Caribbean Trip 2023

It’s finally happening.  No, I’m not referring to Cocaine Bear winning an Oscar; I, of course, mean my newsworthy, headline tour to the Caribbean.

Every time I’ve been prepared to come to this part of the world, I’m inundated with glorious reviews from friends like “it’s beautiful, but everything else sucks”.  I’m paraphrasing, of course – there’s always more swearing.  Yet seeing that 70% of traffic to this site and over 90% of Dorsia clients are American, I figured I’d help y’all out and tell you how much they suck in my own words.  Although seeing how expensive everything is, I’m hoping all prior feedback is some elaborate hoax as punishment for all that colonialism my forefathers did, and it’s, in fact, even better than you’ve all been telling me.  I’m sure it’ll be just as good as the Maldives…

So next week, we fly out to Antigua to try Jumby Bay, part of the Oetker Collection, followed by Richard Branson’s private islands, Moskito Island and Necker Island, part of the Virgin Limited Edition.  Finally, we’ll go to Little Dix Bay, part of Rosewood.  I would have loved to have thrown in some additional properties, like Amanyara, Amanera and Cap Juluca, but alas, my funds are not unlimited.  Especially after I invested my life savings into some NFTs of monkeys – it seemed impossible to fail.  Next, they’ll be telling me it’s not safe to put my money in Silicon Valley banks.

There’s good coverage on Jumby Bay and Little Dix Bay already, so my real interest, and our longest stays, are at Moskito Island and Necker Island.  The latter looks like it could be one of the most impressive properties I’ve ever stayed in.  There are only four villas on the island, each totally unique and capable of hosting between 18 to 22 guests.  I invited all my friends, which translates into us travelling by ourselves.  My children are loud, so hopefully, their shrieks fill the empty spaces.  After only changing my mind three times, I settled on the Branson Estate for our villa because it has a private beach, and I’m sure once this article goes live, the papperazzi will be swarming around the island.

I’m really not sure what I’ve set myself up for with Necker Island, as the notorious party atmosphere was not the place for me pre-kids and certainly isn’t now, where I will kill anything that makes a noise after 7 pm and might ruin my night by waking a child.  But they do have a kid’s menu, which makes them more prepared for kids than Cheval Blanc Courchevel.  And they do have lemurs.  How bad can it be?

This is also the first trip our eldest daughter has to sit in her own seat, as she turned two a few months ago.  A part of me is terrified about how she’s going to handle this, whereas another part gets a kick from knowing how much everyone else in first class is going to be annoyed by it.  I think it’s more like a 25/75 split.  With a nine-hour flight to look forward to, it’s not a coincidence that this is the first trip we’ve hired a nanny to be with us for the majority of it.

As always, reviews will be coming, Instagram will be regularly updated and you can contact me with any questions.


  1. Enjoy! Make sure to have some BBQ at Hog Heaven (it looks down on Mosquito Island).

    Both Jumby Bay and Little Dix need their villas updated; look forward to read your perspectives.

    Know you hate COMO but Parrot Cay is actually worth visiting. Amanyara is better with your kids but PC is truly lovely.

    • I just can’t get excited about the Parrot Cay villas. A buddy loves Parrot Cay, so I’ll definitely at least visit it at some point, but I’m yet to be convinced to stay. I appreciate Amanyara’s beach villas can cost twice as much, but they look 5x better, so mathematically that makes them a bargain? Can’t argue with maths. Dorsia has booked clients into Amanyara beach villas and feedback has always been positive.

      • Spot on. It’s the place (and the staff) that’s special, not the villas. Amanyara is the other way around. If you are unimpressed with PC villas; good luck at Jumby and Little Dix 🙂

  2. finally! you’re traveling to a part of the world (and a luxury market) i know well.

    have to admit, i’m a bit surprised by your choices. having read this entire blog, front to back, they’re not the three choices i’d envision you choosing in the caribbean.

    never been to necker. no interest (though not because of virgin/branson – going to kasbah tamadot in june – just that the setup doesn’t excite). and while LDB and JB are fine properties, no doubt, they’re a bit grande dame-y. i’ve been to both multiple times, felt like they were getting a bit stuffy over the years. though oetkker will clearly up even the already high standards at the former.

    were i to pick three ‘for you’, looking for some variety of locations/terrains/setups, they mighta been jade mountain (views/jungle), cap juluca (beach), and…… maybe something on st barts (all around euro-type luxury).

    • Not convinced by Jade Mountain, but Cap Juluca and St. Barths I agree with were they not so hard to get to from London. When travelling with children I really want convenience – Antigua is a direct and BVI is extremely easy to get to from Antigua. BVI has enough properties (Oil Nut Bay was also a consideration) that moving between properties is easy and we avoid flying. I think any other island would have been too limited or too inconvenient.

      • ahhh right. forgot you’re (senselessly) bringing along your young tikes. man, those are some lucky kids. the best my kids get of the caribbean is atlantis and a disney cruise.
        your choices make more sense to me in light of this.

        think for another trip – and for another vibe – you should give st lucia a good hard look. just for the jungle/mountain vibes. or dominica. something like jade or ladera… that missing fourth wall thing is truly amazing when experie……

        oh right! you’re a bug guy. ok, scratch that entire last paragraph.

        finally, have visited amanyara, thought it looked really nice. thought my lunch was ok. never ever wanted to book it. done parrot cay twice and just can’t imagine yara’s any better. plus, i know i’m not supposed spend any time on TA, but it’s as you say with the maths….. when it gets to a certain number of people, they can’t all be wrong. i’m an aman virgin and will def make one some day, tho it will be most likely be one of the classic properties in asia or europe. just no interest in an ‘aman’ experience in the caribbean, let alone nyc (where i’m from). or even gari with it’s pool and this new one in mexico.

  3. Necker looks like the elephant graveyard from lion king.

    Moskito- heaven. I’d recommend doing mediterranean night one evening as the cuisine, the chef did a lovely job. Smores + brandy with a fire pit on the beach at Branson Estate was also a highlight after dinner one evening.

    And to those talking about Parrot Cay; the service makes up for the lack of villa design. I compare their butler to the one in Mr. Deeds.

    Looking forward to your feedback

  4. To ease your mind, I’ve taken all three of my children to Necker Island 6 times and it’s their favorite trip. There are lots of beverages flowing but the main appeal to Necker is the activities. The water sports team is top notch, so you should definitely take kiteboarding lessons for the week of the wind is good. The tennis games are also fun, and the kids will have a blast if they are old enough to go to kids club…which isn’t really a kids club. It’s more like having your favorite older sister playing with you all day. With all that in mind, this is not a place for polished service. They take a very laid back approach to things, so embrace it for what it is!

  5. FYI: We found Jumby Bay and Little Dix to be boring. I guess it depends on what your after. We like the activities and getting to know people at Necker. We have made some life long friends from our weeks spent there.

  6. LDB has a really lovely beach, and we were pleasantly surprised by F&B. Pool was kind of a joke but not to important with such a beautiful, swimmable beach. Disagree that rooms need updating, IIRC they’re only a few years old? Hard product wasn’t *amazing* but not tired, either. Service was OK, but that’s pretty typical of the Caribbean. Felt the butler service was a waste of time/energy, at least for us (they told us they weren’t able to book us a private boat tour, but we went directly to concierge and they had no problem making it happen quickly). Excited to hear your thoughts on Jumby Bay, that’s high on our list.

  7. FYI Little Dix Bay has a sister resort opening soon – Little Cox Bay.

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