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Fatal Mistakes You or Your Travel Agent May Make When Planning A Visit to Italy & How To Avoid Them

Jesse Andrews by Jesse Andrews
January 8, 2026
in Italy Travel Planning & Tips
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Home Italy Travel Planning & Tips

 

Italy is one of the most beautiful countries in Europe drawing over 40 million visitors a year and the number of tourists traveling to Italy each years is growing, particularly in areas like Florence, Venice, Rome  the Cinque Terre national park and on the Amalfi Coast, and who can blame them!  Italy is not only artistically rich, it is one of the most important centers of Western Civilization and it is as geographically diverse and interesting as its history.

Italy is the longest peninsula in the world, surrounded by astounding islands like Sicily, Sardinia, Capri, Ischia, Procida, Elba and countless others.  The country is home to some of Europe’s highest mountains and most glorious waterfalls, natural hot-springs, incredible coastlines and many of the world’s most important art cities, including Florence, Venice, and Rome.

While the country of Italy  on a map is so small,  because of it’s such varied geography and differing cultures and traditions from north to south, Italy is almost a universe unto itself and so when coming here, keep that in mind.

ITALY LOOKS MUCH SMALLER ON A MAP THAN IT ACTUALLY IS 

WHAT TO AVOID WHEN PLANNING A TRIP TO ITALY

TIP 1:  Don’t Try to See All of Italy in 1 Trip

The old saying goes that Rome wasn’t build in a day and can’t be seen in a life time.  Most first time visitors to Italy try to see Rome in 3 days, Florence in 2 days, the Cinque Terre in 1 day, the Amalfi Coast and Capri in 2 days and Venice in 1 Day.  Maybe you only have 1 week, 10 days or 2 weeks.  While you can certainly fit it all in, doing the normal tourist circuit, which most tourists to Italy are now trying to do is going to leave you tired – not being able to settle in and/or really see anything well.  You’ll be exhausted trying to see all the sites because you will have to transfer, pack and up-pack from one destination to the next.

We suggest you narrow your focus and base yourself longer in one location so as to really enjoy whatever place you choose.

TIP 2:  Book Your Trip to Italy Well in Advance & Know Peak Season Travel Times in Italy before you book.  

Italy is one of the most visited countries on the planet and it’s a busy place for tourism almost all year round particularly in Florence, Venice, Rome, the Amalfi Coast and Cinque Terre which are the most visited destinations in Italy.

The Cinque Terre National Park is a very small territory in Italy with a finite number of hotels that sell out (particularly for groups of 6+) years in advance.   The same is said for Positano and many other towns along the Amalfi Coast, so if you are planning on visiting these areas particularly in the summer or fall months, make sure to book well in advance, because not only is space limited, but pricing is usually fare more competitive,.

Generally speaking, the further in advance you book your trip the more accommodation options you will have at more economical rates.

Italy is not a destination where you want to book a last minute trip.

TIP 2:  Don’t take hotel star ratings in Italy at face value 

Avoid booking your hotel in Italy because it has a 5 star rating.  Star ratings in Italy can be deceiving and misleading, and while you may think you are getting a truly “Luxury” experience, make sure to check out the location of where the establishment you are booking is located, but looks can be deceiving.

Check out our article on why Hotel Star Ratings in Italy Don’t Mean Anything:

 

Why Hotel Star Ratings in Italy Don’t Mean Anything

TIP 4: 

Make sure you and / or your travel agent is booking tickets well in advance to major sites of interest.

Sites like the Cennacolo where Leonardo Da Vinci’s last supper is housed requires reservations well in advance and by well in advance we are talking about 6 months in advance especially if you are traveling with a group of 4+ people.

Milan Last Supper - Stamp

https://www.italyvacationspecialists.com/tours/private-tour-cenacolo-vinciano-milano.htm

Many places like Vatican City in Rome, the Uffizi and Accademmia galleries in Florence, have a limited number of advanced tickets they sell and it is our recommendation you book these tickets well in advance and so so either with a local guide or a tour company like ourselves or another one.

In Milan, the museum to see the last supper fills up with pre-booked tickets sometimes years or months in advance for groups that will by-pass the lines and leave you waiting in line for hours if you haven’t done so alread.

TIP 5:  Avoid the Tourist Menu or Super Touristic Areas in Major Centers for the Best Dining Experiences 

Opt to dine in restaurants which don’t offer “Tourist Menus” and accept recommendations from local guides or locals in the area.  Where you dine – who you dine with – the neighborhood you dine in makes for an important part of your time here in Italy.

When you sit down to eat in Italy, unless it’s a quick sandwich on the go, calculate for at least a 1 hour stay at the very minimum.

Many restaurants offer wine tastings and cellar tours and you can not only dine but have a truly cultural experience by planning in advance, rather than just showing up and hoping for the best – getting poor, rushed in/rushed out tourist service.

TIP 6: For groups of 3+ people always hire a private driver or guide and do private rather than group tours for a better experience 




TIP 7: Avoid Driving in Certain Areas in Italy and NEVER Drink and Driver 

Read our article about places in Italy to avoid driving:

Places to Avoid Driving in Italy

Drivers and guides in Italy can be quite reasonably priced, so instead of risking your life or the lives of others, hire a driver and enjoy yourself responsibly!

Tip 8: Avoid visiting the most Popular Destinations in Italy during Peak Cruise Season and Know Alternatives that are Truly Captivating 

Many destinations in Italy during peak cruise periods can be extremely busy and honestly quite uncomfortable at times, so know before you go!  Read our article all about this here:

Important Information for Cruise-Ship Passengers Coming into Major Ports in Italy

Tip 9: Consider Renting a Private Villa over Staying in a Hotel because it can Save you Money and Give you a Far More Luxurious Experience

Have a look about this topic here and for some great and very economical options get in touch with us!

Why Holidays in Villa Make a for a Truly Economic and Awesome Vacation Experience

10. Consider Farm Estates or Agriturismos as a Great Option and more authentic experience

More information on this topic coming soon!

For the most relevant and up-to-date information about travel in Italy get in touch with the exerts either by phone or email!  We will be back to you with a fast response!

team@italyvacationspecialists.com

 

Live - Travel - Adventure

 

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Jesse Andrews

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Comments 2

  1. Regina Gomes says:
    8 years ago

    I would like to snd a small group (10 to 15 PAX) to Puglia in next April visiting:
    Lecce, Brindisi, Alberobello, Polignano a Mare, Matera, Taranto, Paestum, Naples
    Do ou believe it is a good time?
    Tks and rgds

    Reply
    • Jesse Andrews says:
      8 years ago

      Hi Regina,
      I hope you are well and we can speak about your upcoming trip to Italy very soon! Please let us know when the best time to reach you is!
      Jesse

      Reply

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