Tales & Trails of a Traveling Wiseguy

I haven't even caught up with my backlog of blogs from our trip to Italy last week (they're held up on my time to deal with touching up photos) but already I'm ready with a retrospective. Here are Five Things:

1. Despite a few frustrations around the edges of the trip and a few things that went wrong with the parts my company planned, I very much appreciate being named to Club and getting to go on this trip. There were times I grumbled (privately), Maybe I should skip this trip and plan my own. Well, that would've been expensive. Just the flights alone would've cost us $5,000. The three hotel nights that were included plus the food and misc. expenses were worth another $2,500.


2. The highlight of the trip was our 2½ days in Rome. This was a side-trip we planned— and mostly paid for— on our own. (The Company let us book a stopover on the flights they paid for.) We hired private tours for the Colosseum, ruins of Caesar's palace, the Roman Forum, and Vatican City (the part that's still in my backlog), and augmented that with trekking to the Spanish Steps, the Trevi Fountain, and the Pantheon (also in backlog) on our own.


3. Hiring private tour guides was expensive, eye-wateringly expensive in the case of the Vatican tour, which cost us over $1,200, but there's real value in it. With guides we saved the time of having to do lots of research and planning ourselves, we avoided waiting in lines and wandering around trying to figure out where to go, and we had someone who helped us ensure we saw the best things we could. Yeah, we could have cut the costs maybe in half by booking group tours instead, but we've had mixed experiences with even smaller, 12 person sized group tours. When time's limited, when it might be years, if ever, before you go back to that place again, go big.


4. Our "beach" resort stay, the part paid for by the company, reminded me that when you're at the beach there's an enormous different in really being at the beach. If you can't just walk out the door of the building, across a pool area, and be on the sand, you might as well stay a few miles away and drive to the beach. At the resort in Chia, Sardinia, it literally was a drive; the beach was 4km away from the resort hotel! As a consequence we went to the beach just once. We could have had more fun going back to our favorite splashy pool resort in Phoenix instead.


5. As much fun as visiting Italy/Rome was, and as little a fraction of the whole as we saw, we're kind of done with it. We're definitely not feeling, "Ooh, let's plan another trip to Rome!" Partly that's because we saw the highlights we cared about; partly it's because there's so much else in the world we want to see, too! I could see returning to Italy specifically for Pompeii, to see the ruins; Venice, for its unique canals; and maybe Florence, for its Renaissance architecture. But I don't think I'd want to spend more than a few days in each.

Italy Travelog #21
Chia, Sardinia - Thursday, 29 May 2025, 2pm

We decided to enjoy a take-it-easy day at the resort today. That's a choice with consequence, though. What we've chosen to say No to is a catamaran and snorkeling trip! Alas, as much fun as being out on a boat on azure waters can be, and as much as I've wanted to snorkel since I was a boy, I've found out the hard way, by two failed attempts, that I'm not able to snorkel. Maybe I could with some careful instruction, maybe not. But I definitely can't with just, "Here's a mask and some fins, now jump in!" Plus, Hawk is reluctant even to try because swimming poses to much of a threat to her injured back. But hey, just because we're not going snorkeling doesn't mean we sit around our room swallowing our tears, there's a pool to enjoy!

Update, 6pm Thursday: The whole snorkeling trip was a fail. Due to high winds and problems with the boat, nobody got to snorkel. Now I'm so glad we stayed home and enjoyed the resort!



Ha ha, the joke was on us. That pool is cold. Like, seriously, the only people going in the water are the couple from Minnesota and the couple from Germany. All the rest of us dipped a toe in and said OH HELL NO! 😱

But again, there are more options here than go back to our rooms and swallow tears. There are comfy lounge chairs with beautiful views across the pool and to the ocean beyond.




Some lounge chairs, like the pair we got (photo above) are even in the shade and pair to form a day-bed for two.

Plus, a few minutes later we got drink service, so imagine that picture above with us in it plus a piña colada and a margarita. (Yes, we're drinking like we're in Latin America while being in Italy, but frankly all the Italian drinks on the menu look disgusting.)

We chillaxed on the pool deck for almost 2 hours, until we decided it was time for lunch. We placed an order at the little cafe over to the side. The host came to fetch us when our food was ready.



