Ah, yes, the missionary position. If there’s one sex position that pretty much everyone off top knows what it consists of, the missionary would have to be it. So, where does the name exactly come from? Oddly enough, even though it’s probably the most common sex position there is, there’s conflicting information about how its name actually came to be.
Some say that the Catholic church deemed it to be the only “non-sinful” position, and folks followed suit. Others believe that it’s tied into “patriarchy” since a man being on top puts a woman into a submissive receiving position (I mean, the Bible does tell wives to submit to their husbands, and sex is referenced for married couples, so that tracks — Ephesians 5, Colossians 3:18, I Peter 3:1-7, Genesis 2:24-25, I Corinthians 6:16-20). There are even stories about missionaries teaching people of African, Native American, and Chinese ethnicities that any other position is wrong and so those people came up with the term “missionary position” to make fun of the missionaries (chile).
Whatever the actual backstory is, what we know for sure is the missionary position continues to be super popular (although leave it to millennials to knock it out of first position and replace it with doggystyle these days), a great way to cultivate emotional intimacy (more on that in just a sec) — and it is oftentimes perceived as hella boring.
That last point is what I’m gonna address today. Because since it is indeed a great way to connect with your partner, it makes it easier to hit “your spot” (the G-spot, to be exact), and it’s also easy on your body (you know, if the desire is there but your limbs are not exactly cooperating), in my eyes, the missionary position needs to receive the proper respect that it deserves — and the best way to do that is to give it a few, perhaps much-needed, “upgrades.” Here are 15 of ‘em.
1. Do Some Eye Gazing Before Anything Else
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Recently, I was talking to a male friend of mine who told me that he doesn’t do casual sex in the missionary position. After asking him how he is subtly able to even pull that off (another article, another time), I then wanted to know the method behind his madness: “It’s too intimate and vulnerable. I need to be in something serious with you to be that…into you.”
One might say that literally putting your member into a woman’s vagina is “into her,” yet I digress. Instead, I’ll just focus on the fact that when they say that eyes are the windows to the soul, there is definitely some truth to that. And when it comes to cultivating intimacy with your partner, there is a practice known as eye gazing that can help to connect the two of you in a very special way.
In fact, there are studies to support that you can analyze how someone feels about you by looking into their eyes, you can increase your level of attraction to them by looking into their eyes, and you and your partner can go up a new level in trust if you look into each other’s eyes as well.
How long should the eye gazing last? Some experts say that the goal should be for five minutes while taking deep breaths in between. While doing that might feel awkward at first, look at it this way — y’all are gonna be face to face for a while anyway, right? Why not take the exchange of energy to another level while you’re doing it? And why not get into this mind of headspace by eye gazing as a form of emotional foreplay?
2. Bring Some Jasmine, Ylang-Ylang or Lavender and Vanilla
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One of the best things about the missionary position is it encourages you to shut out the rest of the world, ignore any distractions and really focus on your partner. Matter of fact, a sex therapist once told me that one of the perks of this particular position is it significantly decreases your chances of you and/or your partner fantasizing about other people during coitus (hey, it happens…way more than people care to admit too).
Something that can help to keep you and your partner centered on one another only is the scent of jasmine, ylang-ylang, and a combo of lavender and vanilla. As a bonus, all are also sensual, calming, and relaxing too. You can add a few drops to a carrier oil (like sweet almond or grapeseed) and create a DIY massage oil. You can sprinkle some of them onto your bedding. You can also add a few drops into your sexual pressure points for a nice surprise as far as your partner’s sense of smell goes.
3. Pull in (More) Pillows
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For some reason, I can’t find it now (sorry!), but a few weeks ago, I was cracking up at a video of a guy who was challenging his girlfriend to get into the position of being on top like a man and pushing for more than a minute straight. She failed miserably (it really was hilarious!). After I sent it to a few male friends, one wrote back and said, “Y’all have no idea what being on top can do to a brotha’s back sometimes.”
A workaround that will make everyone happy? Bring in some more pillows. It will elevate your body so that he won’t have to bend over quite so low. Plus, it will help him to penetrate you more deeply, which is almost always a good thing.
You can use the pillows that you already have (they should work just fine). Or you can invest in a sex pillow. They tend to be a bit firmer so that you don’t have to be slippin’ and slidin’ all over the place. Glamour did you a solid by providing a list of some of their favorite sex pillows here; Self did the same by providing their best-of-the-best list here.
