See bottom for the TL;DR.
Awhile back we started our trip south from Stuart Florida planning to go to Marathon. We came down with 2 other sailboats mostly on the inside. The lead boat had made the trip several times so acted as the mother duck.
We stopped in Peck lake just a bit south to make sure everything was working as expected and to get the last few things we forgot.
We stopped in Lake Worth because everyone raved about peanut island. I wasn't amazingly impressed with it. But was worth saying I had been there. I ran aground as we left but that was my fault for listening to someone else.
We stopped in Lake Boca because the timing was good. I kind of liked Lake Boca Raton. There is not really a lot to do but the scenery is nicer than Lake worth. Getting access to the land is tricky but it is doable. Another boat there pulled up a transmission with their anchor chain and we helped them get it off. So there is some junk on the bottom.
Lake Sylvia in lauderdale was pretty nice if a bit tricky to get into. The Los Olas marina is nice and you can land your dinghy there for a reasonable price and get a shower do laundry and get on the bus. The bus system is a bit on the confusing side and not very well documented but some of the bus drivers are helpful. You can call the city bus people and they are very helpful with getting the right bus numbers.
Next stop was Miami and monument island. We went outside to avoid the bridges and sail some but we got tides slowing us in both inlets and the added distance along with the lack of wind kind of made the outside trip moot. We also had to backtrack a couple of miles coming into Miami. The number of powerboat wakes drove us out of the area pretty quick. Getting groceries/liquor and other supplies is quite easy though. Lincoln road in South beach is kind of neat but we were there in the morning and nothing opens until 10 or 11.
No name harbor is a quick trip to the south. This was the only place we could not get internet. it was a weekend so it was very crowded and we just about got swung into by a 68 foot powerboat and one of the boats with us got their anchor line snagged by someone pulling up their anchor. I was too worried about getting run into to leave the boat and see the lighthouse that is on the other side. There is a free pumpout at one end and a place to buy ice at the other end. If you are a rich guy with a big boat and lots of young girls it seems like the place to hang out on the weekends.
We left no name planning to stop at pumpkin key but we finally got our sails up and we made very good time so went on to key largo and anchored in Blackwater sound. There is not much here. Gilberts resort was recommended in our guide but that is pretty much all that is here. The locals seem to have a game where they send you off with bad directions. We wanted some beer and slim jims but ended leaving empty handed late in the morning.
Islamorada was our next stop. Easy access to just about everything in town and they have free showers as well as some interesting free/cheap things to do. I will say that a danforth does not hold well at all here. We drug our anchor 3 times and the other boat with us using a danforth drug twice. I should have used the Rocna knockoff I had but as they say experience is what you get right after you need it. Loraleis has good food and a really good happy hour. The inside route to Islamorada from Blackwater sound is very tricky with 5 feet of draft. The other boats with us were 4'8 and 4'2 and they no trouble. For us with 5 we had a white knuckle trip but we made it with the help of the tide. I doubt I will ever do it again but I can say I did it anyway.
The trip to Marathon on the inside was a very long one with the wind on our bow the whole way. We left at 8:30 and did not get to Marathon until a bit after 6 motoring the whole way. I gotta say Marathon is a pretty big disapointment. Getting to shore for anything is quite hard. Every store we talked to sends us the city marina for a cab. The city marina wants what I think is too much money to park a dinghy and then not be close to anything. The guides say west marine has dinghy access but I guess someone fell and sued the marina that let them and now they don't. Publix/WinDixie/Kmart used to have a bit of water access but its fenced off now and we had to crawl through some trees to get there. For all I heard about it being such a neat place its quite a let down. The city makes it very hard to get into town.
TL;DR Peck lake was fun, Lake worth was not fun, Lake Boca and lake Sylvia were fun. Miami was fun but had issues. No name harbor and Blackwater sound were not fun. Islamorada was fun but held bad. Marathon is the biggest letdown of the whole trip.