Ten Nights in the Southern-But-Definitely-Eastern Caribbean on the Disney Fantasy

Part 1: Overview and the (Very Limited) Negatives

I’m not a big fan of ranking things these days. Opinions shift over time, and how I’m feeling about something can vary for a number of reasons. However, if there is a vacation that I would define as the ultimate embodiment of the word, it remains a cruise on Disney Cruise Line. The service is unmatched, the ability to enjoy a lot of experiences without all the planning that usually entails, and the sensation of being removed from the world outside places a Disney cruise in a league all its own.

Although my family and I have done an annual cruise since my wife first talked me into one in 2022, this was a year of a lot of celebration for us, so my wife and I decided to make an effort to cut a few celebratory expenses and focus on trying to aim for a longer cruise than in recent years. We’ve done 4-, 5-, and 7-night sailings, with the latter two being above the threshold where it really feels like we’re getting a full experience, but the 7-night, which we only did once back in 2023, was our target. However, we discovered that if we were willing to go with an ocean view room and skip the veranda, we could get a very rare 10-night sailing.

We decided that three extra nights beat a balcony, and it meant the added bonus of getting to sail on the Disney Fantasy. I’ve not sailed a ship I didn’t like, but I do find the Dream class, which includes its namesake ship and the Fantasy, to lead the way in design. The Fantasy was our ship for the 7-night itinerary several years ago, but nowadays generally finds itself rotating between 4- and 5-night sailings to the Bahamas and the private islands/beaches. This 10-night sailing was a bit of an anomaly, with the itinerary being a bit of an extended version of the 7-night eastern Caribbean sailing we had on it the last time. Philipsburg, St. Maarten, San Juan, PR, and Castaway Cay were all on the agenda, but added between the first two were Castries, St. Lucia, and St. John’s, Antigua. Also, preceding the Castaway Cay day was a stop at Lookout Cay. The cruise was labeled a southern Caribbean sailing, but I’m pretty sure only St. Lucia met that geographical requirement.

Before going into the trip in any great detail, I want to address the negatives. I never like dwelling on these, so I’d rather just cover them right away and move on to the meat and potatoes of the trip report.

What were the negatives? Well…there were barely any. This is pretty much par for the course on a Disney cruise, especially aboard a Dream-class ship, so most of these are going to be more comical and self-deprecating in nature.

There were only four concerns I really had. The first was the condition of the ship, and I want to be careful to emphasize that we’re talking about an A versus an A+. I don’t want to give the impression that things looked bad, worn, tired, whatever. The biggest issue here were the elevators. Both the forward and aft elevator banks had at least one elevator out of service for much, if not all, of the cruise, and though we were forward on our deck, if we had need of using the aft elevators, we had to go up or down one deck to get it to stop. For the forward side, it didn’t have an elevator completely blacked out like the aft bank, but it did have one elevator show “Call Locked” starting a few days in, and it stayed that way until the end. I generally leave a perfect rating for things that aren’t necessarily perfect because I know how much the staff depend on those, but I did drop this to a 4 out of 5 on the survey because ship upkeep fell outside of the purview of our service team and because especially when it comes to elevators, they shouldn’t be down for a week-plus on a ship not that long out of dry-dock and that otherwise revisits its home base more than once a week. Apparently, the screen in the Buena Vista Theater also had to be replaced, but it supposedly took only a day, and we’d seen all the movies we wanted to see by then.

The second item, and the only other one I rated less than perfect on the survey, was the ease of getting to and from the ship on Lookout Cay. This is old news to anyone who follows DCL news, but I’d caveat this by saying that the walk along that half-mile pier isn’t so bad on its own. The reason I dropped the rating a point is this: there are wagons waiting for you as soon as you get off the ship so you can easily pull your kids along and not subject them to the walk or, worse, find yourself having to carry them the whole way. These wagons then are waiting for you at the end of the day to bring your kids back…

…or so they should have been. We headed back well before all aboard time, only to find no wagons waiting at the pier. These wagons appear to remain on the island, meaning that there’s clearly a way to move them along the pier beyond relying on guests. That they were all sitting by the ship over an hour before all-aboard time wasn’t cool. I’m not trying to sound lazy, as the walk doesn’t bother me, but it’s a lot on small children. I admire the rationale Disney used on putting the dock itself so far out at sea (it’s rooted in environmental protection, one of many selling points of Lookout Cay in general), but it just struck me as a logistical misstep that shouldn’t have happened.

