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I knew that I had to make something for the anniversary, so I worked on this all night.  
Yes, there are imperfections. This is the first image I’ve completed with Photoshop CC. At first, I intended to draw the mane six on the boat, but after coloring in Fluttershy, I decided that just one pony felt more meaningful. Maybe everypony else is below deck, or maybe she’s sailing out there all alone. Regardless, Fluttershy is looking towards Canterlot, thinking about something.
This image took 6+ hours to make. Yeah, I suck. Canterlot and the surrounding mountains were roughly traced, but only because I wanted it to be show-accurate. I also used an image of a sailboat for referencing the hull shape, railings, and furled jib sail.


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Good job on this, it makes me feel, which makes a drawing, any work, the best. I feel kind of lonely and distant with this picture; it makes me imagine a world where Fluttershy find herself leaving Ponyville long before the story, and starting out on another adventure. This makes me feel a twinge of reminiscence, thinking of how short our time with a lot of our friends are. I like this one, reminds me of early Friendship is Magic.