Looking for late October quick trip

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I'd go with Grand Cayman. You can get there on American from Portland with one stop, flight there is a red eye, only $550. I would stay at Cobalt Coast/Reef Divers (AI available) or at Compass Point/Ocean Frontiers. CC is on the Northwest coast, CP is on the East end, very different places, both have fine websites for research. My favorite is the East end, but it's very isolated if you want to be near some non-diving action. As suggested, would get a car for Cobalt Coast, reservation at Compass Point comes with one and is absolutely needed. I've been to both twice, message me with any questions

Good diving, Craig (Portland 1980-8)
 
Costa Rica would be a nice try, in October rainy season is finishing so you could visit Bat Island, where you can see lots of Bull Sharks, also some local diving at Playas del Coco and Ocotal, they have 2 small wrecks at 60ft where you see white tip sharks and lots of rays. If you are lucky enough Catalina Island is the home of giant mantas but they usually start in November.
 
We are fans of the Cayman Islands, particularly Cayman Brac. We've had good luck three times in less than 2 years finding decent airfare from Phoenix. Seems like about 40 days out, the fares have dropped each time we've wanted to plan a trip.
Although many prefer the one dive resort on Brac, you might also consider the nearby condos (Brac Caribbean Beach and Carib Sands) which have a restaurant on the premises but allow cost-savings by having full kitchens, too. One of the 2 Brac dive ops picks up guests right off the dock in front. It worked for our family, in fact, we're heading back soon. Feel free to message me if you have questions.
 
https://www.shearwater.com/products/teric/

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