We are flying Seaborne from San Juan to Tortola later this month. They say they allow one carry on (22"x14x9) and one personal item (14"x14x9). Most 22" carry on bags are slightly larger. Even the 21" carry on bags are about 22.5"x14.5'x9". And, a lot of personal items meet the 37" overall requirement but not in the required dimensions. Can anyone advise on how tight they are with these restrictions? Is the carry on always loaded in the cargo bay so a little larger is not a big deal?
Thanks.

Yes, the larger carry-ons are always loaded in the cargo area. I carry a 21" bag that is probably over 22" and they've never given it a second glance.

The overhead bins on Seaborne aircraft are small and will only accommodate small duffle bags, totes, computer bags, small backpacks, etc. as your "personal item". You will have to gate check any standard Roll-aboard carry-ons be it 22" or smaller. If your carry-on bag is slightly larger (because of wheels or bulging side pockets) there's no need to worry since it will be going in the cargo hold, not inside the cabin.

But, just remember that anything of value should be in your backpack that you keep with you. Those luggage guys in SJU are notorious for separating people from their valuables..

With Seaborne you can carry your bag to the plane and they’ll put in the hold for you and give it back to you when you land.

Good deal. Good to know!

30 lb. weight limit for carry on. They will weigh them.

And your personal item must fit in the tiny over head or under your seat . I had my boat back pack from LLBean which is bulky and my purse and they made me put my purse inside the pack so strict on the one personal item only . We flew seaborn silver tho from SJU to STT which is smaller .

The 30 pound limit, is that for both pieces (the carry on and the personal item) or just the carry on?

Just the carry on

Whew! Just my Nikon and lenses are 10 lbs.
Thanks for the info.