Leave Cold Sands Hold and enter the first outland. You will enter into a valley. In front of you, at the other end of the valley, is Sunclaw's Lair for reference. Turn to your right and travel straight until you reach the beach. Fight smugglers until you reach Smuggler's Cove. As you stand in front of the Cove, look to the left and the hill next to the Cove. Between the rocks is a small opening leading to a small area with four smugglers and a chest. Once you have defeated the Smugglers return to the Cove and kill Vanael the Slicer. There are two chests in the Cove not including the loot from Vanael and the other smugglers.
Getting Into/Out of the Boat - it is somewhat difficult to get into and out of the boat leading to the island where Vanael stands. The best way to deal with this is to wear Helga's ring or use Greenfin Stew.
Leave the Cove and move north up the beach. When you encounter the drake carcass, take the broken tooth. Once you are near Karn, pull some Yuma seeds (for plant locations see crafting section above). Visit Katami and she will tell you about the drake carcass. Visit Vierne and she will tell you to seek out Sunclaw. Sell any goods you want at Hawth's Wares and travel back to Sunclaw's Lair. During this trip, pick yuma seeds.
Getting to Drake Island - you do not have to take the quest from Sunclaw to get to Drake Island. Once you reach Karn, simply swim out from the beach and you will find the island after swimming for a fairly lengthy time. I choose to take the quest because I get to learn the balm recipe and earn more points toward leveling up.
When you speak with Sunclaw, you will discuss her broken tooth. As a result, she will give you the quest I Will Bring You the Balm (1000 exp.) quest. Leave her Lair and return to Karn. During this trip, pick as many yuma seeds as you can.
See Vierne in Karn and she will give you the soothing balm recipe. Make the balm and any potions you might want. If you need more yuma seeds, go back into the desert to pick them. Once you have finished crafting your potions and balm, return to Sunclaw's lair. I usually ride a mount to make the trip quicker.
Complete the I Will Bring You the Balm quest and ask Sunclaw to take you to Drake Island. Once on the island, take a drake egg from the nest and take the emerald in the chest. The emerald is the key to the Temple of Azra (going through the Temple is part of the main quest so you must retrieve the emerald) and the egg gives you a drake mount, which is a great ride. Once you have retrieved the mount and emerald key, return to the spot where Sunclaw dropped you off and ride her back to the entrance to the Temple of Azra.
Enter the Temple of Azra and work your way through it, ending by killing the Ancient Lich and taking the Scepter of Hammara. Return to Callaheim by using the safety ring. Go to the merchants and exchange your loot for things you want. Go to Darius' West Callaheim home and complete the Temple of Azra quest. He will tell you to use the Scepter on Merificus (this is part of the main quest - you must complete it to finish the game; 10,000 exp.). Once you use the Scepter on Merificus, go to the Knights of Aralon and complete the Kill Vanael the Slicer quest.
After Returning to Outland Second Time
Leave Callaheim and go to Cold Sands Hold. Enter the First Outland and go to the Orc cave and Uthu's Fortress. Kill as many orcs as possible, including Uthu. Note - you will not have the Uthu's Fortress quest yet, but you can still complete the tasks from the quest so you only have to make one trip into the desert. Return to Cold Sands Hold and complete The Orc War and Uhu's Fortress (3000 gold, 25,000 exp.) by talking with Captain Fargus. Prepare yourself to enter the Second Outland by stockpiling arrows, poisons/toxins, helpful potions, armor and weapons.
Ride a mount through the first outland (I ride either the drake or wolf) to the mountain pass. Exit the pass into the second outland.