SUP, kayak, or canoe?

[ArmyDaveNY]

Each item you mention has its pluses and minuses. What will you be using the purchase for? That will help a lot in providing useful information.

[roland stockham]

If waves are not a problem it is hard to beat a canoe, they where developed as the waterways equivelent of a truck. Light, eisily handled and will carry heavy loads without having to pack stuff in or tie it down. The ones with a square end take a trolling motor. Not sure about rail storage though as they are somewhat deeper than a kayak.

[Hardhead]

Having spent my youth and young adulthood in both canoes and kayaks, I'd personally much prefer a canoe. Much easier to transport items, and a lot less likelihood of having things slip over the side. Also, much more comfortable in my opinion, as I like to have my legs and feet under my seat. The downside to any of these is probably the difficulty in climbing to and from an anchored boat. (it can be done, but someone with no experience will have a much harder time of it). If using a canoe in heavy wind, the trick is keeping enough weight in the bow. A 5 gallon bucket of water works well if needed.

[jkindredpdx]

I have a 35' sailboat and bought a Sun Dolphin Aruba 8. It's inexpensive, light, convenient, durable, takes up minimal deck space, easily carries 200 lbs... did I mention inexpensive. It isn't the best tracking kayak, but it's quick to launch and super fun around the marina. When someone stole it this winter... I bought another one.

I am thinking of buying an inflatable kayak to go with the Aruba. Although paddling a canoe is great, my guess is that one would be awkward on a 33' deck.

[Scout 30]

For an inflatable kayak I'd go with the Sea Eagle RazorLite. Drop stitch construction like an inflatable SUP which means it's very stiff. I really think that this is the direction all inflatable boats will take.
https://www.seaeagle.com/RazorLite/393rl

[Don C L]

I have friends who hang two rigid SUPs on a rack outside of their lifelines, and they even go sailing out around the local islands that way. So far it works for them. I would REALLY be careful to pick my weather well if I tried that. In your case, not putting open ocean demands on the boat, I think that would be a good choice, and in fact one kayak could fit in that cradle or rack, there are quite a few brands. Google "kayak racks for sailboats" and they will pop up. I like my inflatable kayak a lot, so far it has proven the most versatile non-motorized dinghy I've owned, and it will hold 855lbs (the whole family) and can still be paddled well into a headwind. Mine is a large whitewater model with a dropstitch floor. Sea Eagle makes one, there are others. It doesn't take too long to inflate it. The only drawback for me is that my 29' boat doesn't have much room for inflating a 14' boat on the foredeck!
https://www.seaeagle.com/ExplorerKayaks/420X

[GILow]

Originally Posted by Don C L

I have friends who hang two rigid SUPs on a rack outside of their lifelines...

I really like this idea for storage once safely at anchor. Convenient in terms of launch/retrieval and keeps the deck clear for getting about. I think I'll make something similar to your picture for my boat.