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Italy's Highlights and Best-Kept Secrets: Planning Your Trip

Updated: May 9

Planning a trip to Italy can be both exhilarating and overwhelming, especially when trying to balance visiting iconic sites with immersive, off-the-beaten-path experiences. Over the years, I've helped countless clients craft meaningful and authentic itineraries in Italy that cater to their unique goals and desires. I wanted to peel back the curtain and share my tips to help you plan a well-balanced trip to Italy that combines must-see attractions with hidden gems and immersive experiences, just like I do for my clients!



Step 1: Identify Your Goals and Desired Experiences: Before diving into the planning process, take a moment to reflect on your reasons for visiting Italy. Are you seeking relaxation and self-reflection after a challenging period, or are you looking to reinvigorate your life with new inspiration and experiences? Journaling about your intentions can help clarify your goals and ensure that your itinerary supports them.


Ask yourself questions like, "When I close my eyes and imagine myself in Italy, what do I see? Why? What kinds of experiences and moments would be most meaningful to me?" Remember, it's not about ticking off a list of "must-see" attractions, but rather about crafting a journey that resonates with your soul.


Step 2: Make a List of Desired Destinations and Plot Them on a Map: Now that you have a clear idea of what you want to experience in Italy, make a list of your desired destinations. Plot them on a map to visualize which areas are relatively close to each other and which would require significant travel time. This exercise will help you eliminate destinations that are too far out of the way and focus on those that are more easily accessible.


Step 3: Write Out Your Itinerary: Create two versions of your itinerary. In the first version, include every destination on your list, no matter how far apart they are. In the second version, focus on visiting just one or two of Italy's main destinations and allocate at least four days to a quiet, lesser-known place.



Step 4: Visualize Yourself on the Trip: Close your eyes and imagine yourself on each version of the itinerary. How does it feel? Picture yourself arriving in Rome, jet-lagged and exhausted, but pushing through to do a tour of the Colosseum because it's the only way to fit it in. Then, after just a couple of days of checking off iconic sites in Rome, you're doing it all over again in another city.


Now, visualize yourself on the second itinerary, where you have a week in Rome to explore at your own pace, wander aimlessly, and linger at sidewalk cafes. You can even take a couple of day trips by train or join some off-the-beaten-path experiences led by locals.


After "feeling through" each day of both itineraries, which one most matches the feeling you were going after in step 1? How will you feel when you get back home?

Step 5: Joyfully Remove a Few Things From Your Wish List: Yes, I said joyfully! The more you remove from your must-see list, the more you'll be able to slow down and actually experience Italy. With each city you remove, you're making space for Italy's magic of the unexpected – those little moments that come to us when we're not on a schedule, when we can follow our heart and stumble upon moments that become our favorite memories.



As an Italy travel planner, I walk my clients through these steps and help them plan an itinerary that balances checking off some of the iconic sites and also enjoying some off-the-beaten-path exploration with immersive and meaningful activities in Italy.

If you'd like to discuss custom travel planning for your next trip to Italy, start here. If you're planning your trip on your own, you can sprinkle in just a few of our more unique experiences that are hard to find on your own with our Italy Immersions. For those seeking a balance of iconic sites and hidden gems with like-minded travelers, our small group tours in Italy offer the perfect blend of structure and flexibility.


It would be an honor to help you have a more meaningful and authentic cultural experience in Italy, whether through custom planning, immersive experiences, or small group tours. Let's work together to create the Italy trip of your dreams!

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