How to Plan for a Trip to Italy

Gelato and cold drinks on the street

By now you must know that I enjoy travel planning almost as much as I enjoy traveling…well, not quite. But I do like figuring out my own itinerary when I go to Italy, and I also like the idea of finding the best deals I can.

In fact this is how my fall trip to Italy materialized. My original plan was to wait until next spring, but then the more I heard about others taking trips to Bella Italia, and the more time that went by, I really wanted to go. So I made a deal with myself to go to Italy in the fall, but only if I found a fantastic airfare, since that is one of the most costly parts of a trip to Italy—airfare and accommodations.

Milan’s main train station

Well, I found a nonstop airfare from JFK Airport in NYC to Milan for the incredible price of $643 round trip, half the cost of my last transatlantic flight, which was definitely not a non-stop flight. so that was it and planning for Italy in the fall became a reality. Without needing to worry about vacation requests, since by then I would be retired, I chose the time frame of three weeks and booked my flight.

I spent a couple of months figuring out an itinerary, and have been having fun looking for hotel deals and deciding whether it is better to take a train or a cheap flight within Italy. It turns out that a cheap hour-and-a-half flight from Milan to Naples is a better deal than a four-and-a-half-hour train ride. And not only because of the time but the difference in cost is negligible, even factoring in the €7.50 price for the Malpensa Express bus ride to the airport in Milan.

Since I wanted to make this trip as inexpensive as possible, I have booked a three-night stay in a monastery in Venice, although this is not the same one in which I stayed three years ago; that one is booked.

Venice

So this place is in the Castello sestiere, not too far from the Rialto Bridge, and a neighborhood I would love to explore.

Rialto Bridge on the Grand Canal

Venice is known to be one of the most expensive cities in Italy; it has been my experience that the nice hotels in Rome and in Venice rank as some of the highest. So this is perfect to be able to stay in Venice for three nights for less than $250!

Amalfi

I have also decided to spend time again on the Amalfi Coast and had considered the monastery in Maiori, where I had stayed before. I actually liked the idea of staying in Amalfi this time, so I did a little research and found a great 4-star hotel right in the heart of Amalfi with a view of the sea! (OK Splurge – I have dreamed of writing here and being able to relax.) After making the reservation through Booking.com, I found that the hotel website was actually cheaper. I made a short phone call to Italy via Skype and a pleasant English-speaking receptionist named Vittorio made a reservation for me at the discounted rate. She even made it refundable, up to four days ahead. Sometimes it pays to book directly with a hotel. And guess what? The cost of four nights in this hotel ended up to be only $33 more than the cost of four nights in the monastery.

I am still firming up a few other details and places for this trip, but stay tuned, because I will be blogging from Italy again in just a few more months. I love finding travel deals. If travel agents’ salaries were more lucrative, I would have to seriously consider it. In the meantime, I will keep having fun planning more trips to Italy for as long as I can. Who knows?  This may be the subject for yet another book!

Gelato vendor in Lucca

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