Apparently they don't serve food at the lounge chairs. I guess that makes sense because otherwise people'd generally make a mess of them. So we sat up straight and enjoyed our lunch at a little pool-side cafe table. Hawk ordered a bowl of spaghetti while I played the Ugly American card and ordered the hamburger. BTW these were two of literally only four entree choices on the menu, so it's like we skipped over all the cibo tipico to pick these dishes. Plus, we've recently been unimpressed with the island's cibo tipico.

After lunch we stretched out in our shaded day-bed for a bit longer before heading back down to our room. Hawk has now gone upstairs to the spa for a deep tissue massage— a mea culpa comped for yesterday's fuckup with cibo tipico. I'll join her up there after her massage for us to use the hot tubs together.

Italy Travelog #16
36,000' over the Tyrrhenian Sea - Tuesday, 27 May 2025, 10am

This morning we woke up early, 5:30am, to eat breakfast in our room, check out of our hotel in Rome, and taxi to the airport. We were out the door and in a taxi before 6:30, at the airport by 7:15. We're headed to Cagliari, on the island of Sardinia.

In case you're wondering, "Wait, you only toured Rome for one day?" the answer is No, we had two days there. At this point I've skipped over our Monday tours, leaving them in my blog backlog for now, to avoid getting too far behind. I'll come back around the to the backlog later. For now suffice it to say that Monday was busy. We toured the Vatican for several hours then took the metro back into Rome's city center to visit several sites such as Spanish Steps, the Trevi Fountain, and the Pantheon. It'll probably take me 3 days to catch up on blogging about all of that. And boy, are our feet tired from all the walking!

With this flight to Cagliari we're shifting gears on our trip. Our quick visit to Rome was the "us" part of the trip. Cagliari is the "club" part of the trip. We'll be with work colleagues, the top performers globally from my sales team, for the next few days.

Has this ever happened to you? You set out to book a trip somewhere, and in the process you end up booking a totally different trip somewhere else? And the first trip still isn't planned? It happened to me today. 😂

One of my goals for today has been to book our trip to Club. Club? Yes, President's Club, the annual incentive award for top sellers in many organizations. I won a trip to Club again this year, for the third year in a row. And this year Club is in Sardinia, Italy. I'm excited about that because it breaks the pattern across the past 7+ years where my company has held Club in the Caribbean or Mexico. We've been to those places on our own, and they're closer to home, too, so they seem less special than Italy.

So, we're trying to pick our flights to Italy. The trip's in late May. And I've got to get this done by tomorrow— which, for me, means today, because I'm taking the day off from work tomorrow. Except while researching flight options it struck me, "Hmm, I should start looking at Thanksgiving travel plans to visit family."

At first, looking at Thanksgiving travel to the East Coast seemed like a short tangent... then I went down the rabbit hole on it. Good news? We've got flights booked, and they're at convenient times and much better prices than I expected. Bad news? Those are our Thanksgiving flights. Italy in May, booking deadline tomorrow, is still TBD!

Los Cabos Travelog #19
Viceroy hotel, San Jose del Cabo - Thu, 9 May 2024, 9am

Today's our last morning in Los Cabos. Our flight leaves a bit after noon; our shuttle to the airport leaves at 10am. As I've been waking up at 6am, that actually leaves us me few useful hours to enjoy the resort and/or the beach— if I wanted. Sadly I cannot find the energy to care. Other than socializing a bit with colleagues I passed on the walk over to the breakfast room earlier this morning, I've been content to sit quietly in my room.



It's a comfortable room with a beautiful view, I must point out. But beyond that artificial horizon lies a beach. And probably some of my colleagues. But today I don't care to see either one.

The beach, I don't care about because it's not actually that nice. Oh, it looks beautiful, a wide band of pale brown sand. But it's actually very gravelly and hurts to walk on. And the surf's too rough to enjoy going in further than knee-deep. Oh, and the water's cold, too.

As for my colleagues? I've been feeling a malaise at work for several months now. I'm disengaged and don't care much anymore. Hanging out with colleagues just doesn't seem much fun under the circumstances. Yes, this is the same reason I bailed early from the awards dinner last night. I'm happier keeping my own company here. 😔

Los Cabos Travelog #17
Baja California Sur, Mexico - Wed, 8 May 2024, 3pm

Today we went ATV riding in the Baja desert. It was another of the A-or-B activities arranged for my company club trip. I think the "B" activity was a spa treatment, so yeah, I was totally going with Option A. Hawk, too.