The third concern I have is the survey itself. This is probably the one universal concern I’ve had from these cruises, and until the day comes where the survey gives me the ability to address something without feeling like I’m about to cost an employee a promotion or risk them getting a reprimand. I’m given to understand that this may not be unique to Disney, but I learned back on my cruise on the Wish a couple of years ago that a good number, if not all, questions are going to get applied to the staff onboard. This means that if you don’t like a restaurant, marking that you didn’t like it ends up being a mark against your service team. The overall experience is so far ahead of just about anywhere else in terms of excellence that it’s of little concern, and this is doubly true for the Dream-class ships where the design of the vessel is as good as the service provided by those onboard, but there are times where there may be something that has nothing to do with the onboard staff that I might not want to rate as highly as the rest of the experience. I would like it if the survey gave the option to differentiate a process, design choice, or whatever from the staff themselves.

The last concern had absolutely nothing to do with the cruise itself, but rather the ports. Some places were better than others, and I knew to expect this anyway, but the hawkers in the ports…goodness, it was almost relentless at times. Most took rejection pretty well, to be fair, but it can still be pretty overwhelming, and in St. Maarten, some were downright nasty. They’d get mad at you, they’d get mad at each other, and so on and so forth. We ended up getting a pretty solid deal thanks to some negotiation, but not without our particular vendor copping an attitude over it. I realize that the Caribbean in general is not overly well off and that we’re guests in their lands, but conversely, everything seems to be negotiable, and there is a prevalence of scammers who ruin things for everyone. All told, it can add a great deal of stress to what should be relaxing days.

As for other concerns? Well, in no particular order:

• I botched the rum acquisitions. I didn’t get Topper’s in St. Maarten, which was dumb because it seems hard to get in central Florida. I got the wrong rum in St. Lucia, although it appears I can get what I should’ve bought at a reasonable price here. In Antigua, I should’ve bought the English Harbour 10-year instead of the 5-year as the latter is very good, but the former is likely even better and was considerably cheaper in Antigua than it is here.
• I didn’t get a drink in Meridian. It was one of the very few misses I made onboard. Poor planning on my part.
• Argentina didn’t win the World Cup.
• I didn’t realize how many different options there were when you dial the extension for Pepe the Prawn’s room until I first dialed the extension on maybe the second-to-last day. So many dad jokes missed.
• Too much good food and drink and too little reserve stomach space or wallet space to try it all.
• The maintenance issue we had leaving Castaway Cay that delayed our departure by three hours didn’t delay us enough to get an extra night out of things.

These negatives are mentioned more for the sake of being thorough than for any major impact on the overall experience, and clearly the last batch aren’t even serious. Really, all told, this trip was the standard-bearer for our Disney cruises, which I’ll get into in the upcoming parts of the report.

Part 2: The (Non-Disney) Ports Of Call

Our 7-night itinerary in 2023 included visits to Philipsburg, St. Maarten and San Juan, Puerto Rico for its non-Disney ports of call. These comprised what was considered an eastern Caribbean sailing, and I believe the Disney Treasure, which replaced the Fantasy on Port Canaveral seven-night sailings, still does this route from time to time. This sailing was essentially the deluxe, collector’s edition version of that, placing Castries, St. Lucia and St. John’s, Antigua in between those two ports. Somehow this led to the sailing being considered southern Carribbean, although I’d contend only St. Lucia falls in that category.

St. Maarten was the port I was most excited for in 2023 due to the world-famous Maho Beach, a small beach sitting at the end of the runway at the island’s airport. We got that experience, but it was a bit of a drive. St. Maarten is a beautiful, mountainous island, but getting around much of it can be a little tricky unless you’re feeling adventurous with rideshares or you have an excursion. We skipped excursions on this trip as they can be pricey and our son is too young for most of the interesting ones anyway. Besides, if I’m going to experience someplace, I’d like to give it a few days and really see all there is to see. As a result, we initially planned to stay onboard. However, we popped into the port and discovered the inexpensive water taxis across the small bay to downtown Philipsburg, which sat along a nice stretch of beach. We had to work our way through the relentless waves of hawkers, some of which were actually pretty nasty and didn’t take rejection well, but we ended up on a nice spot on the beach and had several great hours there, with some delicious oxtail to satisfy our appetites. We ended up meeting a nice family from the ship as well, and our kids made friends with theirs that led to time spent together on the Disney islands/beaches later. The town itself wasn’t really anything to write home about, but the location was really convenient, especially with the great water taxi service.

