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Travel To Italy Like An Insider With The Best Local Experts

I absolutely love Italy, for many different reasons. But I hate the way in which many Americans go about planning trips there. Survey after survey shows it is the number one dream destination for U.S. leisure travelers, but the way those travelers get their information and advice gives me nightmares.

Throughout the years I’ve heard people say over and over that “I was told to do this in Italy,” or “I was told not to do this in Italy.” By who? “A friend.” I have close friends who recently planned their entire 12-day trip on the basis of another couple they knew who gave them advice—after their first visit. I’ve heard of many people who skipped Rome because “we heard it was too busy, just another big city.” Or passed on Venice, one of the world’s most magical destinations, because, “I heard it was touristy.”

It goes on and on, but suffice to say, I have been to Italy in the neighborhood of two dozen times, summer and winter, for food, wine, skiing, golf, hiking, cycling and more food, from north to south and east to west and islands too, and I know a lot about Italian cuisine, but I still ask real experts for advice every time I go. I specifically ask for advice on where to eat, what to see, and who to choose as guides. And by experts, I mean people how live in Italy, specialize in particular areas of travel, and know their subject matter.

“We get multiple guests a year who want to wing it,” says Cherrye Moore, owner of My Bella Vita travel. Moore moved to Calabria two decades ago after falling in love with the region on a visit, and opened a bed and breakfast, learning about what her visitors were looking for. Her company now specializes in planning trips—especially foodie and ancestry trips—to the area in Southern Italy where many Italian Americans trace their heritage. “They say, ‘My neighbor just showed up in their family’s hometown and it went great for them,’ or, ‘Our friends went to Italy last year and said we don’t need a driver.’ It’s true that you can rent a car and drive to your family’s hometown, but that experience is vastly different from having a dedicated driver and a heritage specialist who has done research on your family’s history, who has already identified the home your grandfather was born in, and who has arranged meetings with locals upon your arrival.”

I just got back from an exploration of Turin followed by a weeklong hiking trip in surrounding Piemonte, Italy’s most prestigious wine region, which included multiple winery visits. For restaurants and guides and sightseeing in Turin I used an Italian-based travel specialist that is the choice of many of the best luxury travel agents/advisors in this country (the best travel agents are savvy enough to know what they do not know and regularly rely on local experts). For the hiking trip, I used an Italy-based active travel specialist that does nothing else, and does it with a food-centric spin. It was another fantastic Italy trip, one amazing day after another, featuring many meals, wineries and experiences I never would have found by myself, especially by asking random friends or watching You Tube influencer videos by people with far less Italy experience than myself.

“We don’t focus on stars or diamonds, we focus on really special one-of-a-kind experiences and lodging that lets you discover our Italy,” said Heather Dowd, who lives in Turin and along with her Italian husband Beppe Salerno. They run Tourissimo, the active travel company we used. We had several friends hiking with us who were on either their very first or second trip to Italy, and when we reviewed our experiences at the end for the trip, one place we stayed, an 18th century castle turned boutique hotel, was the overwhelming favorite. It did not have whirlpool tubs or Frette linens, it did not have a concierge or room service, but it had excellent food and beautiful gardens in which we had an epic dinner. It had cooking classes, a great location, a fun aperitivo evening cocktail session, and most of all, incredible charm..

It was exactly what my first timers dreamed Italy would be like, and it was a place we never would have found online. It was perfect, and even in Italy not every place is, but the reality is that Heather and Beppe and their guides spend a lot of time behind the scenes visiting small hotels and vetting them, way more time than the people who rate their stays on booking websites. One of my friends was so impressed he is already planning an extended family hiking trip to Sicily with Tourissimo next year.

If you want to have an insider experience in Italy, and see the places locals go, you need a local insider to help you out.

