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I did the Palau Aggressor at about 60-70 dives in. The reef hooks were interesting and there were some current swims but nothing super challenging. Otherwise best trip I’ve done!

If you feel good after Cayman go for it. If you can get to Little Cayman when out there I HIGHLY recommend it. Was there last month.
 
I did the Palau Aggressor at about 60-70 dives in. The reef hooks were interesting and there were some current swims but nothing super challenging. Otherwise best trip I’ve done!

To clarify - I was with a group that chartered out the whole boat. I was with the instructor who had done my OW and AOW. I was one of the least experienced people on the boat but the comfort factor made it feel doable.
 
Ok, so I'm finally starting to narrow down my search. I'd love to get some feedback on my plans so far:
  • As a few here have suggested, I am going to start with a quick "warm up" trip in the Caribbean on a LOB (probably limited to Cuba, bahamas or Roatan due to availability on short notice)
  • Then I will head to Cayman (likely a land based-only trip). This segment of my trip is 100% decided because I will have family there that I will also be visiting at the same time
  • During these two trips I will re-asses my comfort level see how quickly I am advancing. If I still have the stamina at that point and if I think my skills are honed enough, I might try for a third trip to a more remote location and something that's a bit more intermediate in terms of skill level (think maldives, coco, Philippines, polynesia, red sea etc)
It would be great to hear the board's thoughts on bullets # 1 & 3!

Well, I got tired (and poor!) just reading about it, but if you can manage it - then that's great!

Just a comment, if you are planning to hop between different Caribbean islands be aware that you cannot always fly directly to/from your desired destinations. Sometimes folks have to fly back to Miami or Puerto Rico (or someplace else that they don't want to visit) just to make the connections they need between 2 different Caribbean countries.

Since you are definitely going to Grand Cayman, take a look at the Cayman Airways schedule. They offer flights to Havana and Roatan but not every day; but if you can coordinate the dates for your LOB and land-based Caribbean trips then you might be able to transition smoothly between the islands. Maybe you could fly to Cuba or Roatan for the LOB and then fly over to GC for your family visit and then fly home from GCM.

Keep in mind that the "wait to fly rules" will apply to most flights between the islands. Most LOBs schedule the end-of-diving by late morning on the last diving day, because they know that many passengers will be flying home the next day.

https://www.caymanairways.com/SummerSchedule
 
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Well, I got tired (and poor!) just reading about it, but if you can manage it - then that's great!

Just a comment, if you are planning to hop between different Caribbean islands be aware that you cannot always fly directly to/from your desired destinations.

Yeah, admittedly this price tag is going to sting quite a bit. But as I mentioned earlier, this is a once in a lifetime opportunity for me to have this much time on my hands so that's how I feel like I can justify the expense.

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 :)
 
If you can get to Little Cayman when out there I HIGHLY recommend it. Was there last month.

Thanks for the rec, I'd really like to hit all three islands if i can! How much time do you think I would need to spend on each island respectively to make sure I have enough time to hit all of the good dive sites?
 
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Yeah, admittedly this price tag is going to sting quite a bit. But as I mentioned earlier, this is a once in a lifetime opportunity for me to have this much time on my hands so that's how I feel like I can justify the expense.

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 :)

Good for you! There are a lot of people on SB that are very familiar with Cayman diving and dive ops (including me!) What part of the island will you be staying on? How many days of diving will you be able to do? Do you want to do boat dives, shore dives, or both?
 
Thanks for the rec, I'd really like to hit all three islands if i can! How much time do you think I would need to spend on each island respectively to make sure I have enough time to hit all of the good dive sites?

How much time will you have in Cayman? Even though the flights between the 3 islands are short, that pesky "wait to fly" rule does apply - so you could be wasting your time hanging around airports and waiting for your next dive window.

If you only have a week I would suggest sticking with Grand Cayman, or maybe planning a day or two on Little Cayman and the Bloody Bay Wall.

There's very good diving off Cayman Brac but the most popular Brac site is the Russian Frigate wreck.
 
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What part of the island will you be staying on? How many days of diving will you be able to do?

I'd like to dive all three islands if possible. The family will be staying on 7 mile beach on Grand Cayman for 2 weeks, so I will probably want to spend at least 4 or 5 nights on GC to visit them. I am arriving a day earlier than the family though so my thought is to start out on either LC or CB first. I don't necessarily have a time limit on how long I can stay there as I can theoretically stay longer after the family is gone. That being said, the sooner I can wrap up the cayman trip, the more time I will have available for my "bucket list" LOB before I head back to work in September.

Do you want to do boat dives, shore dives, or both?

I'm open to suggestions! What do you think would be best?

How much time will you have in Cayman? Even though the flights between the 3 islands are short, that pesky "wait to fly" rule does apply - so you could be wasting your time hanging around airports and waiting for your next dive window.

