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On this episode: This week the crew kicks things off with sports talk, weekend stories, salsa nights, then gets into what’s happening locally & abroad. We also shine a light on Cayman’s creative community with a deep dive into Underground Sessions — an open mic platform that’s become a real hub for local talent: poets, singers, rappers, instrumentalists, comedians, and more. The conversation covers how it started, why it matters, & how it’s creating space for original art to grow. The crew pivots to sports & youth development with a feature on Stingray Swim Club, one of Cayman’s OG swim clubs. Coach John breaks down what it takes to compete, how training is structured (yes… 5AM practices), the cost of participation, & what support is needed to keep the program inclusive for more young people.

Plus, a special word from CINCO Insurance, reminding you why peace of mind matters on Cayman’s roads.

Providing quality health insurance coverage and peace of mind for Caymanians and residents alike.

Your health matters — and CINICO is here to support you every step of the way.

Underground Sessions

📍 Cayman Drama Society (Prospect Playhouse)

🗓 First Wednesday of the month | 7PM–10PM

Next one mentioned: Wednesday, 4 March

Contact / More Info (as mentioned in the episode)

Stingray Swim Club

📍 Lions Pool (across from John Gray)

🌐 Search “Stingray Swim Club Cayman”

📞 (345) 323-2271

✉️ headcoach@stingrayswimclub.ky

#TheLinkUpPodcast #CaymanIslands #UndergroundSessions #CaymanCreatives #OpenMic #StingraySwimClub #CaymanSports

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Join the ladies of SY30NW on their first book club episode as they discuss being single, what maintaining singleness in a relationship looks like or is there even such a thing? What gems will be dropped in this episode? Only one way to find out… tune in.

TUNE in 👇🏾

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#sy30nw #30something #winetherapy #lifeupdates #dating #relationships #PodLinkUp

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On this episode: Bringing the energy with reoccurring guests Kim & Lana, the cast is joined by Jermaine Sharpe from CayMAS to talk One Carnival. Together we break down the long-awaited unification of Cayman’s Carnival. Jermaine speaks candidly about the years of division, the role of government support, & what “One Carnival” means for the future of cultural tourism/national pride. Viral moments are explored, like the oxtail debate, Caribbean representation at the Super Bowl, shark safety in Cayman waters, & national identity. The crew balances humour, hard truths, and community-focused dialogue, this and much more…

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On this episode: January felt like 8 months long but we’re back with another episode. This episode kicks things off with weekend recaps, Caribbean pop culture moments like Bad Bunny’s Grammy win, & the madness of modern dating of misunderstood “karaoke dates” to financial red flags and Valentine’s Day expectations. All of this before diving into the Chamber of Commerce’s recent comments & the Cuban migrant issue, this & much more..

Plus, a special word from CINCO Insurance, reminding you why peace of mind matters on Cayman’s roads.

Providing quality health insurance coverage and peace of mind for Caymanians and residents alike.

Your health matters — and CINICO is here to support you every step of the way.

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On this episode: The crew returns with unfiltered conversation—covering everything from fashion and cereal debates to work permits, politics, relationships, and ageing. Friend of the podcast Lana joins the table as the discussion jumps from Cayman issues to global headlines and social media drama, leading to heated takes on policy, scooters/insurance, U.S. politics, and the now-iconic “Mr. Earl” moment.
Plus, a special word from Cinco Insurance, reminding you why peace of mind matters on Cayman’s roads.

👇 Don’t forget to like, subscribe, and share.

00:00 – Opening Chat
01:00 – Food talk, cereal cravings
02:40 – 🎯 Cinco Insurance promo
03:18 – Welcome to Episode 154 & intro to the panel
05:00 – OG Lana joins the conversation
06:30 – Weekend recaps & everyday Cayman life
08:30 – Food safety debates & leftovers controversy
10:45 – Online bills vs old-school payments
14:00 – Work permits, population growth & the Cayman economy
18:00 – Jobs Caymanians won’t do & labour realities
21:00 – AFCON drama & football controversies
24:00 – Global politics, media narratives & the U.S.
29:00 – Immigration, human rights & border discussions
33:00 – Cost of living, food security & supply chains
36:30 – Desmond and Kristy breakup & public relationships
41:00 – Cheating, marriage, and public perception
46:00 – 💀 The “Mr. Earl” conversation
52:00 – Ageing, intimacy & relationship expectations
58:00 – E-scooters, insurance & government rollout issues
01:04:00 – Public transport, enforcement & road safety
01:10:00 – Parking chaos, urban planning & frustration
01:18:00 – Comedy, culture & social commentary
01:22:30 – Final thoughts & wrap-up

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On this episode: The crew kicks things off with fashion jokes that quickly turn into the birth of a new nickname, Eggplant Papi - setting the tone for a wide-ranging, unapologetic conversation.

From generational debates and “expert” culture to Starlink officially landing in the Cayman Islands, e-bike and scooter legislation, rising food costs, public transport frustrations, and the realities of living and working in Cayman.

The episode also features a deep and insightful conversation with Alyssa Gilbert, Caymanian creative and founder of WIK Magazine, as she shares her journey through fashion, media, creativity, mental health, and why so many Cayman creatives feel the need to leave in order to grow, with hopes of one day returning home.

The discussion closes with powerful commentary on financial literacy, money mules, online scams, social systems, and why common sense isn’t always common.

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On this episode: The cast reflects on the holidays, parenting teens, first crushes, Christmas chaos, and New Year realities before diving into deeper conversations around discipline, responsibility, and growing up.

From hilarious parenting moments and cultural observations to serious discussions on global politics, Venezuela, U.S. intervention, and leadership accountability — this episode balances humour, honesty, and hard truths.

Proudly Sponsored by CINICO

When you choose CINICO Motor Insurance, you’re not just getting coverage — you’re joining a community that cares about protecting you and your loved ones. Personalized coverage tailored to your needs.

24/7 claims service.

Roadside assistance — from flat tires to towing, anytime, anywhere in Cayman. Peace of mind you can trust.

Ready for a quote? Visit CINICO and stay covered.

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It’s the final episode of the year, and we’re closing out The Link Up Podcast in true Merry & Bright fashion. In this episode, the crew looks back on the year that was and shares laughs, life updates, and real conversations about growth, gratitude, and community.

From marathon achievements and birthday celebrations to Cayman Thanksgiving, holiday traditions, gift debates, traffic frustrations, and what we’re truly looking forward to in the new year.

Thank you for rocking with us all year long. We’ll see you in the new year.

New episodes return in January.

Proudly Sponsored by CINICO

When you choose CINICO Motor Insurance, you’re not just getting coverage — you’re joining a community that cares about protecting you and your loved ones. Personalized coverage tailored to your needs.

24/7 claims service

Roadside assistance — from flat tires to towing, anytime, anywhere in Cayman. Peace of mind you can trust.

Ready for a quote? Visit CINICO and stay covered this holiday.

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