OK Here we go- We live in New England so you remember last year's (2015) snow. Over 4 feet with drifts as high as 7.
We- Dean was out with our Boat Broker, Scott, wandering the New England country and ocean to find our boat for our venture. Went to New York, Connecticut, Rhode Island, Maine to visit different styles, sizes, and cabin orientation that we would find comfortable for our trip. Also, we are looking for a motor sail boat- different from the traditional sailboat in that the engine is a little stronger and it has an enclosed cockpit so when the weather is bad, you can motor from an enclosed area. This helps if you are traveling for an extended period and won't always have nice weather. We (I) also wanted a sailboat that Dean can sail himself  as I am not ready to learn how to sail at my age. And-- did I tell you- he is a power boat person. Limited experience with sails. We live on the South Coast in Massachusetts and wanted a boat we could putter to Block Island, Martha's Vineyard, Nantucket, with some ease.
Many boats were ruled out due to size- length or draft. Many parts of the rivers in the Great Loop are shallow so a short draft is required 4.5ft or less. So that also was a challenge.  We liked some of the sailboats- most were loo long to maneuver in narrow places and had too long a keel (draft). What we did like was the width- most sailboats are at least 12 ft wide-lots of room inside.
Enough for now.