
Back when I was writing for the local paper here in Nashville, I once interviewed a sex therapist. We covered a lot of ground, but one of the things that he said that has remained in my mind to this day is, "A lot of boys learn about sex from porn. A lot of girls learn from chick flicks and Cosmo. Put those two people in a dark room together and you're going to have a big ole' mess on your hands."
After serving as a teen mom director for the local branch of a national non-profit for several years, and also after being a marriage life coach for even longer than that, I must say that when it comes to sexual preparation—especially as it pertains to a long-term commitment—that sex therapist was spot-on. Sex is a significant, relevant and very necessary part of a relationship. Yet, unfortunately, it's something that couples—including engaged and newlywed couples—do not spend nearly enough time hashing out. It's almost like they think, "We love each other, so the sex thing will work itself out." Will it? Will the bills, the in-law issues and who's going to clean what in the home going to miraculously work itself out without some intentional dialogue? No? Well, why should sex be any different?
If you're currently contemplating marriage and you're going to take "'til death parts us" serious (and please do), sex with your future spouse is going to be a part of your life, hopefully for the rest of it. I don't know about you, but that seems like a good enough of a reason to set aside a few conversations to getting some clarity about your man's views, experiences and expectations—as it specifically pertains to sex.
1. “What did your parents teach you about sex?”

Two myths, that I'm always more than happy to debunk, every chance that I get, is 1) Black women don't get married (the real truth is a lot of us have a bucket list that we'd prefer to complete before saying "I do") and 2) most Black kids grow up without dads. You can read articles like "No, Most Black Kids Are Not Fatherless" or check out the totally adorable YouTube channel Beleaf in Fatherhood to know that is a total fallacy. But when it comes to the missing daddy issue, I'd be very irresponsible if I didn't act like it doesn't exist (reportedly one-third of all U.S. children are living with an unmarried parent) and that the repercussions can be truly heartbreaking.
Take the topic of sex, for example. One of my exes? He knew his father, looks just like the man and yet his dad never claimed him. His mother? I can count at least five times when we tried to get into his house, but the door was locked. Through the window, we could hear her having sex—almost each time with a different man. Fast forward to now, and while my ex is a great never-been-married-before father of four, when I asked him what he's taught his kids about sex, he was like, "I started having sex as a kid. Who am I to be judgmental about their decisions?" For me, it came off as flippant, but what I realize is he didn't know what to do because no one taught him.
Although our parents are not solely responsible for who we become, they are a part of our foundation. Knowing what your man was told, taught and modeled can provide you with a glimpse of his views on sex and, quite possibly, the perspective and values that he'll extend to your own children someday.
2. “What was your first experience like?”
Question. How many men in your life, when they speak of their first time, it sounds healthy? And by "healthy", I mean, they weren't a child who had sex with a grown woman (if they were 14 and she was 18 or older, she was a grown woman and it was statutory rape); they weren't pressured by an older brother or some kids at their school; they weren't molested and they weren't babies at the time (14 is a pretty young to me, but I know some guys who claim to have been 9 or 10 when they gave their virginity away).
I was just telling someone earlier this week that I believe there is such a thing as "sex PTSD" and it's not always from sexual abuse or trauma. Sometimes, it's simply engaging in a sexual experience before we're ready or one that we don't really understand the magnitude of. Then, until or unless we get some clarity, we can end up carrying all of that confusion into our other sexual encounters.
One my partner's first time was with a woman that his brother locked him up in a bedroom with; that same guy ended up date raping me. Another one of my partner's first sexual encounter was with one of his female first cousins. Another one of my partners, he was a preteen who participated in a train with a group of his friends. Two had sex with a babysitter.
Contrary to popular opinion, men are not made out of emotional Teflon. And with articles out here like, "Age Of First Sexual Experience Determines Relationship Outcomes Later In Life", "Does Sexual History Affect Marital Happiness?" and "How Does Sex Affect Your Emotions? 12 Things to Know About Attraction and Arousal"—knowing about your man's first encounter can definitely shed light on some things; whether he believes it has directly affected him or not.
3. “What is your biggest past sexual regret?”

