I appreciate the guidance of all 3 of you on these places so much. Genuinely wish I could pay it forward. I'm not that familiar with the Caribbean itself, but I am very, very familiar with all of the Florida cruise port cities-so if you ever need guidance on sights or eats in Jacksonville, Orlando, Tampa, Fort Lauderdale, Miami, I am happy to provide it.
When people talk about private vans (that is exciting to hear, as it sounds like a pretty affordable option), how is the safety factor, seating, etc. for little ones? Specifically, talking about a toddler who is almost 4, here. Would she be allowed, or would we feel comfortable putting her in one of those? As to the first poster, John Bull's, comment about Princess Juliana Airport, the timing guidance is appreciated too-I may look up a specific flight schedule for the day, too, but it it good to know that most (all?) take place in that given time frame.
Re: Brimstone Hill, it does sound as though it is difficult to get there inexpensively through other means, and so it sounds like the default option might be just taking the excursion from the ship. The only other one I saw on a cursory Google search was from Viator, which is a legitimate company, but it was 67, not that much cheaper, and perhaps more concerningly, had no listed reviews. So just considering that as what it is, I suppose it's not a terrible value since it gets us there, and includes multiple stops as well.
The one I saw on BVI is an independent one for $40-I don't know how frequently there are issues, or if one were to come up on the earliest trip of the day, if we would have enough time to improvise on getting back. That was sort of what I was banking on-that if leaving by 7:45 and expecting to be back by 10, that if we encountered problems that we could somehow negotiate them in time. The ship doesn't leave BVI that day until 4.
I hear you on the urbanism and walkability of Basseterre and St. John's overall not being the best, and I will take that into account. The vans to Shirley Heights does sound like a decent idea-I guess my concern again, is without a car seat in a vehicle smaller than a bus if it would feel unsafe? Good reminder on being mindful of waves with the little one too, thanks for that : )
I see people mentioning the water taxi.. is that from Maho Beach back to the ship, or is that from the downtown area of Philipsburg? It does look like only about a 20 minute walk back from the pier to roughly the start of the Philipsburg Boardwalk stretch. That being said, I know it will be quite hot too, and honestly the 7$ spent on that might be fun just for enjoyment of the water taxi itself.
Antigua is best on your itinerary for colonial history: What is it about Antigua overall in terms of either architecture/sights, or just historical events/context, that makes it best for the history? I see the views from Shirley Heights are stunning, but what specifically makes Nelson's Dockyard special or worth seeing? I do see there are a few architectural landmarks in town, such as Museum of Antigua and Barbuda and St. John's Cathedral, but at the same time, not something that would consume an entire day of enjoyable sightseeing either. I also figured that Charlotte Amalie might have more history/architecture, and Philipsburg more walkability, than either St. John's and Basseterre would have. However, because those are officially two new countries for me, I figured I would check if there was an inclination or leaning on which one was better overall just of those 2 : )