Grand Cayman Travel & Food Guide

One of my favorite ways to experience Grand Cayman is to hop in a car and do a little island loop, and you have to stop in Hell (yes, it’s a real place) in West Bay, known for its jagged black limestone formations that look like something straight out of another planet. It’s one of those quick, quirky stops that always makes me laugh you snap a few photos, mail a postcard “from Hell,” and it’s the perfect little break from the beach. Then keep cruising with the windows down until you end up at Rum Point for a lazy lunch and that classic Cayman afternoon. On resort days, I love balancing a full spa reset with pure beach lounging (strawberry daiquiri in hand, obviously), then mixing in a little adventure like paddle boarding, jet skiing, and snorkeling in that unbelievably clear water. It’s the kind of trip that feels fun, easy, and never rushed.

My favorite spots, what to order, and what to wear

If you ask me what Grand Cayman does best (besides the water)… it’s the food. You can keep it casual and beachy, or do a full “dress up and make it a night” dinner, and somehow everything tastes even better when you’ve been in the sun all day. Here are my go-to places, what I order, and what to wear so you feel right for each spot. I always order a tropical drink when in the tropics.

The Wharf (my #1 favorite—I try to go more than once)

• Why it’s special: Oceanfront setting, live cigar roller, and tarpon feeding at 7 pm and 9 pm (yes… I always volunteer to feed them)

• What to eat: Roasted pear & goat cheese, seared diver sea scallops, baked salmon with seared asparagus risotto and truffle dressing. Desserts: warm banana toffee pudding, warm apple strudel, key lime pie.

• What to wear: Resort chic—sundress or linen set for women, nice shorts and collared shirt for men.

Luca

• Why it’s special: Polished, classic, and always such a good meal—one of those dinners that feels like a true “Grand Cayman night.”

• What to eat: Chicken piccata, pumpkin ravioli, pappardelle, braised beef short rib, arugula-beet salad.

• What to wear: Resort chic/date night

Ragazzi Ristorante & Pizzeria

• Why it’s special: A family favorite and you truly can’t go wrong—perfect “easy night out.”

• What to eat: Tuna, Parma ham and melon, Caprese salad or soup, goat cheese salad, octopus pappardelle, spaghetti bolognese, lasagna, chicken marsala, beef short ribs.

• What to wear: Casual—sundress, jeans, or cute shorts set.

Rum Point

• Why it’s special: One of my forever favorites—casual, beachy, and the famous mudslide in hand = perfection.

• What to eat: Mango ceviche, jerk platter, peach and burrata salad, daily catch with creamy jerk mayo.

• What to wear: Swimsuit and cover-up, hat, flip flops (super casual).

Guy Harvey’s Island Grill (Georgetown)

• Why it’s special: Fun lunch stop while shopping around town—and peek into Guy Harvey’s store (I’ve actually seen him there!)

• What to eat: Great casual island lunch spot (perfect mid-shopping break).

• What to wear: Daytime casual—shorts, tanks, comfy sandals.

Guy Harvey’s Boathouse Grill (Georgetown)

• Why it’s special: Another great Georgetown stop—easy, fun, and always a solid meal.

• What to eat: Bang bang shrimp, fritters, calamari, Boathouse, steam pot, blackened mahi, tuna. Dessert: rum cake or key lime pie.

• What to wear: Casual dinner—anything you’d wear to “nice waterfront lunch/dinner”

Morgan’s

• Why it’s special: Perfect for a long lunch or easy dinner after a day on the water.

• What to eat: Escargot, mussels in white wine garlic sauce, Greek salad, classic burger, Drift burger, jerk duck surf & turf, seafood, crêpes, chicken schnitzel.

• What to wear: Resort casual—cute but comfy.

Cracked Conch Restaurant and Macabuca Tiki Bar

• Why it’s special: These two are basically stacked on top of each other right on the rocky coastline with the coolest views. You can literally see people diving at sunset because the water is that clear.

• Cracked Conch Restaurant (more “dinner”): Conch ceviche, conch chowder, coconut oil poached mahi mahi, seared diver scallops, slow-cooked duck.

• Macabuca (more casual/tiki): coconut shrimp, conch fritters, tuna and mahi tacos, fish and chips.

• What to wear: Casual, beachy—sandals, breezy dress, linen, easy shorts set.

Camana Bay (shopping and dinner night)

• Why it’s special: Great for shopping, strolling around, grabbing something sweet, and making it a fun “night out.”

• Where to eat: Brooklyn Pizza & Pasta (easy casual favorite).

• What to wear: Whatever you’ve been in all day—just throw on something cute and comfy.

Now for the Ritz-Carlton favorites (on-property)

Silver Palm

• Why it’s special: My favorite spot for a drink before or after dinner— warm, lively, and the perfect vacation atmosphere.

• What to drink: Anything fun and tropical (this is such a “sit and stay awhile” spot).

• What to wear: Easy resort chic—whatever you wear to dinner works perfectly

Seven (Ritz-Carlton)

• Why it’s special: The breakfast buffet is a total WOW… and dinner is just as good.

• What to eat: Porterhouse, seafood, salmon, pork chop, mushroom risotto and side of bacon, mac & cheese, thirsty seafood platter, soufflé (chocolate or daily special—hands-down fabulous).

• What to wear: A little dressier—“nice dinner” vibes

Andiamo Circolo Sportivo (poolside)

• Why it’s special: Easy, casual, perfect between beach and pool.

• What to eat: Prosciutto and melon, margarita pizza, Capri sandwich, burger. Bonus: rum runner.

• What to wear: Swimsuit and cover-up, sandals, sunglasses.

Saint June

• Why it’s special: Light, sunny lunch spot that feels like vacation.

• What to eat: Chili lime fruit, chips and salsa, tuna bowl, lobster roll.

• What to wear: Beach casual

Taikun

• Why it’s special: Always a hit for sushi nights and trying something new.

• What to eat: Gyoza, sushi, ramen, maki teriyaki chicken.

• What to wear: casual dinner—simple and cute.