This piece is absolutely adorable. I really like the drawing programme you used, and I loved the drawing technique. The humour put into it is also great.
The only thing I would advise is that maybe it could be made just a little bit clearer, like you could have had RD and Scooty hiding somewhere else where you could see their facial expressions.
I think this is a really well thought out piece and very clever. I like how it very clearly reflects the ponies' personalities and traits. It's a really great use of colour and technique. 19 out of 20!
This is possibly the cutest thing ever! I always imagined what they would act like together, and you described that perfectly in this picture. And you also described their personalities awesomely. It seems like exactly what they would if they were kids/pirates.
Also you're detailing is incredible! Everything from the shading to the setting is perfect! But what is truly is amazing, is the expressions. It seems like you got it straight on. You also did the water really well. Specking of water, the texture is awesome. The hair, the flags, and the wood on the boat is all incredible! That's my critique, and I hope you think it's fair, so peace!