Welcome to my upcoming travel report series, which will have a unique twist. This is about a trip I recently finished (mainly) with my dad, and until now, I haven’t shared any “live” updates, so everything will be fresh. Additionally, this series won’t feature formal flight reviews; instead, I’ll share some flight observations and reflections, along with thorough hotel and airport lounge evaluations.
This journey turned out to be incredibly enjoyable, featuring a stay at a fantastic Park Hyatt, visits to two Marriott locations in Germany that I’ve long desired to see, a very special suite at the Sheraton Boston, and more.
In this post:
Reasons we undertook this trip, and why things didn’t go as anticipated
I recently mentioned that I was gearing up for a last-minute trip with my dad, with the two main possibilities being Japan and Morocco. I truly value the fantastic input from OMAAT readers, and I aimed to make the Morocco trip a reality with some quick planning.
Sadly, life interfered with those plans. First, our older son, Miles, fell ill. Then our younger son, Jet, took ill as well. Thankfully, they both bounced back quickly, but I was reluctant to leave Ford alone during their sickness, especially when it could be avoided.
By the time everything settled down, my dad and I had only about five days available for travel, as Ford and I had an (extremely exciting) booking in Boston shortly after. I felt this wouldn’t be enough time to “truly” explore Morocco. My dad is both understanding and adaptable, suggesting we simply postpone.
While I appreciate that adaptability, and we’re set to take that trip in early 2026, I still wanted to do something memorable with him. For one, it was recently my dad’s birthday, and I wanted to commemorate that occasion. Secondly, with my mom having recently passed, I’m eager to travel more with my dad, as I had focused on my mom during her prolonged struggle with cancer.
My dad enjoying his time in the airplane!
The airlines we chose and the last-minute planning involved
As I often note, the prime time to discover award availability often happens last minute, and this trip is a fantastic illustration of that.
On the day I was finally able to travel again (after both kids were feeling well), I discovered Emirates first class award openings from New York (JFK) to Milan (MXP). Emirates first class is my dad’s top choice, and the last time he experienced it was 11 years ago, on a surprise round-the-world journey to celebrate his milestone birthday (some longtime OMAAT followers may recall some of the videos, like the one below).
I knew how delighted my dad would be to fly Emirates first class once more, and I couldn’t pass up that chance. I secured the following in Emirates first class for 102,000 Emirates Skywards miles plus $433.50 in taxes & fees per person (as a reminder, Skywards elite status is required to book awards in first class, obtainable by acquiring an Emirates co-branded credit card):
12/11 EK206 New York to Milan departing 10:20 PM arriving 11:55 AM (+1 day)
I literally booked this without considering our plans on the ground, but I was confident that my dad would enjoy the flight, and that sufficed for me! For instance, when we boarded our flight to Milan, I hadn’t even arranged a return. Fortunately, my dad is an excellent travel companion and is always happy to roll with the punches.
Dom Perignon P2, don’t mind if I indulge!
I subsequently decided we would head to Frankfurt after that, so I booked the following in Air Dolomiti economy class (business class wasn’t available) for 7,500 Air Canada Aeroplan points plus $53.65 in taxes & fees per person:
12/14 EN8805 Milan to Frankfurt departing 1:45 PM arriving 3:00 PM
Espresso (available for purchase) in economy?!?
For our return to the United States, I secured Lufthansa first class just a day before the return, as that’s typically when availability is at its peak. Therefore, I booked the following in Lufthansa first class for 90,000 Air Canada Aeroplan points plus $217.57 in taxes & fees per person:
12/16 LH422 Frankfurt to Boston departing 11:05 AM arriving 1:25 PM
This return was ideal, as Ford and Miles would meet us in Boston, with their flight landing just an hour after ours.
An oldie but a goodie (for 90,000 Aeroplan points)
As mentioned above, I won’t be