Here’s how most people are told to see Italy: Rome, Florence, Venice, maybe Milan. Ten days. Trains in between. Everything ticked off so you can say you’ve “done” Italy.
And it works, in a sense. You’ll see the sites. You’ll come home with your phone full of photos. But you’ll also come home exhausted — genuinely needing a vacation from your vacation — having spent a good portion of your trip in train stations, dragging a suitcase across cobblestones, checking into a fourth hotel, standing in line in the heat, with barely any time to breathe.
Sure, you’ll see a great deal of Italy, but you’ll end up not knowing if you really got to FEEL Italy.
So, you’ll inevitably want to book another trip — this time to make sure you truly feel the Italian experience — but you quickly find out that all the research leaves you overwhelmed trying to find places that aren’t tourist traps, deciding where to go when there’s too much to choose from, searching for a way to balance relaxation with seeing everything, and the constant stress of logistics and figuring out the best way to make it to your next destination.
This is the planning fatigue that nobody warns you about.
And it’s not solved by a better itinerary — it’s solved by travelling differently.
These are the 7 things that changed how we travel Italy:
1. Planning a trip around a bucket list.
We’ve both done the famous things — even Giovanni, who’s Italian, has stood in the same piazzas as every visitor before him. We took the photos, checked off the icons, and came home able to say little beyond the fact that we’d been there.
What we actually remembered were the locals we met along the way, and the friends and family we visited. Lasting memories don’t come from a bucket list. They come from an experience with the people who connect you to a place.
2. Stay longer than the guidebook says to
A guidebook gives a place half a day. Stay a week, and something shifts: the bartender knows your order, you notice which restaurant always needs a reservation, and you stop navigating and start being part of the thread of local life.
Choose wisely, though — stay somewhere too quiet, without enough going on, and you won’t have a great experience either. There’s a balance between immersion and access.
3. An agriturismo isn’t the dream base people make it out to be
They photograph beautifully, and we build genuine agriturismo experiences into our tours — but as a base for an entire trip, they have real drawbacks nobody mentions. You’re out in the countryside, cut off from town, so you never get a real feel for local life. And because Italian law requires them to serve mostly what they produce, you’re eating a lovely but narrow menu, night after night, with no other options nearby.
4.Visiting places that aren’t on everyone’s radar.
Abruzzo. Umbria. Le Marche. Puglia. The Veneto beyond Venice. Every one of these regions gets introduced to visitors the same way — as “the next Tuscany,” the undiscovered Tuscany, Tuscany without the crowds.
It’s meant as a compliment, and it does them no favors. It asks a region to justify itself against somewhere else instead of being understood on its own terms.
Each region has their own grape varieties, their own pasta shapes, their own dialects and festivals and reasons for existing. They aren’t a substitute for anywhere and they deserve to be fully celebrated for their unique culture and culinary identities.
These are the places that ooze the essence of what everyone says when they say they want to experience the real Italy and that’s exactly why we have done the leg work to craft itineraries in these regions – so that you can have a truly authentic Italian experience without the crowds but all the things that drawn people to Italy trip after trip.
Not sure which places are worth your time or not? Click here to grab our curated Guide to Italy’s Best Hidden Gems.
5. Eat in season
It sounds like a small thing. It isn’t. A tomato in August tastes like something you’ll remember for years. The same tomato in February is a different object entirely. It’s not just tomatoes — it’s everything on the table, which means the same region can give you a completely different experience depending on when you arrive.
Spring brings artichokes, asparagus, strawberries, fava beans, wild greens, and the first cherries. Autumn brings grapes, chestnuts, truffles, pumpkin, and the olive harvest — which is exactly what you’ll experience if you join us in Abruzzo for the October departure of Italy’s Epicurean Journey, while the olive mill is actually running. It’s the one time of year you get to taste olio nuovo, the new oil, fresh off the press — green, peppery, still a little cloudy. A sensory experience you won’t forget.
6. Let the tasting menu do the talking
Ordering a fixed tasting menu with no choices, or being welcomed into a family home where they simply bring out what they’ve made, is the easiest way to expand your palate. Often you’ll be served something you would never have ordered yourself — but that’s the beauty of going in blind. You discover new favorite dishes, and wines you were sure you wouldn’t like.
This is the beauty of travel because it opens your eyes and mind to culinary traditions that are meant to be experienced in the place they originated from.
These are the culinary experiences that, no matter how hard you try, you simply cannot replicate at home.
7. Realising the train isn’t the answer.
Everyone will tell you the train is the best way to see Italy. It is — if you’re going to the big cities, which is to say the most populated places, where most of the tourists already are.
The Italy people actually dream about is the other one: the enclaves where the cuisine and culture haven’t bent themselves to visitor expectations, because the crowds don’t really turn up there. Those places aren’t on the line. At minimum, you need a car — and enough of the language to get by.
The one thing that changes everything
But there is a part nobody says out loud: even if you follow all seven of these tips, there’s one thing that changes a trip more than anything else: having someone on the inside to translate the Italian experience. It’s the real door-opener — the difference between eating at an agriturismo and being welcomed into one.
