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Which settlement do you spend the most time in? This includes cities, towns, and mines.
Personally, my Dunmer considers Riften home since the Thieves Guild is there and her husband is at Honeyside. Most of her belongings that matter are squirreled away too, such as an alchemy chest. I think that's the only city I've fully discovered too, tbh. She also spends a lot of time in Whiterun when it's time for a vacation from adventuring to get a week of crafting done. She does a lot of traveling between Whiterun and Riften with a stop for the night at Windhelm as well, so those three holds is where she usually is.

Depends on the character.
However, I can say that my main characters spend most of their time wandering the wilderness. They only go into the cities for quests and bartering. As such, they don't spend more time in one city over another. They go in, and they leave as soon as possible. All of them live outside of cities as well (in Rayek's End, the Hearthfire homes, or Kagrenac's Instant Fortress). The only exception is made for Severin Manor in Raven Rock. They will stay there when on Solstheim, if the house is available.

Dead is Dead characters and my PS3 characters tend to stay in Whiterun for easy access to the crafting supplies. They don't move much, either. Until the higher levels, anyway. Although even then they tend to stay in Whiterun because I'm too lazy to move thousands of items between homes.

^Same here, more or less. All my characters are rovers and vagabonds; my Argonian once stayed away from home so long that Shahvee was peeved and refused to share his bed on his return:lol:, and my Bosmer's neglect of her adopted daughters is bordering on criminal. If there's a city or town I visit more often than the others, it's Whiterun and Riverwood because they're so conveniently placed in the middle of the map, on the way from everywhere to everywhere else, but I rarely stay there for more than a day or two at most.

Whiterun, for logistics and storyline reason, seems to be a place I go to very often. But also Solitude. Even though it's wedged into a rocky corner of the map, it's very big and inviting and has a lot of fun characters and quests. Simple.

That would be Riften for me.
Between quests, I often return to Riften for a little R&R. Gazing over the lake from the Honeyside Porch, hang out at the marketplace, stroll through the woods around town.

Definitely Whiterun, for many reasons. First, I like the place the most, since it seems to have the friendliest NPCs (I like even Heimskr) and is actually quite beautiful (especially after restoring/replacing Gildergreen). Also, most of my characters are warrior types and join the Companions, so I tend to visit Jorrvaskr often. Then, I also often hunt mammoths in the Whiterun tundra to get grand souls, and after that it's only sensible to visit the nearest enchanting table in the Dragonsreach. And speaking of Dragonsreach, Balgruuf is my favourite Jarl so my characters tend to sometimes stop by to say hello. Lastly, it's the most central city in Skyrim, so when travelling on foot from e.g. Dawnstar to Riften it's a convenient halfway stop to sell loot. All in all, it feels so homely and nice I like to visit the place.

The place where I spend second most time is Markarth. I have a love-hate relationship with the city, really. On the other hand there's the dark undercurrent to the city's life, what with all the Silver-Blood corruption and whatnot, which makes the place feel rather gloomy and ominous. And don't even get me started about the cannibals and the haunted house. Basically, only Morthal can compete in creepiness with Markarth.

But then again, the city is very impressive to look at, and there are some interesting quests and NPCs. Speaking of which, I don't know if I should say this, but after Arianne Avenicci I find Ghorza gra-Bagol the most attractive blacksmith in the game. It's not her looks, but there's something in the throaty Orc female voice that I really like. Ahem. Back to the track. Lastly, the Reach is my second favourite hold to explore, and consequently Markarth gets much of my loot business. I wonder that the prices of Forsworn gear haven't dropped dramatically after the heaps of them I've sold.

I mentioned these two, because they are almost only settlements I spend any great lengths of time in. In every other city/village I tend to just sell my stuff, maybe spend a night in the inn and be on my merry way.

I would assume Whiterun is the popular choice for all players.

Riften, simply because after the Reputation Quests it's by far the easiest place to sell stuff.

Riften. There's just something about Riften.

Both of my current characters make their main home in Riften. Character #1 is Thieves Guild Master, but Riften was home long before joining the TG. Character #2 is anti-Thieves Guild, but still thinks Riften is the place to be. Both own vacation homes in Solitude, and neither will acquire any more property.

The only other settlement they spend significant time in is Winterhold. Both are technically members of the CoW but dropped out after a couple of quests. Character #1 still likes to fetch books for the library, and #2's main non-housecarl follower lives at Azura's Shrine. But they stay at the inn instead of using their room at the CoW. Character #1 is Thane and I expect #2 to become Thane, eventually (#1's Thane-ness put her in a bind once, and she had to choose between her Imperial leanings and her duty as Thane - she did her duty as Thane).

They don't really hang out much in the other settlements beyond questing, business, or passing through. They will occasionally go out of their way to drop by Ivarstead, Darkwater Crossing, and Kynesgrove, though.

For my future characters, I intend to change it up so that they favor other locations.

