Can an independent traveler find happiness on an organized tour? 1

Can an independent traveler find happiness on an organized tour?

I traveled solo around the world for 3 years, turning 30 in Hong Kong. I traveled solo in Central America for a year. I traveled parts of the Baltic and Balkan countries as well as  Germany and Israel over 1.5 years. But in all my travels, I had never gone on a “Tour” of a county. I’d taken a day tour or a walking tour once in a while, here and there, but I’d never signed up to see a country or area as part of a tour group.

Over 2,200 days of travel and I decided to sign up for a group tour!

Villa Romana del Casale in Sicily with La RosaWorks Tours

Me on a Tour? Villa Romana del Casale in Sicily with La RosaWorks Tours.

After well over 6 solid years of days traveling on my own, traveling solo, going where I wanted when I wanted, seeing whatever I wanted on my own schedule — I signed up, paid for, committed to, an official 9-day tour.

I have to admit, I have been a bit of a tour snob. I’d watch groups of look-alike people follow a red umbrella or an orange flag, sticking together in a mini-mob, looking at what the guide said to, taking photos even when they seemed not to know why, standing in front of some monument for a photo just to show they’ve been there. That wasn’t my idea of fun or of cultural enlightenment.

I’d heard of tour guides being rude to locals and of tour guides that had never actually been to the place they were guiding and not knowing even the basics they should have known. I certainly never wanted to be stuck with someone like that.

And here I was, actually choosing to become one of those people?!

Well, not really…

Why I signed up to go on a Tour!

Yes, I was going on a group tour. I was committing to travel with a group of people I didn’t know. I was facing the potential to be stuck with people I didn’t know, like, or have anything in common with.

I wasn’t going on some huge tour with some large company where I was just another head and this was just another tour for that company or guide. I opted to see Sicily with Karen La Rosa, a woman who feels a strong personal connection with and love for the country of her family’s heritage.

La RosaWorks is a boutique company that customizes tours to Sicily that introduce visitors to “Sicily’s rich culture, traditions, history, food, and wine.”

And, as I happen to have known Karen La Rosa in my youth, and to have reconnected with her around the time she started La RosaWorks, I knew that what she says on her About page, was truly from her heart.

In short, Karen La Rosa is why I elected to sign up for a Tour. I loved that she spoke of her love of Sicily. I saw that she took/takes/has taken her time to get to know regions, towns, people, businesses, local foods and people/places that grow and prepare them, local artisans, local history and stories. I knew that as each tour is tailored to those who request it or perhaps to a theme, she brings in the appropriate local experts to share their knowledge. I wasn’t booking a custom tour; I joined a tour requested by and arranged for someone else, then opened up to others. It sounded great and I had faith that it would be.

The benefits of the Tour

Rooftop dinner first night

Rooftop dinner first night

As an individual traveler on bicycle through Europe in my 20s I was able to go to most small towns, most out of the way or unique places I heard of. However, traveling by public transportation, I have always been aware that there were fabulous or quaint, historic or aromatic places or events that I’d like to see but couldn’t get to without renting a car. Unless I happened to meet people who were driving there or join a rented car, I simply had to miss these places or events.

There is something great to be said for being able to ride in a comfortable seat in a custom-hired van and get to places such as these.

Adding to that, the van ride itself was typically an education. Each day Karen brought in a tour guide who knew the region, history, archaeology, or such that fit our destination, our outing. And each felt like a friend we could approach and ask questions of. In this van, I learned not only the answers to my own questions but the answers to questions I didn’t know to ask.

I learned the history and other things about the places we visited at such a deeper level than if I’d gotten to those places alone and only read the signage posted by certain displays.

Deb Stomping grapes in Vendetta Sicily

I’m stomping grapes! La RosaWorks worked for me!

One day Karen told us she was changing one of our days’ itinerary. She’d learned of a wine festival in a town that was not on our agenda and she’d arranged to take us to it. The festival was charming — and two of us brave souls actually donned rubber boots and stomped the grapes! I have never been a grape juice fan and I’m not terribly into wine, but the freshly stomped juice that came from our collective grape stomping was oh so sweet and nice.

On my own, I am always able to ask locals for restaurant recommendations — and sometimes the person’s tastes even matched my own. But Karen knows so many people personally that she knew the owners or chefs of each restaurant or eatery she took us to. No one was ever even a tiny bit disappointed by her expert selections. Oh, how we ate on this tour! And as Karen has an Italian wine expertise certification, we enjoyed many a great wine as well.

Actually, we didn’t always dine in restaurants. Karen had even gone as far as to arrange a person dining experience for us in a historic Byzantine Chapel.

Looking back on the Tour

After the tour, I returned to my independent traveling ways. As the tour ended in a beach resort closest to Palermo, I booked myself into the On The Way hostel there in Palermo and made myself at home there for several days. I had work to do for my clients so I spend a good deal of time there (although I also got out to some new places and enjoyed walks around the city).

Each day as I sat in the lobby or the common room/dining room, I heard travelers ask about what to see, where to go, and how to get to various places.

Calascibetta hilltop village above Enna,Sicily. With La RosaWorks Tours

Calascibetta hilltop village above Enna,Sicily

Each of those days and pretty much each of those hours, as they were given advice on where they could go, I wanted to tell people about the places I’d been. Yes, they would get to Siracusa and Ortigia. But they would not be able to get to the remote mountaintop towns such as Calascibetta. (Google maps can’t even map it from the nearby town of Enna and it was a challenge for our driver to squeeze by a parked car without taking us over the side!)

Had I learned about the wine festival on a solo travel day, would I have been able to get to it? I don’t believe so.

There were a few hostel guests who traveled from nearby countries on motorbikes and were able to explore the small mountain villages. One guy had a great local family experience. But the rest of the travelers simply missed those places.

Sometimes by CouchSurfing you can be lucky enough to stay with a local who takes you to the hidden places. Sometimes….

Will I go on tours from now on?

To be honest, I still have my reservations about Tours in general. But when I can find other boutique tours like La RosaWorks Tours and Travel, I’ll be considering them.

Can an independent traveler find happiness on an organized tour? Actually…. YES!

By the way, if you’re an independent traveler but still wish to have a custom itinerary set up by La RosaWorks, you may. Karen creates and arranges custom travel to Sicily for individuals, couples, families, and groups of all sizes.


If you are looking for a disclaimer that I was a guest on this tour or that this is a sponsored post, you won’t find one. I paid my way on this tour and I was not asked to write a reference. In fact, Karen La Rosa has no idea I am posting this. This is simply my own first-ever “Tour” experience. 

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One thought on “Can an independent traveler find happiness on an organized tour?

  • Vickey

    Yes! I’ve been on some exceptional tours–one in Brittany comes to mind–where we had different speakers each day to share their own expertise. They were great! Glad you had such a good time.