“Our goal is for guests to experience Calabria like we do, so we’ve built experiences that aren’t available online,” said My Bella Vita’s Moore. “Nowhere else can you find a multi-course lunch hosted at Zia Pina’s or a picnic prepared and delivered by Signora Francesca. Lunch in the home of our friend, Chef Massimo, isn’t available on Google. When creating or reviewing experiences I always think of my sister in Texas. If she were visiting, would I take her here? If that answer is yes, I know we have a winner.” That is exactly the standard by which I’d like my Italy travels to be judged.

A trip to Italy is a beautiful, special, and almost sacred experience, so don’t screw it up by taking bad advice. I do not know every local specialist—and I hope to keep finding more—but I know several experts I would recommend for different kinds of travel. Or use a good travel advisor, something I recommend for all travel (Read my article Why You Need A Travel Agent More Than Ever here at Forbes), and communicate with them to ensure they are on the same page in terms of sourcing these kinds of local experts. If they are good, they will already be familiar with several of these companies.

Active Travel

Italy has long been the dream destination of cyclists, with Tuscany atop the Bucket List for global road riding destinations. But for the past few years the fastest growing sector of cycling has been “gravel grinding,” and with hundreds of miles of its stunning unpaved “white roads,” Tuscany has also emerged as the world’s top travel spot for gravel lovers. There are also plenty of other amazing places to ride in Italy, including Piemonte, Sardinia, Puglia, the Lakes region, and many other areas. World class hiking abounds, especially the stunning Dolomites—a UNESCO World Heritage Site of beauty unmatched by most other mountain regions on earth. Beyond this there are the Alps in the east, the Cinque Terre, Sardinia, and many other great options.

Italy is so well known for cycling and hiking that every major active travel company in the world runs trips there. But for my last two active trips, one hiking and one biking, I chose a tour operator that is actually based there, founded by an Italian with a passion for cycling and food. Tourissimo may be Italian, but they cater to the American market, and founder Beppe Salerno worked for am American cycling company as a guide before realizing he could do the real Italy better himself—to me, the perfect startup rationale. Over the years since, Tourissimo has grown its library of offerings, with both with an array of scheduled group trips and private custom options. While they do mostly road riding, they are notably one of the only tour operators scheduling gravel trips, and can also arrange custom mountain biking itineraries, with years of expertise in cycling and hiking.

In addition, Tourissimo has also been a pioneer in “Active Culinary Travel,” a hot new category I have written about here at Forbes (and for other magazines and newspapers). They offer an annual series of six group rides (and a hike) each hosted by an acclaimed chef like Mary Sue Milliken, an award-winning chef, restaurateur, cookbook author (five!) and co-host of the popular PBS cooking show Two Hot Tamales. She is also an avid cyclist and has led the Tourissimo Chef Bike Tours for several years, along with other big names. These trips are a unique option for serious foodies who also ride, while the other trips cater to just about anyone. Otherwise they offer several styles of trips, from Bici Basics for new riders to Ambitious Tours for the more hard core.

Tourissimo puts a focus on local, choosing small and often historic hotels that they have curated and vetted (like the castle I just stayed at in Piemonte), places that you would never be able to distinguish from hundreds of other non-chain options online. Same for restaurants, wineries, and all the other ways they take you behind the scenes and into their real Italy. Their Mission Statement? “We don’t want to be the biggest adventure travel company. We want to design and run the best tours in Italy. We strive to be the most authentic and the most beneficial to local communities.” Fantastico!

Bike It! Bellagio offers another insider biking experience on a much different scale, providing a great one-day experience for visitors to Italy’s most famous lake town. This bike shop on Lake Como is run by a former pro racer and his wife. They rent bikes (road, mountain and e-bikes) out, but also offer one-day guided tours with multiple food and drink stops. Given that the owner grew up here and knows everyone, it’s not surprising that the food and drink spots are insider picks. The shop sits near the iconic Madonna del Ghisallo climb, the most famous in the Giro di Lombardia, a race more than a century old, and several days a week the shop offers guided group rides with a climb of the pass, on road or e-bikes—Bianchi bikes of course!