I think i read somewhere that there are ferries between the islands that take anywhere from 30 minutes to an hour, but maybe i misread that. Wouldn't that be a better option if I'm trying to do all 3 back to back so I don't have to wait around for a day in between each?
 
There are no ferries. Little Cayman Beach Resort/Brac Reef Beach resort has a one-time 2 week package, I think it was in Sept, where they were going to transfer people between their resorts on the dive boat. But that is not a regular thing, though it would be nice if it were.

I wouldn't spend less than 5 nights on Little or Brac. If I were to pick one it would be Little, and you may not want to leave after 5. The overhead of moving around too much on a dive trip can result in seeing less, not more, and feeling like you need a vacation after your vacation. There's availability to consider too, the places on LC can book up (though Aug/Sept is sort of a slow season, being hurricane season.)
 
I'd like to dive all three islands if possible. The family will be staying on 7 mile beach on Grand Cayman for 2 weeks, so I will probably want to spend at least 4 or 5 nights on GC to visit them. I am arriving a day earlier than the family though so my thought is to start out on either LC or CB first. I don't necessarily have a time limit on how long I can stay there as I can theoretically stay longer after the family is gone. That being said, the sooner I can wrap up the cayman trip, the more time I will have available for my "bucket list" LOB before I head back to work in September.

I'm open to suggestions! What do you think would be best?

I think i read somewhere that there are ferries between the islands that take anywhere from 30 minutes to an hour, but maybe i misread that. Wouldn't that be a better option if I'm trying to do all 3 back to back so I don't have to wait around for a day in between each?

You have 2 weeks so it makes sense to visit and dive at least 2 of the Cayman islands. There are no ferries so you will have to fly back and forth between the islands.

There are lots of excellent dive ops available in the 7MB area of Grand Cayman, and there is some great diving on GC. 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. There are also several good shore dive sites available and renting tanks and weights is cheap, so perhaps you could work that into your family schedule; do you plan to rent a car? Keep in mind that you will need a buddy to shore dive.

If you stay in the 7MB area you can dive the Kittiwake, SRC, the West and South Sides and the popular North Wall - weather permitting. If you want to see sharks then your best option is to dive the East End, but it is not practical to try and do that from the 7MB/West Bay area. It's too far away and the traffic is bad. You would have to relocate to the East End and stay at a place like Compass Point to dive with Ocean Frontiers or another East End op. But you are sure to see lots of sharks in Cuba, so maybe that's not as important? We generally see some Reef Sharks and Nurse Sharks in Cayman but it is not as "sharky" as some other Caribbean destination. Lots of turtles though, and stingrays (and groupers around the Sister Islands.)

The 2 most popular diver-dedicated, all-inclusive resorts on the small, quiet Sister Islands are the Little Cayman Beach Resort and the Cayman Brac Beach Resort; we have stayed at both and like them a lot.

If you stay at LCBR they offer a half-day trip over to Brac for a couple of dives including the Tibbetts (Russian Frigate) Wreck, weather permitting. And if you stay at the CBBR they will do the same, offering a half-day trip to Little Cayman to dive Bloody Bay Wall, again weather permitting.

Of the two sister islands, the diving is best around Little Cayman (some of the best diving in the Caribbean IMO) as long the weather is good and they can get out to BBW. The weather is usually fine in August as long as there are no storms. It can get windy and rough anywhere in the Caribbean, including Cuba, when there are storms in the area.

I have a suggestion, the LCBR and the CBBR both use Reef Divers as their excellent dive op; and they have another location on Grand Cayman at Cobalt Coast Grand Cayman Resort, which also has onsite shore diving on the house reef. They are close to the North Wall and that is great diving. Cobalt Coast is a bit of a drive north of 7MB but there isn't much traffic in that direction.

Maybe you could contact the Clearly Cayman Resorts and arrange to do some dives at Cobalt Coast (shore dives, Kittiwake, Sting Ray City, etc.) while you are staying with family. And then book a stay at LCBR (if they have availability - it books up fast) or CBBR - and plan on taking the half-day trip over to the other island to dive.

They might offer you a good deal if you are interested in using all of their resorts - perhaps waive the single supplement or something like that? There are other resorts and dive ops on LC but they usually shut down in Aug/Sep for the slow season so LCBR is probably the only choice - and it's great.

But if that is not appealing, there are lots of excellent dive ops on GC that service the 7MB area, and then you can make separate arrangements for the Sister Islands. I am always trying to find the best pricing, and it might be convenient to have the Clearly Cayman Resort Booking agents (Reef Fantaseas) take care of all the arrangements and transfers.

Here is the link for the Clearly Cayman Resorts:

Clearly Cayman
 
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