08/05/2026
Most people don’t enjoy Italy less because of the destination.
They enjoy it less because they try to do too much.
After years of designing custom trips through Italy, these are the mistakes I see most often — and what I recommend instead.
1. Trying to see too many places
Italy is not a country to rush through. Fewer destinations almost always mean a better experience.
2. Staying only one night everywhere
Constant packing and moving takes away the pleasure of traveling. Italy is best enjoyed slowly.
3. Visiting in August without realizing how crowded it gets
The heat, traffic, and crowds can completely change the atmosphere. September and October are often far more enjoyable.
4. Underestimating transfer times
What looks close on a map can easily take half a day. Good pacing is everything.
5. Overbooking museums and activities
You don’t need every hour planned. Some of the best moments in Italy happen spontaneously.
6.Forgetting to slow down
Long lunches, evening walks, a glass of wine at sunset — this is the real Italy people remember.
Save this for your future Italy trip.
Planning Italy 2026? DM me “ITALY” if you’d like help designing a slower, more thoughtful itinerary.