There are scheduled tours Monday through Saturday, as well as wide range of customizable private tours. These are often taken by families with mixed ages, but for more aggressive riders they offer longer road tours, mountain biking and gravel riding, along with a wide range of less demanding e-bike tours, including some even more focused on food and wine. They also offer a handful of multi-day tours and can put these together as custom on demand, usually for groups, including an iconic coast to coast traverse of Italy. If you are a guest of one of the many stunning (and pricey) ultra-luxury hotels around Bellagio, and ask the concierge to arrange a bike tour, they are likely going to call this shop anyway (and mark it up) so just do it yourself.

Luxury Travel in Italy

From planning your entire itinerary with flights, hotels, and transfers to just booking the best tours, guides and VIP access (often to non-public highlights), it pays to use a top local specialist.

Last year I attended the annual Virtuoso Travel Week in Las Vegas, which has been called “the Oscars of the travel industry.” Virtuoso is the leading global luxury travel consortium, and many of the best travel advisors on earth belong, So does just about every top hotel, resort, safari lodge, cruise line, and luxury tour operator. Virtuoso CEO Matthew Upchurch was explaining the many advantages of using a travel advisor (I wholeheartedly agree) and something he said really stuck with me. He explained that with all of the new online tour booking companies, it was easier than ever to book a tour or guide in just about any destination on earth, but harder than ever to judge the quality. The caveat was that, “you can book a guide, but you can’t book my guide.”

The Vatican is the Vatican and the Colosseum is the Colosseum, so when you opt for a guided tour, what really matters and makes it a good, bad or great experience is the guide—and their special access, like a tour of the Vatican when no one else is there.

For my recent trip to Turin, I called Imago Artis Travel, an Italy-based luxury travel specialist. They are what is known in the travel industry as a destination management company or DMC, the same companies luxury travel agents call to arrange local details for their clients. There are great DMCs all over the world, and local knowledge is valuable everywhere, but many of them do not deal directly with travelers, while in Italy the best ones do.

I wanted a private day tour of Turin and its surrounding attractions for my wife and I, most importantly the Reggia di Venaria Reale, aka the “Italian Versailles” (one of two places in Italy with this lofty but accurate nickname). The guide they got for me was a licensed guide, and lifelong resident of Turin, and spoke excellent English, which was all good, but she was also an architect, which was great in a city where so much is driven by architecture. That’s not so easy to find on global tour aggregator website. Imago Artis also gave me a list of their favorite restaurant recommendations, which were spot on, then made my reservations for me. At a minimum this eliminates the language barrier of calling or the technology barrier of booking through often tricky (or non-functional) Italian restaurant reservation websites, but in many cases it also gets you a better table and instant VIP treatment—which definitely does not happen when I book myself.

Imago Artis Travel is a Virtuoso member, which means when you book through them, if you book your luxury hotel, you get extras like room upgrades, late checkout, spa credits etc., one of the big advantages of working with Virtuoso travel advisors. If you have a bigger budget than I do, they can handle all sorts of luxury transport, private jets, helicopters, boat charters, and also offer VIP Meet and Greet services at just about every airport in Italy. They can even arrange private security details. On a more accessible luxury level, they specialize in exclusive experiences, unlocking historic buildings and art collections not open to the public, and taking you behind the scenes with many artisans of Italy, from custom shoemakers to sculptors to jewelry designers. They know food, they know the guides, and I especially like their mission statement, “Our mission is simple: Getting You to the Heart of Italy.” That’s what it is all about.

Another top luxury DMC that is also a member of Virtuoso that I have used in the past with great success is IC Bellagio. They offer a similar array of luxury services and are very well connected, but they also specialize in Villa rentals as well as 5-Star hotels. Differentiating villas in Italy may be the single biggest challenge, more so than restaurants, with so many options and so few valid reviews. IC Bellagio has also boldly acknowledged the overtourism problems some of the most popular parts of Italy face, and are pushing “Slow Season Travel,” which varies in each of the country’s 20 regions but is something they are expert in. Last winter I went to Venice in the off-season, and it was spectacular, and I just traveled in a slow season to Piemonte. It was much, much better than fighting the crowds.

