Read it. Very good. You can tell it meant alot to you and came from a very personal need to tell this story. Mostly for yourself because writing is very therapeutic.
If youll permit me several editorial notes. Dont take these as negatives or critique, sometimes the best thing you can do is have someone else read through a paper because they pick up things your brain just glosses over.
Minor issues but I think you could really punch up your story with these minor additions/subtractions.
Great job
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Discuss the moment you landed and got off the plane. That had to be very powerful and it would seem like a good point to stop and reflect. Its just you build up to going to Italy, how much it means to your grandpa and you, waiting in the terminal for your flight with anticipation. You skip ahead to seeing the landscape as you land and then immediatley jump to taking a 3 day tour of Rome. Its just if you take the time to describe waiting to depart, itd seem like you should also include when you actually landed and any feelings that came up when you stepped onto Italian soil.
page 1, last paragraph "winded our way through the mountains". I dont like the word "winded". Meandered. Snaked. cut. waffed. Just a suggestion. The flow of the story just halts at the word winded because it doesnt fit.
Same sentence "we winded our way through the mountains filled with granite". Is a dangling participle. Is the mountains filled with granite, or are you filled with granite as you wind through the mountains? It sounds ridiculous, but its an important literary detail. "We winded our way through the granite filled mountains".
Page 1, last paragraph. big run on sentence. Start at But and go to the period. That sentence is about 6 lines long. Add a Period after JFK and delete the "as". Thatll clean it up.
1st paragraph page 2. Awesome. Great description.
page 2 paragraph 2. You use "day" twice in a very short sentence. "Would eventually come true". One of the "days" needs to go.
Page 3, paragraph 1. It runs a little long. Starting at "It was until later that evening.." to the end. Break it up a little.
Page 3. In the span of 3 paragraphs, you mention the time span of "...20 years..." 4 times. Pick and choose where its most important. 2 tops.
Page 3. The main point of this part of the story is reflecting upon the fact youve seen the scene that your grandpa painted several times. An awe inspiring view of the mountains and sea from a particular vantage point ( I assume that spot in the church). You should go into a little more detail after your wife tells you to turn around and you see it. How are you seeing it? You said its an exterior staircase, I assume you are on a deck? This is a very important point in the story, dont rush through it. Describe where you are standing. What youre doing. What youre thinking. More detail into what you see. Describe the view for the reader so we can appreciate the beauty as well.