I will be doing a similar run soon. The flight itself and ferry ride isn't the biggest threat. Biggest problem is the night before. If the hotel has a freezer and you can use it that's a big help. AND -if you remember to remove your food from the hotel freezer and take it with you on the plane that's an even BIGGER help. Wrapping the packages tightly in 4 or more sheets of newspaper helps too.
Because my next flight is even earlier than the last and we are carrying more food because we are bare boating the plan is to purchase a few pounds of dry ice the day before we depart to super freeze our chow. That will insure it will stay frozen overnight. The next morning and before flight time I will discard any dry ice that hasn't evaporated because you can't fly with it.
Yes, we bring food every year in 40 qt rolling cooler and few years ago got stuck in Hurricane Irene and had to spend the night in Puerto Rico. My food was still frozen when we arrived on STJ.
Freeze everything and you will be fine.
Another idea - A week or so ahead of your trip make blocks of ice using plastic containers (like Ziplock/Glad storage containers). Make six or 8. Pack your cooler with your well frozen meats and add the ice blocks (even if it requires using two coolers) for your drive and overnight stay. The blocks will last much longer than cubes. Condense into one cooler in AM before your flight and throw out the ice. Have a great trip!
It should. We have done more than 36 hours door to dooron a polar bear. Make sure everything is frozen SOLID. Makensure the cooler is packed tight with no air pockets or dead space. I did a layer of cardboard on the bottom and the top with a layer of techiice, which was probably overkill. Everything was solid on arrival.
I have done it many times. I freeze the cooler with food in it for about week prior to our trip. Have always had frozen food when we arrive. The last trip we even brought butter!
You can't use dry ice. If you're checking the cooler, have extra duct tape inside or a bungee cord. TSA will check it to be sure you don't have dry ice, and you want it to be re-sealed after they do...
A couple of suggestions: NO DRY ICE. Fill the voids with packing peanuts or newspaper. Extra duct tape - to reseal if the airline asks to inspect. And don't use freezer packs or anything that can leak. Just freeze some of the items rock solid and they will keep any non-frozen items cool.
Check your airline regs for details. I travel JetBlue and I prep'd my box exactly as they required ...and had no issues. I wasn't traveling 36hrs ...but I'm sure I could have. I used a commercial seafood box ( waxed cardboard with a styro box insert). Packed it with 15lbs of frozen filet and shrimp along with 16lbs of cooked and de-shelled Maine lobster. Steaks were still frozen solid 24hrs later.
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