4. Light Some Candles
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Back to the eye thing real quick. Yeah, I don’t know how y’all are gonna be able to stare deeply into each other’s eyes if it’s pitch black in the room. And here’s the thing about letting some light shine in; there was a study conducted that said when a light box (like the kind that’s used to treat depression) is brought into a man’s space, it can increase his levels of sexual desire. The reason why is it has a way of boosting his testosterone levels.
However, if you don’t want to feel like you’re standing — well, lying — in a room that has the ridiculous lighting that is in department store dressing rooms, go with candlelight instead. A soft glow can still help him to see your shapes and curves and the two of you to look at each other yet because everything with candles is way more subtle, it can help you to feel less self-conscious if you’re not as confident in the sex department as you would like to be (check out “10 Sensuous Ways To Boost Your Sexual Self-Esteem”).
5. Add Some Flavored Lube
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Although pretty much all of us have heard the saying, “The wetter, the better,” at this point, this tip is a shout-out to the safe sex crowd (since reportedly, only one-third of men and one-quarter of women actually use condoms. SMDH). If you want to make bringing rubbers into a mix a much more pleasurable experience, go with some flavored lubricant. Although you might only think of its use in the context of oral sex (more on that in a bit), dabbing some on your neck (so that he can taste something sweet-er when he kisses you there) or on your wrists or forearm (so that he can lick them while your hands are pinned back) can be a truly welcome surprise.
And what are some of the best-tasting ones on the market these days? No worries. I got you:
6. Modify the Position…a Bit
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As we continue, I will be — no pun intended — deep diving into some tweaks that can be made to the standard missionary position in order to intensify sexual pleasure. For now, I’ll just say that spooning face to face, allowing your partner to pin your legs back, having sex while standing up, letting him ride cowboy (which means he’s literally in the position that you are typically in during the cowgirl) and your partner lying horizontally over your body instead of vertically — these all are twists to the missionary that could cause you to hear “missionary position” with new levels of excitement.
7. Apply the Coital Alignment Technique (CAT)
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Speaking of modifying positions, what do y’all know about the Coital Alignment Technique (CAT)? If you’re staring at your screen like, “What in the world is that?” it’s when your partner gets into the downward-facing dog yoga position while you’re on your back in the missionary one. This causes your partner’s penis to stimulate your clitoris as they are entering you and sometimes as they are going in and out. The (main) benefit is if you’re someone who finds experiencing a vaginal orgasm challenging, you significantly increase your chances of experiencing one since your clitoris will be stimulated during the act of intercourse.
Another bonus is “doing the CAT” can help a man to last longer if premature ejaculation is something that he is prone to experiencing.
8. Get Out of the Bed/Bedroom
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The older we get, the more bedroom sex makes sense. After all, beds were specifically designed to support our bodies. Still, if you’ve been in a long-term relationship for quite some time, just like approaching the missionary position the same way every time can get old, so can always being in your bed — or bedroom.
You’re paying good money to utilize more than just one room in your home, so why not maximize each one’s potential? And as far as the best room in the house to get busy, I recently read an article that said bathrooms and balconies are fan favorites, followed by closets and utility rooms. Personally, I’m with what a Men’s Health article stated, which is the living room is probably the most comfortable (and common) — yet whatever you do, just try and think outside of the box sometimes. In this case, think outside of your bed and bedroom to see what other places are comfortable for you both.
9. Or…Get on the Edge of the Bed
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So, what if you're like, "I hear you, but it's gonna be the bed for me, more times than not?" I hear you. There's a way to upgrade the missionary position and how you use your bed at the same time — have him pull you to the edge of the bed and either penetrate you by lifting your legs over his shoulders, or the two of you can just have "regular sex" that way (so long as he's good at maintaining his balance and keeping you from falling off at the same time).
The perks? For one, if his penis is more on the average side (check out "Sex Hacks For Different Kinds Of Penises (You Heard Me Right)"), he will be able to penetrate you more deeply. Another benefit is if you like to bring vibrators into the mix, it will be easier to do (especially if your legs are up). Another is this is one way to get your clitoris, vagina, and cervix all stimulated all at the same time — in fact, this is why another name for the edge of the bed is "the edge of heaven" (makes sense).
10. Keep Your Bra on — Kinda
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As a doula, whenever new moms talk to me about easing back into sex, it's very common for them to talk about how "conflicted" they are when it comes to their breasts, especially if they are breastfeeding. It makes complete and total sense when you think about the fact that first, our breasts are ours alone, then men come in and use them as foreplay, and then here comes a baby who uses them as a food source. A top suggestion that I give is that moms invest in some super sexy nursing bras. That way, if they want to still keep their breasts covered up, there is something pretty for their partner to look at.
