I made a big batch of shirts with the 100 Pound DXpedition designs this summer and they've stood up pretty well. The original Montserrat team members have already received one of these shirts. The two new fellows will get one, too, when this order ships.
Cafe Press offers two types of printing: direct printing and heat transfer. The first batch of shirts I bought used the direct printing method and the colors were a little faded. That said, they've been through the washer a number of times now and they still look pretty good.
Later in the summer I decided to order a shirt (and some other stuff) and I tried the heat transfer method. Those shirts had images with much better color saturation but I can see how they might not be as durable through many laundry cycles. If you decide to use these guys, I recommend ordering one shirt with each printing technology and assess for yourself which works best for your purposes.
Here's the shirt design (back):
The new Montserrat shirts look even more cool, sporting the Montserrat team logo and our new slogan: Not rare, but well done! As soon as those shirts arrive I'll repackage them and send them off to the team members. I can't wait to do our group picture on the island. That will look great on the QSL card!