Your personalized day by day Italy itinerary
You have been thinking about this trip for a while. Maybe it is a milestone — an anniversary, a first trip with your mother, the one you kept saying you would take when the time was right. You have a rough sense of where you want to go: Tuscany and the Amalfi Coast, or the lakes and the Dolomites, maybe a long loop through Puglia and Sicily.
You have looked at hotels, trains and tours. But the more you research, the harder it gets to turn all of it into something that comes together as a plan in the right order, the right number of nights, and the connections that make sense.
Our itinerary planning service takes the whole thing off your hands. You tell us what matters, we design your complete day-by-day plan from scratch: the route, transport, accommodation, restaurants, and experiences, all chosen for the way you want to travel.
Within 10 business days of your kickoff call, your draft itinerary arrives for you to review. We will then refine based on your feedback. The final itinerary is sent as a handy app and/or PDF file. And you have a direct contact number for our bilingual team throughout your trip, in case emergencies come up on the ground.
Italy Itinerary Planning • $1,250 USD
Have questions? Email us – trips@untolditaly.com
THE BEST CURATED ADVENTURE
THE BEST! If you want a curated Italian adventure, this is your solution. We hired Tyla and the Untold Italy crew to put together our itinerary through Tuscany. We had the vacation of a lifetime! – Jamey I.
WHY TRAVELERS HIRE US
You know what you want from this trip. A winery in Tuscany. A few days on the Amalfi Coast. Time in Rome without spending the whole trip in a queue. Maybe a cooking class, a night somewhere quieter than the main towns, a train journey that connects seamlessly. You have been researching for weeks. You might already have some hotels booked and a rough route sketched out.
But the questions keep piling up. Should you base yourself in Sorrento or work down the coast stop by stop? Is five nights in Tuscany enough, or would three do the same job? Train to Florence or keep the car? Should Naples be on the route at all, or does it eat two days you do not have? These are not questions a travel blog or Reddit thread can answer. They depend on the style of your trip, the pace you travel at, who you are traveling with, and what matters most when something has to give.
That is what our Italy specialists bring. Decades of on-the-ground experience across every region of Italy, a trusted network of local contacts, and the judgment that only comes from having planned hundreds of real trips for real people. It is the Italy that not only looks good on paper but works the way you wanted it to when you are there.
ITALY ITINERARY PLANNING – how it works
• Book and share your trip details. Tell us your dates, who is traveling, where you are thinking of going, and what matters most to you. We read everything before the call so we hit the ground running from the first minute.
• Talk it through with your Italy specialist. Your kickoff call is where we get the full picture — your travel pace, the things that are non-negotiable, the decisions you have already made, and the ones you want us to make for you. The more we know, the better the plan.
• We build your itinerary. This is where we do the work. Route, daily flow, transport connections, accommodation picks, restaurants worth booking ahead, and experiences chosen for the way you travel. Your draft day-by-day plan arrives within 10 business days for you to review and start making bookings.
• Review and refine. Two rounds of revisions to get the plan right. If something needs adjusting — the pace, a destination, a hotel — we work through it with you.
• Final plan. You receive your final day-by-day Italy itinerary in PDF and/or app format. This includes all your booking details – flights, hotels, activities, restaurants – so you have everything in the one place.
• Travel knowing our team has your back. You have a direct contact number for our bilingual team throughout your trip. Not a chatbot. Not an email address. A real person who knows your itinerary, in case anything comes up on the ground.
THOUGHT OF EVERYTHING
The travel professionals at Untold Italy thought of everything when assisting me with my trip to Italy. We cannot thank them enough for their willingness to answer questions, offer options and even assist during our trip when we had questions. – MaryAnn B. – Google review
ITALY ITINERARY PLANNING – summary of deliverables
- A kickoff call with your Italy specialist to map out your trip together
- A complete day-by-day itinerary delivered as a detailed PDF within seven business days — structured from arrival to departure, built to travel with you
- Every confirmed booking included with full details: confirmation numbers, meeting points, check-in times, and anything you need to know before you arrive
- Transport guidance with specific trains, drive times, and transfer details for every move between stops
- Restaurant picks with context — specialties they are known for, when to book ahead, and why we chose them
- Destination introductions and practical tips woven through each day so nothing catches you off guard
- Two review calls to refine the plan before you travel
- A direct phone number for our team in Italy throughout your trip, in case of emergencies while you are in Italy
- Complimentary premium access to the Untold Italy app — practical travel tips, an audio phrasebook, gelato recommendations across Italy, and more
decades of combined italy travel planning expertise
Our team does not just visit Italy. We live it.
