A medical dilating system includes a dilator device configured to penetrate and provide an opening in tissue of a patient, and a plurality of sleeves cooperatively configured to widen the opening in the tissue. The dilator device has an elongated shape with an exterior surface, first and second ends, and an interior wall defining an open interior volume extending from an opening of the second end to one or more openings in a tapered tip at the first end. Each of the plurality of sleeves has an elongated shape with an exterior surface and an interior wall defining an open interior volume extending from an opening of a first end of the sleeve to a second end of the sleeve. The plurality of sleeves include a first sleeve positioned around the exterior surface of the dilator device, and a second sleeve positioned around the exterior surface of the first sleeve.