It’s a shame that so few visitors (other than divers) spend time on more than one island in a single trip. If you have more than a week, you can certainly spend some quality time on both Grand Cayman and one of its Sister Islands.
If You Have 3 Days
Ensconce yourself at a resort along Grand Cayman’s Seven Mile Beach, spending your first day luxuriating on the sand. On Day 2, get your feet wet, if you snorkel or dive, at Stingray City and Sandbar in West Bay, where you can feed the alien-looking gliders by hand. Splurge for a great dinner on your second night, perhaps at Blue by Eric Ripert. On your last day, head into George Town for some shopping. Have lunch with scintillating harbor views at Breezes by the Bay or Casanova before soaking up some last rays of sun.
If You Have 7 Days
Since divers need to decompress before their return flight, the last day should be spent sightseeing on Grand Cayman. The Cayman Turtle Farm, the expensive but exceptional marine theme park, is a fine destination. On the East End you could hike the pristine Mastic Trail, then stroll through the gorgeous grounds at Queen Elizabeth II Botanic Park. Spend your final morning in George Town (perhaps snorkeling Eden Rock). Non-divers, too, should explore a bit farther afield instead of spending all their time at Seven Mile Beach. A full day around West Bay, perhaps beachcombing at savagely beautiful Barkers, is a good choice. If you have a car, explore the East End natural attractions, lunching at the Lighthouse. Head east another day to visit historic Pedro St. James Castle; drive through the original capital, Bodden Town; then spend the afternoon (lunch, swimming, and water sports) at Cayman Kai/Rum Point.
If You Have 10 Days
With 10 days, you can spend time on two or even all three islands. Begin on Cayman Brac; after diving the north coast walls, MV Capt. Keith Tibbetts, and the Lost City of Atlantis (or just lying on the beach), save a morning to hike through the Parrot Reserve, perhaps out to the East End Lighthouse for its sensational views (or climb the Lighthouse Steps, peeking into Peter’s Cave). On Little Cayman, chill out picnicking on Owen Island, and don’t miss the Booby Pond Nature Reserve. Spend at least two nights on Grand Cayman.