Hi Joe, Welcome to this list. We are currently working and unable to get the Loop completed but live in the Great Lakes Region. We have been trailering our 30' Motorcat and find a month evaporates quickly but gives us a chance to have extended time on the boat AND allows for some weather windows. We have not yet trailered over 300 miles to any destination as Michigan is rich in boating opportunities. We contemplate a trip to the Bahamas next year with friends that have the same boat and a proven track record. We will likely haul to Stuart and if a crossing is not favorable cruise the coast and St Johns. Plans just seem much easier and we have more options on a trailer. Things I consider: Configuring canvas and boat takes about 2 hrs to ready for cruising or trailering. Parking for truck and trailer Permits (9' 5") Headwind on the road. Dodge diesel mileage goes down significantly... if I can delay I will but not make a fuss over it. The whole package (boat, trailer, fuel,H2O, stuff) is only around 10,000 lbs but tows like a stone with a strong headwind. We use our boat like a camper and have overnight options most everywhere. Comfort and space will be much different for you in a smaller boat! Maintaining a trailerable boat is much easier and affordable especially if you can do some things yourself. I actually enjoy time aboard, even on the hard, working on projects. The Loop is our goal and if time, money and my relationship with the admiral is amicable on the loop we will do the Down East Loop and then head out West to Lake Powell and the West Coast. Ambitious I know but that is our current plan. Although my comments are weighted to my budget and time I still drool over the larger catamarans and admittedly even monos each month when the new magazines arrive or I walk the docks! Tom R Cat's Away/Oscoda, MI http://oscodabeachbums.blogspot.com/ (09 1 month cruise)