Where to go for Sexy Caribbean Vacation

[majorem]

Hey all,

TLDR: So I need some help on suggestions for the right vacation spot in FL or the Caribbean that is both family friendly but also has potential for a bit of naughtiness. Not Hedo or the like, obviously, but a place you can bring kids, with nice beaches and hotels but also bars or nightclubs with dancing, where a sexy wife could venture out at night to find some men to dance and flirt with... and maybe more...

So I am at the point where my wife knows about my fantasy, eventually admitted it turned her on, we've engaged in dirty talk during sex, role played her being spit-roasted using a dildo, she's gone out with single friends and come home soaking wet after being hit on and flirting with men all night and about a year ago, she finally indicated she "didn't want me to have any regrets" of things we never did before we get old and would "do anything for me." Of course, I know the idea makes her horny and am sure she is definitely not just doing it for me but I think its how she needs me to see it because she can't admit what she wants.

Anyway, I think the only way anything is ever going to happen for real is if I can put her into the right environment, where she can feel relaxed, away from home and her adventurous side can come out (and she used to be quite adventurous before kids). We have a babysitter who has traveled with us before and we went on a vacation with her to one of the islands last year but it turned out to be a very low-key resort, with no real nightlife and maybe a little too family friendly. It didn't help that the kids all got sick 2 days in lol... fml

What we need is a place with the typical nice beaches, an upscale hotel but also some bars, ideally places with dancing, that stay open at least until midnight. The place we were at had no sort of dancing and all the bars closed at 11pm or earlier. I'm not really expecting things to go all the way on this trip but I'd like to at least take a first concrete step and see her to dance with some other men, maybe fool around a bit. My wife can be rather bold and friendly after a couple drinks, in the right environment, so I think there is definitely some potential if we can find the right place.

Any suggestions?

 

[Happyman]

Even I have similar plan. Waiting to see if someone comes back with suggestion.

 

[bigDickZane022]

West plan beach Florida or anywhere outside Orlando on the Atlantic side

 

[Rob12550]

In Florida, you do have West Palm Beach, but it seems there might be more interesting things happening in Tampa (Eyz-Wide-Shut, Secrets Hideaway, etc.). If you go to West Palm Beach, Miami, Tampa, etc. major cities, there should be bars and nightclubs especially in higher end hotels, but they might not be most conducive to what you're looking for. You may want to see if there are swinger clubs or meetings scheduled in the area you go to that you can slip away to a bar/nightclub for a couple hours. In Caribbean, the places with casinos (and good diving) are where we have gone being Aruba and Paradise Island in the Bahamas. Both places had clubs. Had is the operative word since many places may not have fully recovered since COVID. The last time we were in Aruba (which was right after they opened up again after COVID), the clubs really hadn't come back.

Do some googling. You'll find some place to split your lives.

 

[wormwood]

You're bringing the kids and a babysitter along on a holiday and expecting your wife to let down her hair with a feeling of anonymity? Just looking at your last vacation where you were hoping she might find something, but you experienced the kids getting sick and a lack of suitable places. I get that you want something new and wild for her, but you run all sorts of risk when in a strange place or foreign country.
I'm suggesting that maybe you've got the ideal situation closer to home. I'm sure going out with her single friends has put her closer to what you want for her than any vacation wishes. In fact, I'll bet her single friends might encourage her to go a little further than she has so far. If she doesn't want the risk of being judged, encourage her to explore the places she's already been to but on her own. Dress her up and send her out there to find what you are both looking for. She can do so and choose to be as anonymous as she wants without having to worry about the kids or the risks that being in a strange new place would entail. She could also find something on the regular side that would be good for multiple fantasy nights. A regular boyfriend or Bull that she can see when she wants might be just the thing.
I get that a new place might be just the thing you're looking for, but you run the risk of being just as disappointed. You've got the perfect situation closer to home and she can spend multiple nights looking for what you both want.
Just an idea. I'm not trying to flame you or anything. Sometimes we get caught up in the fantasy and forget about what we have at home to work with.

