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2 Separate Hawaiian Vacations or 1 trip to Southern Italy

jehb2

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I'm trying to get rid of my American Airlines frequent flyer miles. Over the past number of years they have become increasingly more difficult to use. I book my tickets 335 days out or as soon as the route opens. Because routes out of my city are very popular if FF seats do become available it is not until much later and then the seats on the final leg of my destination are no longer available. Additionally, a lot of international destination come with a heafty fuel surcharge fee (anything through London $749).

So I have narrowed my choices to either 2 separate vacations to Hawaii or 1 vacation to Southern Italy.

We have been going to Hawaii almost every year for the past 15 years. We love it and have yet to grow tired of it. When we use FF tickets the vacation doesn't cost much more than staying at home. (costco + timeshare = big savings).

This year we did 35 days in Europe. 10 days in HGVC Borgo alle Vigne in Tuscany Italy, Rome, a week in a Scotland timeshare, London, Paris, Amsterdam, Bruges Belgium, & Milan.

We loved Italy and wouldn't mind going back and visiting Southern Italy even though it would mean staying in hotels or apartments.

The way my point situation works is I could go to Italy for a single vacation or I could go to Hawaii twice. This may sound weird but it has to do with actually being able to get tickets (regardless of how far in advance I plan).

Yes my sister has already said I have a "high class problem" :). But if you had to choose which one would you pick?
 
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silentg

TUG Review Crew: Expert
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We flew to Dublin from Orlando non stop, then 3 hours later left Dublin for Rome, stayed 6 days in Rome, flew back to Dublin stayed at our timeshare for a week then back to Orlando.
Next year we are going to Maui. still trying to figure out the best way to go. We have the place just figuring out how to stay longer or maybe adding a city to our trip?
If I were you, I would go to Italy, we want to go back but to southern area or Scicily.
Safe Travels
Silentg
 
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