Small Day Sailor for 2
I think you’ll have a hard time finding a suitable 2 person boat light enough to carry between cabin and dock. Even a Laser has a hull weight of about 130 lbs. I believe and the lightest two person boat I can think of is the Tasar which has a hull weight of about 145 lbs. The Tazar was made in North America by Performance Sailcraft (Ian Bruce’s original Laser manufacturing company) and probably isn’t a good cottage boat – high performance and fragile against rocks and docks – it has a foam cored hull with a thin fibreglass exterior.
If you can manage to store the boat on shore on a dolly, I would suggest taking a look at the Albacore. They’re ubiquitous in Canada, seem pretty rugged and sail well. Since they are very common and have been made by several builders over many years, prices are all over the place and they can be quite affordable.