Latest Planning Guide for Italy from Jane

How to Plan a Trip to Italy

You want to go to Italy.  Where do you start?  Do you hire a travel planner?  Is it possible to do it all yourself?  Is it too overwhelming?

I’m here to say that you CAN plan your own trip.  In fact, it is much more fun to do so and you save a TON of money.  Of course, if money is no object and you want someone else to handle your luggage and shuttle you everywhere, travel companies can do it all for you for a nice sum.  Keep in mind, you will be on their time schedule…up every morning early and on the bus!

If you want to plan your own trip, where do you start?   

1. You need to decide when and where to go!  

The best time of the year is May-Early June, or late September to October.  Why?  The crowds are much less then and so is the heat.  Mosquitoes are not as much of a problem as well.

2. If this is your first trip to Italy?

Then consider visiting Rome, Florence, and Venice, along with Tuscany or the Amalfi Coast.

3. Itinerary.

Create an itinerary….how many days in Rome, how many days in Tuscany, etc.

4. Flights.

Book flights.  Try to keep your flights on the same airline for all your trips and begin earning miles by joining their mileage program.

5. Hotels.

Book hotels for your stay.  I suggest only booking hotel rooms with 100% money back if you cancel up to 3 days from arriving.

How do you choose a hotel?  Check travel blogs, check Trip Advisor for customer ratings (Personally I never stay at a place that doesn’t get Trip Advisor’s Badge of Excellence), check travel experts like Rick Steves, Frommer, and Fodor.  These three experts have books that are easily checked out from your local library.

Also consider your travel companions’ mobility needs. Can they walk comfortably? Do they need to stay near the city center?

6. Tours.

Start thinking about what you want to do when you arrive.  Browse Trip Advisor under Things to Do.  Also, what tourist attractions are a must for you?  What experiences do you want to enjoy?  (For example, visit the Vatican, take a golf cart tour around Rome, go on a food tour!)  These will be the things you remember the most.  Start talking to people, see who are posting about Italy on Instagram, etc., etc. Go to Viator or Get Your Guide or AirBnb Experiences and look at their offerings.  Many allow you to book with no cancellation fee, asking for payment 72 hours before the experience.

7. Transportation.

How will you get from city to city…..rental car, hire a driver, trains?

Check Trenitalia or Italiarail to book train trips.  Again, always buy refundable tickets.  You may need to book trains as soon as you can, as they fill up quickly.  

8. Print out everything.

Train tickets, Hotel confirmations, Vouchers for tours, Restaurant Reservations.  Take them with you to check in, just in case the wifi is not working where you are.

9. Establish files.

Hotels, Meals, Tours, Transportation, etc

10. Book Restaurant Reservations.  A Must!

Again, check Trip Advisor, travel books, Instagram Influencers.  Remember in Italy, if you want to experience the local culture, book a little later than you would at home.  We like 8:00 (20:00) for most meals.

11. Check YouTube for anything you are unsure about.  

I even found a YouTube video showing me how to use the PeopleMover in Venice, and how to get from the train station to my hotel.

12. Consult your Hotel Concierge for directions and details.  

While you may be able to consult your phone for directions, depending on your plan, your Concierge or desk clerk probably can tell you what you need to know, like where to catch the vaperetto to Burano and when it leaves(in Venice).

13. Go with the Flow. 

Things will happen.  You may need to be flexible.  Breathe.  Laugh.  Enjoy.