A bus took us to a spot over an hour away. Fourteen of us were aboard for the activity.

After the difficulty I had with snorkeling yesterday you might wonder if I'd want to try another physical activity. Hell yes! It's not the physicality.; it's my familiarity with the equipment. While I've never driven an ATV before I have been driving 4x4 vehicles for 27 years. I'm very confident with reading trails and picking the right line through obstacles. As I took the while after a quick briefing on the controls, I thought to myself, "This is like a Jeep and a lawnmower had a baby."

The photo above/right of me in my gear is the only one I have from this activity. The guides told us multiple times not to try using phones or cameras during the trip. "You'll need to keep both hands on the wheel and pay attention to driving," they advised us. Which was totally reasonable. But it was also because they were taking pictures for us to sell at absolutely hideous prices. How hideous? Over $100 for a digital download of 20 or so pics they made. $72 for single photo printed as a souvenir. Fuck no.

The ATV I drove was a two-seater, front and back. I had wanted a solo ATV but Hawk didn't want to drive. Thus she rode as my passenger for the full hour.

While we were out on the trail we saw other groups in the same area. Other outfitters offer ATV rides, too. And some offer a much more classic 4x4 way of traversing the desert....



I was amused we saw camels in the same area as Hawk had spotted beach camel rides a couple weeks ago when we were planning activities for our Los Cabos trip. I was way more interested in ATVs than camels, though. "Compared to ATVs," I warned, "Camels are stinky and mean."

Los Cabos Travelog #12
Viceroy San Jose del Cabo - Mon, 6 May 2024, 4pm

Today around lunchtime we headed back to San Jose... but not the one near our home. Now we're in San Jose del Cabo, Baja California Sur, MX instead of San Jose, California, US. This is officially the club part of our club trip. The next 3 nights at the Viceroy hotel in San Jose BCS are being paid for by my company.

In a previous blog I wrote about what I saw as the difference between 4.5 and 5 star hotels based on the distinctive service at the Waldorf Astoria. By that rubric the Viceroy is at hest a 4.5 star hotel. The rooms may be nice— though we wouldn't know, because we haven't been assigned a room yet— but other than that it's just a normal, large hotel. When we arrived the lobby was busy with people checking in, and we had to wait. At the Waldorf there was never a line, for anything. There were always enough staff on hand to greet us immediately.



Like I said, our room wasn't ready yet when we arrived, so we left our luggage with the bellmen and grabbed our beach bag to head down to the pools and the beach. The pools and beach are out across this... water court, I'll call it for lack of a better term... and then down a few levels. Descending those levels on ramps feels like leaving the Ziggurat.

We staked out a couple of beach chairs and put on suntan lotion. We headed first for the surf. That was mostly a no-go as the waves were pounding too hard to want to go in deeper than our knees. And Brr, the water was cold! Oh, and the sand was rough, too. It hurt my bare feet to walk across it. We retreated to our beach chairs and ordered lunch from the beach-side cafe.

Lunch was... edible. I.e;, it was bland Mexican food. And overpriced, though not $133-for-two-people bougie.

After eating we hung out at the pool for a while. Many of my colleagues were there. Some of them were already pretty well liquored up even at 2pm. Ah, day-drinking. It's a younger man's sport.



Around 3 we headed back up to the lobby to see if our room was ready yet. It was. They just hadn't texted me like they said they would. We went to the room, started to unpack, then thought to make walk-through videos like the one above. 😅 And it's not just for showing off. Making and narrating a short video like this is a great way to remember things months or years later. I'm trying to remember to make short videos more often of cool places I go.

Los Cabos Travelog #0
At home - Fri, 4 May 2024, 10:00pm

This evening Hawk and I have been packing for our next adventure trip. I know, I'm not even done posting blogs from our New Zealand trip— I've got probably 15 journal entries still to go!— and here were are getting ready to head out again. And no, it's not Alaska. Though I wrote earlier today about planning an Alaska trip, that's not 'til June. It's not even the next trip. It's, like, four trips away in the future. Tomorrow morning we're leaving for a nine days in Los Cabos, Mexico and Phoenix, Arizona.

