You can pretty much book with the company offering the best deal for your needs. Check Expedia Kayak or Orbitz. Based on fluctuations in availability and fleet refresh, its difficult to say you has the nicer condition cars at any given moment. We generally use Thrifty, they've done us many solids over the years, but have also used Andy's, Firefly, Budget and Marshall's.
Keep in mind if you don't obtain an International Driver's Permit (you can use AAA to obtain), you'll need to spend $20 USD on top of the quoted price to get a local visitor's driving permit. All insurance is optional, hopefully you have a no foreign transaction fee credit card that will cover the Collision and Damage waiver. If so, it would just be up to you if you want to purchase 3rd party liability.
The drive to Rum Point is about 45 minutes from the airport. Cayman follows the British rules of the road with driving on the left, but speeds posted in MPH. Rental cars may have metric displays only, make on the fly speed conversion a fun task.
Once you leave the George Town environs, it is pretty much one road and little traffic, but some folks get flummoxed at the round-a-bouts. If you do get lost or think you are lost, by all means stop and ask for directions. Most folks will be all to happy to assist. Just plan on getting lost, so you don't get too frustrated if you actually do.
Google Maps is available for off-line, no data service needed, turn-by-turn navigation to just about any address or location on the island. Keep your phone in airplane mode or turn data services off and you can still get directions. Just search for "Grand Cayman" on the Google Map App and crop so that the entire island is selected for download. Here's the how-to:
Andriod PhonesIphonesWe recommend buying groceries on your way to the condo at one of the bigger stores on the other side of the island. Please be advised, if arriving on a Sunday when the grocery stores are closed (all, except gas station mini-marts and Chisholm's mini-mart ), you may want to consider a shopping service who will stock the unit with items from the shopping list you provide. There are two smaller local grocery/convenience stores which are best for items you may have forgotten to purchase at one of the bigger stores or if you have run out of something.
Some sights along North Side to check out are: Crystal Caves, Starfish Point, A Bio-luminescent bay tour, Sting Ray City.
