How to Fly to Italy for Free!

JAXsonville to Firenze (Florence/Rome) Trip for 2

A friend of mine who is new to the Travel Hacking game was intrigued about the possibility of going to one of my favorite places in the world, Florence Italy, for Free.  Unfortunately, NO Airlines fly directly into Firenze (FLR) , but you can fly into Rome (FCO) and take a peaceful* Train 1.5 hours to Florence a couple cities away.  FYI this is also the Region of Tuscany, so you can combine the rich history of Renaissance Florence with the rolling hills of Tuscan wine country in one trip.  The decision to test your foot on the winding roads of Italy will be a big factor in how easily you can visit wine country and other surrounding areas of Italy… I would prefer to not drive there even as a speaker of their language.   I don’t care for the stress of driving on crowded Roman roads or being uncertain of what street signs say.

So to keep this simple, we’ll focus on the easiest redemptions for someone new to this hobby.  AwardAce is a great resource for checking if any particular airline is much cheaper flying into Rome than others.  Unfortunately, their figures are ‘ideal’ redemptions and not always 100% accurate.  Some of those prices are only for ‘main hub cities‘ or during the low season.  For example, ANA shows 55,000, but they don’t tell you that’s only if you’re flying into one of the few ANA ‘Hubs’ int he US.  Never the less, you can expect that 60,000 points in almost any currency will get you there.


We’ll start by knocking out the traditionally worst option:  American Airlines (bad availability) and then United – who is sometimes great, sometimes awful depending on timing.

American Airlines:   You’ll notice that for this date in May and many others, they have a ridiculous 26 hour ‘Total Flight Time.‘  This is a critical piece of info you’re looking for.

In this case the crappy 3 segment flight would cost 30K each way…. I searched other dates for April and July, and the options were just as bad.  This is mainly because Jacksonville, like Cleveland, is not a ‘Hub’ city.  Which means if you want to go anywhere, you have to connect in a Bigger City first.  This immediately adds one extra leg (segment) to your flight.)  In a perfect world, THAT city would then fly directly to Rome… which as you can see, is simply not the case for AA.  Same goes for United.



United Airlines

While I’ve had some great experiences with United, I hate their ‘gotcha!’ pricing model they now use.  See that awesome 1 stop, 12 hour flight?  AwesomeBut wait–  Its DOUBLE the Points to spite you. You could fly for the standard 30K each way, but you’d have an extra stop and it would take 17 hours instead… What are 5 hours of your time worth while on vacation?   We also put in the ‘Calendar View’ for March and July and got basically the same results… Also tried Tuesdays (often the best) and weekends for comparison.  They did have a e Mar 7  2 stops 14h 25m flight which might be tolerable.  However, the only SAVER awards available coming home would be 6 or 18 days out, and still be the long crappier 2 stop flights.

Alaskan Airlines

Truth be Told, I have very little experience with Alaska.  But I DO know their Search Engine for Award Flights is praised by many.  It shows partner award space, AND lets you refine your filters better than the others.

Props to the IT Team behind Alaska’s Search Tool!

Obviously you’d want the shortest flight here, #1840 / #720 at only 12 hours and change. But wait, there’s More!  Mileage Plan (Alaska’s Program) only charges you 20,000 points for each leg!  So for 40K RT you get a better flight!   Keep in mind, you’ll pay 9-11 /  Taxes on ALL flights, even when you pay with Points.


Return Flight – Slightly Longer Layovers but still worthwhile… Unfortunately no flights available on certain days.

What’s the catch!?  Mileage Plan Points are harder to come by, as they are only offered by Alaska Airlines directly OR Transferred from an SPG Card.  SPG has 2 Cards – a Personal and Biz version through Amex. Each give at least 25,000 Points, which would be 25,000 Mileage Plan Miles after you Transfer them.  (5K bonus for every 20K Transferred.)  You can get 35,000 during special or targeted offers seen here.

For Alaska Branded Credit Cards, read this article on obtaining their 30,000 Mile Personal or Business cards through Bank of America.  For THIS scenario (40K requirement) you would either need to get a Personal card, spend the $1K to get 31,000 miles (total)…and then spend $9K organically to get to the 40K point... OR open a Personal and BUSINESS version of the card, to amass a total of 62,000 Points...  These cards are also more ‘Churnable‘ than others, which means you can get the points, cancel, and apply again after 91 days.

Lastly, we’ll check out Delta – who as we mentioned has a variable points pricing model.


Delta can be a sweet spot if you’re lucky to be in a city that they serve well.  In my search for this particular itinerary, I used multiple months and the prices varied by 100% (in points.)

The average is 70,000, which sounds like a lot…Except when you consider you can obtain 63,000 Delta Points pretty easily with their Gold Amex Business or Personal Cards.  ProTip: You can apply for ANY Business Cards with your SSN as a ‘Sole Proprietor’ – and list on the application that you sell stuff online (or whatever your real side business does.)  Alternatively, if you have no qualms about it, you can use your employer’s EIN # and business details, and if you use your own mailing address they will never find out about it, because YOU are the only one responsible for the debt / card.

They do have some 60,000 point fares available at various times in the season, but they are almost always the slightly longer 16 or 20 hour flights.   That being said, Since the Delta card has no annual fee, AND comes with a $50 statement credit (after purchasing a $50 Delta Gift Card) – this might still be worth considering.  The Delta search engine starts off nicely, but seems to run into problems or give different values from time to time when searching.

As you can see here, a 60,000 Round Trip (x2) Flight to Italy can be had for just $155 for taxes and fees for two people.  This flight averages $1,100 bucks, so you’re getting a ‘Value‘ of 1.8 CPP. To make this happen, you and your partner would both have to apply for the Amex Gold Delta cards, spend $3K, and then use your 60,000 points to book two identical Delta Flights (shown here.)  I don’t believe you can combine miles with Delta like you can with certain other programs.  However, if you search for availability for TWO you should have no problem.  Enjoy Florence!!


One thought on “How to Fly to Italy for Free!

  1. Zach says:

    We recommend you hit up Venice (Venenzia) while you’re in the Tuscany area!

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