We have been running TI's since 2010, we do a lot of ocean sailing off Islands (mostly Key West). Our TI is now our only family boat, we got rid of our Searay 24ft, and all our other Hobie kayaks (yea we had bunches of em). We use our TI for anything and everything. You get a great bonus with these boats as a kayak (no sails and ama's). The darn thing is the best and fastest kayak we have ever owned, (lol Hobie doesn't even advertise that aspect). I'm familiar with your area and what is neccessary for Island sailing, which is way different from most of the people on the forum who mostly sail inland lakes and close coastal waters, (a different world). Island sailing is way more dangerous and with these boats I would call high risk, (the stock boat from the factory is not recommended for offshore sailing (CE class 'C'). The TI is a CE class 'D' craft, (mostly protected waters) as shipped from the factory. Of course these classifications are not mandatory in the us, but really are common sense and shouldn't be ignored, (sailing is bigger in europe than here). Yes the boat can be hardened and modified to be more sea worthy, (what we did with ours). It's pretty important to pay attention here. First off the TI is a great boat and the mirage pedal system makes it an incredible boat, however the sail is rather small and the boat doesn't point upwind very well (we are talking 45-50 degrees off the wind upwind). And typical sailing speed is around .6 windspeed. On lakes and close coastal waters this is not a problem. When sailing off remote islands this can be fatal, (before modifying our rig we got washed out to sea several times and couldn't get back to the island, ( in our case next stop Cuba). In other words if you plan on going off shore it's pretty important to have an outboard, even if you never use it, it's there for safety backup to get you home and back to the island. I'm not going to bore you with all my harrowing offshore experiences, but wind changes occur, winds die, and sudden unforcast storms come in almost daily in the summer in the keys, plus the currents are fierce in the keys, as I'm sure yours are. I actually have twin Honda 2.3 outboards on ours, mostly because we travel great distances, plus the likelyhood of both failing is very slim. We always carry a couple hundred mile fuel on board, (our daily range is 100 miles). When tilted up, the motor doesn't effect your sailing at all. In the grand scheme of things, that extra 27lbs (the Honda motor weight) means nothing, doesn't effect performance at all. Just for safety reasons I always carry an extra 2 gallons of fuel, I can't recall the last time I used them, (refill the fuel tanks while out on the water) most of our trips (typically under 25-30 miles) are well within the built in fuel tank range. But they are always on the ready if we get in trouble. I'm not knocking the battery/electrics (like the torqeedo 403), but my worst nightmare would be being caught in the gulfstream or really unfavorable winds 5 miles out with only enough juice to get me to 3 mile out. Just sayin, the ocean is unforgiving.
You get out into open ocean (more than 3miles out), it can get pretty rough out there, you need to harden your AMA's to keep them from folding in when waves hit, (plenty of posts about that on this forum).
Off key west there are lots of coral heads, you will be breaking your rudder pin (we have broke plenty, offshore even just waves hitting you wrong can break a rudder pin). You are not going to steer these boats with a paddle (just sayin), another reason for the outboard (needs to be able to steer, basically that's your backup steering, we have had to use ours (outboard for steering) plenty of times. Basically if your 5 miles offshore in open ocean in 15mph winds and 3ft chop, you are not going to be able to replace your rudder pin, (I've tried many times), very dangerous and scared the wits out of me. I'm not tryin to scare you or anything, or tryin to talk you out of a TI. My main point being know your boats real capabilities, not imagined. When modified and hardened these boats can be quite durable and handle most conditions within reason, however the boat sits very low in the water, your goin to get really wet. Since we scuba dive (your area is the meca), we have the tramps (re-enforced so they can handle our weight with tanks on), and we often have too many people on board ours (another reason for the tramps, we've been out plenty of times with 6 on board (adults and kids of course), and only on really safe water obviously). Actually we normally tow an inflatable dingy behind our boat for all the extra gear and sometimes people. I would definately get the tramps if it were me. For offshore I recommend the Hobie spinnaker, we have both spinnakers and jibs (all custom) on ours (up to 260 sq ft of sail area, but thats a different story). We have a guardian g4 (maybe g5 don't remember for sure) that works well on the sand bottoms in the keys, I also hear the cooper (mentioned above) is very good. Of course all the offshore safety stuff like FM radio, eprb, or spot, flares, compass and paper charts, (gps's can fail), etc. We have been caught out way after dark many times (usually from changing conditions, never on purpose), I have two complete sets of Atwood full nav lights (red/green, white), and always at least two waterproof led flashlights, (you literally can't see anything on a moonless night). Keep it all in a dry box in the bow, along with tools, flare pistol, first aid kit, etc. Some will tell you you only need just a white lite, our TI under power is about the same speed as a pontoon boat when we really need it, so to avoid confusion we have full lights, good bad or indifferent, that's what we got, works for us, we have an absolute blast with ours, I'm sure you will too. One nice thing about these boats is they are easily modified to do anything you can imagine, some of the offshore game fishing guys rigs are a sight to behold with sonar and everything, ( the ultimate fish slayer). Hope this helps FE
Edit: If your planning an aluminum trailer, I would just use that as a launch cart ( that's what we do). If you slide the boat back a bit on the trailer so it's balanced on the axle, the put just one strap on to hold it, the trailer with boat walks very easily in the bearing axles and the road tires. I added a cheap harbor freight winch that I operate with a cordless drill. I don't remember the last time we used our scupper cart, (it's been years).
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