What a day. Great trips always require the initial departure and I love a good early start. They’re exhausting, but they’re also exciting. So this one must’ve been super exciting because it began at roughly 3 AM Pacific Time.

We always have things ready to go the night before, but with a 6am flight out it is even more important. And traveling as a pack of 8 makes it more important still but simply increasing the potential for something to go wrong. But it didn’t, at least not related to the members of our party.

Check in at Las Vegas was predictably smooth. I’m always impressed with American Airlines and their priority service. It took while due to the size of our group and it being an international trip, but everything seemed fine. More on that later.

Flight to Chicago was easy; there were no bumps and some of us caught up on sleep. Due to busy schedules some of us were running on less than 8 hours of sleep over the past couple days, so it wasn’t a problem to catch up a bit.

We had a few hours to kill at O’Hare, but plenty of food options and the buzz of excitement about the trip had us in good spirits. A stop at Dunks and one at Starbucks – which ended in a beverage casualty – didn’t hurt. We grabbed food before heading over to the international departure area at Terminal 5 using the shuttle. Super easy process.

Once at T5 we found our gate and settled in a bit. Chloe and I went for a long walk and explored the rest of the terminal as we’d never been there before. It was much bigger than we expected even if oddly spread and laid out. Clearly the airport commission knows this as there are quite a few renovation projects seeking to improve the area and it’s utility. I’m guessing it will be a great facility once complete, and the far end of the terminal with the Southwest gates may be set up for larger aircraft and not strictly used by their 737s.

Getting back to our seats we noticed that our plane was rolling up to the gate. Before I continue and look like a total nutcase it makes sense to make an admission: I’m an aircraft nerd. I can’t help it. They’ve always interested me. Endless conversations with my grandfather as a young boy didn’t hurt. And years working as a contractor for US Airways, and others, inside their corporate operations and maintenance facilities only fueled my interest. So my excitement was obvious when the giant Airbus A380 was rolling our direction.

If you’ve never seen one in person, I don’t know any other way to say it: the aircraft is massive. Pictures won’t do it justice, but watching it roll smoothly and powerfully to the gate was a thing of beauty. (See? Nerd.) The double level jetway with no stairs and the gate architecture had me almost as excited to experience the boarded process under the watchful management of British Airways, and I was quite certain it would be almost as efficient as the giant Rolls Royce engines hanging from the wings.

But. Before we could get there, we had to recheck at the desk. What most people don’t ever remember, and most codeshare partners will deny, is that our check in with American doesn’t count as a qualifying Passport check for an international departure on a flight operated by a different airline. In todays world, that means even though you have a seamless purchase, ticketing, and baggage check process, you still need to go to the gate and get a new boarding pass for your international leg prior to departure. Other than a long line and minor nuisance it is usually a simple step. Except when it isn’t.

I should’ve seen this coming. I should’ve taken the next half step. I didn’t. When we booked this trip, many months ago, we booked through American. It was no surprise to see that most of the flights were operated by British Airways. Totally fine. Until flight schedules and routing started changing and reservations started getting goofy.

Where this got strangely complicated was because Milan, our entry point to Italy, is served by two airports. Malpensa is the larger of the two and receives most international traffic. We were flying through Linate, the smaller airport with no train station connection so a shuttle would be required, but schedule and pricing made it a better choice. We had always chosen Linate, but somehow a couple weeks before departure BA was showing that we had reservations from London to both Malpensa and Linate, but only Linate had been ticketed. Still sounds okay. But upon check in, apparently American’s coding of the bag tags was sending all of the bags to Linate correctly, except mine which had the Linate airport code by the barcode was for Malpensa. Fortunately the gate agent in Chicago caught that on my bag when rechecking the passports and fixed it. We wouldn’t know until we landed if it worked.

When we started boarding in Chicago, we noticed that my ticket had me sitting in the row in front of Michelle. Nothing says happy family vacation to spend time with said family like not sitting with them. Since we’d been told the flight was oversold, we hatched a plan to ask the occupant of the seat next to her to switch. It was a like-for-like so we expected it to be fine. Shortly after boarding my non-Michelle seat mate showed up and we were talking. Great guy, would’ve been fun to sit with him, and he offered to switch with her if the other person wouldn’t. But, no one showed up, so I just moved, and my new friend had two seats to himself. Everyone was happy.

I could easily do a whole post just about the A380, but I’ll spare you all and just say “wow.” It was insanely quiet, incredibly smooth, and the way every flight should be. Service was typical BA, and we enjoyed a few small bottles of wine with dinner.

Once we landed in Heathrow we were packing up our things to deplane and I realized I’d spent the 8 hour flight sitting on the passport in my back pocket. Shocked, I took it and put it in my backpack for the walk to customs. I even checked twice to make sure it was in there. What happened next is a bit of a mystery. As we were walking off the plane and through the long corridor to the train that would take us to customs, i was struggling to find my passport in my bag. I was thinking I just couldn’t get my fingers on it, because I knew I’d put it in there, so. I didn’t want to stop and look only to delay us unnecessarily. Just then I heard a woman yelling my last name and turned to find a BA employee holding my passport. It hadn’t been in my bag. I know after I put it in that I shuffled things in my backpack. But I must have pulled something out far enough for my passport to fall out and I had no idea. I was incredibly lucky. I took the appropriate amount of flack from the group.

As we were boarding the train to customs our group cut off in the mob. My family and one of the Keating girls made the train, the Keating parents and one daughter, did not. The crush of people was significant and then stopped just as the doors closed and they were left behind. But given that the are Heathrow newbies, they did great. Met us right before customs and all was good.