I say it often because it's something that I wholeheartedly believe. I don't trust anyone who says that there is nothing in their life that they don't regret. It's one thing to say you feel like all that you did played a purpose in where you are now; it's something else to say that when you look back over all of the things that you've said or done, you have absolutely no remorse (which is what regret is).
Unless you're about to marry a virgin, I think it's close to impossible for someone to not have any regrets when it comes to their past sexual choices. I regret having sex for the first time in my boyfriend's mother's bed with his little sister asleep in the same room. I regret having sex with people's boyfriends. I regret agreeing to pick up a guy at the side of a dumpster one night, so no one would have to know we were gonna have sex. I regret my abortions.
And here's the thing—had I not made the time to really process and heal from my regrets, I know I would've ended up carrying a bit of bitterness, resentment and baggage into my future marriage bed. It's not just me who feels like this either. Some husbands have told me that now that they are married, they wish they had handled their season of singleness differently too. So yeah, it's a good idea to ask your partner if he has any regrets. If he does, follow that question up with if he's done anything to feel better about the situation—or situations. If he hasn't, encourage him to do so.
4. “Is there any sexual trauma that we should discuss?”
Reportedly, 1 in 6 boys have been molested by the time they turn 18.
I believe it's a lot more than that because at least half of the men in my own world have shared with me that it is a part of their history. As a result, it has made it hard for them to trust, they admit to having some really complicated views about sex and, some of them have made some really toxic sexual decisions, as a way to "process" their sexuality (for instance, some told me that they had sex with lots of women because a man molested them and they were trying to "prove to themselves" that they are heterosexual).
Someone I care deeply for once told me that although he gets plenty—and I do mean, plenty—of female attention, he's not sure if he'll "ever be healthy sexually" due to his childhood sexual abuse. That's a really vulnerable and insightful thing for him to say. But just think about how many men have been molested or raped and don't share their feelings about it. Not enough women ask their partners if there is sexual trauma in their past. But for the sake of a stable and thriving intimacy life, it's one that is beyond valid.
5. “Are all of your sexual relationships and situationships FULLY resolved?”

There's a guy I know who once told me that, for a decade, he had an affair with a married woman. Now that he's married, he still finds himself hittin' that woman up on social media from time to time. In his mind, it's just to see how she's doing. In my mind, he's playing with fire (and yes, I've told him so).
The reason why I say that is because a lot of my exes are married at this point. One of them, because we were homies before sex ever entered into the picture, I used to think it was OK for him to hit me up too. But conversations always eventually turned into a slick sexual statement or strolling down sexual memory's lane which is all kinds of inappropriate. So, even though we used to be friends, because we also used to be more than that and we never really closed that chapter, I had to totally and completely let him go. Otherwise, it was gonna be a slippery slope if we remained in communication.
A lot of married couples deal with jealousy and even slight paranoia in their relationship, not because their spouse has a past, but because they can tell that the past has never been fully resolved. It might hurt to know that your partner still has some "residue" laying around somewhere, but it's better to ask and encourage him to close those doors now than to find out the hard way later that he didn't via an emotional affair—or worse.
6. “What are your sexual expectations?”
When people hear that I have no problem spending 5-6 weeks on intimacy in premarital counseling sessions, they think that I'm being excessive. Whatever. If they knew how much sexual dysfunction I hear about while dealing with couples after they say "I do", they'd get why it's such a priority to me. Being that a lack of intimacy continues to be a leading cause of divorce, and also because I know that a lot of dating couples feel like intimacy is not something that they need to put a lot of forethought into (I mean, we love each other, so what is there to worry about? We got this), that's why I think that intimacy should be explored, almost ad nauseam.
It never fails. Whenever a married couple comes to me about their issues and challenges, it's very rare that sex doesn't come up in the conversation. Someone isn't getting as much as they want, someone isn't getting the kind that they desire, or someone thought that the entire sexual part of their relationship was going to be different.
We all know what assuming can do to a person and having expectations without discussing them first is a form of making assumptions. Whether you've had sex prior to marriage or the plan is to wait until after getting married, you are going to do your future sex life a world of good by asking each other what your expectations are, beforehand.
7. “Do you have any sex-related deal-breakers or hang ups?”

