You’ve been thinking about Italy for a while. Maybe you have a stack of saved posts, a spreadsheet, and several versions of the same itinerary. The more you research, the harder it gets to decide what belongs in the trip.
That’s often when people start looking for a travel agent for Italy. They want someone who knows the country and can help them make sense of all the possibilities.
I’ve spent more than 35 years traveling in Italy. I split my time between the U.S. and my home in Lucca, Tuscany, and I plan custom trips for people who want to experience more than a list of famous sights. Here are a few things I’d ask before choosing someone to help plan yours.
Travel agent or travel advisor? Ask what they’ll do for you
You’ll see both “travel agent” and “travel advisor.” People use the titles in different ways, so I wouldn’t choose someone based on the label alone.
Ask how they work. Do they book hotels and tours you’ve already chosen? Do they help you decide which regions fit your interests, how many places to stay, and how to make the days flow? Do they plan the trip with you, or mainly handle reservations?
There’s no single right answer. You may need help with a few bookings, or you may want someone to shape the whole trip. If you’re looking for a custom travel agent, ask how your interests and pace will shape the itinerary. Be clear about what you’re looking for, and make sure their service matches.
Look for someone who really knows Italy
Italy is 20 regions, each with its own food, character, and pace. The right place for someone who loves food and wine may be different from the right place for someone who wants to hike or spend time by the sea.
Ask a potential advisor about the regions you’re considering. Ask when they were last there and how they decide which places and properties to recommend. You want someone who can explain why a particular place suits your trip, not just send you a list of popular hotels.
I also think it matters that an advisor knows what not to recommend. I’ve walked into hotels and restaurants that looked right online and decided they weren’t a fit. That kind of firsthand judgment is part of planning, too.
Ask what they can arrange that you can’t find online
Most of what you find online is available to everyone. That’s why the same restaurants, tours, and towns appear on every list, and why so many Italy trips start to look alike.
Some of the most memorable experiences in Italy don’t advertise at all. A small wine estate that welcomes guests by introduction. An artisan’s workshop that isn’t open to the public. A table held because someone called ahead. You won’t find these by searching, and not every travel advisor can arrange them.
That kind of access comes from relationships built over years, not from a booking system. There’s a difference between having a contact and having a relationship.
So ask: what’s something you’ve arranged for a client that they couldn’t have booked on their own? A specific answer tells you a lot. A vague one does too.
Ask how they would start planning your trip
Ask: “How would you start planning my trip?”
Listen for whether they’re curious about you. How do you like to spend a morning? What makes a day feel good? Are you passionate about food and wine, art and history, being outdoors, or do you want to feel like a local? Those answers should shape the itinerary.
I start with the traveler, then we talk about places. That’s the thinking behind my S.L.O.W. approach:
- Select a region that fits your travel style, rather than choosing only by name recognition.
- Limit the number of stops. One or two home bases in a week mean less time packing and moving, and more time to experience Italy.
- Opt for a place to stay that suits the trip, whether that’s an agriturismo, a small hotel, or something else.
- Weave in everyday Italy: a cappuccino in the morning, the passeggiata in the early evening, or simply lingering at a cafe in a piazza watching the world go by.
The right number of stops depends on the trip, but six cities in ten days can leave you spending a lot of time packing and moving. A good advisor should be able to talk that through with you, even if it means changing the itinerary you first imagined.
Ask how the travel agent is paid
It’s completely reasonable to ask about fees at the beginning. A good advisor should explain what’s included and what you’ll pay before you decide to move forward.
Travel agents may earn commission from hotels and other suppliers they book. Some Italy specialists also charge a planning or design fee for the time they spend creating a custom trip. Fee structures vary, so ask what applies to the service you’re considering.
My first conversation with you is complimentary. We can talk about the trip you have in mind and whether my planning service is suited to your needs. Before any planning begins, I’ll explain the fee, what it includes, and how the process works. You can find more details on my services page.
The trips I plan typically start at around €1,000 per person per day, and most are 10 to 12 nights. If you have questions about the investment or what’s included, we can talk them through in that first conversation.
Ask who you can reach while you’re in Italy
Things don’t always go as planned while you’re traveling. A train strike or canceled ferry can change your plans. You might feel unwell, have trouble finding your way in a rental car, or arrive to a room that isn’t what you expected. Ask what kind of support is included, who you’ll contact, and when they’re available.
When I plan your trip, you’ll have an assigned local concierge who stays in touch on WhatsApp throughout the trip. Someone is on the ground in Italy and available to help, whether you need a last-minute restaurant reservation or support with something more serious.
When you may not need a travel agent for Italy
Not everyone needs help planning Italy. If you’re going for about a week, want to see the major cities, and enjoy doing the research, you may be happy planning it yourself. The same may be true if you’re looking for a simple trip and would rather put your budget toward the travel itself.
Where I often see people get stuck is a trip they’ve been imagining for years: an anniversary, a retirement, or a family trip. They’ve spent months researching, but still aren’t sure what to choose or how to fit it all together.
A trip like this is a meaningful investment of money, time, and anticipation. I believe in taking care of that investment by planning around what matters to you, so the trip reflects what you hoped it would be.
That’s a good time to consider asking for help. Not because you can’t plan it yourself, but because you may want someone alongside you to sort through the decisions.
What working with me looks like
- You fill out my inquiry form and tell me what you’re picturing.
- We have a complimentary video call to talk about your travel style and whether my approach is the right fit for you.
- I’ll explain the planning fee, what it includes, and what the planning process looks like. Then you can decide whether you’d like to move forward.
- I design your trip, region by region and stay by stay, with my Italy-based team.
- We refine the plan together. Then the arrangements are booked.
- While you travel, your assigned local concierge is available to you on WhatsApp throughout the trip.
If you’ve been carrying this trip around in your head for a while, you don’t have to figure out every detail by yourself. Let’s start planning your Italy trip.
Frequently asked questions
How much does a travel agent for Italy cost?
It depends on the agent and the service. Some travel agents earn commission from bookings; some Italy specialists also charge a planning or design fee. Ask what the fee covers and how it works. I explain my planning fee before you decide whether to move ahead.
Do I need a travel agent for Italy?
Not always. A short trip to the major cities can be straightforward to plan yourself. If you’re planning a longer trip around your interests and want help with the decisions, an Italy specialist may be useful.
What’s the difference between a travel agent and a travel advisor?
The titles overlap. Ask what the person will actually do: make bookings, help design the itinerary, or both.
Can a travel advisor arrange experiences I can’t book online?
Some can. It depends on the relationships they’ve built in Italy over time. Ask for a specific example of something they’ve arranged that a client couldn’t have booked on their own.
What should I ask before hiring an Italy travel agent?
Start with these: How would you begin planning my trip? How many trips to Italy do you plan per year? When were you last in Italy, and which regions do you know well? What support can I reach while I’m there?