Along these same lines (kinda sorta), consider keeping your own bra on during missionary — well, kind of. Either get one that is extremely sheer or pull your breasts out so that they are hanging out over the front of your bra. Why? Well, a lot of men have told me over the years that while nothing really tops a woman in her birthday suit, the peek-a-boo effect of breasts over bras and crotchless panties turns them on in a way that they can't fully articulate. Plus, if you're a bit insecure, this can help you out like it can a new mom (believe it or not), especially if you're going to bring some lighting in (like I suggested earlier).
11. Enjoy His Nipples
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Speaking of breasts…although not everyone finds their nipples to be the ultimate erogenous zone (check out “So, What If ‘Typical Erogenous Zones’ Annoy TF Outta You?”), don’t automatically assume that your partner is one of them. The reality is men have the same glands and nerve endings that we do when it comes to their nipples which means a lot of them find their nipples getting some TLC to be super erotic and enjoyable.
A husband client of mine once told me in a session that he wished that his wife would lick on his nipples more, especially during intercourse, because it takes his orgasms to a completely different level. When his wife heard that, she asked, since she’s not a contortionist, how could she possibly pull that off in a comfortable way? This actually brings us to the next point.
12. Try Some Kama Sutra Piercing
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On the heels of what I just said, what do you know about the Kama Sutra approach known as piercing? It’s kind of similar to CAT, only with a twist. This time, a man should position his shoulders to where they are directly over your head — that way, as he is moving in and out, you can get direct clitoral stimulation.
How is this any different from the CAT? Well, with that position, his arch is backed farther away from you. Plus, it tends to feel the most amazing upon entry only. On the other hand, piercing makes it possible for you to do the whole nipple thing that we just talked about while he’s able to stimulate your clitoris more intentionally the entire time. A win/win for everyone, wouldn’t you say?
13. Engage in (Some or More) Edging
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Another way to almost guarantee that your orgasms will be next level is to engage in a bit of edging. If you're familiar with the word, yet you've never exactly researched and/or tried it before — let's just say that it's the kind of act that requires some stamina (on his part) and some self-discipline (for you both). The reason why I say that is because edging is all about having intercourse, your partner stopping for 15-30 seconds, and then you both starting back up all over again.
And why would someone want to send themselves through this mind of, in a way, mind f-ck? It builds anticipation and excitement, which can actually make your orgasms super intense. Hell, it could even lead to multiple orgasms if y'all play your cards right. Anyway, you can learn more about edging by reading "All About Edging: The Ways Prolonging Pleasure Makes For Mind-Blowing Orgasms" on our platform.
14. Stop. And Switch.
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As I was in the process of penning this piece, I asked a few people to share why they felt that some people take a ho-hum attitude about the missionary position. The general consensus was if that’s all you do the entire time, things can get old really quick.
Good point. That’s why it’s also a good idea to keep in mind that, just because you start off in missionary, no rule says that you have to stay there (unless you happen to live in Florida because, apparently, only the missionary is legal there; Florida stays wilin’ out). No rule says that once you start having sex that you can’t do some other, eh hem, activities in between positions too.
My vote? Be down to get into some oral, especially if you want to increase your chances of having an orgasm. A “good giver” is gonna get off so much on pleasuring you that you probably won’t have to worry about him needing to maintain an erection even if he spends a few moments downtown (cue SWV’s song). Oral sex intermissions are so unsung. Whew, chile.
15. Moan ‘N Whisper
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The last and final point. "Dirty talk" is always gonna be a winner when it comes to sex, period; however, when you're in the missionary position, it's really amazin' considering you're both right next to each other's ears.
And what if dirty talk isn't something that you've exactly mastered (yet)? The key is to not overthink it. Moan. Whisper the things that you like being done to you (or that you want him to try). Ask him what he likes (or wants more of). When he's got it right, praise him. If he's got a pet name, use it. If you want to go with his government name, he probably won't mind that either.
The main point here is to remember that great sex incorporates all of the senses — touch, taste, sight, smell, and hearing. And since words are our most effective form of communication, you can't go wrong with using some in the bedroom…especially when you're giving it all that you've got in the missionary position…especially as you're adding in some of these upgrades that I just shared.
Enjoy, sis. EN-freakin’-JOY!
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RELATED
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
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