I've shared in one of these articles before that a husband once told me that, in premarital counseling, he expressed how important fellatio was to him. His fiancée was so intent on getting married that she said, in counseling, that she loved to give head; that him getting it on the regular would be no problem. Fast forward to almost a decade into their marriage and, according to him, he only got it twice. He ended up cheating.
Another husband? When he was dating his wife, he told her that sex every day was preferred but if not that, sex every other day was desired. She not only agreed but professed that her drive was also really high. They ended up having sex about once a week. They were married for almost 12 years. They're divorced now.
You can say whatever you want to say about these men and what they wanted going into their marriage, but it's what they wanted. If it's something that sounds ridiculous to you, you're actually proving my point about why it's a good idea to ask your own man this question on the front end.
I know some people who didn't know their partner hates oral or doesn't like to try new things or only wants to have sex in the dark before they married them. They are pretty close to being miserable now. So yeah, figuring out what the potential deal-breakers or hang ups are before marriage is definitely something that should also be discussed. It can only benefit you if you do.
8. “How much of a priority is your health?”
This question might seem like a bit of a wild card, but here's why it's relevant. There's a wife I know who, while she was dating her now-husband, he gave her the impression that she was gonna be swinging from the chandeliers from their wedding night on. He talked such a big game that she was a little intimidated, going into their honeymoon. But from their wedding night on, he has had trouble maintaining an erection because he's overweight and has to take blood pressure medication. It's been well over a decade now. Guess who's the one who isn't sexually satisfied?
Married sex is wonderful. It really is. It's also a responsibility in marriage. And in order to act responsibly when it comes to marital intimacy, one's health must be taken into account. So yeah, inquire about that too.
9. “Do you think there is a difference between single and married sex?”

Single sex can be all kinds of false advertising, boy. After all, when you're single, you are your top priority and so, it's pretty common to mostly and mainly consider yourself, even when it comes to sex.
If you take out the time to read "10 Wonderful Reasons Why Consistent Sex In Marriage Is So Important", hopefully you'll see that married sex is very different from sex you may be having as a single individual. Shoot, the "forever exclusivity" of the dynamic is enough to set it apart.
Even while dating, different couples have different "rules". Maybe you don't mind your man going to a strip club with his friends. Maybe you're not as upset if you find out he watches porn. Maybe there are certain things that he wants you to do that you concede to because "It's not like it's all of the time."
Most of the men that I know, they are pretty literal. When it comes to this topic, what I mean by that is if you give your partner the impression that nothing has to change from his single life, it probably won't. So, if you've got other thoughts, this would be the time to bring them up. Stat.
10. “How important are my needs going to be?”
Something that I had to learn the hard way about sex—and by sex, I mean good sex—is sometimes, even your pleasure is all about a man's ego. What I mean by that is some men aren't great in bed because they are trying to connect with their partner and meet her needs. Sometimes they are, just so they can feel good about themselves; it's all about patting themselves on the back (by the way, I believe that there is even such a thing as "sexual narcissism"; you can read more about it here). The problem with this kind of individual is they tend to not emotionally invest well. Plus, the sex will only be good if they want it to be that way. Who wants to spend forever with an individual like that?!
So yeah, it would be ludicrous of me to not close this out with a question that could've been the first one, to tell you the truth. Before marrying "him", discuss what your own sexual needs and desires are, get a read for how he feels about each and every one of them, and discuss if they are going to be a priority or not.
Marriage is supposed to be for life. Both partners should be willing to spend a lifetime pleasing one another in the best ways possible; this includes sexually. A good way to know if that is a part of your partner's plan is to well, ask him.
Want more stories like this? Sign up for our newsletter here and check out the related reads below:
10 Married Couples Share The Keys To Their Totally Off-The-Chain Sex Life
How PCOS Strengthened This Couple's 4-Year Marriage
If You're In A Committed Relationship, Avoid These Sex Mistakes At All Costs
6 Tips For Dealing With A Sexually Incompatible Spouse
Feature image by Giphy
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Your December 2025 Monthly Horoscopes Are All About Surrender & Alignment
December is about letting go. We end the year with the need for more peace, reflection, and rejuvenation, and that is exactly what December is providing for us. The Sun is in Sagittarius, and anything is possible. This is the month to believe in that and to know that the universe is supporting you. With a Supermoon in Gemini as we begin the month as well, we have an opportunity to gain the closure we have been looking for this year and to wrap up old projects, ideas, and communication breakthroughs.
