I’m not making any loops my 1st voyage. I’m considering hanging out in the Gulf of Mexico for quite awhile to get experience doing basic boating maneuvers such as anchoring, docking for refueling, mooring which I think is maybe anchoring, and just learning to be courteous to other boaters. Also what it takes to change from salt water to fresh as I will go up the Mississippi River to around Blytheville AR where I have family in Jonesboro. I’ve briefly read where a person can tie off to mooring buoys for a nightish so there is another learning curve. I am adding the other intents of loop travel to see what is the most advantageous boat to get. I will also be taking classes from both registered instructors and people I know in southeast Texas who charter deep sea fishing guides.
In my mind, the difficulty with doing the loop is, it might take 2-3 years to complete if, you are going to stop and see the things along the way. Folks go north from FL and at some point, they stop because of the winter and cold weather and ice, come back the next year to do the Great Lakes, around MI, though the Industrial Canal .... making your way south.... So many things can go wrong and break down.... stuff you nor I know how to fix, so that means, finding the good folks to do the repair...
Once on the Mississippi another can of worms.... avoiding the commercial traffic..... Finding anchorages for the night might be a problem w/o good prior planning. This it why I suggest to join the wagon train of folks doing the loop. Take good notes on your charts and in your note book for maybe 3 reasons, 1. in case you want to do it again, 2. have something to read in your later life and finally 3. pass the information onto someone who wants to do the loop.
There is an computer organization of 'loopers'.... (someone else can tell you the name.)
I would like to do the loop.... but I doubt if I ever will. I was blessed to bring my Nordhavn46 down from Long Island to Ft Lauderdale.... we would run inside and at night, outside (stabilizers) My tool kit consisted of pliers, an adjustable wring and 2 stumpy strew drivers and 2 regular screw drivers and no spare parts. Outside, one night, the professional captain came up saw the water breaking over the bow and up against the pilot house windows and promptly got 'a little concerned' until I reminded him, the N46 could take worse weather than we could survive. Oh yea, that made him feel good. LOL
Naturally, I told the midship berth (I was the owner) he tried the forward cabin and saloon. I think maybe he would sneak into the owner's cabin while I was standing watch at the helm. I didn't care. He would mysterious go though a case of beer during 2 or 3 night, open the board door and pee over the side. I told him, he had to stop doing that because if he fell over the side, I would not know until it was my turn to stand watch. This was back in the early 90s so I purchased an expensive really really basic hand held GPS. There was a LORAN system onboard but, no current chips. He made fun of my GPS but after we complete the trip, he admitted, he used it all the way down.
I am pretty sure, we carried 1000 gallons of fuel so once we filled up in NY, we had no worries.... we had 5 water tanks but neither of us understood the valving system.... we ran out of water about 12 before our final destination.... only later did I discover, we had a 5th tank of about 150 gallons... unused. LOL The 1986 used water as ballast.
When outside, we ran WOT, fuel usage be daymned. SMIRK. inside.... we tried not to create a wake.
So you see, I am not a looper... not even a 1/2 looper.... IF I had to do it over, I might have take twice the time and stopped along the way to enjoy the sights. We spent a night at a marina w/o a reservation but the owner had LOTS of room. One other night at an unnamed dock behind someone's house, quietly leaving early before they woke.
My only regret was not circling the Statue of Liberty.... he was in a hurry to get out into the ocean and it was beginning to get dark.
The N46 purred at WOT, never used my "tool kit", the fuel must have been clean because it was never necessary to change filter.
So you see, God really does protect fools. LOL
My recommendation, hook up with other loopers have fun but realize, you may have leave the boat for the winter.