Risk is largely a matter of perception.
When flying a Westwind from Puerto Rico back to the States, I put away my chart once we passed Grand Turk and started pointing out places in the Bahamas that I had flown to years ago, when I had my own Arrow and was building flight time during the last Aviation Depression (1991-1996.
As I passed Crooked Island and pointed out the lighthouse, my FO said, "You have been out here in a single-engine aircraft?" when I told him I had, not only once but many times, he said, "You're crazy! We're over 350 miles from shore!".
I pointed out that we weren't 350 miles from shore, only from the US, and that flying a single out here was reasonable if you did it right.
In my case, I was flying my own plane, which meant I was more in touch with it mechanically (Knew any/all sqwaks, aware of normal fuel and oil consumption, normal sounds, vibration levels, etc).
I always flew on an IFR flight plan. I would always fly at the higher altitiudes, keeping in touch with FSS. Since you had to be above 6000' to reach them on the radio, you would fly to the island of intended landing, cancel from altitude and spiral down over the landing field. Same with the departure- spiral up to altitude, file and open your flight plan, and then depart land. I would also advise using a cellphone from altitude to let a resposible person also know your departure, route, and when and whom you want them to notify if they haven;t heard from you by a set time.
Load the airplane in a way that you can get out with a raft. Discuss ditching with your pax beforehand, including how to secure the liferaft so it doesn;t float away, nor get pulled under with the aircraft. Make sure they know to pop the door before touchdown so it doesn;t jam shut.
Always track the nearest land, keeping ships in sight as well. Monitor several nav sources. We used to use Loran, which could be spotty at times in he Bahamas. Invest in a Pilot's Guide to the Bahamas and Caribbean- it's a great source.
Years later, I got a job flying a CE402 throughout the Bahamas, but it was never as much fun as it was in my Arrow, with a cooler full of food and beer and our snorkeling gear, blasting off for a week in the out islands . . . far from the tourist crowds, eating with locals and swilling rum out under the stars at night, listening to nothing but the waves.
Risk. . . . low. Benefit . . . high.