This is the month to make your peace the priority and let go of trying to control the way the tides are turning. Trust in your new beginning, and give yourself time to prepare for it this month.
A big part of the clarity that is coming through this month is due to Neptune going direct in Pisces on December 10, after being retrograde here since July. With Neptune now direct, we are able to see our inspiration and creativity a little more clearly, providing the perfect energy for dreams and manifestation to be built upon. The smoke is clearing, and it’s up to you to decide what you want to do with this newfound clarity that this transit is bringing. Mercury also moves back into Sagittarius on December 11, which is great for communication and clarity, and the adventures you were trying to see through at the beginning of November come around for you again with greater purpose and support.
On December 15, Mars enters Capricorn until the end of January 2026, and this is the extra push we need to make important changes and to be on the path towards greater abundance, stability, and prosperity. Mars in Capricorn takes care of business, and we have extra energy at our disposal during this time to do so. This transit is an ideal time to focus on your career or financial goals for next year and to start putting some of these plans into motion now. A few days later, we have the New Moon of the month, which will be in Sagittarius on December 19, and this is the perfect New Moon to manifest.
The energy is high, magic is in the air, and it’s all about moving forward with the new beginnings that are inspiring you and bringing you joy to think about right now.
Capricorn Season officially begins on December 21, and this earth sign energy is how we heal, gain closure, and build new foundations in our world. With Venus also moving into a Capricorn a few days later, there is something about peace, prosperity, and security that we are gaining in life and in love as we close out the year, and this is what we need right now. This month is about reflecting on what was, letting go of old hurt, and renewing. December is an ending and a new beginning in one, and there is magic in this space to be created.
Read for your sun and rising sign below to see what December 2025 has in store for you.
AriesKyra Jay for xoNecoleARIES
December is a full-circle moment for you, Aries. You are seeing the gifts in your world and have a lot of gratitude for the way things have come about for you as of late. There are culminations in your world that are providing you with more abundance, stability, and community, and you are exactly where you are meant to be this month. With the Sun in a fellow fire sign and in your 9th house of travel for most of the month, December is a good time to get out of your comfort zone, explore the world around you, and get your body moving.
Mars, your ruling planet, also makes a change and moves into Capricorn on December 15, which will fuel your inspiration and power in your career space. You are making a lot of professional progress as we close out the year; however, make sure to be more mindful of your competitive drive right now. The New Moon on December 19 is the perfect opportunity for you to create some new plans and goals when it comes to traveling, education, and where you want to gain some new inspiration in your world. Overall, this is a month of things coming together for you serendipitously.
TaurusKyra Jay for xoNecoleTAURUS
December is about trusting your intuition, Taurus. You have a lot on your mind this month, and it’s best to delegate, communicate, and allow yourself some relief by opening up to someone and not feeling like you have to hold everything in. As we begin the month, we have a Supermoon in Gemini happening in your house of income, and the plans and projects you have been building here come to fruition for you now. This is the time to gain clarity on your financial world and to take a look at what spending habits you want to let go of here as well.
With Venus in your 8th house of shared resources for most of the month, you are doing a cleanse on your commitments, partnerships, and business ventures. You are taking a look at what you want to dedicate yourself to in the future, and what commitments you may need to let go of now in order to be in the space you truly want to be, both financially and within some of your relationship dynamics. Before we end the month, we have a New Moon in this same area of your chart, and it’s time to look at the opportunities that are presenting themselves and to trust your internal guidance system to lead you forward.
GeminiKyra Jay for xoNecoleGEMINI
You are moving forward fearlessly this month, Gemini. December is your month of love, passion, and dignity, and you are owning the light that you shine. We begin the month with the last Supermoon of the year, happening in your sign, and you are stepping up to the plate. You are showing up, owning how much you have grown this year, and allowing yourself to heal while also acknowledging that you have done your best and you deserve to have fun in the midst of the changes you are creating.
