Who has done a "Grand Tour" around Skyrim? I am talking about going around the world in one big circle. Any tips on it?

This actually sounds interesting..I'm doing this tomorrow...tips? I guess bring a follower, you don't wanna be lonely

Start at Riften, go trough Helgen to Falkreath. From Falkreath you can get to Markarth and then Solitude and Morthal. From Solitude you can go to Dawnstar and then to Winterhold. From Winterhold you can go to Wildhelm and then to Riften again.

(If you want to pass by Whiterun you can go there between Falkreath and Markarth or between Windhelm and Riften)

I can recommend the 'coastal road'. Starting at Windhelm, around the coastline, past the College of Winterhold then making your way along the coast through Dawnstar and onto Solitude. Around the peninsula and right the way around to Mor Khazgur - it's all very scenic, and lots of different encounters en route.

An area that I really like is the area between Riften's Plateau and Windhelm, the place has some Pine Tress, but isn't as dense as Falkreath and has a beautiful river.

I would say don't hesitate to suspend the tour to adventure into something interesting or to get rid of loot and restart your tour where you left off. Remember that when you enter a dungeon or other locations you lock in the level of the enemies. While ducking in and back out might sound like a good idea to make things easier later when you come back with your character leveled up, you will have locked the loot in those places at lower levels too.

Don't forget the pickaxe!

I did a perimeter tour, pushing the edges in a complete circuit (including into the sea up north), and it was just what I needed to stay fresh.

This is a fantastic idea! Road trip!!! Seriously, it would be fun to take all of the roads around Skyrim. Although most of the fun stuff is off of the beaten path, some of the most scenic views (as well as some choice random encounters) are found on the roads. I think either starting or ending in Solitude would be a good idea, since there's only one road leading to it, and it ends/begins there. I'm going to have to plot out a route and start hiking!

I walk (drag my follower(s)) between regions now. It is exciting to be attacked by Dragons, Wizard types or Bandits out of the blue.

Tis good for the legs.

I hate the Forts where the evil wizard types look for passing bodies to necromancer on. I usually go in blades and magic resistance blazing. I hate being attacked like that.

I plan to exclude the cities actually and to limit myself on what to carry and not having to go back to a shop in the city. Sleeping in bedrolls that I find a long the way and trade with only hunters, farmers and miners. I know some will buy what I hunt, pick and mine. It sure will be interesting.

Most important thing that came to my mind is to get a few Cure Disease potions and not to forget the dog. I hope it will survive .......