For the purposes of this demonstration, I'm using a standard-sized rolling suitcase -- the size that you (usually) can carry onto the plane. Remember that airlines allow you to carry on one piece of luggage and one smaller bag, such as a pocketbook, computer bag, etc., that can fit under the seat in front of you. If you're in a hurry to get to your Caribbean resort destination once you land (and who isn't?) it's always a good idea to carry your luggage on rather than checking it. Just be careful to follow the TSA rules regarding liquids when you do. Liquids like shampoos, mouthwash, etc., must be 3 ounces or less and be packed in a clear bag for inspection.