Crazy, Sexy, Chill: These Jamaica Baecation Itineraries Have Something For Everyone

Who doesn’t love a good baecation, especially if it involves taking flights and knocking back shots in an international locale? And where, in the world, is more alluring—with diverse options for almost every couple—than Jamaica?
It is undoubtedly my favorite island in the world, and recently I got the chance to try out a few amazing new experiences with my man, taking us from the east to the west, from sexy excitement and fun mayhem, to alluring sightseeing and connection. If you’re looking to take your bae to the Caribbean (or give your partner a few hints for your next trip), try these itineraries curated by yours truly.
CRAZY… BUT WORTH IT: Cross-Island Road Trip
Start your road trip in Westmoreland Parish and make your final destination an oasis of rum. On this trip, bae and I drove through nine of the island’s 14 parishes in 24 hours. Rent a car or hire a driver and get on the road. Jamaica is best seen and experienced by car for sure!
Where To Stay
Traveller’s Beach Resort, Negril
Start in Negril on Seven Mile Beach, and skip the big resorts to enjoy a bit more bang for your buck with the vibes, modern amenities, and beachfront access here. It’s affordable, the rooms are cute, and you’ll be in a prime location to take the main roads for this trip.
Hot Stops
1st: Cool Oasis, Negril
It’s the largest indigenous fuel provider in Jamaica, the prices are great, and the gas price matches the quality. It's a great place to get all the snacks, extra cash for tolls, and drinks you need to enjoy a road trip for two. After gassing up and getting snacks and drinks, we hit the road along Seven Mile Beach, on through Hanover and into the next parishes of St. James, Trewlawney, and St. Ann, and on into Clarendon.
2nd: Murrays Fish And Jerk Hut, Clarendon
Located in Clarendon, this stop is a must if you’re taking any sort of trip west to east. And while there are dozens of jerk centers across the island, this is one of the best simply due to the unique taste and smoke of the meats. Bae likes the chicken but this is the only time I cheat and eat pork ever. (When it's your turn to order, just say "I want a quarter pork please." It's a portion perfect for one.) Add festival, (a fried slightly sweet bread that tastes a little like hushpuppies but better) to your order, and thank me later.
3rd: Worthy Park Estate Rum Distillery, St. Catherine
Just getting up the winding hilly terrain for this attraction is scenic (and borderline scary) enough, and once you arrive, you’ll find the trip was well worth it. The lushness of the expansive property embraces you, and your tour, which originates at their welcome center, begins with rum punch served by the in-house bartender.
You’ll then be immersed in the history of the company, how their diverse brands of rum are made (with my favorite being Rum Bar Rum Cream), and a full walking tour of their distillery (which could actually give any California winery a run for its money when it comes to the alluring atmosphere, cool-comfy valley breezes, and the delightful sticky-sweet smell of fresh barrels of liquor).
The tour, of course, ended with a tasting of four samples of different types of rum (and a bottle of water to sip in between). And of course, one of us had to take one sip and call it quits since we had some more driving to do.
We headed on through St. Catherine (passing near Linstead and Spanish Town to be exact), then through the southern part of Clarendon, and then on to Manchester (where there are big beautiful homes and the weather can get cold like in the States). We then went through St. Elizabeth to pass through my second-favorite town, White House, then finally to Savanna-la-Mar, and on to where we started, Negril.
SEXY & CHILL: Club-Hopping, Cocktails, And Cannabis
For this trip, bae and I wanted to let loose and explore a little wild fun. We hadn't had a crazy, drunken, throw-caution-to-the-wind weekend since the day we met, so we wanted to lounge, do a little partying, and try a few new things. To spice things up, we were able to check a few things off our "We Ain't Too Old Yet" bucket list.
Where To Stay
Deja Resort, Montego Bay
It’s right on the Hip Strip, across the street from Doctor’s Cove Beach and literally steps away from any and every popular restaurant (think, Margaritaville). You can enjoy the open bar and the complimentary breakfast, and after one too many rum-punch rounds, slide on into a little secluded rendezvous with your boo in the upper-level hot tub. The area gives sensual vibes by sunset, and the added shade of the palm trees and other greenary around the pool just adds to the allure. (Again, keep it on the hush, sis, and take heed to discretion. There are several little hidden nooks that it’s just irresistible, but if you get caught, you’re on your own!)