Skiing

Skiing in Italy remains a bit under the radar for Europe, especially compared to France and Switzerland. Well, let the crowds go to other countries, because Italy has two different major ski regions, both of which have hosted the Winter Olympics, and the Games are returning to Milan and Cortina in 2026. The interconnected Dolomiti SuperSki lift and trail network in the Dolomites is arguably the largest “ski resort” in the world, and inarguably one of the most beautiful mountain landscapes on the planet. The towns are charming, the food is great, there are spectacular hotels from non-chain independent hidden gems to world-class luxury (Aman, Mandarin Oriental, Relais & Chateaux, etc.) and it’s cheaper than much of the rest of Europe. Did I mention the food?

I first went to the Dolomites to go hiking, and was so wowed I thought, “I have to come back and ski here.” I came back the next winter and skied, and the following year I got a group of friends together and went back. I have skied all over the U.S., and all over the world and never had the same compulsion to return to the same place immediately. That’s how good skiing in Italy is (read much more in my Italy skiing piece here at Forbes).

I’ve only used one company for ski travel in Italy and see no reason to switch gears, especially since the local logistics (a great guide/instructor, transfers, the best on-mountain meals and staying a couple of nights in the region’s unique on-mountain rifugios) is very hard to organize on your own. The company is Dolomite Mountains, a specialist in both resort ski vacations and backcountry touring trips (using skins and alpine touring or AT gear). They too are a U.S. facing company with mainly American clientele.

Like many active travel companies, they offer both group trip scheduled departure options and private custom trips to fit whatever you want. The group option is called the Dolomites Ski Safari and is a 7-day trip mixing stays in amazing rifugios with in-town hotels (4 and 5-stars on the Italian system) and includes all breakfasts and dinners, a full-time guide, ski pass, luggage transfers and more. Custom options include the same kind of trip for your own group, or anything you want, and while its name suggests local expertise—quite true—Dolomite Mountains also handles ski trips in the rest of Italy, like Courmayeur, and connected border regions of France, Switzerland and Austria, as many lift systems here know no national boundaries (ski with your passport!). They are also a Virtuoso member.

Calabria & Southern Italy

My Bella Vita travel focuses on this area, including both small group trips and custom privates. Their specialties include “Heritage Tours” for those interested in their ancestry, and a food focus for the rest of us. For instance, Taste of the South is a 12-day gastronomic journey through Calabria, Basilicata and Naples—the birthplace of pizza! Food & Wine of Calabria is an 11-daty trip and just what it sounds like.

These are some of the scheduled small group tours offered, but the rest of their business is private trip planning and custom options.

“Italy is deceivingly large, and travelers think two weeks is enough time to see everything. It isn’t,” insists Moore. “You can’t even experience all of Calabria in two weeks. Our team collectively spends about six months a year scouting new hotels, restaurants, and experiences in Calabria and we are constantly re-evaluating and tweaking our recommendations.”

There are some other Italy specialists I have not personally experienced, but that come highly recommended by some of my other experts:

Sicily

My Bella Vita’s Cherrye Moore says, “ In Sicily, I recommend Lucia Davies of Sicily Tour, one of a trio of British expats who have lived in Siracusa, Sicily for decades.” A family-owned tour-guiding company based in Siracusa, they have nearly 40 years of experience on the island and create trips fostering cultural exchange between Italy and English-speaking visitors, specializing in small group and custom tours.

Food & Wine

Beppe and Heather Dowd of Tourissimo recommend Lazy Italian Culinary Adventures, a company that has also earned kudos from other travel industry folks I know. Owner Francesca Montillo grew up in Southern Italy where her father was greengrocer. An Italian-American cookbook author, she launched the company a decade ago, and she personally leads the tours. She does numerous scheduled tours to different regions each year, and also offers custom private itineraries.

Ciao!