Honestly, I can't read all the posts above, so I'm going to just chuck in my two cents worth.
MdR through the Canal ( do you have the $ for the canal?) and east is all to Windward, after the Canal. I'm sorry but I'd bet you dollars to donuts that you'll be so beaten up by the time you get to St Martin, you'll sell the boat.
Way back when, the charter boats from the Caribbean would sail to Greece in the spring and we'd return to the Caribbean for the winter season. The trip east across the Atlantic was always hit or miss. Some years it was a pleasure cruise, another motoring most of the way to the Azores. And then there were those trips when one wished for a rough day traversing the Cape, over what one was experiencing at that time.
So, that leaves going westward with the wind. Many, many cruisers have done that. Other than the Suez Canal (no locks, but minimum speed requirement, and non-stop) the sail up the Red Sea should be 50% running and 50% beating. I honestly believe that your electric motor will basically be unusable, even for getting in/out of ports, at times. That leaves your boat an engine-less sail boat when conditions are particularly difficult. Folks have been doing that for eons, and there is nothing wrong with that, if you are OK with all that extra work.
However, being realistic not political, we aren't very popular overseas these days, and that might make the voyage a lot less pleasant. You are going to need visas for every place you stop, before you arrive, which may be very inconvenient, and there are areas that you might not to wish to sail through, unless you are accompanied by a battle ship.
Either way, you are contemplating a difficult and perilous voyage, seriously. Just so you know, you will not be allowed firearms of any kind. As a delivery skipper, when my normal rate was $2.00 a mile, I'd probably ask double for a voyage like that. And $75.00 per day for each crew member. If you were really lucky, had the weather gods' love and devotion, pushed yourself and your crew really hard, you could probably do the voyage in 60 to 70 days, but that's without breakdowns, sailing nearly every day. No weather windows on that one. Dock, clear in, shop for provisions where you can, then clear out and be on your way that same day.
Good luck, either way, and I wish I was the one contemplating that voyage, or at least living in Greece.
My suggestion would be to sell your boat now, and check out what's available when you get there.
