Cayman Islands

The only full 18 on the island, and it's better than it has any right to be. Originally a Jack Nicklaus design from the Britannia days, redone by Roy Case — open, breezy, and exposed enough that the wind off the sound is the real defense. Conditioning is solid year-round and the staff actually gets you out fast in the morning.

Nine holes, private, and the fairways are tight enough to embarrass anyone who got cocky at North Sound. Access is through member introduction or sometimes resort concierge — most visitors never even hear about it. If you can get on, you should.

Greg Norman-designed nine-holer for Ritz-Carlton guests and members only — short, manicured, and built across the property's narrow inland strip. Not a destination round but a respectable way to get more golf in if you're staying on site. Multiple tee sets so you can play it as 18.

The default splurge on Seven Mile, and the only hotel on the island with its own course (Blue Tip). Service is tight, the beach is right there, and Eric Ripert's Blue is downstairs when you want one big dinner. Pricing is what you'd expect — expect to pay Miami-plus rates in season.

Newer than the Ritz, sleeker design, and arguably the better pool scene if your group skews younger. Same Seven Mile Beach access, easier price tag than the Ritz in shoulder season, and the on-site restaurants (Coccoloba, Avecita) are good enough that you don't have to leave on a tired night.

The smart-money play. Same beach as the Ritz and Kimpton at noticeably less money, full resort with multiple pools and restaurants, and you're a five-minute drive from North Sound. Not as stylish as the newer properties but the location is identical.

Boutique, art-driven, and a different gear from the chain resorts down the beach. Tillies is on property and is one of the better restaurants on the island. Right call for a foursome that's bored of resort sameness and wants the dinner walk to be ten steps.

Three-bedroom oceanfront condos directly on Seven Mile — the move for a group of four to eight that wants space, a kitchen, and beach access without resort markup on every bottle of rum. Luca restaurant is on the ground floor. Books out fast in season.

For groups of six-plus, a Seven Mile condo or villa beats any hotel on math. Look at Plantana, Coral Stone, or Lacovia — three-bedroom units on the sand, walkable to restaurants, with a kitchen for the breakfast that doesn't need to be a $90 buffet.

Le Bernardin's chef has had this seafood tasting menu running at the Ritz for two decades and it's still the best meal on the island. Six or seven courses, jacket not strictly required but you'll feel underdressed in shorts. Reserve weeks out in season.

Palm Heights' beach restaurant — Mediterranean-leaning, big shareable plates, and the kind of room where a long lunch turns into a longer afternoon. Get the whole fish and the orzo. Best brunch on the island, full stop.

Camana Bay, Italian-Peruvian, and the locals' answer for a serious dinner that isn't at a resort. Ceviches and pastas are both worth the trip — split a few of each. Easier reservation than Blue, almost as good a meal.

On the water in West Bay, painted bright Caribbean colors, and famous for the sticky toffee pudding that everyone tells you to order — they're right, order it. Whole snapper, conch fritters, and a long lunch facing the boats.

A shack in West Bay, cash only, no reservations, picnic tables under a tree. Fish tea, jerk chicken, oxtail. This is the local Caymanian food the resorts can't replicate. Hours are whenever they're open — call ahead or just drive by.

Open-air, on the water at the northwest tip, and the right answer for a sunset beer after diving Cemetery Reef or the Kittiwake. Conch fritters, cold Caybrew, and a happy hour that feels earned. Don't expect a tablecloth.

Rum Point area, on the north side. Lunch downstairs is barefoot and beach-table; Luca upstairs is the real dinner. Most groups make a half-day of it — boat over from Seven Mile, swim, eat, drink, repeat. Earn your Sunday afternoon back here.

Roadside, no fuss, and home of the Sunshine Burger that locals will fight you over. The right post-round lunch when nobody wants to put on a shirt with buttons. Cheap by Cayman standards, which is to say merely reasonable.

East End, Vivine's house, plastic chairs in the yard, and some of the best home-cooked Caymanian food on the island. Curry goat, stew beef, fried fish. You're not going for ambience — you're going because this is what people actually eat here.

Tacos, ceviche, and frozen drinks at the Kimpton Seafire's beachside spot. Casual lunch or first-night dinner when nobody wants to commit to two hours. The Baja shrimp tacos and a margarita and you're set.