I'm not sure this is the board to give you the best advice.

I have first-hand knowledge of St. Kitts and Nevis and can verify that they are rather conservative islands in general.

But in my recent visit to Nevis, i did see a couple of same sex couples who were clearly repeat visitors. These were at smaller hotels. I don't know about the Four Seasons.

I would have recommended the French side of St. Martin but reading what Statia says, maybe it's not a good time.

I think you'll be fine no matter where you go, if you are aware of local sensibilities. Make your decision on other island/hotel amenities and activities (i.e. good snorkeling, hiking, white beaches etc.).

Let us know what you decide upon.

CW

A dictionary definition of a Gentleman is "a man of refinement", and as such a gentleman will be someone who is aware of their surroundings, local culture and sensibilities.

A traveller is basically the same thing (as opposed to a tourist :))

What I am trying to say is that I can't imagine any Caribbean island would be an issue for two gentlemen travelling together, it is all a question of respect for ones surroundings, and that applies to all visitors.

As you are lookng at high end resorts, I would rule out my place (The Reef), as we don't offer the kind of "hot and cold running bathrobes" service I think you are looking for.... but you would certainly be at home and welcome here (we do welcome many "gentlemen/ladies travelling together" as you put it !)

I feel sure that the same would be true at any resort in Cayman, so you may wish to consider the Ritz Carlton.

All the best with your research.

I think Caneel would be a great choice!! We just returned and the seclusion, privacy, and quiet was amazing.

Congratulations on your upcoming vacation!

I have been to:

Caneel - with a girlfriend
Peter Island - solo
Cuisinart (Anguilla) with a male buddy
Little Dix - solo

I think you and your friend would be welcomed and comfortable at all of the above.

The AI thing is pretty much a given at PI and at Little Dix - not many (any?) other choices.

I would not recommend AI on Anguilla or St. John because there are so many great places to eat off campus.

At all of these places I have seen all kinds of people in all kinds of groups. I don't think it will matter to anyone and I think you will feel comfortable. If someone has a problem, it is pretty much their problem anyway. (you are safe at all of the resorts regardless of what people might think.)

I agree with other posters that you may find a more conservative (Christian/Taliban?) view of "stuff" on the islands than you might find in NYC or SFO, but unless you are doing a lot of "in your face" stuff the issue won't come up.

Go where you want and have the vacation YOU want. These are all places to cater to worldly Americans and they won't give you and your friend a second glance - at least at the resort.

Of the places you mention, Peter Island is the most isolated and self contained. I would not hesitate to visit there with a buddy. Last time I was there was in August and it was mostly younger couples, but it was very low key and everyone was very friendly...food is great. Beach front rooms are much nicer than the chalet/harbor rooms, but also much more expensive. It is a nice resort for very low key relaxing. There is not much to do except the beach and a nice dinner. Little Dix is similar, but has the option of some other beaches and a couple of off campus places to eat...perhaps more kids at LD.

Caneel has the most to offer in terms of off campus activities - exploring St John and St. Thomas, hiking the national park, renting a boat, finding off the beaten path beaches, fun bars and places to eat - or just vegging on the 7 Caneel beaches - mostly couples and a lot of older people. If you have not been to the Carib a lot, St. John is a nice mix.

No experience with 4S Nevis or Jumby. Based on experience with other 4S resorts, I suspect you will find many couples who are not experienced world travelers (whatever that means)at 4S...they buy by price and hope for the best, but I doubt you would feel awkward there.

On Anguilla...I am not sure CJ is worth the price... check out Cuisinart and eat a meal or 2 at CJ.

Feel free to ask more specific questions and I will gladly respond.

Eileen,
I will comment on it as best as I can for you. The people that were on the beach down by Sunshine's were down there because there is service right down there as well as a rest room and a new adult only pool. The people on the other side were there because that is the side for children. In the middle I think people just prefer to be poolside (like us! We live on water and have our own beach so we find a pool to be more special)as there are no rules about putting your chairs anywhere. As far as lining them up, all of the resorts I've stayed in, at the end of the day, the staff has cleaned up and just lined the chairs up in an orderly fashion. But the following day, as more and more people came out and used the chairs and placed them where they wished, they weren't lined up anymore. Unless they wanted to be. Or didn't know any better. The other possibility is that the bonfire ring is right in front there and it's possible that they may have been planning on cleaning the area or had just cleaned it and no one had ventured out there yet. I just looked through my pictures the other day though and there are chairs all over the place in every one of them. I do know the FS was not full when we were there and I know that they have times when they are. We were told by the staff that during the holidays they get the repeat customers and they really get FULL! We loved it there. Great bathrooms and the beds, oh my!

I have some friends in the life who enjoy Caneel Bay. Lots to do and they felt welcomed.