 

[majorem]

You're bringing the kids and a babysitter along on a holiday and expecting your wife to let down her hair with a feeling of anonymity? Just looking at your last vacation where you were hoping she might find something, but you experienced the kids getting sick and a lack of suitable places. I get that you want something new and wild for her, but you run all sorts of risk when in a strange place or foreign country.
I'm suggesting that maybe you've got the ideal situation closer to home. I'm sure going out with her single friends has put her closer to what you want for her than any vacation wishes. In fact, I'll bet her single friends might encourage her to go a little further than she has so far. If she doesn't want the risk of being judged, encourage her to explore the places she's already been to but on her own. Dress her up and send her out there to find what you are both looking for. She can do so and choose to be as anonymous as she wants without having to worry about the kids or the risks that being in a strange new place would entail. She could also find something on the regular side that would be good for multiple fantasy nights. A regular boyfriend or Bull that she can see when she wants might be just the thing.
I get that a new place might be just the thing you're looking for, but you run the risk of being just as disappointed. You've got the perfect situation closer to home and she can spend multiple nights looking for what you both want.
Just an idea. I'm not trying to flame you or anything. Sometimes we get caught up in the fantasy and forget about what we have at home to work with.

Hah, I think you misunderstand the intent - I'm still in the "laying the groundwork" stage. There is zero chance sex with anyone else is going to happen on this vacation or at home, at this point. Also, she just ran out of single friends, so unfortunately that's not a thing at the moment. Need to wait for some divorces or something lol.

I'm just looking for an environment where she could be hit on, flirt with some dudes, maybe dance. Maybe her and I do something risque in public.

I mean, last vacation we fucked by pool outside our villa, in view of the beach and other units, which was at least something. On a previous one in FL we didn't have a sitter so I hung out with the kids one night while she went in the hot-tub wearing an extremely revealing thong bathing-suit I picked out, while there was another couple there (had been hoping for a dude or two but still got her horny).

I'm just looking to fool around and do some stuff of that nature in a fun environment where there is something more going on than just a beach and bars that close at 10pm. I'm still in little league here... haha

No offense taken though, I appreciate the idea.

 

[Rob12550]

"something more going on than just a beach and bars that close at 10pm" There's the problem. Many places still do shut down earlier. That's the COVID legacy. Either it is the local laws or places found out their "profitability" dropped off after 10 PM or wait staff no longer wanted to work until 2 AM.

What you might need to do is ditch the kids with grandparents, bite the bullet, and go to Hedo in Jamaica. Total sensual environment where people are basically on the same page and get naked in the hot tubs late at night.

Best of luck.

 

[crissynh50pt]

"something more going on than just a beach and bars that close at 10pm" There's the problem. Many places still do shut down earlier. That's the COVID legacy. Either it is the local laws or places found out their "profitability" dropped off after 10 PM or wait staff no longer wanted to work until 2 AM.

What you might need to do is ditch the kids with grandparents, bite the bullet, and go to Hedo in Jamaica. Total sensual environment where people are basically on the same page and get naked in the hot tubs late at night.

Best of luck.

yup... as a long time both player and hotwife.. i can tell you (SHE) CAN get her some fun strange..(likely without ..YOU around) while having kids on vaca... but just do what the Robs say here and get what you both want!!🙂 crissy

 

[majorem]

"What you might need to do is ditch the kids with grandparents, bite the bullet, and go to Hedo in Jamaica. Total sensual environment where people are basically on the same page and get naked in the hot tubs late at night.

Best of luck."

Heh, if only.... Unfortunately there's no one we could leave the kids with as grandparents are either ...... or in poor health. Also, she's not ready to just straight up head to hedo. That's like taking it to 11, when I think she's only ready for a 6.

Even though she's 5 years younger than me, was a party-girl club-slut when we met, and still periodically goes to watch female strippers at gentlemen's clubs with her friends, she is surprisingly uptight about swingers clubs or anything like that. Her perception is that they're just full of desperate weirdos (without realizing all men, including her husband, are desperate weirdos deep down lol).

I also don't see her agreeing to knowingly sign up for something like that in advance, in a totally sober frame of mind, with the expectation something might happen. My difficulty is, she is more the type who needs to be in the right mood / environment, where she gets wild and allows something to happen. It would probably be a small step initially though, like sexy dancing with a stranger, flirting in a hot tub, letting someone touch her, doing something with me in front of someone else...

I think I may have found some options though - saw some resorts have adults-only sections, with adult pools / bars, so she can at least feel free to wear her skimpiest thong bathing suits without being in view of children. 😏

 

[Hwcouple702]

Look into the Desire resorts south of Cancun and Temptation resort. Find one of the family type resorts nearby and pick up some day or night passes to the resorts....leave the kids with your traveling babysitter...there's opportunity to play, most others staying at the resorts will have rooms available if it goes well. If nothing else, you can just get a bit of the "vibe" from the lifestyle with no pressure on her. Temptation is topless optional and not strictly a "lifestyle" resort, but anything you want goes on. The Desire resorts are "nude optional" but she can stay clothed in her skimpy bikini. In all honesty, she will want to get at least topless pretty quickly. I have no idea if she's "hot" (no offense) or confident with her body. There are all types at those resorts but sometimes a woman who is not comfortable with her body can have problems. It does seem though, that since she's confident in a string bikini then she's fine with her body. All of the resorts have late night nightlife (loud disco type with sexy dress up) and late night hot tubs where everything you want you can find. (at least at Desire resorts)

Also, there is quite a bit to do on family days as well. Xcaret nature park, with underground river, Mayan ruins, etc...