As it is our job to travel throughout Italy, we come across this constantly when we travel. People who’ve been in Italy two weeks, sometimes a month — occasionally on their fifth trip to the country — and once they learn Giovanni is Italian and that we live here, the questions start rolling in. What should I order here? Is it rude if I…? What is this, exactly?
They’re not lost. They’re just unsure — because Italy isn’t one culture. Each region is closer to its own country, and understanding that takes more than a yearly trip. Which is why becoming regional experts mean visiting, having genuine locals connections, and living throughout the entire country, not just one big city or one main region.
It’s exactly why Forbes called us the “perfect guides to translate the Italian experience.” Because we personally craft each tour from the ground up from our local connections crafted from years of living and traveling the country, in addition to have lived abroad. What’s why you get the best of both worlds, two tour hosts that understand your culture and the local culture in a way that we seamlessly translate so that you get to live like a local and leave Italy having uncovered it’s stories.
Which is also why we host every single tour ourselves and keep our groups small — just twelve guests. To ensure you get to interact with the locals one-on-one, get your questions answered and have an immersive travel experience where you feel like you’re traveling with friends instead of feeling like just another tourist following a tour guide with a waving umbrella through crowded monuments and long lineups. When you tour with us you’ll return rest, fulfilled and deeply grateful for every unhurried moment we’ve planned into our itineraries.
Best Italy tours by region
Instead one grand tour of Italy, we run four small-group, personally hosted itineraries — each built around one to two regions so you actually experience it, rather than pass through it. Making them the Best Italy Tours to experience every region we take you to:
- Umbria Undiscovered — learn to cook with an Italian mamma on an award-winning organic olive oil farm, visit family-run wine cellars, and the first Regenerative Organic Agriculture (ROA) certified pasta producer in Italy. Based in Gubbio, the town known as the Most Beautiful Medieval City in Umbria.
- Italy’s Epicurean Journey — Le Marche (region where Giovanni grew up in and where we were married) and Abruzzo in September and October, including the first-pressing olive mill experience in Abruzzo (October only) and truffle hunting in Le Marche’s hinterlands.
- Passport to Puglia — Giovanni’s family region, running in both April and October. On this trip you’ll experience Puglia at the best time of year to escape the crowds and enjoy the creamiest burrata you’ll ever sink your teeth into.
- Northern Italian Delights — the Veneto beyond Venice: Prosecco hills, Palladian villas, an artisanal grappa distillery, cooking with a talented chef in his family home and a multigenerational organic cheesemaker, based in Castelfranco Veneto.
Every tour is capped at twelve guests and hosted personally by the two of us on every departure.
See all available dates by clicking here
Frequently asked questions
A grand tour typically covers multiple major cities (most which are subject to the negative impacts of over tourism) — Rome, Florence, Venice, Milan — in a short window, with heavy travel time between stops. A regional tour stays in one area long enough to actually settle into it, trading breadth for depth. Our tours concentrating on the quality of the experiences over quantity and focus on supporting local small business and not big chain hospitality conglomerates.
Tours built around regions outside the standard circuit — Umbria, Le Marche, Abruzzo, Puglia, and the Veneto beyond Venice — tend to avoid the crowds that concentrate in Rome, Florence, and Venice, while still delivering the food, wine, and culture people associate with “real” Italy. However, it’s very important to choose a regional tour that doesn’t stay in a location that is isolated like a typical farm house or you’ll feel cut off during your free time. This is exactly why all of our tours choose locations that are either in the historic center are close to all the amenities of a town where the local life is vibrant. Too small and you’ll also feel like an outsider, which is something else to consider when choosing the right trip. Not sure what is the best Italy tour for avoiding the crowds? Click here to take our quiz!
Are small-group Italy tours better than large tour groups?
Smaller groups generally allow for more access — family homes, working olive mills, and multigenerational producers rarely host large groups — and make personal hosting by people who actually live in the region possible. When you travel with large groups you won’t necessarily be able to reach these places as not only can they not accommodate big groups, the coach buses can’t reach there and you don’t have the chance for 1:1 time with the culinary keepers and cultural experts in the area. Meaning large groups can give you a lot of see in a concentrated amount of time, but it is very surface level and doesn’t offer the type of experience that results in connecting with locals and memories that last a lifetime.
It depends on what you want to eat and see. Spring (artichokes, asparagus, fava beans, wild greens) and autumn (truffles, the olive harvest, grape harvest) each offer a distinct seasonal experience — for example, the olive mill experience in Abruzzo is only available during the October harvest. And truffle hunting (not simulated truffle experiences) are only available during select months when truffle are in season and foraging for them is permitted. Each of our tours have taken into account the best cuisine, the crowd variability, and the seasonal experiences, which is why we only offer a few set-date departures per year for each tour.
The Italian On Tour® hosts small-group, personally guided journeys through Umbria, Le Marche, Abruzzo, Puglia, and the Veneto — capped at twelve guests, hosted by us on every departure.