Whiterun for three of my characters. All of my characters own all of the houses except for Windhelm (haven't done the Stormcloak questline yet), but these ones "live" at Heljarchen Hall. It's an easy run from there to Whiterun, Riverwood, and Falkreath in one direction, and to Windhelm or Dawnstar in other directions. Whiterun has many merchants (eight, unless I've miscounted) and the hold is pretty and relatively safe, apart from giants. So it's a nice place to call home.

My Argonian "lives" at Riften. She's in the Thieves Guild, so it's most convenient for her. She travels wherever she's needed on Thieves Guild business, but her home is in Riften and she spends most time there.

It would be interesting if there was some way of measuring in which holds/settlements I spend the most time.

I tend to try and avoid cities unless I'm doing quests, selling stuff, or going to a house.

And since HF, I don't often pick a city house.

Buuut for the topic, I would have to say Whiterun on most characters because of the small merchants area, with 5 merchants being so close together.

However, any Thieves Guild characters spend more time in Riften, or at least they do once it's upgraded.

My current guy (Nord Dwemer Archaeologist) lives in Riverside near Falkreath, its a pleasant manor situated in an area which is regularly visited by dragons, vampires, giants and bandits who come to enjoy the view. I am considering buying a place in Markarth due to his interests but I'm not sure, I dont really like that place much

my thief lives in Riften cos he's an imperial lackey and they have great connections with that town,

and my Dunmer has homes in Whiterun, Solitude and Solstheim> WHiterun was amazingly useful as it is cheap and next door to a blacksmith (and the merchants up the road) and also home to my favourite Jarl in the game , Proudspire manor was his "rich man's" house but now he seems to enjoy the visits to his Morrowind home

I think the convenience and fact you discover it very early makes Whiterun an obvious choice, and i like the fire pit and alchemy lab all being downstairs.. in many ways a smaller home suits my style of playing

Whiterun is my main base, but isn't my first choice. But it does have several things going for it. Its centrally located, all the important merchants are all on the main street, and Skyforge and Jorrvaskr. As Mattbott said, convenience. Then add in Breezehome, its my favorite vanilla home as is. But, I always use a mod called Breezehome Fully Upgradable. This mod adds in lots of storage, all the crafting stations that are linked to storage chests, and a lot of other things.

If I could move my modded Breezehome to any town in Skyrim I would definitely end up in Riverwood. I like the small town atmosphere you find there. Too bad they did not have a purchasable home there in the vanilla game. The fact that its not in its own cell, that you have to load as you go in the gates, but part of the open world. I know Open cities would do this for all the other towns but it conflicts with so many other mods, I have given up on using it.

(I'm sorry for injecting mods into the discussion but the house mod I mentioned is the key reason I use Whiterun as my main base.)

Whiterun is the central hub, so I always go there the most. Usually though, I stick to the road. Can't be tied to down to one place in anyway.

Felina and Onmund split their year between Windhelm and their marsh homestead. Felina loves the marsh. She likes to explore it while gathering ingredients for her poisons. She's quite the loner, preferring her solitude in the marshes over cities.

Lieth and Vilkas spend most of the year in the Rift because its her favorite area to hunt. She finds the trees in the Rift to be the most beautiful. She enjoys living in Riften, and being gossiped about by the jealous hags of the town. The summers they live in Falkreath.

My main character only has one house, in Whiterun, but has just purchased the deed for one of the Hearthfire homes so he'll probably move into that once it's built.

My 'bad guy' doesn't have a dedicated home yet. She spends her time mostly between the thieves' guild and the dark brotherhood, but she really hasn't found 'her place' yet so she sells off whatever she can't carry.

I spend a lot of time in Whiterun at the start of the game, mostly to get a house to store all the loot I have.

I usually spend most of my time in Whiterun, but a bit later in the game I go to Markarth.

Main Nord: Markath, Whiterun, and Windhelm.
Orc: Riften
Nord Spellsword: lolsettlements. She isn't much of a settlement person.
Dunmer: Winterhold, Solitude, and Whiterun.
Bosmer: Riften, Markath, Solitude, and Whiterun.

There is a motif.

DikaSmausha wrote:I spend a lot of time in Whiterun at the start of the game, mostly to get a house to store all the loot I have.

Breezehome is way too small. Its like having the Dovahkiin's family living in a closet.

You couldn't do anything in that house without everyone hearing you.

It depends on the character but I spend a lot of time inside Whiterun.

I've spend most time in Riften for Quests, but mainly Whiterun feels like my home base mainly because smithing is trained easily here.
I also spend a lot of time roaming skyrims wild lands.

I really like Falkreaths location, even if the town is sorta "bad" and the count is a stuck up wimp.

edit. Also Dawnstar. Dawnstar really owns too but it's a shame that it is such a small town. I miss big towns like in Oblivion.

You spend time in the small towns. I like doing that, but get bored.