As an Italian and a local expat, over the years we’ve helped many guests in their retirement years avoid common pitfalls that can put a damper on an Italian vacation. That’s why we’ve put together a comprehensive guide to retirees’ biggest mistakes when planning a trip to Italy. Put these tips into action to plan your Italian adventure today!

#1: Not Planning for Emergencies

No retiree wants to consider that the worst could happen when traveling to Italy – but if you have pre-existing conditions that could lead to a medical emergency, or even if you don’t – review your insurance company’s policies on expenses incurred out of your home country, and arrange for accommodations when needed. American Medicare, for example, will not cover these costs. Read more about travel insurance HERE!

If you get sick or injured while visiting Italy, you’ll have to pay all costs out-of-pocket until your policy kicks in — which could be thousands of dollars! That’s why it’s essential to purchase travel insurance before leaving home and ensure it includes emergency evacuation coverage (an unfortunate lesson from the pandemic!). You’ll also want to plan for any medications – ensure that you have extras packed in an emergency. 

What To Do Instead: Review your insurance company’s policy on coverage of expenses incurred abroad and arrange an additional policy if needed. To insure yourself against any unforeseen circumstances, cancel-for-any-reason is highly recommended.

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#2: Not Properly Planning Your Air Travel

We all know that air travel can be stressful. The last thing you want is to arrive in Italy with your battery wholly depleted from the stress of delayed flights, rushing through airport security, or waiting in lines! Don’t start your Italy trip off on the wrong foot with a horror story of lost luggage or trouble at customs. 

What to Do Instead: While the unexpected may catch you off guard, you can still protect yourself against these hiccups as much as possible! Invest in services like TSA PreCheck or Global Entry to make security a breeze, arrive at the airport with plenty of time, and periodically check your airline’s app or website for updates on your flight. 

Pro-Tip: Make sure there’s enough time between flight changes so that you do not find yourself frantically running from your gate of arrival to the gate of departure, hoping you won’t miss your flight.

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#3: Wasting Your Time & Energy on Lines, Tourist Traps, or Transportation

The best way to completely ruin your Italian experience as a retiree? Spend it waiting in long lines (especially terrible in under the hot sun), wasting your precious time and energy! Is the only way to do Italy as a retiree packed like a sardine on a big bus tour or DIYing it with TripAdvisor and Groupon? We’re pleased to tell you that there IS another way! 

What To Do Instead: Book a small group tour that will allow you to indulge in personalized service, authentic cuisine, and real Italian life! Find your perfect itinerary here.

italy trips for retirees

#4: Overpacking

Packing for an extended trip overseas can be overwhelming. You may feel like you need to pack up your entire house “just in case!” But, we often find that the extra weight may put a damper on your trip. If your luggage is too heavy, you may wish to shed those extra pounds while lugging it onto trains! You don’t want to leave behind those one-of-a-kind Italian artisan goods or brand-new genuine leather bags because you filled your suitcase before you even landed in Italy!

What to Do Instead: Make getting around on and off trains a breeze by packing light. Create a packing list with only the essentials, and stick to it! Upon packing, ensure that you have enough room in your luggage to fit any items you plan to purchase while abroad. 

Want the inside scoop on Italian travel? Grab your FREE Italian Insider’s Guide HERE to see the Top 10 Mistakes even the savviest travelers make on their trip to Italy – and what to do instead!

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#5: Booking your Flight Before Booking All your Tours and Activities

Nobody wants to miss out on taking the tour of a lifetime because the flights you already booked don’t align with the tour you want to take. Flights are flexible, but tours and other activities are once-in-a-lifetime opportunities often with limited departures and available time slots.

What To Do Instead: Book all your bucket-list experiences before your flight! Additionally, we recommend leaving some flexibility in your schedule. You can do this by planning to arrive a few days before your scheduled activities, which can help with jet lag, or by leaving a few days after to explore other iconic locations, such as Rome or Florence. 

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#6: SELECTING Accommodations Outside the City Center

Under the Tuscan Sun may have you dreaming of a Villa stay in the Italian countryside, until you realize getting anywhere requires driving a vehicle.  A BIG stress, cost, and time waster that many retirees don’t factor in when planning their trip to Italy.  

That’s why all of our tours include 4-star boutique accommodations that are centrally located so that when you join us on tour you’ll be walking distance to some of Italy’s Most beautiful squares, historic cafes, award-winning pizzerias and Michelin-starred restaurants. Giving you access to all the amenities without ever needing to rent a vehicle or getting lost trying to find your way from point A to B.

Ready to explore the Italian countryside, experience the real Italy all while taking the guesswork out of your next trip to Italy?

Click here to get STARTED!

What To Do Instead: Carefully research the accommodations for your trip ensuring that you’re walking distance to all the amenities.

italy trips for retirees

#7: Staying on the Beaten Path & Choosing the Destination Over the Experience

What comes to mind when you think of Italian travel? Many retirees envision the picturesque city squares, rolling vineyards, or charming villas they’ve seen in movies or on TV. Others may think of the classic and historic landmarks of Rome, Tuscany, or Venice. 

While these locations are iconic, it’s important to remember that heavy tourism may affect your experience. Many travelers may feel like “just another number” and leave wishing their experience was like what they’d seen in the movies or heard from friends. 

What To Do Instead: You want a life-changing experience where you get to immerse yourself in the local culture and experience the real Italy that so many travelers who visit Italy numerous times never get to experience.  All you need to do is get off the beaten path and travel like a local! Sounds simple, right?

Traveling like a local sounds dreamy, but it can be complicated. This type of experience requires someone on the inside who can guide you on your trip – and that’s precisely where The Italian on Tour steps in!

Want to experience the REAL Italy, unpack ONCE at a four-star hotel just steps away from one of Italy’s most charming squares, and uncover the nuances of everyday Italian life? Discover your next Italian adventure today! 



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