Caribbean Cruise – Beginnings/Prep


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We had planned to take a ‘big trip’ for our 40th wedding anniversary in 2024. But COVID got in the way. Discussions had begun sometime in 2023, but we hadn’t really settled on where we wanted to go and when it would be safe to do so. So we postponed for a year.

Thanks to our previous trips, we get almost daily catalogs from various tour companies (Viking, Road Scholar, National Geographic, etc.) At some point we got one from the Smithsonian. We didn’t realize they did tours. And I think it may be a relatively new thing for them. Anyway, Marion discovered a tour of the Windward Islands of the Caribbean. A ‘small boat’ tour (which I prefer) with stops at 5 or 6 islands. And at each stop, there is a choice of various things you can do (snorkel/swim, take a tour, etc.). So we could both hopefully find something we wanted to do. I’m not usually a ‘tropical’ trip person given my propensity to burn in the sun (or on cloudy days for that matter) and thus having to slather myself in sunscreen every morning. But Marion was so excited about the prospect that I couldn’t say no. And I’ve always wanted to go there too.
First step, and critical for this log, was figuring out how to spell Caribbean. Two b’s and one r as it turns out (I always want to do the reverse). But now, having resolved that, we can move on.

The second step, and one that shouldn’t have been all that complicated but was, was figuring out when to get to the boat and how. The cruise leaves from St. Lucia, which is not a big place. We are doing a pre-tour add-on so that we can get there early enough to ensure we make the boat and to adjust to the time zone. The tour will pick us up, but for reasons that were never quite clear, they said we had to arrive by 2:30p local time. Well, it’s a 5-7 hour flight from Portland and a 3 hour time change just to get to the east coast, let alone to St Lucia so that’s a little tricky. And God help you if you don’t get a direct flight to a city that has a direct St. Lucia flight. It becomes a 20+ hour ordeal (vs 10 or 11 which is bad enough).

There’s a flight to Miami with under an hour layover that gets in with plenty of time. With a reasonable layover, it gets in at 2:45. That seems close enough to me. But can we get anyone at the tour company to respond to an email asking if that’s ok? No.

We really want to fly through Raleigh, NC rather than Miami if possible anyway. Our one experience at the Miami airport was that it’s not much different than flying into a third world country. I want to say there were live chickens in someone’s luggage. But I may be imagining that. When I look for flights though, I can’t find one available to Charlotte. So ultimately, I booked the earlier Miami one and hoped we’d make the connection. But Marion insisted the flight was available. And reminded me that when searching for flights I actually needed to start on the day *before* we were to arrive because all of these flights were overnight. Oh, right… Oops. And when I looked it up that way, lo and behold, a flight. Luckily, I had booked changeable tickets and made the swap and one problem solved.

Except no. A few weeks later, another mail that our flights had been changed again. Basically changed back. There are no flights from Charlotte anymore. Presumably because of hurricane Helene. We’re now back to arriving 10 minutes ‘late’ and returning with a too short layover in Miami.

So, I try to change them again. I chat with someone online. Or maybe it’s a bot. I tried to ‘Turing Test’ them (look it up) and still couldn’t tell. Anyway, they found reasonable flights and I thought all was well. Until the next day when I checked and it hadn’t changed. And when I looked, those flights didn’t exist. So I left it.

Then a few weeks later, another update. We now get in at 2:25. So just under the wire for the arbitrary cutoff from the tour company (assuming we’re on time, and that’s just wheels down I’m sure). And now we have 1.5 hours of layover on the way back. Which I’m sure is *plenty* of time to get through customs and to our flight in Miami. But all other options involve overnighting somewhere (22-25 hour total) so we’re going to give it a try and hope for the best.

But no, another ‘your flight has changed’ email from American Airlines. I look and it looks the same to me. I try to find a human who can tell me what changed. The best I can do is a chat and it turns out it’s only a few minutes change. Do you want to stay overnight in Miami and take the direct flight to Portland the next day (at 7:30 pm)? No, no I do not. So fine.
But… no. The next day YET ANOTHER mail that the flight has changed. Apparently, the layover time was not acceptable to American. And after a bit of Google research to confirm what I really did know in my heart anyway, I saw they were right. We were never going to make it. But what did they change us to? A few hours layover in Miami, fly to Phoenix, land at midnight and leave at 8 in the morning. Really? Um, no. What was wrong with the direct flight to Portland the next day they asked me if I wanted just a few days ago?

So, some more Google research and I determine there’s a flight out to Phoenix late morning the next day, and an afternoon flight to Portland and we still get in before the 7:30pm direct flight. So let’s try that. I call the customer service line and the wait time is ‘approximately 1.5 hours’. Should we call you back? Yes, let’s do that. But in the meantime, let’s try the chat. 45 minutes later and for reasons I won’t go into, they are unable to change the flights. This rule, that rule. It’s not a separate flight, blah blah blah. Thanks for nothing. But, finally, a human calls back, I tell him what I want to do, he says fine, bing bang boom, it’s done. What the huh? But ok, fine. So now we’re spending the night in Miami, getting a good night’s sleep hopefully, and flying home via Phoenix the next day. Hopefully with our checked bag in hand but if not, so be it.

As 2024 turned into 2025 and we were only a few weeks away from the trip, the next concerns were what clothes to bring (there are a couple of ‘fancy’ dinners on the boat, some of the excursions suggest hiking shoes, etc.), what the power requirements are (forgot about that), international dialing plans, what food/snacks to bring and the like. The clothing especially was a problem. The trip description made it sound like you were expected to dress up for dinner (slacks and a real shirt at least). Which resulted in essentially packing two sets of clothes per day. As it turned out, that wasn’t necessary (of course), but all things are clear in hindsight.

I found a cool device that has USB ports and various types of plugs in it and thought we were good. Until I discovered my portable CPAP (or the evil machine as I call it), doesn’t voltage shift like most electronics devices today. And, that the only 110V plug in the cabin is in the bathroom. So, I had to order a power converter too, which conveniently also does everything the ‘cool device’ does, plus convert. Ah well.

Everything is stacking up in the spare bedroom. Marion, the packer extraordinaire, claims she can get it all into two suitcases and under 50 lbs and I believe her. We’ll see.
And one last snag to worry about. I woke up the Monday before we were leaving all congested. It seemed awfully sudden and not like a usual cold. Is it COVID? Will they not let us board (you have to stipulate you aren’t sick)? Did we get the ‘cancel for any reason’ trip insurance? No, we did not. Uh oh. But tests were negative and by Thursday I was feeling pretty good with still a few days to go before our Sunday night departure. As it turned out, all was well. Just a little bonus anxiety.

As it turns out, the 147 shirts I selected to bring (okay, not that many) actually didn’t all fit in the suitcase. And after some discussion, the A team was selected and Marion got it all stuffed in. 45-ish pounds. It turns out she was a bit overly ambitious about what she could bring as well. So some things had to go. She’s right on the 50lb line so we’ll see. We agreed we will need to go to some more warm weather climes in the future so the clothes that didn’t make the team this time will get a chance to play.

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