I've been north on this route, and have been closely contemplating my future of bringing my Willard 36 from Ensenada (near San Diego) to our home in St Pete, so will be repeating the trip north in about 2-years and have been doing my research. As I write, I am on the beach in Akumal, 60-miles south of Isla Mujeres.
1. Heading south from Dry Tortugas is definitely doable, even though the Gulf Stream is opposite. Try FastSeas - awful for waves, but good for current projections. PredictWind requires an upgrade from $250/yr to $500/yr to get current predictions. Given this is the only stretch you really need it, not sure it's worth the extra money, at least for me. Note, there is no VHF or cellular comms at Dry Tortugas, so SSB or perhaps Satellite for weather.
2. Jimmy Cornell's World Cruising Routes is setup for sailors who need wind vs flat seas that powerboats prefer. It's a great source, but you have to consider that it's setup for sailors who may opt for Great Circle Routes to get decent wind.
3. Pilot Charts. Age-old approach - I forget exactly, but a few months ago, I was looking and there was a 6-week seasonal weather windo in the May timeframe to go from St Pete to Rio Dulce and back, but check as this is from memory. Heading south for the long haul is better than headed north even with the favorable northbound gulf stream - you can cross the stream at right-angles and hug the coast to knock-down much of the effect.
4. Rio Dulce. I've never been, but it seems like a great place to cruise a bit. It's about 800 nms from St Petersburg, probably 600 from Dry Tortugas. Might be a worthy stop. If you head south from here though, it does, however, put you close to some waters known for piracy (see below - I want to cruise this area, but will approach from Providenias - more below).
5. Cuba. Never been - watch Sailing Project Atticus YouTube channel for shoe-string cruising on south side of Cuba. Given your boat, doubt it's your style, but good info anyway. According to Atticus videos, many areas are not open to cruisers due to Cuban govt restrictions.
6. Diving and Fishing. Again, "Sailing Project Atticus." A young couple sailing on a shoestring. They have free-dived the reefs near Honduras. I have ear problems so it's not for me, but looks amazing if you're a diver and into remote anchorages. This couple are spear-fishermen. I'm an awful fisherman, so the last person to ask.
7. The person with the KK42 who responded right before me and has done this run would have very good information - PM him and get his best thinking.
8. Piracy - further south, off Nicaragua. When you look at the charts, it's tough to get far enough offshore to be safe. This was a heart-stopper for me, and changed my thinking - in 2004 when I delivered a N57 from Dana Pt to Ft Lauderdale, I was within 12-miles of Gracias de Dios (thank God), the norther point of Nicaragua that juts out before cutting in towards Honduras. Either I didn't know the piracy danger, or it didn't exist back then. But now, I't scares me due to piracy concerns. I will steer well clear of Nicaragua, perhaps most of Honduras too - a challenge if Rio Dulce is in the cruising plan. Providencia appears to be a decent target given it's location in the middle of the Caribbean. Again, Sailing Project Atticus recently stopped there so a decent discussion. Check out Noonsite.com. Don't mean to scare you off, but proper planning is better than surprises.
Website that updates piracy in the area:
https://safetyandsecuritynet.org/zo...interactive-infographic-risk-assessment-tool/
Overall, this is a really great trip, but it's beyond simple coastal cruising in safe waters. It is immensely do-ablel, but planning is preferred (at least for me). I don't know your Ocean 62, but my guess is that throtteled back, it has decent range, at least 1000 nms plus reserve. Less is still doable, but with more caution.
It's a good run, but takes some planning. Have a great time - I'm envious!
Peter
