I do tend to overthink and analyze things, just my nature I guess. With this being a huge transition for us, I want to make as informed choice as I can, and gather as much information as I can.
Some others have suggested chartering different model 1st and I think that is a very wise move, so I will definitely be doing that. However there is no point in chartering a Nordhavn, if its overkill in capabilities for what I need, and out of my budget.
I have a friend in Florida who does some runs out to the Bahamas, and he sees plenty of Carver, Sea Ray, Doral, Regal in south Florida and Bahamas. Being a Canadian I always thought they were more suited as lake cruisers, however they are significantly cheaper then what I would be paying for a Nordhavn or even other trawler type boats like a Sabre, or Backcove, Helmsman, etc.
I know those boats would be fine around Bahama's its the longer stretches to the other islands that concern me. Other then the obvious fuel capacity requirements to reach the other islands, for example going from Turks & Cacios to BVI I think would be the longest stretch (bypassing Hati, DR, PR)
Would any of those Cruiser style boats (ea Ray, Doral, Regal, etc) be recommended by experienced island hopping cruisers? From what I read, the models with diesel can get similar fuel economy when running slow then for example a single screw trawler.
Random Example of what I mean:
https://www.yachtworld.com/barche/2004/sea-ray-420-sundancer-3731630/
Wifey B: Good morning from wherever I am. It never gets dark here so ^#^% confusing.
Now, sharked. You're so far away in Toronto from where you plan to be? Must walk before you run and run a lot before you enter a marathon. Hope you know this won't be your last boat?
So it might not be the do all, end all.
The Sundancer can run all around in the Caribbean......but......wouldn't say the Doral or Regal and many Carvers.....but......but #2....range....and now the big but....#3. Less captable the boat, fewer days you can use it. Less capable the boat, the less you and family will want to use it.
We have all these tomfoolery talks sometimes on blue water boats but the real question is blue water boaters. A lot of things can be done safely, but miserably to the average boater.
A 42' Sundancer will do better than a 35' but a 45' even better. The drive types in a Sundancer make a difference even. Might consider some Grand Banks and North Pacific's and similar though. They'll do 90% of what the Sundancer will and 50% more. Sundancer style isn't the best for long, long, long, long, long times living on boats. Not what it's designed for.
Look at different boats in person and on YW. Decide how slow you can go or how fast you prefer and correlate with what you're prepared to spend on fuel as it sort of goes together. I was just reading a word document from a friend here again this morning and he dared to say "one must go SLOW. (Is that word even in your vocabulary??)" to us. Guess he knows us well. I can spell SLOW but really don't like doing it.
But most here prefer it greatly. Only you can decide for you.
This big blue water thing isn't necessarily as threatening or big or huge as some make it appear. However, you must base weather windows and crossings on your boat, on yourself, on those aboard with you. We have friends who are avid boaters with us and we splash across pretty big seas at speed. But we'd never take newbies out in those conditions. Instead of giggling and laughing and yelling more, we'd get screams and wanting to stop and go in and never get back on a boat. I must warn you that one bad experience can lead someone, such as a spouse, to say never again and end all the fun.
Sort of like "fun fun fun till my daddy took the T-Bird away." Boating can be fun until it isn't anymore and you need to make sure it never reaches that point.
I don't know your finances or your family or much of anything about you. But I'd go one of the following two routes.
The coastal route-Buy a boat adequate for the coast and the Bahamas and enjoy it and then ultimately decide whether you want to go further in it or a new boat.
or......
The all-the-way route-Within your finances, get the most boat you can that you know can handle the Caribbean.
One last thing I must say. You said (bypassing Hati, DR, PR). Yes, I left the i out just like you did. No, no, no. Did I say
. I mean I would currently bypass Haiti. However, it's only something like 130 nm or so, depending on where in Turks and Caicos, to Puerto Plata, DR, which is a super place to visit as is Samana, DR, as is much of PR and the USVI and then the BVI. You're wanting to do controlled jumps, at least at first, so don't start bypassing yet.
Rent, charter, explore new and different areas. Be respectful but not intimidated and please, don't fall victim to that few who will tell you that if you go to these areas on any boat other than the one the push, you're doomed. Plenty of people who live there have far less seaworthy boats. Moorings in the BVI only uses Power Catamarans from 40-53' for their power boats.
So research but don't overthink and only you know what that is for you as some of us must do more than others to be happy. Then go boating.