I would find a good broker to help you. The purchaser's broker is paid by the seller so there is no direct cost to you. A knowledgeable broker can take your budget and list of needs and wants and find suitable boats.
Heading back to Lake Ontario for this summer. Relatively few stops along the way from Grenada. Martinique, Guadeloupe, St. Martin (must have something to do with the French food), then Bermuda, New England and up the Hudson/Erie Canal. We were going to go via Newfoundland and Labrador but June remembered that one of the kids is getting married this summer - details, details!