Mercury, your ruling planet, is officially out of retrograde, and you can use this energy to the fullest potential now. With Mercury in your 7th house of love, it’s time to speak from the heart and to talk about the things that matter and that are inspiring you right now to your loved ones. You never know what kind of epiphanies you may have when you open up the conversation to others. Before the month ends, you have a New Moon in this same love area of your chart, and this New Moon is all about manifesting romance, commitment, and abundance in your world.
CancerKyra Jay for xoNecoleCANCER
December is an opening for more love, more joy, and more freedom in your life, Cancer. You have come to a place where you hold so much gratitude in your heart for where you are today and where your heart is shining, and things come together for you with more ease right now. With the Sun in your 6th house of health, work, and daily routines for most of the month, you are getting your ducks in a row while also putting more energy and effort into taking care of yourself, your priorities, and your well-being. This month surprises you in many ways, and it’s because you are showing up.
Mars and Venus both move into your house of love, relationships, marriage, and abundance this month, and you are making strides in your love life. You have both of these opposing forces on your side and are being recognized for the love you are while also receiving the love you want. This month, overall, is about focusing more on the positives in your world and letting your heart have its joy. Before December comes to an end, there is a New Moon in Sagittarius, and this is the perfect opportunity to create the plans you want to see through next year, especially when it comes to your work life, colleagues, business ventures, and health.
LeoKyra Jay for xoNecoleLEO
The scales of karma are balancing, and they are balancing in your favor this month, Leo. December is your month of truth, and of seeing it clearly in your world. The Sun is in your house of romance, pleasure, and happiness for most of the month, and it’s time to relax, be in the present moment, and allow what is meant to be, to be. With a Supermoon in your 11th house of manifestation as December begins, this is a powerful month for seeing your dreams come to fruition, and for feeling like the intentions you have set this year are finally here for you now.
Mars also moves into your 6th house mid-month, and this is the perfect energy to have to move into the new year. You have extra energy at your disposal right now and are feeling fearless with what is possible for you and your daily routine. Before the month ends, we also have a New Moon in a fellow fire sign, Sagittarius, and this is a breakthrough moment for you and your heart. December, overall, wants to show you how loved and supported you are and will be doing so in magical, unexpected, and concrete ways.
VirgoKyra Jay for xoNecoleVIRGO
December is a month of victory, Virgo. You are showing up and experiencing some new successes in your world that move you forward on your path in life. With a Supermoon in your 10th house of career as we begin the month, the effort and intentions you have made this year come into full bloom, and you are being recognized for who you are and the good work you have done. This month is all about showing up and allowing yourself to be seen and loved, knowing that you deserve the support and opportunities you are receiving.
Mars moves into Capricorn on December 15, which brings the passion and excitement into your love life, hobbies, and little pleasures in life that light you up. You want to have fun this month and are going to be walking into the new year with this fearless, happy, and spontaneous energy within you. Before the month ends, Venus also enters Capricorn, and in this same area of your chart, you have a lot to look forward to and believe in right now. Overall, December wants you to be happy and will be doing everything possible to make that happen for you. This is your month to shine, Virgo.
LibraKyra Jay for xoNecoleLIBRA
December is a month of opportunity for you, Libra. New doors open, and you are financially making breakthroughs this month because of it. December begins with a Supermoon in your 9th house, and you are getting a clearer view of where you have been making strides in your life and how it has all brought you here to this present moment of freedom. This month is showing you what happens when you are fearless with your purpose and when you believe in yourself and what you are worthy of.
Moving further into December, Mars moves into your 4th house of home and family mid-month, and you are closing out the year in your safe spaces. You are spending more time with your loved ones and taking the time to quiet your mind and listen to what your heart has been telling you. Before the month ends, we have a New Moon in Sagittarius, happening in an area of your life that deals with communication. This is a great time for getting the answers you have been looking for and for feeling more clear-headed and confident about the decisions you are making as you move into the new year.
