about the land it came from, and gastronomic experiences are how you get close to a region as someone who understands what shaped it.
I plan around that depth — from the family trattoria that has never needed to advertise to the Michelin-starred restaurant worth the three-month wait, and the experiences that only exist where you are: Parmigiano Reggiano in Emilia, balsamic vinegar in Modena, red oranges in Sicily. Every region has its own food story. I make sure you taste it.
I handle every experience personally, communicate dietary requirements directly, and choose every table for the region you’re in and the trip you’re on.
Why fee-only changes everything
I don't take commissions.
— that changes everything.
A commission-based agent recommends what earns them the most. I can’t and don’t. Every hotel, guide, and experience I recommend is chosen purely on quality and fit for your specific trip. You see the net cost of every item. No markups, no hidden margins, no reason to recommend anything other than the right thing.
What clients say
In their own words.
“Even while we were travelling, Vanya talked to us on most days to adjust plans as needed. We will use her every time we go to Italy.”
M. Gollan
One month, family trip · Australia · Signature plan
“She rescheduled a missed Colosseum visit on the spot. From Venice to Naples, every detail was handled.”
K. Sutherland
Venice to Naples · Australia · Signature plan
“Attention to detail and ease of use of the itinerary made it possible for us to have a completely relaxed family holiday.”
L. Burke.
14 Days, family trip · Ireland · Signature plan
“Suggested unique itineraries and attractions we would never have discovered on our own.”
D. Reeks
Milan, Lake Como, Verona · UK · Signature plan
Planning fees — flat, transparent, all-in
The right level of planning
— for your specific trip.
Every Italy trip planning service is fee-only. One flat fee. No markups on hotels, guides, or transport. What you see is what you pay.
Essential Italy Trip Planning
For travellers with a direction but gaps to fill. Three services, chosen by you.
€450 flat fee
Signature Italy Trip Planning
Complete end-to-end planning, from first conversation to return home. Every detail handled personally. Built for the trips that mark something.
€2500 10 days/up to 6 travellers
✓ Real-time in-trip support
✓ Accommodation research & booking
✓ All tours, guides & experiences
✓ Transport & ZTL logistics
✓ Unlimited revisions
✓ Itemised cost breakdown
Immersive Italy Trip Planning
Everything in Signature, built for larger groups and multi-generational families.
Contact us for custom quote
✓ Group flow & pace consultation
✓ Multi-room & group transport
✓ Large-table reservations (6+)
✓ Private event & milestone support
✓ One central contact for the group
Your Italy itinerary — one document
Every Signature Italy trip planning service includes a single digital document with everything in it — available offline, no hunting through emails, no separate booking confirmations. One file. Complete before you leave home.
Stay & Sightseeing
Movement & Logistics
Dining & Support
The first conversation is free.
— no commitment, no packages, just your trip.
If you have questions about the planning process or the fee model before we speak, the planning process and Italy Travel FAQ are there. But the fastest way to know if this is right for your trip is a conversation.
A few things worth knowing
— before we speak.
Do you plan trips for specific occasions like anniversaries or milestone birthdays?
Yes, and for most of my clients, the occasion is exactly where the planning starts. A 25th anniversary, a 50th birthday, a retirement trip long postponed. These aren’t just context for the itinerary, they shape every decision in it. The hotel, the pacing, the signature dinner, the moment that marks the day itself.
My Italy trip planning services are built around the occasion from the first conversation. Not as an add-on. As the reason the trip exists.
What makes your recommendations different from what I'd find myself?
The honest answer is: sometimes calibration, sometimes access, often both.
For most hotels, restaurants, and experiences, the difference isn’t that I found something you couldn’t. It’s that I know whether it’s actually right for your specific trip, your occasion, and the pace you’re after. A hotel can be highly rated and still wrong for you or your special occasion. A food tour can be well-reviewed and still not right for a family with an eleven-year-old and a teenager.
But some things genuinely aren’t findable. After-hours access to the Last Supper. Private tours of Palladian villas that don’t take public bookings. Producers and artisans I’ve met directly, who work through a relationship rather than a booking platform. That network takes years to build and keeps expanding. I meet suppliers directly and continuously, specifically so my clients reach places and people that don’t appear in any search result.
Can you plan Italy for multigenerational families and mixed-age groups?
Yes, and it’s one of the most rewarding trips to design well.
The challenge with multigenerational Italy travel isn’t finding things to do. It’s building a trip where a six-year-old and a seventeen-year-old are both genuinely engaged, where grandparents can pace themselves without the trip feeling compromised, and where the parents in the middle aren’t managing logistics instead of enjoying Italy.
I’ve planned multigenerational family holidays across Italy — from lake-based trips in the north designed around mixed activity levels, to itineraries that built specific moments around individual family members. A private guided tour of Bologna built around a daughter who had just graduated in criminal justice. A Via Ferrata in the Dolomites that worked for a family of eight with children spanning nine to twenty-two. A pizza class in Naples for children aged six to eleven.
The itinerary works when every person in the group has at least one moment that was built for them specifically. That’s what I plan for.
What happens if something goes wrong while we're in Italy?
I stay available throughout your trip, directly reachable for anything that comes up on the ground.
If something doesn’t go as planned, I deal with it. The Signature plan includes real-time in-trip support specifically because Italy — however well planned — is still Italy. Trains run late. Weather changes a coastal itinerary overnight. What changes with proper planning isn’t whether things occasionally go wrong. It’s whether you’re dealing with it alone in a town where nobody speaks English, or sending one message to someone who already knows your trip, your itinerary, and exactly who to call.
"Messaged her numerous times for help and she rescued us every time. We showed up late for our check-in — after posted hours. She tracked the person down and arranged for us to get checked in. Without her I think we'd have been out on the street."
— L. Dietrich · USA · Signature plan
How far in advance should I contact you?
As early as possible, and earlier than you think.
The experiences and properties that define a well-planned Italy trip book out months in advance. After-hours access to the Last Supper, the right private guide for a specific region, a restaurant worth protecting, these aren’t available on short notice. High season in particular closes options quickly, and the best ones go first.
For a Signature plan, I recommend reaching out at least five to six months before your travel dates. For milestone trips — an anniversary, a significant birthday, a once-in-a-lifetime itinerary — six to twelve months gives the planning the space it deserves.
That said, if your dates are closer than that, reach out anyway. I’ll tell you honestly what’s possible.
Want to go deeper
— before we speak.
• Why a Slow Travel Italy Itinerary is the Secret to Seeing More — the pacing logic behind every itinerary I build, and why moving less means experiencing more.
• Tailor-Made Trips to Italy: What They Are, What They Cost, and How to Plan One — real client cases, real numbers, and what the difference between a planned and self-planned Italy trip actually looks like.
• Custom Italy Itineraries for Families and Couples Beyond the One-Time Consultation – the difference between paying for Italy travel advice and having someone take full ownership of your trip from first call to return home.
Ready When You are
Ready to Plan Your Italy?
Let's Talk
The first conversation is free. No packages, no pressure – just a real discussion about your Italy trip planning and whether I am the right fit for each other.