In 2012 I went on a Solo Trip to Italy, England and Ireland. I had already been to Italy before, but missed out on Florence. London and Ireland have always been high on my ‘To See’ List, and I was excited to do some traveling Alone for the 1st time in my life.
I was still new to the Credit Card Churning game at this point, and was happy just to use a $300 voucher from AirCanada for this flight.
The Chase Ink Plus Business Card is currently offering 60,000 points when you spend $5,000 in 3 months. This can be achieved in one month using the Target RedCard in this post.
Those 60,000 Points would be transferred to American Airlines for a Round Trip ticket from the US to Rome.
The Barclay Arrival OR similar Card (Capital One Venture) will ‘Cover’ the Ancillary Travel expenses. Those will include Travel from Rome to Pisa / Florence via Train, flight from Rome to London (discount airline), and ferry or flight to Dublin.
With proper Planning, you could also use various Hilton or Hyatt Cards to get 1-4 nights of free Hotel stays in any of these cities.
ProTip: If you ever have a bad experience / long delays during a flight, it pays to call / Email and complain. The worst thing that can happen is nothing, or you might make $300.