The Los Cabos part of the trip is the President's Club trip I won at work. Well, part of it is club. The club trip is 4 days and starts Monday. We chose to extend the trip, at our own cost, for an extra two days, flying down there Saturday morning. We'll be off on our own at a beautiful resort (more on that soon!) before joining the company group after two days at a different hotel.

Club is over on Thursday. Instead of flying home or extending another three days in Los Cabos (the five we've planned are plenty) we'll fly to Phoenix, Arizona. We'll be there for three days at a nice hotel with a waterpark. Splashing around in pools at a hotel in the US is kind of more our speed than visiting an overly commercialized, "foreign lite"  resort. And my in-laws are flying out from Pennsylvania to join us for those 3 days in Phoenix. That Sunday we'll fly home... and they'll fly with us, to visit us in California for a few days.

Anyway, it's late Friday night here. Our flight leaves in about 10 hours. We're pretty much all packed. And we're packed fairly lightly. This trip is all leisure, no work. No work clothes, no work computer. Just shorts, light shirts, two pair of sandals, two swim trunks, and a few bottles of suntan lotion.

I got word on Friday that "Club" this year, aka President's Club, aka the annual resort trip for top performers in my company's sales organization that I won in February, will be in San Jose del Cabo, Mexico this year. We'll be at a fairly swank resort hotel on the beach for 4 days in May. If I go.

Wait, what do I mean "if"? Well, over the past few weeks I've been thinking about the places club might be this year. Cabo has been on the short list. It's a predictable tourist destination for this sort of thing. And I've been thinking, "Enh, if it's Cabo I'm only 50/50 for going."

I've been to Cabo before. For club, even. It was back in 2019. It was a... reasonably good... trip but also one that left me not wanting to go back for more. See my 5 Takeaways from the Cabo Trip for details.

And this trip being 4 days, that's 2 days that are part travel so there are only 2 full days at the resort. It's not a big trip. I'd rather spend the time off from work going somewhere of my own choosing, even at the cost of paying my own way. The main thing that keeps me "in" for this trip is the fact it's face-time with leaders and key coworkers.

It's only what, 9 days since we actually finished our trip to Grand Cayman? And I've just finishing catching up on my blog backlog. I would've caught up sooner, maybe only 2 days late, except that I've had two other trips in the meantime. And now one of them, the San Antonio trip, is getting backlogged. At least that one should only finish 36 hours behind. But now that I'm caught up on travelogs from Grand Cayman it's time to do a trip retrospective. Here are Five Things:

• Our choice to extend the trip 2 days was a good one. Yes, it was expensive. Those extra 2 days on our dime cost over $1,200. That's a lot of dimes. But much as we expected, the 3 nights paid for by Club would have been too brief of a stay on the island, especially considering the travel time there and back.


• Our choice to book flights that allowed an overnight in a hotel on the outbound trip was a good one. It turned out that with a flight delayed 2 hours we didn't get much sleep. But that was better than flying a redeye— or worse, missing a redeye connection, which happened to a few of my colleagues.


• I've said many times before that every trip I forget one thing. That's not a hard-and-fast rule, of course, Some trips I don't forget anything. This trip I almost forgot one biggie: the hotel overnight in Houston on the outbound leg. The day before the trip I was reviewing plans for Sunday and tried finding which hotel I'd booked to see what dinner options would be available at/near the hotel. That's when I realized that I hadn't booked a hotel. 😱 I'd looked at options and more or less picked one... but I didn't actually make the booking. 😧 Well, I did get around to it... one day ahead of time. 😅 Lesson: always recheck your plans 24 hours before you leave.


• Our choice to travel with only carry-on luggage was the right one. It meant not taking dressier clothes (e.g., trousers and loafers for me) but we absolutely didn't miss dressing up. We also considered checking a bag just to not have to lug carry-ons around the airports, but the time we'd have lost checking and reclaiming that bag 4 times would've made every airport more of a hassle.


• Finally, the good experiences we had with guided tours on this trip, particularly swimming with the manta rays and snorkeling (even though it was a bust for me), make me more interested in looking for guides on future trips. One of the reasons I've been reluctant is that outfitters are hit-or-miss. We've had a few flops when we've hired tours. I feel more comfortable traveling by my own wits than outsourcing it to someone who may take my money, a lot of money, and give me a shit experience and not care— wasting, at that point, not only my money but also my opportunity. Maybe I need to be more willing to take that risk.