I am currently anchored in a bay with about 100 boats in it in Grenada, ranging from seven figures (a new Amel 54) to a lot less (a Canadian Chrysler 26ish, that I would want to check carefully before sailing across Lake Ontario). This has made me think about the interminable discussion about cruising on $X dollars a month or can I take my Whatever 36 into bluewater. This applies for people on the east coast of the US and Canada and the Great Lakes. There will be variations with different starting places.
Get a boat that you can afford, make sure you have some money to do upgrades after purchase and after you start cruising and just go.
At any point in the process you may decide - the boat isn't up to what comes next and/or I am not up to it/or it isn't really what I expected. If the former, you need to get a different boat and start the process again. If the latter, head home and either cruise locally or take up golf.
Discussing chainplates and anchors endlessly on the Internet will not get you sailing and cruising.
Get a boat that you can afford, make sure you have some money to do upgrades after purchase and after you start cruising and just go.
- Go down the east coast, ICW and hop offshore when you can. Fix and upgrade boat as needed and as affordable.
- Go to the Bahamas for the winter. Return to Florida before hurricane season. Fix and upgrade as needed. Note that this will be the last chance to fix your boat really cheaply.
- Go to the Eastern Caribbean via the Thorny Path. You guessed it - fix the boat (St Martin and Trinidad are best).
- Still having fun and want more adventure. Head to Panama and go through the canal. Fix and upgrade as needed.
- Rinse and repeat this process as necessary as you head to wherever you head for.
At any point in the process you may decide - the boat isn't up to what comes next and/or I am not up to it/or it isn't really what I expected. If the former, you need to get a different boat and start the process again. If the latter, head home and either cruise locally or take up golf.
Discussing chainplates and anchors endlessly on the Internet will not get you sailing and cruising.