Let me clarify a couple things.
I'm not hell bent on crossing an ocean. I just assumed that was the only way to see the South Pacific Islands and/or the Greek Isles in my own vessel. I honestly didn't think about the shipping option.
Another question....do you still need a "ocean going trawler" if you ship the boat and sail around Europe? Same thing with the Bahamas and the Caribbean? I've done the Bahamas several times in my own boats but I have never ventured into the Trawler world. I guess I'm simply ignorant on the differences between a coastal cruising trawler and an Ocean going one? Is it recommended for those in the USA to cruise the Bahama Islands and even stretch it to the Caribbean Islands in a coastal Trawler?
You require less boat to cruise around Europe on in the Bahamas or to the Eastern Caribbean than you do to cross an ocean. Two of the biggest factors are:
1-Range
2-Weather window
Crossing oceans requires fuel range of over 2000 nm. Crossing oceans takes typically 14 days or so, although can be more or less but it's long enough that weather can change considerably during your trip and that your ability to bail out and get back to safety is very limited.
You could easily spend years along the coasts, do the Big U, then do the Eastern Caribbean, then ship the boat to the Mediterranean and from there cruise Europe for a few years. Next ship it to the South Pacific and enjoy Australia and New Zealand for a few years.
Another approach is to get the boat that will do everything but cross oceans, ship it, then if at some point crossing oceans is essential to your pleasure, upgrade, but by then perhaps you have a better knowledge of what is required and more skill and experience yourselves.
We've done a tremendous amount of cruising the last 6 1/2 years, over 100,000 nm and my wife and I both are 500 Ton Captains and we do intend to cross oceans. However, we wouldn't dare head across the Atlantic by ourselves in any boat today. We don't have the mechanical experience ourselves and I'm not talking just normal maintenance, but how to handle emergency needs in the middle of an ocean, so we'd want an engineer or that type and the first time would like someone who has crossed with us. Plus, and this is personal, but we'd want more than two persons capable of operating the boat aboard. At the least we'd want three so at least we'd only have to do eight hours a day each. To actually enjoy the crossing probably more. If you're fighting elements, fighting fatigue, fighting lack of sleep, then what fun is it anyway? Mark Pierce will tell you to go on a cruise ship. I don't agree with that, but then I don't agree with the idea of just trying to prove what you can do without help.
When I see someone talking about crossing oceans so early in the process it scares me a bit. I think of those on the sailing site who say just go do it because they can tell you all those who did so and survived with no experience. They don't tell you those who failed or those who died trying. Just in North America, without even including the Bahamas but you would have to go through Central America to get from one area to another, you can cover 20,000 nm before you ever go to a place the second time.
We've done 100,000 nm and only been in North America and the Caribbean, and Central America as we used the Panama Canal to get from one side to the other and we've only touched the surface. If you're in an 8 knot boat, just think how long that would take you. While seeing other parts of the world sounds wonderful, there's years worth to see here.
One other concept is to get the boat to cruise this area and then go to Europe one year and rent a canal boat or charter for a while or go to Australia and charter.
I guess what I'm trying to say is there are year's of fresh, exciting, new boating to do before you ever exhaust what's near and even need to think of crossing an ocean.