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I think you will have an awesome time...and I say go for it! My wife am I did that trip in our boat about 2 years ago. We dropped in at Ft Lauderdale and took the intercoastal down to Cudjoe key about 21 miles shy of key west. One big problem is parking your truck and trailer, in Miami its about 12 bucks a day and not very secure. The marina we dropped at was Habour town in ft Laud. they have security and are reasonable. The is a hotel in key largo you will pass it on the intercostal, but you can slip your boat right outside the room and they have decent rates. Glad to hear you have thegarmin, it really was a life saver for us.Thanks for the replies. All very useful information from my standpoint. We are very excited about the option of having our own boat down in the keys. Although I am an experienced boater on our local lakes and rivers and even in our intercoastal waterways here I know that boating in the Keys is totally different. That being the main reason for my concern. Although, I figure if I do some research and learn the do and don'ts/rules and regs of boating in the Keys as moneysaver mentioned and take my time and be careful when I do get there I feel like I will be okay. I have a Garmin chartplotter with the most up to date Bluechart G2 Vision card for the area so that will be an invaluable tool I am sure. I think we're definitely gonna try it and see what happens. We have decided however that we are only going to attempt to dive from our own boat if the weather cooperates and is really nice. Otherwise, we will probably dive with Horizon and save the boat for simply cruising around and enjoying being on the water in the keys. How awesome is that? We can't wait. Thanks again for the replies and feel free to offer up any other tips you may have.
And when you near the tail end of the pike, aka Dade County, clinch your cheeks, cross your fingers, say a couple of hail marys, click your heels, and pray for Florida City to come quick. Then roll your windows down, pop in your favorite CD, inhale the intoxicating aroma of the mangroves along US1, and begin to feel life's stresses fade away.
Have Fun! There's nothing like having the freedom to explore in your own boat. Use your common sense and you'll be just fine.