I recently read an article on Reddit.com in which a passenger had their baby stroller gate checked when they boarded a flight. It ended up damaged with a broken handle. It turned out that it was basically useless.
Uppababy makes a really good stroller that costs a small fortune. They stand by their products with their warranty against manufacturing defects but they specifically exclude damage caused by air travel. I understand the desire to have a really nice stroller for your child but airlines are not known for their Tender Loving Care when dealing with luggage.
What can you do if you are travelling with an infant? As I see it there are a few possibilities. First, you can rent a stroller at your destination. This works well at tourist spot like Disney World. You are able to rent a stroller from Disney World for $15 a day there (of course you will have to add insurance on top of it in case it is stolen or it breaks). This way, you do not have to worry about packing and transporting the stroller. But there are downsides in that you do not have a stroller in the airport or outside of the park.
The second possibility if you have an Uppababy stroller is to buy an Uppababy Travel Bag for $249 (under their TravelSafe Program). This padded travel bag guarantees against any air travel damage for 4 years. It is basically a padded insurance policy for your stroller. If the stroller is damaged then all you have to do is contact Uppababy and they will fix or replace your stroller. The downside is the cost and it only applies to the Vista stroller.
The third option is to buy a travel stroller. In other words, you can purchase a less expensive stroller and not be too concerned if it is stolen or damaged. You can choose between a ZoeBaby stroller for $250, a stroller on Amazon (which can range in price from $170 to $250) or a stroller on Ali Express between $150 and $200. The downside is that you are purchasing a stroller that will be inferior to your daily stroller just for the time you travel.
If traveling with a baby, there are a whole lot of things that you need to take with you especially if you are going to remote destination. These travels can be extremely stressful. The goal in any planning is to reduce your stress level so you can have the best trip possible. In my mind, worrying about an airline breaking a stroller or someone deciding that they like your stroller more than theirs (and taking it) can ruin a vacation. So even with the Uppababy TravelSafe Program, I would not feel comfortable with taking a high-end stroller on vacation for fear of damage or loss. I would much prefer an inexpensive travel stroller that can be easily replaced without too much expense.