Where To Go
Taboo, Montego Bay
I’d heard about the location in Kingston, but since I’m always traveling to the western parts of Jamaica, I’d never visited. I’m no stranger to strip clubs (well, the ones that employ women) so I thought it would be a good idea to check the Montego Bay location out.
We went on a Wednesday, and it wasn't too crowded. The entertainers there were fun, down-to-earth, and beautiful in a way that was inviting and relatable. They really didn’t hold back, to the point where my man—a born-and-raised Jamaican who is 10 years my senior, has several children and has been well around the block several times— was even blushing. We both got private as well as couple's dances and enjoyed every minute of it.
Added bonus: The drinks were exotic, strong, and worth every penny.
Lounge 2727, Montego Bay
This is another spot on Montego Bay’s Hip Strip, and if strippers aren’t your thing, you can get your party, drink, and eat on here. They have hookah, beer, wine, and cocktails, and again, the views, the views, the views! Depending on the night, you can dance (or lounge) to the soundtrack of dancehall, hip-hop, and R&B hits, and, as a bonus, it’s steps away from Island Strains, a marijuana dispensary that, on my first visit, I actually accidentally walked into thinking it was a lounge. (And do I have to spell it out for you sis? This has all the makings of a potentially Hangover-worthy spontaneous sexy adventure waiting to happen.)
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This Is How To Keep 'Holiday Season Stress' From Infecting Your Relationship
Hmph. Maybe it’s just me, but it seems like there is something really weird happening in the fall season air (because winter doesn’t officially begin until December 21) that cuddle season is in full swing while break-up season is as well. In fact, did you know that break-ups are so popular during the holiday season that December 11 is deemed Break-Up Day?
The reasons why relationships shift around this time vary; however, I did both roll my eyes and chuckle when I read that a very popular one is because it’s an easy way to get out of getting one’s significant other a Christmas present. SMDH.
Anyway, I personally think that the less shallow folks out here may contemplate calling things “quits” or they at least distance themselves a bit from their partner (and what I’m referring to is serious relationships) due to all of the stress and strain that oftentimes comes with the holidays whether it be financial, familial, due to their tight schedules or something else.
Listen, I would hate for you and your man to miss the fun and happiness of experiencing this time of year, all because you are so overwhelmed or irritated that you can’t really enjoy it. That’s why I have a few practical tips for how to avoid allowing the typical holiday season stress from INFECTING your relationship.
Manage Your Expectations
GiphyUnmanaged expectations. If there is a main reason why the holiday season tends to be so stress-filled for so many people, I’d bet good money that this is the cause. And when you’re in a long-term relationship, expectations can manifest themselves in all sorts of cryptic and/or unexpected ways. You might have relatives who assume that you are going to be with them for Thanksgiving or Christmas when you have other plans in mind. You might be thinking that you are going to spend one amount for presents while your man is thinking something totally different. When it comes to scheduling, your signals may be crossed.
And you know what? To all of these scenarios, this is where clear and consistent communication come in. Don’t assume anything. Don’t dictate anything either. From now until New Year’s, mutually decide to check in once a week, just to make sure that you are both on the same page as it relates to the holidays and what you both are thinking will come along with it. The less blindsided you both feel, the less stressed out you will be. Trust me on this.
Set (and Keep) a Budget
GiphyOkay, so I read that last year, 36 percent of Americans incurred some type of holiday-related debt. Hmph. Last year, there was still some sense of normalcy in this country, chile, so I can only imagine what finances are gonna look like over the next several weeks. That said, since I don’t know a lot of people who don’t find being broke stressful, make sure that you and your bae set a budget and then stick to it this year — no ifs, ands or buts.
Because really, y’all — it doesn’t make sense to deplete savings and/or max out credit cards for a few days of giggles only to be damn near losing your mind because you don’t know how to make ends meet come Dr. Martin Luther King, Jr. Day.
And by the way, this tip doesn’t just speak to things like food and gifts; I also mean travel. If it doesn’t make a ton of sense (or cents) to be all over the place this year — DON’T BE.