ScorpioKyra Jay for xoNecoleSCORPIO
Patience is a virtue this month, Scorpio. December is all about remaining patient and vigilant with what you are creating in your world, and knowing that the universe has your back. It’s time to be reminded of the power of hope, and this month is an opening to greater clarity in your life. There is a lot of energy in your financial zones right now, and this is providing you with new opportunities and new insight; however, the speed at which things come about for you may feel daunting. Keep your head up and eyes focused on what you want and know that you are more than worthy of receiving it.
With Mercury in your 2nd house of income this month, December is a good time to plant new seeds and to think about where you want to be financially a month from now or even a year. This month is asking you to think bigger and to think more long-term so that you can set the appropriate plans into motion now. We also have a New Moon in your house of income before the month ends, and this is when you will see more of your dreams come to fruition in this area of your life, and have more opportunities to build. Overall, December will be teaching you a lot, Scorpio.
SagittariusKyra Jay for xoNecoleSAGITTARIUS
Sagittarius Season is here, and there is a lot in store for you this month, Sag. December is all about what you are dedicating yourself to. It’s about setting your intentions and putting the work in to back up your dreams, and about getting things in order so that when the new beginnings come, you are ready for them. The Sun and Venus are in your sign for most of this month, and there are a lot of eyes on you right now. You have the potential to create a new beginning for yourself, and it’s time to invest in yourself, your love life, and your dreams.
Mercury moves into Sagittarius on December 11, and this is giving you another opportunity to see through some of the plans that you had initiated in November. Mercury was retrograde in your sign last month, and there may have been some disruptions to your vision and plans for the future, and now this energy is turning around for you. Before the month ends, we also have a New Moon in Sagittarius, and you are walking through new doors fearlessly. You are catching others by surprise by your growth this month, and you are thinking a lot about your purpose, future, and plans for the new year.
CapricornKyra Jay for xoNecoleCAPRICORN
December is all about the vision, Capricorn. You are moving through a lot of changes and transformations this month, yet they are giving you a chance at a new beginning in the process. You are focused more on the future and what goals you want to manifest for yourself right now, and are ready to let go of what hasn’t been working for you. With the Sun in your 12th house of closure for most of December, this is your time for healing, but remember, healing doesn’t have to be isolating or boring; you can thrive while you renew, and you are this month.
Mid-month, the excitement picks up for you, and you are feeling more energized than you have in a while. Mars moves into Capricorn until the end of January 2026, and you are being proactive with your goals, intentions, and passions. You are a force to be reckoned with this month, and you are making things happen for yourself with confidence. Capricorn Season officially begins on December 21 this year, and this is definitely speeding up your healing process. You are breaking free from what was, and with Venus also moving into Capricorn before the month ends, you are leaving this year in high spirits and with love opening a new door for you.
AquariusKyra Jay for xoNecoleAQUARIUS
December is all about community, creativity, and manifestation, Aquarius. This is the month to work together with others to help bring your dreams to life. You are in a space of inspiration, empowerment, and beauty, and are creating more of this energy around you and in your world. Look out for what support comes your way this month and know that you don’t have to do everything alone to succeed. With the Sun in your 11th house of manifestation and friendship, your intentions are coming to fruition, and it’s time to celebrate with the people you love and to own how far you have come this year.
On December 19, we have a New Moon in Sagittarius, lighting up your life in all of the best ways possible. This is your New Moon of freedom, victory, and magic, and you are seeing new beginnings appear that you were once just hoping for. Before the month comes to an end, Venus moves into your 12th house of closure, and after an active and successful month, you are ready to relax, heal, and give your heart some of the attention it has been asking for. You are moving into the new year with the need to release and renew what hasn’t been working in your relationships, and you are finally ready to.
PiscesKyra Jay for xoNecolePISCES
December is a big month for you, Pisces. You are making some huge accomplishments this month, and are feeling like everything you have been through this year has been worth it for these moments that are coming to fruition for you now. The Sun is in your 10th house of career and reputation for most of the month, and this is where a lot of your focus is right now. You are claiming your successes and putting yourself out there in ways that not only serve you, but that inspire others as well.
