Vehicles
The environment in GTMO is pretty harsh when it comes to vehicles and the roads aren't exactly kind. The climate is similar to the desert southwest with little rain and year-round tropical sun. Add to that the salt air of the Caribbean Sea and it's easy to see that it's tough to keep a new car looking good.
Fuel is something to consider. There's only one gas station and 89 octane is the only choice (other than diesel).
If you're planning on diving then bring a truck, preferably one you won't mind getting beat up a bit. Shore diving involves driving off road and not all areas have water available to clean your gear.
It would be good to prepare your vehicle by getting new tires, charging the AC, and having everything checked.
Transporting a POV
Typically, your vehicle is shipped from your home of record to the Blount Island shipping facility in Jacksonville, FL. From there, it's put on a barge and shipped to Guantanamo Bay.
Once the vehicle arrives in GTMO, you'll pick it up from Schuyler Line and then register it at the Vehicle Registration Office (more information is available below)
You'll need a temporary tag from the VRO in order to pick up the vehicle from Schuyler. It's recommended that you get the tag from the VRO days before your vehicle arrives. The VRO is only open Tuesdays and Thursdays for registrations.
During peak PCS seasons, it may take longer for your vehicle to be transported on and off the island.
Buying Locally
There are occasionally vehicles for sale. Often these are the "GTMO Beaters" that wouldn't pass a vehicle inspection back in the states.
Insurance
USAA is the only insurance provider that offers coverage in GTMO. Membership is open to active, retired, and seperated veterans and their dependents. For more information, visit USAA.
If USAA is not an option, one alternative is Trustpoint Insurance
Registration
In order to register a vehicle, you'll need the following:
Drivers license
Proof of ownership
Insurance
Registering a vehicle is done through the Vehicle Registration Office.
Your vehicle will need to pass an inspection performed at the VRO. There is no cost for the inspection and the registration is free of charge.
You may have your vehicle inspected at AutoSkills for $10.
Maintenance
Vehicle maintenance is done at the Auto Port.
You can work on your vehicle yourself at the AutoSkills Center.
Motorcycles
Motorcycles over 50cc require a motorcycle endorsement on your drivers license. You must have the endorsement prior to arriving in GTMO.
While USAA does not offer motorcycle insurance in the states, they do provide coverage in GTMO. In fact, they're the only major insurance provider that offers motorcycle insurance in GTMO.
As a bonus, once you return stateside, USAA will grandfather you in and continue to provide motorcycle insurance.