Littler, but Just as Grand

72 Hours in the Cayman Sister Islands


A Caribbean island can be perfectly indulgent. You’ve got a week or a long weekend, a couple of plane tickets, a pretty gal and a nice leather duffle. It’s a few hours from anywhere on the East Coast and once you’re there, you’re there. Take a taxi to your hotel, where a waterfall of earnest “gourmet” food is constantly thrust upon you and service is a button away. Hell, the most difficult thing to figure out is the outlet and Wi-Fi situation. But the trappings of modern resort life can also bring a modicum of staleness. That’s why you go the extra mile.

Or, in the case of the Caymans, 60 miles. Beyond Grand Cayman — famous for Seven Mile Beach and Stingray City — are the Sister Islands, Cayman Brac and Little Cayman. Here, you can relax under a palm tree, no advertisements in sight (except the odd tropical beer poster), and listen to the sounds of the ocean and the wind. Walk a beach without running into anyone, or bike the span of the islands without the fear of getting hit by other tourists on a moped. Both islands are explorers’ and photographers’ reveries, refreshingly Caribbean and just a puddle-jump away.


Stay-Gear-Patrol Where to Stay
The Cayman Sister Islands aren’t big — around 120 people live on Little Cayman, which just got electricity in 1990, and about 1,200 live on Cayman Brac — so don’t expect to stay in a luxury resort. Rather, the accommodations are earnest and personal, more closely related to inns than hotels. On Cayman Brac, stay at the Brac Reef Beach Resort, located near the airport, or the more affordable Alexander Hotel. On Little Cayman, the Southern Cross Club features multi-colored bungalows right on the beach, and many visitors return annually to Pirate’s Point, which offers eleven tasteful cottages on seven acres of white-sand beach.
Eat-Gear-Patrol Where to Eat
Because the islands are so small, most of its restaurants are located in the hotels, and cater to both vacationers and locals alike. The Palms Restaurant, part of the Brac Beach Resort, offers air conditioning, but for a more relaxed atmosphere, check out the Tipsy Turtle, which offers live music, cold beers and a popular pub quiz. On Little Cayman, the owner of the Pirate’s Point Dining Room frequently invites patrons into his living room for cocktails and local delicacies.
Venture-Out-Gear-Patrol What to Do
Dive, dive, dive: it’s the Cayman Islands’ unofficial motto. On Cayman Brac, swim down to the MV Captain Keith Tibbetts, a 330-foot Russian frigate that sunk in 1996. When you get bored of swimming, the 12-mile-long island also features more than 170 caves to explore, or take a hike up to The Bluff, the highest point on the island, where you can walk right up to the tenacious boobies that make their nests in the craggy limestone.

Once you land in Little Cayman, visit the charming heritage center — conveniently located right next to the airport — and then ride a bike to your hotel. In terms of diving, Little Cayman offers the Bloody Bay Wall, a 3,000 foot drop where divers can see giant lobsters and friendly turtles. Another popular activity is a visit to Owen Island. Swim or take a kayak to the private island, located just south of the 10-mile-long Little Cayman, for a picnic.

Sunshine-Grill-Gear-Patrol Venture Out
If you happen to plan your trip to Little Cayman during the Oscars, bring some fancier clothes — locals celebrate the awards ceremony with a “Black Tie Oscar Party”, featuring a watch party, banquet-style dinner and their own awards. And if you do spend some time in Grand Cayman, don’t miss the legendary fish tacos at the Sunshine Grill, tucked behind the Sunshine Suites Resort, or the jumbo prawn and a cocktail at the Westin Hotel.
Additional reporting by K.B. Gould