Where to Go and What to do in Italy?

Planning a vacation in Italy is a wonderful puzzle and a delightful discussion with your travel companions. There are so many places to visit and wonderful things to enjoy, you should take into account the experiences and interests of your traveling companions.

Here are a few questions to ponder with input from our experts:

Countryside versus city vacations?

  • The marvelous countryside is best Spring through October. Most properties rent Saturday/Saturday.
  • Cities are welcoming year-round. Busy with tourists during peak summer months May, June, July.
  • To enjoy beaches in Italy, purchase a pass to a beach club with full amenities.  More information.
  • Country villas are designed for relaxing so day trips will take some planning and some driving. Evening meals easiest in the property, versus nighttime drive on dark country roads after some vino. Answers to questions about villas you didn’t know to ask.
  • While in a city, you can pop in and out of your apartment to enjoy sights and meals.
  • Teenagers may enjoy exploring cities more than countryside stays. “Moooom, I’m bored, there is nothing to do, the internet connection is slow….”
  • Of course you can visit both cities and countryside. Talk to us before nailing things down for best sequence.

What do we want to do?

  • First timers often want to see the top 10 sights whereas returning travelers may want to visit fascinating sights that are on a longer list. For a mixed group, consider staying some place where folks can go in different directions.
  • Some travelers go deep into fascinating layers of Italy with explorations such as the history of concrete, walking the city walls, off-the-beaten path museums.
  • Getting around. Consider mobility issues. You end up walking a lot through the fascinating cities. Not all buildings have elevators.
  • Driving conditions vary. Does your group have a calm and confident driver used to a range of driving conditions? The road systems are excellent, but sometimes crowded, narrow, winding and hilly.
  • Do we want to just relax in a beautiful setting with a few day trips from a countryside property?


  • The popular locations and sights can be crowded during peak travel time. Some places are always mobbed. Consider:
    • early morning visits before the tour buses/ships arrive
    • hire a personal guide who can adjust the itinerary on the fly
    • going during the winter
    • avoid the top 10 sights, go deeper; the possibilities are infinite



  • Who wants to see the incredible art collections in Italy’s museums and palaces? Some wonderful museums are moderate in size, so even those somewhat allergic to museums can find small jewels.
  • Who wants to hike, bike and explore the outdoors? Advance planning required.
  • Fun with food. You can enjoy Italy’s marvelous food every day with just a little discrimination. Some prep required if you want to take cooking lessons or eat at top restaurants.
  • Art hunt. Masterpieces of architecture and art are found all across the country in palaces and churches. Nothing like finding a Caravaggio or Byzantine masterpiece in a spiritual cathedral. The huge and most prestigious art exhibit in the world is at the Venice Biennale.
  • Music. Perennial favorites in Italy’s opera houses (or in the ruins of ancient Rome) and seasonal programs balance out your activities.

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