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Here is the link for the 2 island offer in late September that @Damselfish mentioned for LCBR and CBBR (with boat transfers between the 2 islands) but I don't think the dates would work for you. Maybe they could offer something similar in August for 8 or 10 days?

2 Islands. 14 Days. 42 Dives.
 
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@Dish is very familiar with Cayman and can provide some insight on how best to allocate your time. :)

Kind words, @outofofficebrb and thanks. @KathyV is always my recommended “go to” for Cayman questions and I can’t add anything to what she has already posted.
 
..The 2 most popular Cayman dives are Stingray City and the Kittiwake wreck and most dive ops will take you to those sites, but they go on different days and at different times so you would have to work that out with your schedule...

BTW, when I said that Stingray City and the Kittiwake are the most popular dives on Grand Cayman, I didn't mean to suggest that they are the BEST dives you can find on GC, just the most popular. However, they are good dive experiences and worth doing at least once.

But I advise against going to these popular tourist spots during the peak times when cruise ship passengers invade Grand Cayman. They are usually all over the place between 10 am to 3 pm; so try to go early (or late) or maybe on Sunday. Ask your dive op for advice, they will have the best information.

Also stay away from George Town while the cruise ships are in port, it can really be a zoo!
 
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...My Cuba leg is now on the books, staying on the Tortuga! And I found a cheap direct flights arriving from nyc and departing to Grand Cayman from Havana. The 7 hour bus ride to/from Havana will suck, but I think its worth it for the direct flights plus I get to spend a couple nights in Havana as a US citizen, which is a cool opportunity. Now, time to coordinate dives for the Cayman leg :)

@Scuba_Smitty Please remember to post trip reports after you return from all your dive travels this summer and fall! I am especially interested to hear about the Tortuga LOB because we don't get many trip reports about Cuba.
 
@Scuba_Smitty Please remember to post trip reports after you return from all your dive travels this summer and fall! I am especially interested to hear about the Tortuga LOB because we don't get many trip reports about Cuba.

Will do! Thanks again for the help!
 
@Scuba_Smitty Please remember to post trip reports after you return from all your dive travels this summer and fall! I am especially interested to hear about the Tortuga LOB because we don't get many trip reports about Cuba.

Will do! Thanks again for the help!

I have a question for you. Were you able to book single accommodations on Tortuga, or did you have to pay a surcharge for a single traveler? Just interested, thanks!
 

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