Untold Italy trip consultants know Italy from top to toe. We live, travel and work across multiple Italian regions and maintain real relationships with local contacts — built over many decades, not sourced from a directory.
We have helped thousands of travelers design trips that actually delivered, from first-timers who wanted to get it right to seasoned travelers who wanted to explore somewhere new.
Our podcast has reached millions of listeners, not because we repeat what is already online, but because we show people what makes a trip worth taking.
our team of italy experts
Want to plan a multi-generational trip, a solo adventure or rent a villa with friends in Tuscany or Puglia? We can help. Each of our Italy travel specialists has different passions – for particular places, travel styles and interests. From the best ski school in the Alps to favorite cooking classes in Tuscany and Sicily, favorite restaurants in Rome and even vintage markets in Puglia – our clients access an unparalleled depth of resources across the whole of Italy.
KATY CLARKE
Founder of Untold Italy and host of a podcast with over 5 million downloads, Katy has been traveling Italy since the 1990s and has visited more time than she can remember. She built these services on the belief that great Italy planning comes from depth of experience, not a list.
OLIVIA WINDSOR
An Australian living in Italy for five years (Turin and Rome), Olivia specializes in Rome, Tuscany, Piedmont, Umbria, Sicily, and Puglia, with a particular focus on food experiences and Italian wine. She is also the consultant to speak to about traveling in Italy with a baby.
SARAH MARANO
Based in Umbria where she has run an agriturismo near Gubbio for over 15 years, Sarah specialises in Umbria, the Dolomites, and off-the-beaten-path country escapes. She is the consultant to speak to if you want to get beyond the tourist trail and connect with local people, food, and culture.
CASSANDRA TRESL
An American living in Abruzzo, Cassandra specialises in southern Italy, Puglia, Calabria, Naples, the Dolomites, and road trips, with a particular strength in family travel. She is the consultant to book if you are planning a road trip, heading south, or traveling to Italy with children.
HENNA GARRISON
Now based in Liguria after eight years living and working at a cooking school in Sicily, Henna holds a Master's degree in food and gastronomy and specialises in Sicily, Liguria, Puglia, Piedmont, Rome, Venice, and Bologna. Food and wine are at the heart of everything she plans.
CARRIE SMITH
With over 15 years of planning Italian itineraries, Carrie specialises in Tuscany, Liguria, Puglia, unique accommodation, and family and multi-generational travel. She is the consultant to book if you are traveling as a group or need a classic Italian trip done exceptionally well.
TYLA TRAIN
Having lived in Florence, Milan, and Trieste, Tyla specialises in Florence, Tuscany, Milan, Venice, the Italian Lakes, the Dolomites, and winter trips. She is the consultant to book if you are planning a classic northern or central Italy trip, or considering Italy for a skiing vacation.
KRISTEN JACKSON
Kristen specialises in Rome, Florence, Cinque Terre, Sorrento, Ischia, Lucca, and Orvieto, with a particular focus on immersive travel and solo travel. She is equally at home planning a first trip to Italy's big cities as she is helping returning visitors get further off the beaten track.
Frequently Asked Questions
Can you make bookings for us?
No. We are not travel agents. We give you specific hotel recommendations, restaurants worth reserving ahead, transport options with realistic timings, and a clear picture of what needs to be locked in before you go. You book direct, knowing exactly what you are getting and why.
Can you work to our budget?
Yes. We tailor every recommendation to your budget and priorities. Tell us what you are working with and your priorities when you book and we build from there.
