Where should we eat in Grand Cayman?

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Thanks for the reviews. For me, the challenge on grand Cayman is not finding good food; it's finding good food at reasonable prices. I'm glad that the OP reviewed places at both ends of the price spectrum.
 
Don't forget MyBar at Sunset House, southeast of George Town, the Red Conch Chowder is delicious!

https://www.sunsethouse.com/island-info-my-bar-a-local-favorite

I also want to mention the George Town Yacht Club. It's on the Bacadere Marina and only a few minutes from the airport. Not only is it a good place for breakfast on the weekends, but it is owned by the same people that own the Cracked Conch and Macabuca. The food is good, the ambience is lovely (indoor or outside) and I feel that they serve the best cracked conch on the island. You can also take advantage of their free shuttle to escape from the airport and enjoy a nice meal while you are waiting to get on a plane.

George Town Yacht Club

Some of our favorites in Bodden Town and the East End/North Side include:

Grapetree Café
http://www.grapetreecafe.ky/

Czech Inn
http://czechinngrill.com/

Over the Edge
https://www.tripadvisor.com/Restaurant_Review-g1973858-d817589-Reviews-Over_the_Edge-Old_Man_Bay_Grand_Cayman_Cayman_Islands.html

Tukka's
https://www.tukka.ky/

And if you are looking for a reasonably priced and funny dinner show, try the Wyndham Reef on Thursday nights for the show by the Barefootman. The prix fixe menu is nothing special (reminds me of wedding reception food) but it's fine for a very enjoyable evening:
https://www.barefootman.com/whassup.html
 
This is interesting because Sticky Toffee Pudding is a popular dessert on Cayman, and why wouldn't it be popular?! I just came across a 2016 review of the George Town Yacht Club that says that the Sticky Toffee Pudding is better at the GTYC than it is at the Ritz; I will have to give it a try the next time we visit!

https://cnslocallife.com/2016/07/golden-spoons-review-george-town-yacht-club/

Golden Spoons Review: George Town Yacht Club

Cayman News | 05/07/2016

“…For dessert we shared a very generous portion of sticky toffee pudding, which was excellent. I recently tried the much-lauded sticky toffee pudding at the Ritz, but this was better. The cake incorporates cassava, which is a nice touch and gives it another layer of flavour. I’m not fond of the local heavy cake because of the texture but I like the taste of cassava cake.

This melded a desert favourite with an undercurrent flavour of cassava cake, still very moist and pudding-like but without the gelatinous feel of heavy cake. It comes served with caramel sauce and ice cream, both served in a separate dishes.”
 
I just remembered another one!

We enjoyed a lovely Friday Night Happy Hour (2 for 1 drinks) at the Outpost Bar at Pedro St. James Castle in Savannah. It was a beautiful sunset evening and the crowd was a mix of locals and visitors just relaxing and having fun, and Seven Fathoms Rums were the featured liquor. See the link below:

The Outpost Bar
 
Macabuca/Cracked Conch consistently good, even if the tarpon have moved on. Last time we were at Macabuca, Don Julio was having a promotion. Not exactly sure how we got back to Sunset House...
 
This is interesting because Sticky Toffee Pudding is a popular dessert on Cayman, and why wouldn't it be popular?! I just came across a 2016 review of the George Town Yacht Club that says that the Sticky Toffee Pudding is better at the GTYC than it is at the Ritz; I will have to give it a try the next time we visit!

https://cnslocallife.com/2016/07/golden-spoons-review-george-town-yacht-club/

Golden Spoons Review: George Town Yacht Club

Cayman News | 05/07/2016

“…For dessert we shared a very generous portion of sticky toffee pudding, which was excellent. I recently tried the much-lauded sticky toffee pudding at the Ritz, but this was better. The cake incorporates cassava, which is a nice touch and gives it another layer of flavour. I’m not fond of the local heavy cake because of the texture but I like the taste of cassava cake.

This melded a desert favourite with an undercurrent flavour of cassava cake, still very moist and pudding-like but without the gelatinous feel of heavy cake. It comes served with caramel sauce and ice cream, both served in a separate dishes.”

Thanks for the info. Sticky toffee pudding is my wife's favorite dessert, and she's made it a point to try it at every place we've eaten on GC that serves it (and she also makes our guests try it). For whatever reason, we've never eaten at the Yacht Club, so now I'll definitely have to get her over there!
 
Too many options and I can agree and disagree with just about any list that is published.

For the record I have eaten at Calico Jack's. It's bar food. Good bar food, though, of course (this is Cayman!). I wouldn't go there for a meal, but it caters well to the "man I could use something to eat" while sitting on the beach thing.

I usually split my list into High-end, mid-range, casual and "thinking outside the box".
My High-end fave right now is Bacaro, then the Brasserie
Mid-range I like Morgans, the Brooklyn
Casual I find it hard to beat Macabuca, Chicken! Chicken! or Craft
and Thinking outside the box goes to VIVO and Bread and Chocolate.

I have a much longer list or preferences for different occasions but I will leave this post at this,
 
An award winning Sticky Toffee Pudding can be had at Thai Orchid! Hemingway’s from the old Hyatt days had an awesome one. Don’t recall it on the RC restaurant menus but was perhaps at Periwinkle back in the day. Calypso Grille also had an excellent version. Have had it in the UK years ago and the Cayman versions compare very favorably for this wonderful old classic.
 
There are many many food threads for GC on this board. What is unique about Tony's original post is that it represents favorites of the local DMs and not us, the tourists. I appreciate the insider opinion.
 
Yes. That is very true. For the DMs leaving from the GT area Rackhams is a regular spot. The far side of the bar is their meeting spot to hash out the day. That said Tony’s post did give us the wonderful opportunity to yet again relive happy food thoughts!! Brings back fond memories of The Lone Star of yesteryear before it was revamped and group owned. In the restaurant part there were T-shirts and badges from dive ops and fire, police and special emergency depts from all over the world - it was fascinating! The DMs lined up at the bar for lunch in between dives — the good old days for sure!!!
 

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