Island-Hopping in the Cayman Islands

An airplane runway on a long flat island. Clouds drift overhead.

Are you the sort of traveler who can’t sit still? Do you always want to see what is around the next bend and what the next town over offers? If you think that a Caribbean vacation is for the more sedentary type of traveler, then the Cayman Islands, and this itinerary, will come as a pleasant surprise. Here’s a trip designed for those of us who want to always be on the move. You’ll spend some time not only on Grand Cayman, home of the islands’ capital and the world-famous Seven Mile Beach, but also the archipelago’s two smaller islands: Cayman Brac and Little Cayman. It even includes a visit to tiny, uninhabited Owen Island, where you can feel like Robinson Crusoe for a day—with the luxury of knowing cold beers and conch fritters are awaiting when you return to civilization.

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Caves of Cayman Brac

The magnificent caves of Cayman Brac with their stunning chambers, many filled with stalagmite and stalactites, can be explored even by amateur spelunkers.
Ignacio Maza


Ignacio Maza

Born in Cuba and raised in Latin America, Ignacio held senior roles at Virtuoso and American Express’ Travel Related Services division before joining Signature Travel Network in 2004 as Executive Vice President. In his current role, Ignacio is responsible for developing the network’s luxury travel business.
People sit in a warmly lit plaza at sunset.

DAY 1Arrive in Grand Cayman

Seven Mile Beach might be the most familiar destination in the Cayman Islands for many—the postcard-perfect crescent of white sand frequently tops lists of the world’s best beaches and it is lined with many of Grand Cayman’s top resorts. You’ll stay at the Marriott Grand Cayman Beach Resort which recreates the casual atmosphere of a cool friend’s seaside home—fondly referred to as The Beach House. Choose from yoga on the beach, borrowing a Linus bike (included with your resort fee) to explore the island, checking out a GoPro to create your own adventure show, or just hang out at the pool.

The Beach House encourages visitors to explore the local culture, a sentiment we agree with. After you have settled in your room, hop on a Linus and pedal to the National Gallery of the Cayman Islands (or you can walk, it’s only about a half-mile away), where you can explore the sculpture gardens and the works by local artists in the permanent collection plus amazing international exhibits you may not expect to see in the Caribbean.

This evening you’ll dine at the one of the restaurants at Camana Bay, a waterfront “town” that is one of the Cayman Islands’ premier shopping and dining destinations. The Brooklyn Pizza + Pasta satisfies locals and visitors alike with its popular and tasty Italian-American dishes.
A portside town on an island



DAY 2George Town

Spend this morning exploring the sites of the Cayman Island’s capital, George Town. On a self-guided walking tour you can start at the Cayman Islands National Museum for an introduction to the history of the island. Continue on to the Craft Market to shop for locally made gifts to take home, and then explore some of the town’s historic and contemporary sites: the new Legislative Assembly, the Library completed in 1939, and the Town Hall from the 1920s.

Stop for lunch at the nearby Paradise Grill, where you can snorkel among the fish before sitting down to a meal of their signature fish sandwich, seasoned island-style.

Spend this afternoon enjoying some time by the pool or beach at your hotel, either lounging with a book or taking advantage of some of the water sports offered there. In the evening you can explore more of the bars and restaurants along Seven Mile Beach.
A pristine beach on the ocean

DAY 3Little Cayman

This morning you’ll head to the second island in your tour of the Cayman Islands, Little Cayman, the smallest in the archipelago and home to only around 200 residents. Your base for the next two nights will be the Southern Cross Club, the oldest resort on the island which first opened in 1958 as a fishing club. Fourteen cottages in vibrant pink, yellow, turquoise and other tropical colors welcome guests to this barefoot chic property. The emphasis remains on fishing, as well as diving, and the resort arranges dives and fishing charters for guests. If you’d rather explore the sites on dry ground, it is easy to get around Little Cayman by bike or scooter.

At the eastern tip of the island, you’ll find Point of Sand, one of the island’s most beautiful beaches with shallow waters that are home to loggerhead turtles and has views of neighboring Cayman Brac. It’s a great place to search for seashells and snorkel too, or simply enjoy the quiet of this unique barely inhabited island. You’ll dine tonight at the Southern Cross Club.
A boat on green waters

DAY 4Owen Island

If you aren’t headed out on a dive today, you can enjoy a Robinson Crusoe experience on tiny Owen Island. Just off shore from the Southern Cross Club, this speck of land is uninhabited and there are no permanent structures. Bring a picnic lunch ordered at your hotel, and kayak the short distance for a day spent exploring this pristine little islet.

Once you are ready to talk to humans again, return to the “mainland” of Little Cayman and make your way to the Hungry Iguana restaurant, with its breezy verandah overlooking the sea. Like everywhere on the island, the atmosphere is casual and you can meet locals and other visitors while enjoying a cold beer.
A cliff on the sea.

DAY 5 & 6Cayman Brac

Cayman Brac is larger than its neighbor, but not by much—it measures some 12 miles long by a mile wide and is home to just over 2,000 residents. As on Little Cayman, iguanas probably outnumber humans and here, too, most visitors come to dive the island’s world-class sites. The Brac in the name is from a Gaelic word that means bluff—it runs the entire length of the island. Reaching a height of around 150 feet, it includes the highest spot in the entire nation.

You’ll spend the night at the Cayman Brac Beach Resort, renovated in 2015. The atmosphere is casual and friendly and the rooms are simple. Opt for a second-floor room for better views, or one of the junior suites if it’s in your budget.

If you are a certified diver, you’ll want to spend your stay on Cayman Brac exploring some of the legendary sites, especially its wall dives or the Capt. Keith Tibbetts wreck. If you aren’t certified, there are also some good snorkeling spots. Or you can explore the caves that are another of Cayman Brac’s most famous features.
A rusted anti-aircraft gun underwater.

DAY 7Leave Paradise

Your airport transfer is included in your room rate at the Cayman Brac Beach Resort, which will perhaps make it a little easier when it comes time to leave and begin the journey back home. Now that you have sampled all the Cayman Islands, however, you’ll know which ones you want to spend more time exploring on your next visit.
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