Can I check a stroller

Slight edge to hard-sided luggage. Doesn't mean it couldn't crack, but it's theoretically more protected than soft-sided luggage.
To avoid cracks, always pack your hard-sided luggage so that it’s full & firm. You want to avoid having empty space inside if possible, because the sides aren’t designed be deflected inwards, so it increases the chance the hard shell could crack. Make sure you are using the size of suitcase that is appropriate for the amount of things you’re packing. I have had a few cracks because of using a larger size than needed so I had space for souvenirs.

For soft side luggage, I’ve heard both theories— bulging sides are more likely to get caught on sharp protrusions that could cause cuts or splits; and alternatively, luggage with sagging sides have no resistance to sharp protrusions that could cut through. I think appropriately packed luggage, that’s not under-, or over-stuffed is going to fare best. Luggage is designed to be filled to a particular fullness, and it stands to reason that the further you vary from that optimal fullness, the more risk of damage. I will say that luggage covers or sleeves or whatever they’re called now, do help protect your luggage from scuffs, and might also serve as a sacrificial layer that will bear the brunt of any snags or tears. If nothing else, they help you identify your bags faster in a sea of other same-colored, similar-shaped suitcases. And you’re more likely to notice if someone else is walking away with them.
 
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Can I check a stroller at the cruise terminal at the same time as our luggage to be brought to our room? I want to bring 2 strollers for lookout
If the two strollers don’t work out, lookout has wagons just off the ship and more when you exit the tram. If there aren’t any, just wait a few mins and you’ll see golf carts pulling dozens of wagons back to the starting point. We loaded up a wagon with our 4 year old, seven year old (when he was too tired), towels, and beach bag. We Used it until we got to the tram stop. Then picked up another wagon when we got off the tram and used it all day long. It worked out so well for us. I believe I also saw strollers near the wheelchairs, but I can’t remember where exactly I spotted them. Just some alternatives if your plans don’t work out just so.
 
If the two strollers don’t work out, lookout has wagons just off the ship and more when you exit the tram. If there aren’t any, just wait a few mins and you’ll see golf carts pulling dozens of wagons back to the starting point. We loaded up a wagon with our 4 year old, seven year old (when he was too tired), towels, and beach bag. We Used it until we got to the tram stop. Then picked up another wagon when we got off the tram and used it all day long. It worked out so well for us. I believe I also saw strollers near the wheelchairs, but I can’t remember where exactly I spotted them. Just some alternatives if your plans don’t work out just so.
My cruise was a couple weeks ago. I decided not to check any strollers and yes we used a wagon. There were plenty to use
 

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