When I was younger, reckless, and naive I traveled great distances with small boats and outboards. If you travel the world by boat you will find some fisherman with outboards well away from shore in open water.

In very general terms check to see which way the wind and current are moving if the motor dies or you end up in the water you will travel with the current, the wind or both. If either one of those are moving in the direction of open water think twice.

If you must travel outside of the anchorage where you will be alone without other boats in earshot. Consider throwing the flare kit in the boat, consider taking a gallon of drinking water, consider putting a cell phone connected to the network in something water proof. Certainly take a hand held VHF if you have it. Note: The range down at the surface of the water will be very limited. Do not count on anyone hearing you. Always bring a PFD that you do not mind wearing in the water for a long time and a good hat. A piece of soft line to tie everyone who might end up in the water together might also be a good idea. Lastly the low profile boat can easily be missed by a larger boat's helmsman focused on his newest bit of electronics, romance, or finding the beer someone else put away. There are many reasons to consider not putting yourself in a small boat with no one else around for the moment.

To some real world experience. Upwind and downwind can be very different. I can think of one late afternoon trip from the Caneel Bay anchorage to US C&I. The boat was full with more females than males. Most of the ladies were sporting arms full of stuff they thought they needed for the big trip to St. John. The trip over was uneventful and the same with C&I. All a great day until the time came to turn the dingy around with the sun setting and head upwind. By the time we got back to our boat. Everyone and their stuff was drenched and all the girls were cold and unhappy. The guy(me) driving the boat will always get the blame.

One night in North Sound I saw a group head off in a packed dinghy for dinner downwind. Later that night as they were returning I heard and witnessed one of the finest display of lady profanity I have ever experienced. The girls got drenched in their "good" clothes with their "good" stuff. Hubby in all the distraction trying to drive a dingy upwind at night managed to foul the dinghy prop in a super yacht toy painter hanging off the stern... note to all... sometimes wet wives can be a lot like wet cats.

So after all the dribble I would recommend if you are going to leave the mooring field with a dinghy you do so upwind. If you start off downwind you may not know what going upwind will be like to return at the other end.

As a standing safety order on our boats anyone who leaves in a dinghy, kayak, or paddle board is expected to leave a note on the nav table stating what time they left and what direction they left in. If you ever have to go looking for someone? You will want to know how long they have been gone and what direction the went off in. This can be very important when you have active early risers aboard.

In any small boat upwind can be very different than downwind and fetch will change the sea state the further you get downwind. Just because you can go both ways next to the boat does not mean you will be able to make safe progress upwind at the turnaround point.

PM me if you want to hear a more adult story on not paddling off downwind....