How far ahead should we start?
Six months is ideal. In peak season, good hotels in popular areas fill fast, and the better restaurants book out weeks ahead. If your trip is sooner, reach out to trips@untolditaly.com and we will tell you what is possible. The later you leave it, the narrower the options on the table.
What does the itinerary cover?
The standard service covers up to 14 days, four to five destinations, and up to six travelers. It includes your complete day-by-day route, specific train options or drive times between stops, up to three hotel options per destination, restaurant picks, and experience recommendations — all chosen for your travel style and budget. Your first draft arrives within seven business days of your kickoff call.
How do the revision rounds work?
You get two rounds of revisions after your first draft arrives. Small adjustments to pacing, a hotel swap, a change to an experience — all fine within those rounds. If the route changes significantly after the plan is delivered, we will talk through what that means for scope.
We already have flights and some accommodation booked. Can you still help?
Yes. Most clients arrive with something already confirmed. We work around what you have, tell you honestly if anything does not fit, and fill in the rest.
We are worried about transport — trains, rental cars, driving in Italy.
Transport logistics is one of the most common questions we hear. The right answer depends entirely on your route. Tuscany with a car is a different trip from Tuscany without one. The Amalfi Coast by rental car in summer is a mistake most people only make once. We sort out what makes sense for your specific itinerary.
Will you be available during our trip?
Yes. You have a direct contact number for our bilingual team throughout your trip in case of emergencies. Not an email address. A real person who knows your itinerary, there if anything urgent comes up on the ground.
We have a large group or a longer trip in mind. Can you help?
Yes. Reach out to trips@untolditaly.com with the details and we will let you know what is possible. Custom pricing applies for groups beyond six travelers and trips longer than 2 weeks.
This is a milestone trip — an anniversary, a honeymoon, a once-in-a-lifetime visit. We cannot get it wrong.
Nearly a third of our clients are celebrating something significant. They want the trip to feel considered, not just efficient. We will ask what the trip needs to mean and build from there.
Are you a travel agency?
No. Untold Italy is an Italy travel planning company. Our consultants plan your trip with you. They do not make bookings on your behalf. What that means: every reservation you make stays in your control. We give you the knowledge, the itinerary, and the recommendations. You book direct, knowing exactly what you are getting and why.
Is this the right service for me?
Itinerary Planning works best when you want every detail of your trip figured out before you leave — route, transport, accommodation, restaurants, and experiences, all in one complete day-by-day plan. If you have a rough idea of where you want to go and need an expert to shape it into a plan, the Trip Consultation is a better fit. If you only have one or two specific questions, choose the Quick Fix Chat.
We are returning visitors. Italy is not new to us. Can you still add value?
Often our most interesting calls are with people who already love Italy and know what they do not know. They come with great questions and are ready for the version of Italy that takes a few trips to find. Returning visitors make up roughly half our bookings, and we love sharing a mutual passion for Italy.
Can I reschedule my call?
Yes. Reach out to your consultant directly and they will find another time that works.
What do you need from us before the call?
You fill in a short form when you book: who is traveling, rough destinations, dates, interests, and what is on your mind. The more specific you are, the better the call will be. Write down the questions you are stuck on. If you have a draft itinerary, share it. We read everything before we speak to you.
Can I pay in my own currency?
Our services are priced in US dollars. We also accept Australian dollars, New Zealand dollars, Canadian dollars, British pounds, and Euros. Email trips@untolditaly.com for a quote in your currency.
I have more questions before I book.
Email us at trips@untolditaly.com and we will get back to you.
Client Feedback
Thank you! Now excited about our Italy vacation
I just did a 1hr consult with Untold Italy and it was invaluable! I recommend it highly! I went from completely overwhelmed to having a solid plan and booking.
Wonderful time in Italy
Thank you so much for your help with our trip to Italy.. I thoroughly enjoyed our time in Italy and the lovely hotels you suggested helped tremendously. We loved them all. The views from the terraces, the breakfasts, the position, the service, all great!
