I did the trip from pensacola to the exumas and had a blast. There was a good learning curve but not many problems if you read all you can,stay away from the marina folks whom never leave the docks. Prep your boat and watch weather. As you leave you WILL meet other cruisers and travel with help.But go at your own pace. A 35 can be large enough but remember don't take to much junk. As in over pack. But you can do it. We did it on a endeavour 37 with our dog Molly and just fine. Glad to answer or help in any way. Mark