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OK, so the Odyssey is pretty much the same as the Oasis which is one of the two Mirage drive kayaks that I currently own. I have modified my Oasis to make it (IMO) a better sailer - and it sails very well indeed - there is no reason to suppose the Odyssey would be any different but there are some compromises/differences that I think you should be aware of and take into account. What I did was an easy mod and from what I see would pretty much translate directly to the Odyssey...
...BUT as Matt says you would be well advised to think about fitting a rudder (not sure that I like that idea of steering with a paddle - might well work but an Odyssey 2-up would be a big heavy boat to steer - just my thoughts, no experience) that you can control; this part may not be easy and I cannot attest to how you would do this. My advice only relates to the "how to install a sail" part.
I dunno if you are already a sailor - if not you may struggle a bit with some of the sailing terms and logic; in this case you can take what I say verbatim and you pretty much won't go wrong - if you are you might want to think thru my suggestions based on what you know about sailing theory to get your head round what I am saying & why.
The Oasis comes with a mast base between the seats as standard and no daggerboard but, obviously you have the fins on the drives to provide some lateral resistance.
Because the position of the mastbase is in the centre of the boat with the centre of effort aft of the point of lateral resistance, there is a tendency for a sail in this position to push the boat upwind. Because of the lack of powerful lateral resistance (no daggerboard) the Oasis doesn't sail particularly well upwind compared with a boat that does have a daggerboard/keel (good example at the same tiny scale = Hobie Adventure). I am not saying it won't go upwind: I am just saying that its upwind performance is marginal.
On the Odyssey there is no daggerboard at all (no fins) so the upwind performance will be substantially less than the Oasis' marginal upwind abilities - to the point that I would suggest that the est you are realistically likely to get is downwind (close reach, broad reach and due downwind) - you may get across wind sailing but there is likely to be considerable leeway (sideslipping) which will mean basically that you may get your boat pointing across the wind but you will probably still be travelling slightly downwind.
Don't be put off by the lack of any real upwind ability because, set up as I will now describe, the Oasis sails beeyoootifully downwind, and the Oasis should do exactly the same (and possibly even slightly better - you will see why if you read on...).
What I did was to add a second mast base under the Hobie sticker on the foredeck - so that I now have a schooner (2 sails one between the seats, the other at the front). As a schooner the Oasis is quick, engaging, stable - despite 2x the canvas aloft, and very tweakable. But in a light to moderate breeze with a single sail in the front mast base on a downwind course it really is a total delight.
A sail at the front of the boat has the centre of effort in front of the point of lateral resistance so it naturally wants to push the boat downwind. If you are sailing downwind there is less pressure in the sail because you are travelling with the wind, and more of the wind's power goes into providing forward momentum. So even 2-up with a single sail the Oasis can produce very reasonable-for-a-sailing-kayak speeds without feeling overpressed or tippy, whereas sailing the Oasis 2-up with a single sail between the seats the boat tends to want to turn upwind and it just doesn't seem to sail as well, even downwind. And with a single sail at the front (no mast in the centre) you only need a single sheet unlike the 2 sheets you need to sail it as a schooner - so there's no rope to flog the crew's ears.
So IMO the ideal location for a mastbase on the Oasis/Odyssey is at the bow rather than between the seats, though this will compromise the already-somewhat-compromised upwind sailing ability of the boat further... and you have to be willing to forgo much/any upwind performance for the very real pleasures and benefits of capable, stable and enjoyable downwind (close reach - broad reach - run) sailing capabilities of the boat.
The mod is easy - you get a Hobie mast base as a spare part. You get some scotchweld DP8010 glue (and optionally scrounge or borrow a plastic welder) and a length of stiff, strong tube or rod that will fit tightly into the bottom of the mast base.
You then remove the Hobie sticker on the foredeck and drill a circular hole to allow the mast base to slide in through the deck (obviously, I hope, it must not be able to drop all the way through but the flange must sit above the deck and the hole provide a tight fit between the tube shaft and the deck to provide lateral & fore and aft rigidity).