Neptune officially goes direct on December 10, after being retrograde in your sign since July, and you are finally seeing things a little more clearly. You are feeling renewed inspiration and passion in your life, and your intuition is your strongest asset right now. Before December comes to an end, we also have a New Moon in your 10th house of career, and what happens now not only changes things for you in the present, but it also opens new doors and what is possible for you in the new year as well. Overall, you are on top of your game this month and are owning the joy and empowerment you feel.
Featured image by Kyra Jay for xoNecole
Why The Cayman Islands Is The Ideal Soft-Life Island-Hopping Destination
It's always a pleasure to add a new stamp to the passport, especially when it's an opportunity to visit a country you've never been to. When invited to explore the Cayman Islands, I was very familiar with Grand Cayman—the largest among the three islands, known for its stunning clear-blue beaches, and modern city comforts—but I seriously slept on Cayman Brac.
On a six-day trip, I knew Grand Cayman would be that girl, but the smaller sister island Cayman Brac? She’s the captivating, low-key spot that is a whole soft-life fantasy.
This trip was my first time in the destination, via the Cayman Islands Department of Tourism (@visitcaymanislands) and it had all the luxe chill and exploration that makes for great memories that will prompt anybody to want to return again and again. Plus, it was the tail end of rainy season, which is basically my jam because off-peak travel makes me feel like a VIP. I get the beauty, the beaches, the food, the people—without the crowds and noise.
Let’s get into how you can pack your Cayman Islands itinerary with cultural exploration, elevated cuisine, deep restoration, and an island-hopping adventure along the way.
GRAND CAYMAN
Grand Cayman hits you with that effortless island confidence from the moment you land. It’s the largest of the Cayman Islands, known for crystal-clear Caribbean waters and a culture that blends British influence with laid-back island charm.
Visitors pull up for Seven Mile Beach, stingray encounters, fresh seafood, and those luxe resorts and villas that make unplugging way too easy.
Where To Stay

Courtesy/Grand Cayman Marriott Resort
Grand Cayman Marriott Resort: This property offers ocean views, polished comfort, with easy access to everything near Seven Mile Beach. (Marriott stays are often a go-to for me when I’m in the mood for a resort stay where the standards are consistent no matter the destination).
The spacious rooms, warm staff, and a pool area perfect for quick resets between adventures were a hit for me. Despite the patchy rain, lounging by the pool felt like a reset button.
I popped into the gift shop and found pieces from Isy B, the Cayman-based brand created by Isy Obi, a Black woman who pivoted from finance to fashion. The designs are bold, colorful, full of vibes I love to reference when returning home.
Botanica Luxury Cottages: The cluster boutique cottages blend island-chic décor with modern touches. My cabin had vaulted ceilings, washer and dryer, roomy showers, a cozy lounge area, and a private outdoor nook with stylish umbrellas and seating perfect for reading, sunbathing, or unwinding. A pool is just a short walk away on the property and Seven Mile Beach was just a quick drive. I took a two-mile stroll along the shoreline where families, chilled-out tourists, and sleek beach clubs lended to a balanced and laid-back but lively environment.

Courtesy/Botanica Luxury Cottages
Where To Eat
Pom Pom: This breezy rooftop lounge serving curated cocktails with a relaxed, stylish vibe and mellow music was the perfect evening welcome to the island. And the sunsets are divine.
Avecita Chef’s Table: It’s an amazing multi-course dining experience where chefs craft global flavor fusions right in front of you. Expect bubbles, bold tastes, and an ambiance that feels refined without being pretentious. This is one experience I definitely plan to fly back to Cayman for in the new year.
Pepper’s Bar & Grill: Conveniently located just across the street from the resort, it’s a local casual spot with live music and unique takes on Caribbean meal staples. The Cayman-style jerk pork was a favorite.
Ristorante Pappagallo: Set on a 14-acre bird sanctuary overlooking a saltwater lagoon, this brunch delivered everything from sushi to risotto to curry goat to barbacoa tacos. The white tablecloth elegance paired with homestyle warmth and peaceful water views made the whole experience feel elevated yet comforting.Bacaro
Bacaro: This is where we had our farewell dinner, enjoying their Venetian-inspired small plates and curated cocktails. If you want a final night with your partner or even your best girl group, this is the spot.