 

[Memories54]

Wife and I had great success with the night clerk in St Marteens and a security guard and massage man in St Kitts..
Both were very good resorts with great beaches and some clubs..Men are there, just need to show interest in them.
Night clerk flirted with her when we checked in, and she flirted back. Later that evening I suggested she put on her bikini and go past desk to pool..he was there so they chatted as he walked her to the pool right outside our room so I could watch..Later she came back, so I suggested she change and go talk some more..she put on short denim skirt, blouse and no bra and no panties.....she was gone about 90 minutes..found out he took her up on top of bldg to see ocean and moon..kissed her, laid a towel down for her so they made out..he took her to a suite and took nice care of her.
In St Kitts, she got a partial massage on beach...I asked him if he did room service which he did...He took real good care of her in room...
Security guard , she just flirted with him, he came to room two nights in a row..supposedly I didnt know about it but we were both in on it.
Condoms in use.....good luck

 

[majorem]

Look into the Desire resorts south of Cancun and Temptation resort. Find one of the family type resorts nearby and pick up some day or night passes to the resorts....leave the kids with your traveling babysitter...there's opportunity to play, most others staying at the resorts will have rooms available if it goes well. If nothing else, you can just get a bit of the "vibe" from the lifestyle with no pressure on her. Temptation is topless optional and not strictly a "lifestyle" resort, but anything you want goes on. The Desire resorts are "nude optional" but she can stay clothed in her skimpy bikini. In all honesty, she will want to get at least topless pretty quickly. I have no idea if she's "hot" (no offense) or confident with her body. There are all types at those resorts but sometimes a woman who is not comfortable with her body can have problems. It does seem though, that since she's confident in a string bikini then she's fine with her body. All of the resorts have late night nightlife (loud disco type with sexy dress up) and late night hot tubs where everything you want you can find. (at least at Desire resorts)

Also, there is quite a bit to do on family days as well. Xcaret nature park, with underground river, Mayan ruins, etc...

Ah yeah, you know, I actually thought about that and wondered if that was a possibility - thanks for the advice and info. I think I may try to find something in the Temptations neighborhood for the next trip. I feel like she would never agree to go on a vacation to one of these places but if we happened to be staying nearby, I think she would be up for checking it out.

Haha, she's not a swimsuit model but she gets hit on all the time. Despite the attention she gets, she isn't super confident about her body as she is fixated on relatively minor things but, yeah, she's gotten over it enough she'll put on a pretty revealing bathing suit.

 

[Seapride]

I understand the desire to go someplace you are not known. But your first comment stated she was coming home real wet after a night out with friends. Have you considered she might already be further along than you are thinking? She might not tell you what actually happened on her girls night out adventure. I would encourage her to keep going out with her horny friends. Doesn’t matter if they are single or not. Lots of married women fuck around. Tell her she is free to do anything she wants and you want details when she comes home. Bet she opens up more.

 

[majorem]

I understand the desire to go someplace you are not known. But your first comment stated she was coming home real wet after a night out with friends. Have you considered she might already be further along than you are thinking? She might not tell you what actually happened on her girls night out adventure. I would encourage her to keep going out with her horny friends. Doesn’t matter if they are single or not. Lots of married women fuck around. Tell her she is free to do anything she wants and you want details when she comes home. Bet she opens up more.

Heh, I wish... It's not "that kind of wet" and while I am sure she wouldn't tell me everything that actually happened, there is just no chance, given the circumstances of her outings that anything significant even could happen. Unfortunately, the one horny friend she had is in a relationship and not going out lately. Sounds like that relationship may be coming to an end though, so might be back in business.

"Tell her she is free to do anything she wants and you want details when she comes home. Bet she opens up more."

Not exactly what I'm looking but also wouldn't work for her either - she would be weirded out if I said that and even if she did something, she probably wouldn't tell me lol.

In the meantime, we're going on vacation anyway, so why not make it something fun.

 

[hotratz]

Stay at Sandals, Negril. Next door to Hedo2. Get her a day or evening pass. A few hours in the nude pool does wonders for a woman (or a man, lol)