Best Beach Bar & Grill Calico Jacks

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Calico Jacks Best Beach Fun Ever! 

 Passenger Picks finally caught up with  Sian Weinzweig, no stranger to Calico Jacks and knows how to pull off the best or should I say "Epic Events" on the island!

  • PP Why is Calico Jacks the post popular Bar and Grill on the island? What is the draw?

SW Calico Jacks is right on beautiful seven mile beach and just steps away from the incredible clear blue water that Grand Cayman is known for . As well as that Calico's has a very casual and fun atmosphere with some of the cheapest drinks on island.

  • PP I know casual is key for I have seen some major volley ball tournaments take place on the sand at Calico Jacks! This bar is a magnet to the young and old! Not fancy just fun!


SW You got that right! But tons of folks are drawn to excellent entertainment and excitement!


  • PP Yes the sunsets on Seven Mile Beach are amazing! Many folks hit the Beach right before sunset to witness the sun cascading into the sea 

  • PP What is the significance of the Pirate outside the Bar? Where did the name come from Calico Jack?



SW The pirate was called Calico Jack Rackam, When the owner opened Calico Jacks he also still owned Rackams downtown so it made sense for him to name this new bar Calico Jacks! 

PP Folks Love the food at Calico Jacks! Especially the BBQ? Can You tell me more?

SW The food is great! Jerk chicken, pan fries grouper are both cooked with authentic Caribbean recipes. The quesadillas are to die for -  many call them the best on island!

PP My husband Dave is addicted to the Jerk Chicken right off the Grill!
  • PP Hundreds gather for your various events, feed back I receive is that the events are high energy, fun and always different? The full Moon Events seem to get a lot of buzz!
SW Yes most definitely the full moon parties are island renowned and it brings huge crowds every time. I think people enjoy partying under the stars on the sand which is why Calico Jacks is the perfect venue for big parties!




  • PP  Who plans these events? How do you get the big names? 
SW Epic Day Entertainment plans most of the big events and they have great contacts to bigger names and  I won' t spoil their secret on how they get them! 




  • PP What are some of the Events Coming up in the Future?


SW Full moons are obviously a favorite in fact the next Full Moon Party is August 28th! But I personally love New Years Eve also. EVERYBODY goes out on NYE and its just such a great atmosphere! Epic Day Entertainment usually brings in a big name DJ every year and it's become the place to go. 1500 people were on the beach last year!




  • PP  You started out at Calico Jacks working the bar area tell us about the culture,the fun factor,the folks you draw!
SW Calico's is just such a great place- the bar staff are really fun - everyone is really good at what they do and enjoys doing it. GREAT staff is something Calico's has prided itself on since opening. when tourists visit Cayman, they find out pretty quickly that Calico's is a place they must visit, plus its a very local hang out! All round great place!




Calico Jacks is a busy beach bar with beautiful sunsets, great events, delicious local dishes and entertaining staff. They host an Open Mic Jam every Tuesday night where people are encouraged to bring their instruments and get up and join in the fun. Saturdays are Jackpot Saturdays at Calico Jacks where a DJ spins funky, progressive house on the beach - Calico Jacks is THE place to be on a Saturday night. Every Full Moon also sees a big party on the beach at Calicos so if you happen to be on island during a Full Moon this is definitely worth a stop in to check out. Call 1 345 945 7850 or email sianwales@gmail.com for more details. Opening hours 9am - 1am Monday to Friday, 9am - 12am Saturday and 11am - 12am Sunday.

Calico Jacks is a 2015 Passenger Pick 
https://www.facebook.com/CalicoJacksGrandCayman

Comments

  1. KGJuly 11, 2026 at 2:37 AM

    This is such a great list! I'm a huge fan of beach bars — there's just something special about having a cold drink with your feet in the sand and the ocean right there. 🌊🍹

    I've been lucky enough to visit quite a few beach bars around the Caribbean, and one that really stood out was Barefoot In The Bar in Speightstown, Barbados. It's exactly what you imagine when you think of the perfect beach bar — no walls, no dress code, just wooden tables on the sand, palm trees swaying overhead, and the most incredible turquoise water stretching out in front of you.

    The food is authentic Bajan — their Flying Fish Cutter is a must-try, and the Grilled Fish with macaroni pie was honestly one of the best meals I've had anywhere. They have 18 signature cocktails including a traditional Rum Punch that's made fresh to order, plus ice-cold local beers with bucket deals if you're with a group.

    What really made it special though was the live music. Every Friday, Saturday, and Sunday from sundown they have local musicians playing steel pan, reggae, and acoustic sets right on the beach. There's something magical about dancing barefoot in the sand as the sun sets.

    If you're ever in Barbados, definitely add it to your list. It's one of those places you'll remember long after the tan fades. 🏝️🌅

    📍 Queens Street, Speightstown, Saint Peter, Barbados
    🕙 Open Daily 10AM – 11PM

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