In a factory mastbase installation the bottom of the tube is cut to length for the boat and it locates over a raised knob on the floor of the hull - you need to replicate this, either by glueing or welding a suitable knob on the bottom of your boat ONTO which your mastbase will fit - or glueing or locating a suitable raised circle INTO which your mast base will fit. The decision between raised knob vs rasied circle will be guided by your confidence in the strength of your glue/your plastic welding and whether or not you have bought a tube or a rod to extend the standard mast base with. Clearly you need to line the fixture up with the deck hole so that the mast will stand straight up - or your boat may look decidedly odd on the water!
I think Hobie's factory approach is to mould a brass fitting into the bottom of the hull (I suspect it is a nut) around which the raised plastic accumulates - this would be worth a try if you are going to plastic weld. if you are going to glue you need to choose the right glue - Scotchweld DP8010 is the ONLY way to go IMO (things like epoxies will probably fail at some point but DP8010 can and does stick like you know what to blanket) - the other consideration is surface area of the glued surface - I am guessing that even DP8010 might fail if all you have is half a square centimeter of glue taking all the load of the sail - so I would suggest that glueing a broad raised circle might be the safest way to go if you glue. FWIW what I did was to cut part of the part of the hull containing the raised knob from an old oasis hull and glue that to the inside of my hull - the profiles were pretty much the same, the surface area greater, and the glue has held so far with no indication of any sort of failure likely (not that there would be much warning!).
The what you do is cut your extension rod/tube to length so that it locates into/onto your fitting on the floor of the boat and into the bottom of the mastbase with the mastbase sitting snugly on the deck of the boat. Then you fit it all together, glueing where you want extra confidence, seal the deck-mastbase flange joint, and leave it to set according to the recommendations for the glue. I think I did not glue the extension rod over the raised knob in my boat, nor do I remember glueing my extension rod (aluminium towel rail) into the bottom of the mast base, but I definitely did glue the mast base into the deck of the boat.
When it is all set off you go. The person in the front cockpit is responsible for raising/lowering the mast on our boat - it is a long stretch over the mirage drive but doable - will be easier on an Odyssey; you could set the sail up on the shore using a furling kit to stow the sail but we prefer not to suffer from the additional windage and I think that any paddler would be the same. When not sailing our mast & sail is stowed rolled up on the gunwale using simple bungee loops. We use a single sheet and the sail is trimmed from the rear cockpit as this gives the best sheet lead for good sail shape. If you were to sail singlehanded from the rear cockpit you would probably need to use ballast in the front cockpit but be aware that, counter-intuitively, a sail at the bow has a tendency to hold the bow of a boat down, not lift it up, so don't think that the sail is going to make things worse; you will also need to be agile enough to skip between the cockpits to set your sail up if you don't have it already in place - this is certainly doable for a reasonably agile, not overweight person but it can be a bit "interesting" in a choppy sea.
I think that the Odyssey will almost certainly prove a better (downwind) sailer than the Oasis because the Odyssey hull doesn't have the additional drag of the Mirage drive holes and fins but I do think that a rudder with either one-handed (you need the other one for the sail sheet!) or foot steering is a requirement!! Oh, and of course you are gonna need to buy a sail - there may be better ones on the market but I just use the standard Hobie one. Depending on the wind conditions where you sail and the all up weight of skipper and crew, then a larger sail may suit you better, but we find that there are enough good wind conditions where we are in NZ for gentle to enjoyable to slightly exciting sailing on our Oasis. Personally I don't think outriggers are needed - with 2 medium sized posteriors in the seats of our Oasis there is easily enough ballast low-enough down to keep our boat stable and nicely trimmed in any conditions of wind & wave that we would want to be out in, and in any case, downwind sailing can be less tippy than upwind.
Hope you find this helpful!
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