How to Plan for a Trip to Italy

Gelato and cold drinks on the street
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.

Milano Centrale
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.


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
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!


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, 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
Gelato vendor in Lucca

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24 Responses

  1. hometoitaly

    when i start to plan a trip Home to Italy, it seems i become Italian all over again!
    i see you use also. I have used them for the past 5 years but have not heard of the one on the amalfi coast, shall have to check on that. however, I HATE the bus so if i cant walk to a location, I have to look elsewhere. my goal is to find a convent that also has dinner….a great way to meet other travelers.

    shall watch your posts, I may be in Italy again in Nov and shall follow your adventure
    have a great trip

  2. twoblackdoggies

    I am so envious of your trips to Italy, we are planning another one towards the end of next year (although I am always planning holidays to Italy) when airfares are around $1800 AUD because flights to Europe are quite expensive from Australia. Would love to know where you are staying in Venice, we stayed in the Castello area and spent many hours wandering the little alleyways, it was fabulous and I certainly want to return and explore more.

  3. Sherry

    I’m learning so much about traveling from here to there. It was very different when I lived there with the military and then traveled everywhere I wanted to by car. Going there now, flying, finding places to stay, well it seems so much more daunting being 60 instead of 21. Haha So, I’m excited for you, envious as all get out and am going to learn and watch in fascination. And I can NOT wait for pictures!!

    • margieinitaly

      Thank you Sherry – I will be posting photos as I go and have built in relaxing time this trip so I can write..Yes travel is very different no especially with smartphones and other means of communicating. I do not feel isolated at all as I travel alone in Italy. Thank you for sharing your experiences

  4. timelessitaly

    Margie, I’m so excited for you! Can I go in your back pocket? So looking forward to your posts from bella Italia! Blow it a kiss for me:)

  5. Debra Kolkka

    As Littleitaliandreams said, we pay a lot to travel from Australia…it is a long way from Europe. I can also vouch for the 3day pass in Venice. It is so easy to get on and off when you want to without buying a ticket each time, cheaper too.

    • margieinitaly

      Yes Debra – Just becoming aware of the high cost for Aussies to visit Italy. Looking forward to finally meeting you in person this trip!

  6. ishitasood

    I so Agree with you Margie. It is very costly to travel from India but I do want to meet you in Amalfi or Venice some day. Hope we can.. I love planning a trip but the airfares happen to be pretty much and forget that, the cost of eating staying is scary right now!!Hope I can manage soon… happy travelling and packing 😉

  7. jennyandstephenmilan

    Ciao Margie,
    I have been meaning to send you a message to say how much I enjoyed reading your e book. It is a wonderfully detailed account of your trips to the south of Italy. I particularly enjoyed your stories about the very friendly locals that you met and their incredibly generous hospitality. I really can’t wait to visit the south. We hope to make it to Sicily in Novemeber.

    If you are staying in Milan for a night or two do let me know. I’d love to show you a couple of spots for a Milanese aperitivo or perhaps you’d prefer la paste e cafe? I’d also suggest that you consider using the Malpensa Express train (11euros one way) if you are arriving during the daytime as the buses can be very slow going through the traffic.

    • margieinitaly

      Thank you and I am so glad that you are enjoying the book! I also hope you make it to Sicily in November!
      Grazie for the tips from a local! I will have a look at taking the train rather than the bus. I will be in Milan a short time and have some arrangements already but I will check my schedule as it gets closer and if we can meet up, let’s!

  8. Paula

    This is exactly what I have only just finished organising for this September in Italy, although my airfare was considerably more since I am coming from Australia! Also have booked some lovely B& B’s this time in Venice, Florence and Positano. I am also giving the Italo trains a try out between each place. Yes it is fun to plan the trip that’s for sure. Love Italy!

    • margieinitaly

      Sounds great Paula- I have heard that the Italo trains are wonderful, so please keep me posted on your experience. I am only now learning about the high airfare cost from Australia to Italy! I guess I shouldn’t complain.

  9. margieinitaly

    Thank you so much Marnie for your timely comments. Wow – had no idea that it was so expensive to fly from Australia to Italy! And yes thanks for the tip on the vaporetto 3-day pass. I have been to Venice several times and you are right – it is totally worth it!! Glad to connect with another italophile.

  10. littleitaliandreams

    I am totally in agreement with you. I love planning a trip, scoping out the best deals, the most interesting travelling options, stopovers, side tracks, researching regional dishes, festivals and so on. Given my time over again I would gladly work as a travel agent, just for the staff discounts I think! Spare a thought for us Aussies though… the economy airfare from Sydney to Milan is around US$2300, and our summer holidays are in Dec-Jan, so high season airfares happen twice a year for us, not once. Hopefully you know when you get to Venice to buy a three-day tourist pass for the ferries? Its well worth the cost if you plan to see a few different places. happy travelling! Marnie

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