Keep Matthew 5:37 at the Forefront
GiphyIf off the top of your head, you don’t know what Matthew 5:37 says, no worries, here ya go: “But let your ‘Yes’ be ‘Yes,’ and your ‘No,’ ‘No.’ For whatever is more than these is from the evil one.” That verse right there? Oh, it’s a boundaries lifesaver! I say that because do you see “maybe” or “I’ll think about it” in there? Nope. LOL. It says that you should tell people “yes” or “no” and leave it at that — and that complements Anne Lamott’s quote, “’No’ is a complete sentence” impeccably well. Yeah, you’ve got to remember that anything beyond a yes or no to a request is privileged information; you don’t owe anyone details or an explanation.
Besides, if you are really honest with yourself, when someone asks you something and you give a “Umm, let me think about it” kind of reply, more times than not, you already know what your answer is going to be — so why not let you both off of the hook? Give your response. Commit to that. And let everyone (including yourself) get on with their lives and schedules.
I promise you that when it comes to those holiday parties, you are pissing more folks off by not RSVP’ing or doing so and not showing up than just saying, “Thank you but not this year” off the rip.
Remember That Your Personal Space Is Privilege Not a Right
GiphyA friend of mine recently bought a new house and invited me over to come see it. He’s a single man with no children, so as I was taking in all of the space that he had, especially as I walked through his finished basement, I joked about relatives coming to live with him. “Hell no” and “absolutely not” were pretty much his immediate responses as he went on to say that some folks even had the nerve to be offended when he told them that he had no intentions on taking DNA in.
Ain’t it wild how people think that your stuff is their right? And yes, that brings me to my next point. Your home is your sanctuary space. If you want to host folks this year — cool. If not, ALSO COOL. Please don’t let folks (family included) guilt you into how they want you to act or even into what they would do if the shoe was on the other foot. You are not them — and as one of my favorite quotes states, “If two people were exactly alike, one of them would be unnecessary.” (A man by the name Larry Dixon said that.)
Hell, my friends? They know that I am good for sending them random things that they need or even want all throughout the year. Coming over to hang out at my pace, though. Uh-uh. Chalk it up to being a card-carrying member of the ambivert club yet I like keeping my living space personal — and I sleep like a baby, each and every night, for feeling that way.
Always remember that your space, your time, your resources, your energy and shoot, yourself period (including your relationship), are all things that are your own. You get to choose how, when and why you want to share them. The holiday season is certainly no exception.
Cultivate Some “You Two Only” Traditions
GiphyIt’s not uncommon for some couples to hit me up after the holiday season to “detox.” Sometimes it’s due to the financial drama (and sometimes trauma) that they experienced. Sometimes it’s because they allowed their relatives (especially in-laws) to get more into their personal business than they should’ve. More than anything, though, it tends to be because they didn’t get enough quality time together and so ended up feeling “disconnected.”
Please don’t let that happen. Listen, I’m not even a holidays kind of woman and yet, I will absolutely sit myself down with some hot chocolate and chocolate chip cookies to enjoy a Hallmark holiday film or two. Aside from the fact that most of them are lighthearted and sweet, I also like that they usually focus on couples loving on each other amidst all of the holiday beauty and ambiance — which is something that all couples should set aside some time to do.
Maybe it’s a vacation. Maybe it’s a staycation. Or maybe it’s my personal favorite, A SEXCATION. Whether it’s for a few days, the weekend or even overnight — don’t you let the holidays go by without setting aside time for you and your man to celebrate one another. Don’t you dare (check out “Are You Ready To Have Some Very Merry 'Christmas Sex'?”).
GET. SOME. REST.
GiphyI once read that 8 out of 10 people get stressed out over the holidays and 3 out of 10 lose sleep during to it — and when you’re stress-filled and sleep-deprived, that can absolutely lead to hypersensitivity, making mountains out of molehills and even not being in the mood for sex.
Your relationship can’t afford to go through any of this, so definitely make sure to prioritize rest. I don’t care how unrealistic it might seem during this time, sleep should never be seen as a luxury; it will always and forever be a great necessity.
