Looking for FL keys recommendations for early/mid November

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There is plenty of diving in Key Largo for you. No need to make the drive down to KW unless you really want to go. Largo has the Speigel, the Duane, the Bib, and the Eagle. Molasses deep and French deep are also good deep reef sites (70'-90', they are usually drift dives).

I've done ~50 dives with Rainbow Reef and have nothing but good things to say about them. They are professional, the guides are great, and they are reasonably priced. They have a lot of customers so if you're looking for the 6-pack experience then you'll have to look elsewhere. That being said, I've never felt like their boats were crowded and I never felt herded or rushed. The benefit with RR is that they run 8 boats, 6 of which are either 42' or 46' Newton Dive Specials so they are comfortable on crappy weather days and downright luxurious on nice days. They also provide a good variety of dive sites on any given day.

Islamorda Dive Center is another dive operation you might want to try. I don't have personal experience with them but I've heard good things.

Novemeber can be tricky weather-wise. As long as you're not expecting flat days on the water you should be ok though (again the bigger boats make for a much more comfortable ride).

I'm another vote for staying in Homestead or Florida City. I've stayed at both the Florida City Travel Lodge and the Quality Inn. I had a good experience at both. Average price per night is $65-$75 all-in. I know the Travel Lodge lets you cancel for free up to 24 hours before, which is a big perk if you're watching the weather.
 
If you want to maximize your dive time ... Friday - Monday I also agree to drive down to Key Largo on Thursday. From Miami its only 1 1/2 hr drive. I also recommend Rainbow Reef as you can buy a package and save $$. They may even have a night dive that day. As others have stated, weather's iffy around that time so you dont want to waste a good dive day driving to your next location.

Option #2 is just like above but after your Sunday morning dive and lunch drive about 2.5 hrs North to Jupiter so you can dive there on Monday. Still Florida but very different than Key Largo and great diving. And you'll be closer to Orlando for that fun drive after all that diving
Jupiter Dive Center, or Narcosis in West Palm beach are great ops
 
Rainbow Reef does have a good packaged hotel/dive deal.

I've done it a few times. Also threw in one day of diving with another dive shop (Conch) that was going to more interesting sites on a particular day
 
When will you be going? I'm diving Blue Heron Bridge on the evening of Nov 9, and then Key Largo with Rainbow Reef from Nov 10-14.
 
Novemeber can be tricky weather-wise. As long as you're not expecting flat days on the water you should be ok though (again the bigger boats make for a much more comfortable ride).

I’m honestly not sure what I’m expecting... what SHOULD I be expecting?

Option #2 is just like above but after your Sunday morning dive and lunch drive about 2.5 North to Jupiter so you can dive there on Monday. Still Florida but very different than Key Largo and great diving. And you'll be closer to Orlando for that fun drive after all that diving
Jupiter Dive Center, or Narcosis in West Palm beach are great ops

I was already considering something like that when somebody mentioned diving in Pompano Beach earlier in this thread. Splitting the drive to Orlando, especially after a morning of diving (most likely) is appealing.
 
When will you be going? I'm diving Blue Heron Bridge on the evening of Nov 9, and then Key Largo with Rainbow Reef from Nov 10-14.

Likely flying in on Nov 7, planning to be in Orlando the evening of the 12th.
 
I’m honestly not sure what I’m expecting... what SHOULD I be expecting?

You should expect good diving regardless of the weather conditions. Just don't expect every day to be perfect out on the water. November is sort of the beginning of the windy season for South FL. so you may get some days where it's blowing 20+ mph with 3-4 footers or you may get days when it's blowing <10 mph and waves are less than a foot. You just don't know. As long as you don't mind a bumpy boat ride and some surge near the surface you'll be fine regardless of the conditions. It's all the same at depth anyway!
 
Another thing to note, however, if NOAA issues a small craft advisory, most, if not all, of the dive dive operations will keep their boats at the dock that day.
 
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