I just got back from a 13 day cruise from Ft Myers to the Keys and back to St. Petersburg. I cruised the Abacos 25 years ago on a chartered sailboat.
The high lights of my Keys cruise was the 10,000 island chain, Long point Key just north of Marathon and Key West. We had excellent weather as we usually do in May.*
Ft. Myers is a great layover and the folks at Legacy Harbor will treat you right. A 10 min walk will get you to the historic upscale downtown area and a 5 min cab ride to the Edison museum. Try Joe's Crap Shack at the marina for a great but expensive dinner.*
Cruise up the river a bit and just east of the Franklin locks check out Rialto Harbor, a marina B&B.*
Smokehouse Bay in Marco Island offers a great anchorage or tie up your choice, and a great on site restaurant.*
We stopped off at Indian Key in the 10,000 island chain. This breaks up the long cruise from Marco to Marathon. Indian Key has one of the few beaches in the area, but gets a bit skinny at high tide. Great place to walk the dog, but be careful of the currents.
We stayed 2 days in Boot Harbor near Marathon, but I will skip this next time. A great mooring area with good facilities but nothing much else to do. The moorings fill up in the winter but there were plenty when we were there.** The town is nothing to see though there is a museum depicting the building of the original railroad. I'll probably get some disagreement on this, but there are much better areas to spend time IMO. Long Pt key just north of Marathon is a good anchorage with clear water and mostly a sand bottom. Great place to see the sunset floating on your boat cushion behind the boat.
Marathon to Key West offers some great anchorages and I wish we had the time to visit some. Sombrero Key off Marathon has moorings for a great place to snorkel as well as Sand Key off Key West.*
Key West Bight is the place to stay in Key West as there are I believe 4 marinas offering slips. A 15 min walk will get you to most places in Key West, but bikes will expand your offerings. Plan on a least 3 days in Key West.
Its 90 miles from Key West to Marco so watch the weather. We refueled in Marco and continued to Pelican bay a total distance of 150 miles and 10 ½ hours. A long day with a thunderstorm meeting us on arrival at Pelican Bay.
Returning north, Pelican Bay off Cayo Costa just south of Boca Grand is one of my favorites. Just do the research on how to enter the large anchorage as you will run aground without it.
Moores anchorage on the north end of Longboat Key is also one of our favorites, but has lost some of its charm due to the recession. The many stores within walking distance have all closed, but the Mar Vista restaurant is still open and very popular with both the locals and cruising folks.
The Tampa bay area is next and Don Moon is probably better able to help you on this area.
Our next cruise will be the Abacos.
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