Wow, it is almost like O'Day 25's are taking over the lake!!!! But, that is the beauty of a trailerable boat. You can take it where you want and enjoy it. Bayfield, as mentioned, does have a city ramp, but parking your truck and trailer there is limited to 3 days. Right next to the ramp is the Black Hawk Marina and the owner there might be of some value to you in terms of a transient slip and a place to keep your truck and trailer. If you are planning on spending the night in the islands your boat needs to be equipped with the proper safety equipment, which you probably have for the most part, but one thing many trailerable boats might not have is an anchor light. This must be turned on at posted sun down (not when it gets dark) and must be on all night long or you might be confronted by a park ranger. No big deal, you don't want anyone to run into you in the middle of the night anyway. There are places you can dock (first come first serve), such as the dock in Quarry Bay or in the small marina (both on Stockton Island), but it is $10 for overnighting. If you have a dinghy with an outboard on it, make sure you have battery powered legal lights if you intend to motor after dark. A VHF radio is a must for weather reports and to see where the winds are so you can find yourself a calm anchorage in the lee of an island or mainland. Charts are a good idea (even a place mat chart which is available at the Apostle Islands Marina will offer up a good reference for getting about the islands), but GPS is real handy (but not necessary if you have charts). Line of sight navigation is pretty easy if you just keep alert and stay in the islands. Charts are good so you know how much water you have underneath you too. The lake is very deep, but there are shoal hazards here and there. It can be cool or very hot. Depends on the time of the year and mother nature. Later in the summer jumping in the water is not all that bad and if you are in the shallows of a place like Long Island, the water is more like bath water.....very warm. If it is very foggy, not recommended that you venture out, but fog really is not so frequent. If it is blowing like stink you might want to sail with reservations as well, but usually sailors are praying for wind and have to motor too much, but when it blows, it can blow hard. Lots of protection with the islands, however, but like any big or small body of water, you have to use common sense. It is a beautiful area, great sailing and if you get on some islands, great hiking and some of the light houses are open for tours as well (that info on the web). Bayfield is a charming little fresh water seaport with lots of shops and restaurants and watering holes. Madeline Island is charming as well with more restaurants and entertainment at Tom's (twice) burned down cafe, if you like that sort of thing. It's a sailors haven on Lake Superior. If you want more specifics, feel free to message me with questions, etc.