Rockland, to Vinalhaven area, to Stonington area is a nice journey, but it's quite committing water. If you are not experienced with long crossings, tidal currents, and large boat traffic, then you might not want to start with that trip.
Each summer I hear about a few distress calls from groups of kayakers that decide to make that trip and get overwhelmed for whatever reason.
2-3 Canoe/Kayak Trailer
Kayak & Canoe Covers
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