Destination: Your Customized Italian Dream Vacation


A travel boutique that fosters your personal connection to Italy by personalizing your experience while there.

One of the most challenging aspects of planning a trip to Italy is plotting out an itinerary. One can quickly become overwhelmed with questions, leading to more stress than excitement and anticipation. Just look at the million travel websites such as Trip Advisor and you’ll find a barrage of posts filled with a certain sense of panic: Can I really hit all these places in the two week vacation time I took off from work? Is two days in Rome too little — or three days in Venice too long? How can I ensure an authentic Italian experience when I have to cram in all the must-see sites that are overrun with tourists? And the frenzy goes on…

Enter Diana Maiola-Cirino, an Italian travel expert with an artistic spirit who lives in a town just west of Cleveland, Ohio. For the past 43 years, Diana has been traveling back and forth from Italy, immersing herself all the culture has to offer while sharing those familiar experiences with others in search of the same thing.

Imagine having a good friend as a travel companion — one who tailors the day to your own personal tastes, but one who also knows when to take a step back and give you space to find your own connections. That’s the balance Diana likes to strike when creating and guiding custom trips for her clients.

With Italian Tours and Travel by Diana, it is possible to know just how much time should be spent where, what an appropriate itinerary is, and, most importantly, how to find an Italian experience that is meaningful to you. After all, this isn’t some behemoth, commercial travel agency. This is a small team of Italy-enthusiasts who want you to take in the homeland through the filter of your own unique spirit.

To give you a better idea of what, exactly, this small but remarkable travel company is all about we asked Diana a few questions. Her answers provide a little insight to the magic her services can provide, taking the panic out of planning and making your next visit to Italy just what it should be: A reflective journey of a lifetime.

Diana, what does your heritage mean to you? 

It means everything. It’s my life-blood. I am intensely passionate about my Italian heritage. It guides my values and family life every day. And, I am fortunate to have my heritage involved in my everyday business. I love sharing my background with others on a daily basis.

You offer some amazing services for Americans looking to travel to Italy, including fully accompanied tours and individually customized vacations.  Can you tell us a bit about your philosophy when planning a trip or tour?

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Diana Maiola-Cirino

Our philosophy when planning a trip is striking a balance between planned time and time at leisure within each destination. This gives a well-rounded experience of each destination and truly allows travelers to understand the history while tasting the culture of each place.

When planning, we also like to do some research, discover what is of interest to you, and organize as much in advance as possible. This way, when you arrive, you can relax, take one day at a time, live in the moment, and leave yourself open to new opportunities.

If you could share just one travel tip with people planning a trip to Italy, what would it be? 

In the most honest and genuine way, I would say work with a qualified expert for whichever country you travel to. That way, you can get the most out of your journey abroad.

For example, I’ve formed strong relationships with our suppliers in Italy over the last 10-12 years, which clients benefit greatly from. It means they travel as our guests in Italy, rather than tourists.

Everything an expert can set you up with is tried and true hundreds of times over, which ensures a memorable and authentic journey.

Also, don’t expect to find America in Italy!

What is your personal favorite Italian destination?

That’s an extremely difficult question! The Amalfi Coast is a highlight as far as seaside areas go. My favorite country area is the south of Toscana, specifically Montalcino and Pienza. I like soulful reflection in Matera and Basilicata also.

To begin planning your next trip to Italy, visit Diana’s website to learn more about her services or contact her today.

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