You've had a range of responses, but I would find it hard to respond myself not knowing what your paddling experience has been to date and how you were equipped.
What kind of boats are you planning to use? Rented rec boats and paddles? Touring kayaks that you are already familiar with? That will affect speed and safety a great deal. What kind of gear do you plan on taking as far as clothing and safety equipment? Your comment on "sleeping in shifts on the water" concerns me. Are you in tandems and hoping one person can sleep while the other paddles? Not realistic. Or were you planning to tow each other (even more unrealistic -- this is a difficult thing to do even in short term rescue situations.) Have you ever spent a continuous period of time even just sitting in a kayak? Do you have the flexibility and stamina for this? Just being "athletic" and competent in one or more other sports doesn't mean your could hold up to this one. I have often taken very fit athletes (fitter than myself, in fact) out on daytime kayaking tours in well outfitted boat and had them whining about back pain, sore hands and leg cramps within a few hours or less.
Last of all, why, as novices in the sport, would you be planning a very long and probably exhausting trip that even experienced paddlers might have second thoughts about when you have no idea how fast you can paddle and have never tried paddling in the dark or continuously anywhere? Planning time/distance challenges like this should only be done when you have a realistic concept of the effort involved and know already how you will hold up and what you need to bring.
Maybe you do have good answers to these questions. But I think they need to be laid out before anybody can comment realistically on this planned outing.
Perhaps we are being overly concerned about this expedition. My instinct is that all of you would bail before midnight Friday, haul out and hitchhike back to your cars at the put in.
The Kayak Wing
Gedi Convertible Helmet
URCHIN Portable Anchor
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