Top All-Inclusive Cayman Islands Resorts

The Cayman Islands may be a centerpiece of the international banking world and a clichéd reference in spy caper movies (think “offshore holdings”), but they also happen to be dotted with gorgeous beaches, nature preserves, and world-class diving opportunities.

There are three Cayman Islands: Grand Cayman is much larger, with plenty of big resorts, and is a regular cruise ship stop-off, so those who prefer to really slow down might prefer Little Cayman or Cayman Brac—both being more remote, but just as charming.

Dining is generally expensive here, so the rare all-inclusive package or hotel can make a stay much less stressful. If you’re more of a “bring me a drink in a coconut” traveler than a “let’s cook all our meals at this condo” traveler, here are a few places to fully unwind with inclusive package deals.

Cobalt Coast Grand Cayman

Love to dive? This relaxed spot tucked away at the tip of Grand Cayman just north of Seven Mile Beach has aquatic packages aplenty. One scuba-centric deal includes two morning dives daily in addition to all three meals and five beverages per day, taxes, services, gratuities (except for scuba staff) and ground services. Premium drinks and rental gear are additional. That’ll run you $721 per person for three nights.

This is a petite resort with top-notch homey food and service as opposed to the sleek, luxe trappings and oontz-oontz soundtrack you might find at a mega-resort. For a lot of its fans, the groovy, laid-back vibe is part of the appeal—as is the nearby strip of shopping, restaurants, and things to do if you feel the need to take a break from the resort.

Cayman Brac Beach

About 12 miles long and 1 mile wide, Cayman Brac—the easternmost sibling to Grand Cayman—is home to only a few thousand people, and it feels like it. It’s the sort of place where, if you’re walking down the street, someone might slow their car to ask you if you need a ride. You can’t get there by boat; you have to fly, but the local resorts tend to make it easy for you, helping arrange transport.

This one in particular is the sort of place serious divers go—along with those who just want to completely take it easy. Most people arrive and don’t leave the resort, a rep tells us, taking advantage of package deals that start at three-night stays. As is true of its sibling outpost on Grand Cayman, those start at three nights and longer, depending on availability, for double occupancy. The “Clearly Cayman” package includes all three meals, ground transfers, three drinks nightly, taxes, tips for waitstaff and housekeeping, and some dives.

Wyndham Reef Resort Grand Cayman

Points hoarders, listen up! You can use your Wyndham points here, a resort situated far from the hubbub of Seven Mile Beach on the opposite end of Grand Cayman. Stay five nights or longer and take advantage of the all-inclusive plan, which, yes, entails a wristband, but means you don’t have to carry cash around with you. It’s $189 extra per person per day for adults, $60 daily for kids between 3 and 17, and free for the littlest ones.

Like to party and want to do it up? Well, you can (responsibly!) drink as many house brand drinks as you want, including frozen cocktails—and there's no extra charge for tiny umbrellas. Stay active and burn off the three included meals by kayaking, snorkeling, pedal boating, or paddle-boarding, or duck into the fitness center. And if you really like to blow it out on vacay, tack on a $50 surcharge daily for premium add-ons such as New York strip steak, lobster, and top-shelf spirits.

Pirates Point Resort

For those who like to truly get off the grid, there is Little Cayman, the smallest and least populated of the three islands. Ten miles long and a mile wide, there are only a few places to stay, and those who love it are over the moon for how remote this place feels.

Pirates Point—a tiny, simple spot with only 11 rooms in cottages—offers a few well-priced packages, with one tailored to heavier drinkers and heartier divers, and one that is not. (We love that both include unrestricted use of bicycles; the island is perfectly sized for a ride!)

Packages don’t include an additional 15 percent service charge that covers all gratuities, nor does it cover the $10.40 nightly tax per room, but all-inclusive meal packages including a room, wine at dinner, airport transfers, and a welcoming tropical drink start at $250 per night per person, which is among the better deals we’ve seen in this part of the world.