Introduction: Good Morning Milan, Goodnight Moon

Welcome to my next trip report series, which will be a bit different than usual. That’s because this is about a trip that I just completed (primarily) with my dad, and up until now, I haven’t provided any “live” updates, so everything will be new. Furthermore, there won’t be any formal flight reviews with this series, but rather, I’ll just have some flight observations and musings, plus detailed hotel and airport lounge reviews.

This trip ended up being super fun, including a stay at an excellent Park Hyatt, two Marriott properties in Germany that have long interested me, a very special suite at the Sheraton Boston, and more.

Why we took this trip, and why it didn’t go as planned

I recently wrote about how I was planning on taking a last minute trip with my dad, and the two primary destinations I was considering were Japan and Morocco. I really appreciate the incredible feedback that OMAAT readers provided, and my plan was to make the Morocco trip happen, with last minute planning.

Unfortunately life kind of got in the way of those plans, though. First our older son, Miles, got sick. Then our younger son, Jet, got sick. Fortunately they both quickly recovered, but I didn’t want to leave Ford alone when either of our kids is sick, especially when it can be avoided.

By the time everything was good again, my dad and I only had a period of around five days to travel, because Ford and I had a (very exciting) booking in Boston after that. I felt like this wasn’t enough time to “properly” do Morocco. My dad is really understanding and flexible, and suggested that we simply reschedule.

While I appreciate that flexibility, and while we’re planning on taking that trip in early 2026, I still wanted to do something special with him. For one, it was recently my dad’s birthday, and I wanted to celebrate that. Second, with my mom having recently passed, I’m now trying to do more travel again with my dad, since I had prioritized my mom during her six plus year battle with cancer.

The airlines we flew, and how last minute we planned it

As I often say, the best time to find award availability can be last minute, and this trip was the perfect example of that.

The day that I was able to travel once again (after both of our kids were feeling better), I found Emirates first class award availability from New York (JFK) to Milan (MXP). Emirates first class is my dad’s favorite first class product, and the last time he flew it was 11 years ago, for a surprise round the world trip to celebrate his “round” birthday (some longtime OMAAT readers may remember some of the videos, like the below one).

So I knew how much joy it would bring my dad to fly Emirates first class again, and I couldn’t turn down that opportunity. I booked the following in Emirates first class for 102,000 Emirates Skywards miles plus $433.50 in taxes & fees per person (as a reminder, you need Skywards elite status to be able to book awards in first class, but you can get that by picking up an Emirates co-branded credit card):

12/11 EK206 New York to Milan departing 10:20PM arriving 11:55AM (+1 day)

I literally booked this without even thinking about what we’d do on the ground, but I knew my dad would love the flight, and that was good enough for me! Like, when we boarded our flight to Milan, I had no return journey booked. Fortunately my dad is a great travel companion, and is so happy to just go along with whatever.

I then decided we’d go 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 1:45PM arriving 3:00PM

To return to the United States, I locked in Lufthansa first class one day before the return, since that’s when availability tends to be the best. So 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 11:05AM arriving 1:25PM

This return was perfect, since Ford and Miles would meet us in Boston, and their flight landed just an hour after our flight.

As mentioned above, I won’t be fully reviewing the flights, but instead, will just share some musings. Why?

• I’ve reviewed Emirates’ A380 first class many times before, including on this route
• There’s not much to review on an Air Dolomiti economy flight that lasts under an hour
• The return was on Lufthansa’s A340-600, which will be retired soon, and I’ve reviewed the carrier’s A340 first class

Fortunately you can expect some full hotel reviews, including of some hotels that I found to be super interesting. Ford, Miles, and I, also traveled to Philadelphia after Boston, so you can expect reviews of the new American Flagship Lounge Philadelphia, as well as the new Chase Sapphire Lounge Philadelphia.

The interesting collection of hotels we stayed at on this trip

For the first hotel stay of our trip, my dad and I spent two nights at the Park Hyatt Milan. This is a hotel I hadn’t otherwise stayed at since pre-pandemic, and the hotel has since undergone a full renovation. This remains a spectacular hotel with a central location, and I’d recommend it in a heartbeat.

As you can tell based on our flight schedule, we ended up having two nights in the Frankfurt area. So my dad and I agreed to stay at two different hotels, both of which have been on my radar for such a long time (and I think OMAAT readers will find these to be very interesting).

For years I’ve been curious about the two Marriott Autograph Collection properties in Königstein im Taunus, not far from Frankfurt. Specifically, I’m talking about the Falkenstein Grand and Villa Rothschild. I couldn’t decide whether these properties would be awesome or just very past their prime and mediocre.

I thought both hotels were incredibly interesting, and I’m so happy I finally had the chance to stay at them, as I have lots of thoughts. In particular, the latter property has just 22 rooms, so it must be among the smallest properties in Marriott’s portfolio — it really feels like staying in someone’s (very big) country estate…

Then after returning to the United States, we met up with Ford and Miles, as we’d be spending a night in a very special suite. For a period of several months, the Sheraton Boston has a special suite themed after the children’s book “Goodnight Moon.” This was Ford’s favorite book growing up, and it’s also one that we’ve long been reading to Miles.

So Ford was actually the one who spotted this several weeks back when it was announced, and we booked right away. I’m happy we did, because it ended up getting a lot of national press, and was ultimately booked out within days.

What a special experience this was!

We then bid farewell to my dad, and Ford, Miles, and I, flew to Philadelphia for a couple of nights, where we checked out the Four Seasons Philadelphia.

I was excited about this on a couple of levels. For one, I’ve heard nothing but good things about the property, and many have said it’s among the best large city hotels in the United States. Passing through Philadelphia would also allow me to check out some lounges that have been on my radar.

Bottom line

I just wrapped up a great family trip, with the main portion of the trip being with my dad, but then the second portion being with Ford and Miles.

While we didn’t quite make it to Morocco or Japan as hoped (though I’m now planning that for early 2026), we still had an absolutely amazing time, and it shows how the enjoyment you get out of travel largely comes down to company.

I’ll try to publish this review series pretty quickly, with flight musings, and full hotel reviews. Thanks for reading, and stay tuned!