We went back through security for our connection only to learn it was delayed. Not significantly, at least at that time, but enough that I had to check with the shuttle company about our ride to the Milan train station. They saw the delay and all was on track. Again, at that time. Now, just had to keep hoping that my bag went to the right airport.

We camped out at an empty gate near a flight board so we would know when our gate was assigned. I took a few minutes and went to the American First Class lounge to talk with their top tier customer service people about my bag and ask about our return flight since the same strange ticketing fiasco around Milan existed on the return. Chloe came along for the walk.

When we arrived at the lounge the nice lady didn’t really want to let Chloe in because she wasn’t carrying her ticket or her passport. But, based on my status with American, regardless of the class I’m flying in, I have access to the lounge with a guest. We were obviously both tired, because we went what I will call “politely feral” on her like a well orchestrated pack. She immediately hit a couple keys on the keyboard, and we were admitted. Shocking.

The service agent was literally a rock star. She hit a few buttons and made a couple calls to people who answered on less than a ring. Not long after she muttered “there’s a lot of nonsense on these tickets” all was right in the world. She assured me my bag would be okay and thanked me for my patience and patronage.

We walked through the lounge and back to our seats then broke into groups to grab food. My family stayed true to their roots and hit Pret, one of our favorite spots in the UK for coffee and take away sandwiches while traveling. I opted instead for itsu, because I simply can’t pass it up.

Warning, soap box moment coming. Michelle and I went together. She got a fresh egg salad sandwich, bottle of ginger lemonade, and bag of crisps. It was €9, or $9. I had a tray of salmon sashimi, salmon maki, salmon avocado roll, and wasabi salmon sashimi with a large bottle of sparkling water, €12. It was an insane amount of fresh food, for a ridiculously low price. This is not a circumstance you could repeat in the US. We would’ve been stuck with nasty hamburgers and fries, for at least $25 a person and would’ve felt like crap. Huge upgrade.

And we were glad we ate because our Milan flight kept getting delayed. And delayed. By the time we boarded the math wasn’t pleasant. Milan is one hour ahead of London and it is a two hour flight from London to Milan. A 20 minute ride from the Milan airport to the Central Milan Train Station to catch a 4:10pm flight. We took off from London at rough 12:30pm after a delay at the ramp. That was 1:30 pm in Milan. We landed a little ahead of schedule. Then deplaned down stairs. Rode a shuttle bus to the airport terminal. Then waited to clear a passport control checkpoint before grabbing our bags. It was shockingly efficient and only took at 15 minutes, plus our bags – yes all of them! – were coming off the belt. We bolted from the customs zone out to find our shuttle. But we couldn’t find him. After a few minutes of looking, I called and received a text response informing me that since our flight was late, the driver took someone else (we are working on the issues associated with the service failure). We grabbed cabs and took off for the train station at 3:46pm. I could do a whole long selective edit and storytelling session in the spirit of the Amazing Race, but I won’t. We missed it. By 3 minutes. That was the second train I’ve missed at the Milan station in five years.

So, we had to find a new train. That wasn’t easy for eight people. We reviewed locals with multiple stops or strange connections. But we found a direct express route with seats available. Of course it was an Italo executive car. For eight people. That left in another three hours. Fortunately at the elevated price point, we got access to the Italo lounge to kill time. There were snacks and naps. And the saving grace for the day, some wine. Not good wine, but it was enough to make us relax a bit while we waited. Oh, it also gave us time to rearrange dinner plans, as there was no chance we’d make our 7pm reservation since the train didn’t arrive until 9. So we developed a list of options instead.

The train from Milan to Florence couldn’t have been easier. It was on time. The car was comfortable and we only had to share with a couple other people. Frankly, the biggest concern was everyone melting into a deep sleep and is missing our stop, which would have landed in on Rome. After today, that didn’t seem impossible. So after scoring a few minutes of sleep, I stayed awake for the last 40 minutes of our ride to make we got off. It really was a pity that we had to come into Florence at night. The train from Milan can be quite pretty and we missed it.

Our hotel was a short ten minute walk from the station, and aside from the cobblestones was relaxing. What we saw of Florence looked great, but we were primarily fixated on food and bed, maybe not always in that order.

We are staying at Hotel Pendini, a conveniently located hotel that has all the charms of old Florence. Another win by my wife. Strongly recommend. The rooms are amazing, and the staff phenomenal. There is even a free breakfast tomorrow.

Once we got into our rooms, it was time for food. At after 10pm local time we tried to be sensitive to closing hours, but found two places less than a two minute walk from the hotel: Hard Rock Cafe and Bella Italia. No chance I’m going to Hard Rock when authentic Italian is readily available.

Bella Italia was a perfect first night stop. The menu was wide and varied, they had an outdoor patio complete with a heater for the 52 degree night. we ate. A lot. Everyone had a meal, there were deserts. A bottle of wine selected by the manager, and of course a limoncello shot for everyone. For €187 for all eight of us. It was awesome. If we were here another night, I bet we’d go back.

This was an epic first “day.” It was challenging, exhausting, and a lot of fun. We are off to a great start.

As a wrap up, I have to make a few comments about travel.

First, expect things go wrong and for there to be challenges. It really is part of what makes the trip memorable and a learning experience.

Second, the bigger your group, the less resilient you are to change, and the more expensive it will be to deal with the unexpected. BE PREPARED. If you let traveling in a group of 8 and you have to punt on travel or a hotel, be aware that you are likely forfeiting the money of the initial arrangement and the cost of the rebook. It can be expensive. Make sure you have access to money.

Finally, make a plan but don’t be afraid to deviate from it and don’t hesitate to let it go. Staying stick to a plan can be crippling. You have tools – smartphones and people – both are interactive and able to help. Travel is about growing and the experience. And today had plenty of both.