Getting to the Islands: There are plenty of nonstop flights to Grand Cayman (GCM) from the United States; then you can hop over to the Brac (CYB) and Little Cayman (LYB) on a small plane.
Hassle Factor: Low for Grand Cayman; medium to high for Little Cayman and Cayman Brac.
Nonstops: You can fly nonstop to Grand Cayman from Atlanta (Delta, three times weekly), Boston (US Airways and JetBlue once weekly), Charlotte (US Airways), Detroit (Delta once weekly), Fort Lauderdale (Cayman Airways), Houston (United once weekly), Miami (American, Cayman Airways), Minneapolis (Delta once weekly), New York–JFK (Cayman Airways daily, JetBlue three times weekly, Delta once weekly), New York–Newark (United once weekly), Philadelphia (US Airways once weekly), and Tampa (Cayman Airways).
On the Ground: In Grand Cayman you must take a taxi or rent a car at the airport, since most hotels are not permitted to offer airport shuttles. Hotel pickup is more readily available on Cayman Brac and Little Cayman.
Renting a Car: It's possible to get by without a car on Grand Cayman if you are staying in the Seven Mile Beach area. If you want to explore the rest of the island—or if you are staying elsewhere—you'll need a car. Though less necessary on Cayman Brac or Little Cayman, cars are available on both islands. Driving is on the left, and you need a local driving permit, available at the car-rental office for US$20.