That said, try to get no less than six hours of shut-eye in (check out “6 Fascinating Ways Sex And Sleep Definitely Go Hand In Hand”) and even ask your bae to take a nap with you sometimes (check out “Wanna Have Some Next-Level Sex? Take A Nap, Sis.”). Not only will sleep help to restore your mind, body and spirit but, when it’s with your partner, it’s an act of intimacy that can make you both feel super connected, even in the midst of what might feel like chaos.
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Holiday season stress is real. Still, never give it the permission or power to throw your relationship off. Put you and your man first and let the holidays be what they are gonna be, chile.
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Sergio Hudson On Designing With Intention And Who Gets Left Out Of The Industry
Sergio Hudson dreamt big as a young South Carolina boy staring out of the window of his mom’s Volvo driving down the Ridgeway, South Carolina streets. Those dreams led him to design opulent tailoring that’s been worn by Beyoncé, Queen Latifah, former Vice President Kamala Harris and Forever First Lady Michelle Obama, just to name a few.
Those dreams have come full circle in a new way as he recently collaborated with Volvo for a mini capsule collection suitable for chic and stylish moments this fall. The 40-year-old designer follows a long legacy of fashion aficionados who’ve used their innovation to push the automotive industry forward, including Virgil Abloh, Eddie Bauer, Paul Smith and Jeremy Scott.
Using the same material from the interior of the Volvo EX90, Hudson crafted a wool-blend car coat and waistbelt that combine the vehicle’s Scandinavian design with his signature tailoring and intention. The exclusive collection launched on October 20, and each piece is made-to-order by Sergio Hudson Collections.

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In October, I traveled to Charleston with a group of journalists to get a firsthand look at Hudson and Volvo’s location. During a fitting, Hudson said his goal is to make “great work that can stand the test of time.”
“People can look back on and say, ‘I remember when Sergio did that collaboration with Volvo,’” he continued. “Thinking about aligning yourself with classic brands that speak to where you want to go. And I think that's what this collaboration kind of means to me and my business.”
Hudson pinpoints his mom as the biggest influence for his designs. This collaboration was no different.
“This particular coat reminded me of the swing coats that my mom used to wear in the early 90s. You know, diva girls in the early 90s had Sandra suits,” he said, referring to Jackée Harry’s character in 227. “My mom wore those and she would have these matching swing coats to go over them. And that's where the initial idea came. This would be around the same time that we had our Volvo. So she would put on her suit, her swing coat, get in that red Volvo, and go to church.”

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With this capsule and beyond, Hudson wants to see more staples rotating in and out of closets this fall. He advises fashionistas to build her closet out with essentials to mix and match that aren’t just stylish but also sustainable.
“It's just those special pieces,” he said. “You can wear the same shirt and pants every day and nobody will notice. But if you have a special boot, a special coat, a special bill, a special bag, that kind of speaks to everything that your style stands about, that is something you should focus on.”
These are the same kind of staple pieces that return to our Pinterest boards and TikTok feeds season after season. Fast fashion has never been Hudson’s aim. “I'm trying to create a special pieces that can stand the test of time,” he said in his warm, Southern accent. “I'm only creating those kind of pieces from here on out.”

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For Hudson, this collaboration is revolutionary. It’s his first time working with a car company and experimenting outside of his wheelhouse in this way.
“This is a Scandinavian brand, and, you know, it's 70 years old. I'm an African-American boy from South Carolina that has had a brand for 10 years. So I think bridging those two worlds and seeing the similarities was the beauty of this project,” he explained.
Though Hudson and his partner and CEO of Sergio Hudson Collections Inga Beckham have made massive strides in just 10 years, Hudson said the industry is far from where he wants to see it when it comes to Black representation. He pointed to how few Black designers were at this year’s Met Gala despite the theme being Black dandyism.
“The fact that I dressed 18 people speaks to how many of us weren't there,” he said. He implored more of industries, fashion and beyond, to collaborate with Black designers often.
“Allow mentorship. Allow funding. Allow great design to shine through,” he implored. “When it comes to being a designer of African descent, when you can't get the funding that your counterparts have, you can't compete. When you get opportunities like doing a collaboration with Volvo, or you get opportunities to be at the Met Gala, that's putting us on the equal playing field, but really the funding behind it is what we need to take it to that desk level.”
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