Things To Do:

Courtesy/Island Soul
Floating Sound Bath with Island Soul: The floating meditation was calming, grounding, and deeply restorative. We had the sky and breeze as a backdrop and listened to music, prompts and chimes that allowed us to simply float and be.
Anchor & Den Cocktail Class at the Grand Cayman Marriott Resort: I thoroughly enjoyed this lively, hands-on cocktail-making session which would be fun for couples, friends, or anyone wanting a playful evening activity without leaving the property.
The Grove: This is a foodie and art-lover's delight with its dining and culture scene that features spots like Island Naturals, a chill café with plant-forward dishes—where the mushroom tacos were everything, and the tuna poke nachos are a must—and upscale spots like Mykonos Steak Club. After eating, stop by Carlos Garcia’s gallery, a working studio and public exhibition space that supports a collective of local and international artists, and regularly hosts events, pop-ups, and live painting.
Pirates Week Festival: This was a welcome surprise addition to our itinerary, and it's an event held in November across the Cayman Islands, with the major events happening in the heart of Grand Cayman's George Town. During the finale, I was out there jumping and whining to Nessa Preppy and Faith Callender, rum in hand, surrounded by locals and pure island joy. As a woman who loves soca, that moment lit me up. It was the perfect last hurrah with a slice of home, culture, and celebration.
Bonny Moon Beach Club: It’s a Tik Tok-famous stylish beachfront lounge experience that, for me, actually matched the good reviews. The octopus ceviche and everything from the woodfired portion of the menu were a hit and the DJ added the right amount of energy. We ate just steps from the ocean. It's swanky, atmospheric, and ideal for date night, girls’ trips, or baecations.
CAYMAN BRAC
Known for dramatic limestone cliffs, caves, and some of the best diving in the Caribbean, the vibe in Cayman Brac is slower, more local, and perfect if you want nature, real island culture, and adventure without the crowds. I took a quick Cayman Airways flight from Grand Cayman and spent two days there.
The visit was honestly one of the most peaceful, soul-nourishing parts of my trip. The moment I landed, the island reeled me in—raw, mysterious, almost cinematic in its quiet beauty. There’s a softness that feels like an alluring secret.
Where to Stay

Courtesy/Le Soleil d'Or
Le Soleil d’Or: This is a farm-focused boutique haven with luxury villas, a restaurant, a pool, and its own beach club. Our villa was huge, complete with a kitchen, living room, laundry space, game room, and the modern luxury master suite of my dreams.
The bathroom had a soaking tub that fit my 5’7"-plus frame, a large shower, and his-and-her sinks. The bedroom had tons of storage, a large comfy bed, and a mini fridge, plus a TV lounge and veranda opening to the pool. Honestly, my suite could’ve been a full studio apartment back home—I was blown away.
The farm-to-table meals, which I could enjoy at the restaurant just steps away from my suite, were rich, fresh, and soulful. My morning walks on the property were serene, wrapped in nothing but nature and quiet.
If you want an escape from the tourist and business buzz of Grand Cayman, this is the perfect hideaway for a baecation, girls trip, or solo venture.

Courtesy/Le Soleil D'Or
Things To Do & Good Eats
Rock Iguana Yoga: This soothing yoga and therapeutic art experience was set in lush island terrain and was a grounding, earthy immersion that eased my back pain from stress, and was a great quiet time to reflect and release. The instructor was patient, graceful, and welcoming.
Le Soleil D’Or Beach Club: It's a chill open beachfront that offers a peaceful, quiet experience in the off season. Think serene solitude, gentle waves, and open space to unwind—far from the typical beach club scene with loud DJs, pumping music, and high-energy crowds.
Star Island Restaurant: This restaurant reminded me of my favorite local spots in Jamaica where you can get food with spices and tastes like your Caribbean grandma or auntie made the meals with love. The menu includes Caribbean dishes like jerk chicken and Cayman's national dish, stewed turtle.
I’ve been to several islands across the Caribbean—with my tried-and-true all-time favorite being Jamaica—and I must say, if you want that soft-life island-hopping luxury adventure paired with opportunities to connect with a rich arts, music, and culinary scene, a trip to the Cayman Islands is exactly that.
Featured image via Shutterstock









