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I'm just curious and want to hear from anyone who has experience towing there kayak instead of hauling it up on deck. I've done it both ways, hauling it on deck is a pain and it takes up way to much room. Towing it so far has gone well. I've had it in moderate chop on the Pamlico sound and she just bounced and bobbed around and stayed bone dry inside. However I do have a fear of ending up in heavy weather and losing her. I'm planning about a 30 mile trip on the Pamlico this coming weekend to a new anchorage, forecast is looking good. Am I worried about nothing or am I gambling? I don't have a cockpit cover, it would probably be a good idea though. Here are some photos to show you what I'm working with. Thanks
 

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I think a cockpit cover would be a good idea.

We tried towing on a couple of occasions - we have had the kayak randomly flip a few times, never sure exactly why, just looked behind and saw it upside down after feeling a 'slow down'.

We keep ours amidships inside the lifelines, but if it's 'in the way' Garhauer makes some simple kayak racks that mount to the stanchions and carry the boats outside the deck line.

KR1 KAYAK RACKS - (pair)
 

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I tow my 2 seat kayak all the time and you really need to have a cockpit cover to avoid swamping it by the waves. It may still flip (having some weight in it always helps, I keep extra water cans in there, tied down low so they are not moving) but will not flood.
Get a good cover. Seals have a great selection and reasonable prices: Seals Sprayskirts - Cockpit Covers
I have been toying with an idea to make a bimini top with my inverted kayak, but that is a lot of extra weight aloft and on a small boat like mine it makes little sense.
 

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My kayaks sat vertical outside the mizzen shrouds ,bow in a baggy on a deadeye and stern up thru a belt loop at the appropriate height. Ok and I'm not racing anyway.
 

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You could also consider the ORU kayak , I saw this on the shark tank show, It's a foldable kayak that look though enough and apparently they work really well. Once folded they could be easily store.
 

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We strap our kayaks from the stanchions outside the lifelines. This works well as they are very light weight kayaks (about 25 lbs), so very easy to load and deploy on the water. They also serve as fenders when docking!

In heavy seas, the leeward kayak sometimes bounces a little on the waves, but they are the sit on top type, so can't flood.

The only other downside is that they block some light and view from the ports, but they are hung low enough that they don't block the view from the cockpit.

We also sail in the Pamlico.
 
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