I had this problem too. It's another stupid glitch. This worked for me:
Go outside the Fletcher shop, from the door looking out southwest jump over the small wall, landing on the Angeline's Aromatics. Then you have to jumpclimb to the small little ledge on the south side of the roof, and face south. Use Whirlwind Sprint to zip across the street to the roof of Bits and Pieces. Go a little west to the edge of the roof, and look south to the roof of Radiant Raiment. If you look at the roofs of Bits and Pieces and Radiant Raiment, you'll notice the two roofs kinda mash into each other. Walk onto that mashed roof section, which is to the south, and you should HOPEFULLY just drop straight down beneath the town, onto the rocky/mountain/hill terrain that the city is on. Go down the hill slowly (don't fall). For me he was near the shore.
Taken from: http://www.gamefaqs.com/boards/615803-the-elder-scrolls-v-skyrim/61006342?page=1