Castries, St. Lucia came the following day. St. Lucia seems to be regarded as one of the most beautiful islands of the Caribbean, replete with some impressive attractions. However, the island is not particularly small, and the cruise port in Castries is a considerable distance from the parts of the island with the various attractions. I’m told the roads are pretty adventurous as well, so our time there basically involved our kids going to the kids’ club onboard and us doing little more than going to a grocery store to get treats and rum. As I mentioned, I botched even that, although I’m told that as far as entry-level spiced rums go, my purchase of locally-distilled Bounty Spiced Rum was among the better acquisitions one can make. Thankfully, I can get the island’s famous Chairman’s Reserve locally…I think…at only a small markup from what it was there.

St. John’s, Antigua, was similar in terms of locational challenges to Castries, albeit not quite as severe. We did consider trying for a beach day, but the water taxi to a nice beach nearby was significantly pricier than it was in St. Maarten, so we passed. Thankfully, St. John’s is the main population center, so we explored town a little more, but it still ended up being little more than a magnet and rum acquisition. I went with locally-distilled English Harbour, choosing the 5-year over the renowned 10-year to save a few bucks. I’m sort of kicking myself, but even the 5-year is the first rum I actually enjoy as a sipper, so I’m not totally mad. I’d really like to come back to Antigua, as it looked to be a very beautiful island and one I’d like to see more of in the future.

Last up was THE port of ports of all the cruises I’ve done: San Juan, Puerto Rico. This was the port for which even the crew was excited. Given the enormous amount of air service San Juan has, especially from all over the east coast, it may seem a somewhat unimaginative choice for best port, but it wins because several of the cruise piers are right in the heart of Viejo San Juan, the old city and home to all sorts of places that the locals go. Walk just a few minutes and you’ve left the world of Señor Frog’s behind, instead finding yourself amidst all sorts of great local places to eat and shop. It’s not even a long walk to some of the city’s famous historical sites, although it is a steep uphill climb to much of it. Here we spent a good bit of time walking around, getting lunch at a nice local spot, visiting a great local chocolatier, and taking in some of the beautiful city sites. San Juan was the best choice to close out four days of port visits, and it lived up to all the great memories from our last cruise that stopped there. We saw a good amount of crew take it all in, and it seemed that the crew, who were in good spirits the whole time, were rather invigorated by the day themselves. I’m not entirely sure where they went or what they did, but they apparently had quite a day. Getting through dinner was almost a struggle because we were all laughing so much. They were already a pretty funny duo, but it was next-level that night.

As the islands went, I’d happily go back to see any one of them. Each one is probably worth a few days to really see it all, but even for what little exposure I got, I did enjoy them. It was pretty cool venturing a bit further afield, and I only wish that it was a bit easier to get to those islands for further exploration.

I have desperately tried to do an itinerary with San Juan, but it's never the right timing or origin. I find the other Caribbean ports to be meh, but I don't know anyone who hasn't fallen in love with San Juan. Outside of their owned properties, I rarely get off in the Caribbean ports. Jamaica just because the immediate area has stores with rum and jerk spice. Totally different situation in Europe and Alaska. Your ports don't typically show on the east and west itineraries, and I think the crew was right to be excited about San Juan.

The survey is never ideal because of the constraints you mention. It still doesn't have a box at the end to just fill in whatever. I often email shoreside for things that don't fit in the survey, good or bad. I'll send you a PM with it.

I love the Fantasy (and Dream), in no small part because Skyline is one of the best bars anywhere, and I like having all of the adult space in one spot (Meridian is kind of there too, since it's just an elevator ride). Dream will be sailing out of Canaveral when Wish crosses for dry dock next summer, and I'm pretty excited about that. Still, not gonna lie, we did Treasure for a week last year, and the theme and shows and decor all hit better. That might be my favorite.

Just out of curiosity, how much does oxtail cost on a Caribbean island? I love it and you can find it in Texas, but it is insanely expensive. It's double the cost of every other plate at one of the lunch places I frequent.

My wife and kid stopped at San Juan on a girls cruise several years ago and came back raving about it.