Cayboss Charters

01/02/2026

Cayboss Charters now offers easy online booking through our website — choose your trip, select your date, and you’re set.
Private charters. Crystal-clear water. Zero stress. 🇰🇾🇰🇾

04/10/2025

Sometimes the best way to reset is with rod in hand and open water ahead.
At Cayboss Charters, we take care of everything so you can focus on the fishing. Whether you’re chasing your next big catch or just enjoying a day on Grand Cayman’s beautiful waters, we make sure your experience is seamless, stress-free, and unforgettable. 🇰🇾🇰🇾🇰🇾
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24/12/2024

08/12/2024

🎉 CHRISTMAS GIVEAWAY TIME! 🎉

We’re giving away some amazing prizes to choose from just in time for the holidays! Here’s what’s up for grabs:

✨ $500 Kirk Freeport Gift Certificate
✨ $500 Cayman Airways Travel Voucher
✨ $700 Private Boat Charter (4 Hours) with CayBoss Charters 🇰🇾

Want to enter? It’s easy! Just follow these simple steps:

1️⃣ Follow us on Facebook and Instagram
2️⃣ Share this post and tag some of your friends
3️⃣ Enter your name and email on our giveaway form at caybosscharters.com

Giveaway ends December 15th, 2024 – winner will be announced that day! We will never send you links via social media. We will only contact the winner via email on the day the giveaway ends. Do not let scammers trick you. As we have already had claims of winning the prize.

Good luck! 🍀

Cayboss Charters is a local family owned private boat charter company in the Cayman Islands. Come be your "Own Boss" of your adventure and book with us!

04/12/2024

IMPORTANT SECURITY NOTICE: SCAM ALERT

We have been informed that scammers are impersonating our company here on Facebook, claiming users have been randomly selected for our giveaway and urging them to click on links in the message.

Please DO NOT click on any links and ignore the message as it is fraudulent.

While we are indeed running a giveaway, we will ONLY contact the winner via email on 15 December, the day our giveaway ends. Any communications through other channels is not legitimate.

Please share and thank you for your attention to this matter.

Best regards

Cayboss Charters