Anonymous
Post 06/04/2025 07:51     Subject: Caribbean at Christmas - I know...

Anguilla Aurora: Plenty of beach chairs, two beachfronts. I was there last year; I left around the 20th and one of the beachfronts was often completely empty. The other wasn’t full either. They might see more traffic during Christmas, but I doubt it’s full.

You can also look into other islands like Cancun, Cayman Islands
Anonymous
Post 06/03/2025 20:40     Subject: Caribbean at Christmas - I know...

Anonymous wrote:You don't need a bigger beach, you need a more exclusive hotel. We have never had to fight for chairs at a Four Seasons and that's not even that exclusive. I rec Four Seasons Anguilla.


This, though I can’t vouch for Christmas week.

And truth is, we’ve even had issues at some four seasons hotels. We stayed at the FS Maui (before it was on the white lotus, so it wasn’t even as wildly popular as it is now). You could probably get some seats by the pool or beach throughout the morning, but the afternoons could be a challenge and if you wanted a seat at the adults only pool, you had to be waiting by 6 or 7am - was nuts!

But yes in general more exclusive hotels where the capacity isn’t much bigger than the pool or beach capacity. Or a place where you can prepay for beach seats online (some properties in Aruba and Oahu offer this)
Anonymous
Post 06/03/2025 20:18     Subject: Caribbean at Christmas - I know...

Anonymous wrote:Condo on seven mile beach in grand cayman. Find a low rise condo like Aqua Bay Club. Rent a car.

St. James Club on Antigua.

Smaller property on Aruba like Divi.



That is what I would do. You can still use the bars and restaurants at nearby hotels.
Anonymous
Post 06/03/2025 20:18     Subject: Re:Caribbean at Christmas - I know...

Do a cruise instead. Or go somewhere like Bermuda where it's not going to be super hot.
Anonymous
Post 06/03/2025 20:17     Subject: Caribbean at Christmas - I know...

Condo on seven mile beach in grand cayman. Find a low rise condo like Aqua Bay Club. Rent a car.

St. James Club on Antigua.

Smaller property on Aruba like Divi.

Anonymous
Post 06/03/2025 20:00     Subject: Caribbean at Christmas - I know...

We like Windjammer Landing in St Lucia. I’d recommend the direct flight out of Philly. The only downside of St Lucia is the ride from the airport.
Anonymous
Post 06/03/2025 19:52     Subject: Caribbean at Christmas - I know...

Anonymous wrote:
Anonymous wrote:You don't need a bigger beach, you need a more exclusive hotel. We have never had to fight for chairs at a Four Seasons and that's not even that exclusive. I rec Four Seasons Anguilla.


There's absolutely no way we can do Four Seasons anywhere for that amount that week.

We were in the DR.


Ah, I see you need 2 rooms. 4S are almost all booked that week anyhow. I just checked a few.

I'd look at a villa in St. John.
Anonymous
Post 06/03/2025 19:49     Subject: Caribbean at Christmas - I know...

Should be able to find someplace on PR (incl Vieques). Maybe airbnb?
Anonymous
Post 06/03/2025 19:47     Subject: Caribbean at Christmas - I know...

Terre-de-haut, off of Guadeloupe. 7 empty beaches, one for every day of the week, all quite different. Cool village to explore, hiking trails across the hills, a pain de sucre…look at Bois Jolie hotel…But there are many other hotels and little houses to rent.
Anonymous
Post 06/03/2025 19:35     Subject: Caribbean at Christmas - I know...

Anonymous wrote:You don't need a bigger beach, you need a more exclusive hotel. We have never had to fight for chairs at a Four Seasons and that's not even that exclusive. I rec Four Seasons Anguilla.


There's absolutely no way we can do Four Seasons anywhere for that amount that week.

We were in the DR.
Anonymous
Post 06/03/2025 19:31     Subject: Caribbean at Christmas - I know...

Westin in St John. It’s not on a beach of course because nothing is in St John but there are tons of beaches to where you won’t feel crowded unless you pick the most popular 1 or 2.
Anonymous
Post 06/03/2025 19:27     Subject: Caribbean at Christmas - I know...

Anonymous wrote:Tell us where you went before and had the bad experience so we have a better sense of what you don’t want.

Have you been to Grand Cayman?


We had to fight for chairs at the Ritz in Grand Cayman, it was awful. Service not good either. The workers at the beach seemed more interested in hanging around talking to each other than helping guests.
Anonymous
Post 06/03/2025 19:26     Subject: Caribbean at Christmas - I know...

You don't need a bigger beach, you need a more exclusive hotel. We have never had to fight for chairs at a Four Seasons and that's not even that exclusive. I rec Four Seasons Anguilla.
Anonymous
Post 06/03/2025 19:24     Subject: Caribbean at Christmas - I know...

Tell us where you went before and had the bad experience so we have a better sense of what you don’t want.

Have you been to Grand Cayman?
Anonymous
Post 06/03/2025 19:07     Subject: Caribbean at Christmas - I know...

DH wants to go to the Caribbean between xmas and NY.

Backstory - We went to an island a few years ago and it was terrible -- small beach and couldn't get chairs there and had to fight with pool guy to get one there at 9am ("Sorry miss, they're all taken," yet there is one person in the pool and one person sitting in a chair.) Everyone hated it, but DH is insistent we try again.

Is there a hotel you recommend that has access to a big beach that we don't have to fight over that week? Bonus for easy flight and not many drunk people. I know it's outrageously expensive that week, but we can do ~$17-20K for 7 nights, but need two rooms, so it looks like a mid-range-ish place. Can be adults-only as kids are college-aged.

Is Cancun a possibility? Or, is that a bad idea?

Please help!