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11-1/2' skiff, 16' Jewelbox Jr. cat yawl, San Juan 21
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My wife and I figure on towing a San Juan 21 sloop to Florida next winter for three or four month floating vacation and I reckon we'll be needing a tender.

I have been reading a bit here and it seems that for a tender most folk favor as big an inflatable boat as possible, with as big an outboard clamped on the back as possible.

But I just need a tender for a small trailer-sailor for coastal cruising. No way is it gonna have a motor, we really don't want one for our sloop much less one for the tender.

The wife HATES rowing.

I do have two 16 foot canoes and was considering one of those, but I have nightmares imagining getting into and out of a canoe from the sloop. A canoe is not the best boat to stand in, but of course it can be done.

I think a canoe has much going for it, simplicity, easy to lug on land, seaworthy enough when properly handled. They certainly have great capacity for the weight.

Anyway, so how about an outrigger canoe? I happen to have designed one last winter and have started construction of it.

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Am I mad to even contemplate towing such a thing behind a sloop?
It would be nice to have a capable, light weight, stable, sail and paddle craft handy for trips to civilization for shopping, exploring the mangroves and side trips.

I gather towing a tender can be "bad". Bumping into the sloop when at anchor at night, not to mention the drag when sailing
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Is it really a big deal for coastal waters?
 

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I would do it just to show the smug yachties it can be done...

No reason not to really. A good canoeist can manage a lot of coastal conditions. An empty canoe is that much more bouyant.

Put in some floatation either by design or float bags so she's easier to recover in case she swamps some how.
 

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We used to tow a 16ft canoe but only in protected waters. It really didn't track very well in seas, and it did swamp once. In general it was a pain in the butt, and not a very good tender. Our next tender was a 10ft Whitehall rowboat which was a vastly superior tender in pretty much every way.

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Consider inflatable kayaks. Compact and seaworthy (not the box store type--more like Walker Bay, I have one). Or folding kayaks by Oru (I have one). I also like hard sit-in kayaks (have 2). I have a lot of kayaks :)sneaky:). But I'm not much for 2-person kayaks, just a personal dislike.
 

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I took my Advanced Elements inflatable kayak instead of my dinghy on a couple of short cruises last summer. Worked out fine. But even though the AE kayak is very stable for a small kayak, it still was a bit tricky to get into from the stern ladder.

Nothing wrong with towing a small dinghy and rowing it or using a small light outboard if you want to go any distance.
 

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I took my Advanced Elements inflatable kayak instead of my dinghy on a couple of short cruises last summer. Worked out fine. But even though the AE kayak is very stable for a small kayak, it still was a bit tricky to get into from the stern ladder.

Nothing wrong with towing a small dinghy and rowing it or using a small light outboard if you want to go any distance.
We have carried 3 inflatable kayaks when cruising for many years. They package up nice and small, and are a great option to get ashore. We tow a RIB with us these days, but still use the kayaks more than the tender.


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Herreshoff/Vaitses Meadowlark
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I have a half-built outrigger canoe in my basement, to a Michael Storer design:


I've mused about using as a tender on my ketch, once I have that configured for more than daysailing.

I've thought about making it nestable, so that it would fit more easily on deck:


I'm long way from putting this in the water, let alone trying to tow it.
 

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I've towed a 12' sit on top kayak behind my 26'. Pulling it in close the drag wasn't so bad. Using some shock cord to damp the painter help keep it from banging on the transom as much. With a canoe, I'd worry about it swamping if you get into some weather or when you get waked.
 

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We used to tow a 16ft canoe but only in protected waters. It really didn't track very well in seas, and it did swamp once. In general it was a pain in the butt, and not a very good tender. Our next tender was a 10ft Whitehall rowboat which was a vastly superior tender in pretty much every way.

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But, the op isn't asking about a regular plain Jane kevlar, aluminum or royalex canoe. Asking about a proa or double outrigger canoe with a sail rig. Along the lines of a Polynesian sailing canoe or double outrigger canoe. These are very different critters than our back country canoes.

For one, more stable, harder to swamp, often have a steering appendage that will move CLR aft. Just need a tow ring mounted low enough like you would have on a rib, and I think they should tow fine.
 
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