Shelter Cove to Bear Harbor- Camp and Return

The dream when I bought my TI was to sail to Bear Harbor, camp and then paddle/peddle/sail (wind permitting) home.  Along those lines I have a few questions.

1st is the trip... It's not something I'm going to jump into, but rather will build up to, when I am comfortable with the distance... but I'm wondering what people think in general about the paddle north against the current and wind.

2nd... launching and beaching at bear harbor in swell... it seems to be somewhat protected, and I have launched kayaks at bear harbor and beached, but I did flip one surfing it in... what is the max height of swell people are comfortable with (take into account my somewhat limited experience), and shoot me some recommendations.

3rd  It seems there is no way to register and pay for the campground without physically going to the parking lot at bear harbor, that is a long drive around, or a good hike, neither of which is really what I'm after.

I'm sure there's plenty of things I haven't considered at all, in planning and executing a trip like this, and I would be honored to have any advice on things I haven't thought of.  Cheers.

I'd love to do this trip, and your point about the campground registration is a good one - I think you could just send it in prior to the trip and ask for a refund if you had to bail.

As for the logistics, I'd do it on a calm stretch of summer weather where you could predict light wind early.  I think it's only about 8 miles from the Cove to BH - that sounds like 4 hours work, but the current and wind definitely factor in big.  A good training mission would be to troll for salmon to about 4 miles south and a mile out, then come back along the nearshore and see how it goes.  We commonly do 10 to 14 mile days with gear out, so 4 with and 4 without shouldn't be an issue.

With any of these plans it would be really nice to have a powerboat backup for emergencies, but a seasoned group of ocean kayakers could pull this off with no problems.

Up to 8 foot North swell, but preferrably below 6 and ideally 4 or less.

Bear Harbor is a magical place.   

thanks man... great info... I love bear harbor and haven't been down there since the road washed out.  I will call them and see about mailing in the reg. Sometime in June would be epic, and I will keep my eyes on the swell... I have a buddy with a powerboat that might be game too, and as my experience is limited I would be looking to fleet up with some folks. If you're interested lets keep talking about it.