OK so I get the idea, but really at a loss as to how to make it actually work!
Either no obvious options as to what to do, or way too many options as to what to do, and I'm kind of flummoxed but would like to give it a try.
A flow chart of options in each chapter would be great . . . unfortunately not in the book!
How about this for a general outline? Then you can explore areas in more depth as you get to them. If the sandbox nature of the thing is overwhelming, feel free to make it more linear. And feel free to cut out huge sections that don't add directly to what you're trying to do, or you don't understand, or that aren't obvious.
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Outline
Opening Quests
I. Intro/hooks
a. receive fake burgomaster letter, head to Barovia
II. Death House - right when they get into town, the party is drawn to the crying child
a. explore all the upstairs
b. rest, head downstairs, final battle, escape!
III. Barovia
a. find out about Mad Mary (optional)
b. go to Inn, meet Ismark: he talks about Ireena (sister) and Strahd (vampire) and sets up most of the plot and gives them all kinds of info about Barovia
i. Vistani approach and tell the characters to see Madame Eva (critical)
c. go to his house, meet Ireena
i. she asks them to help bury her father
d. go to church
i. find Doru
ii. kill Doru
iii. comfort priest
iv. agree to come back in the morning for burial
e. stop by shop on the way out of town (optional)
f. meet hag, do dream pastries encounter on the way out of town (optional)
IV. Tser Pool - make sure players know they should head there
a. at the crossroads turn RIGHT
b. get fortunes read
c. leave
V. Windmill (optional - also insanely dangerous so try not to let them get in a fight)
a. talk to the hags
b. negotiate for release of children (optional)
VI. Vallaki
a. find the church first (change or ignore the map); introduce quest to find bones
b. Inn; quest to find more wine from Winery
i. mention that people in Krezk will know more
c. Stockyard; discover tiger (optional)
d. coffin maker shop
i destroy vampires and get bones (insanely dangerous so reduce vampire spawn total or give them an "out" like burning it down) to complete church quest
ii. Ireena can now stay there safely (quest complete)
e. introduce burgomaster of this town
i. invited to festival coming up
ii. introduce his bodyguard and how he's a bad guy
f. NPCs mention Vistani on the edge of town
i. get quest to find girl at the lake
ii. finish that quest
g. NPCs mention haunted mansion west of town "Argynvostholt", probably treasures are hidden there
h. NPCs mention haunted, abandoned town south of town
VII. Stay in Vallaki
a. festival starts
i. guy is arrested for laughing, party decides to help or not
ii. if they help, the burgomaster gets mad and starts to have them arrested, but either way...
iii. tiger is loose! Must help the town get the tiger captured or kill it; Rictavio skips town
b. party is either already under arrest or implicated in the tiger fiasco; either way the burgomaster sends bad guy bodyguard after them
i. kill him or flee; either way, party isn't welcome in town and the townspeople fear them - but then they get an invitation to the Watcher House
c. Watcher House
i. creepy woman tries to get them to kill the burgomaster; either way she also hires Vistani to kill the party
ii. more fighting; the party discovers the double-cross and can try to confront the Watcher woman or not; either way they will have to fight someone
d. new boss, same as the old boss?
i. if the current burgomaster is killed, Watcher takes over and the town is worse off and she still tries to kill the PCs
ii. if Watcher is killed, the current burgomaster forgives the players and decides to reform (not in the book but easier)
iii. if both are killed, the innkeepers take over the town (not in the book but easier)
VIII. Find Wine
a. head to Krezk
i. frosty reception; these guys want wine, too! They tell the party where the Winery is
b. head to Winery
i. the current owners intercept the party and let them know the winery is under attack
ii. lots of encounters with druids! lots of fighting; PCs win; owners happy
c. new quests: find the missing gems (optional)
i. they think one was stolen by druids: here is where the druids live
ii. they think the other was stolen by an old witch: she lives in the haunted, abandoned town south of Vallaki
d. turns out there's enough wine for both Krezk and the Inn in Vallaki if they get both gems!
IX. Spooky Mansion - cut this place down a lot and reduce the encounters
a. find the wagon and run into Ezmerelda - major companion
i. she suggests finding Rictavio; there's a tower nearby - new quest (optional)
b. go in, meet ghosts, find out they need a skull from the castle to light a beacon and be happy again - new quest
X. Where the Druids Live
a. get close; fight some guys
b. druids start a ritual - must be stopped! (Strahd is supposed to show up - do not include this, as it is insanely dangerous that way)
i. stop the druids: defeat them, get the gem
ii. don't stop the druids: defeat the monster they create, then get the gem
XI. An Old Witch
a. check out abandoned town south of Vallaki
b. run into wereraven woman (Muriel) who can help them by telling them the witch has a secret which can be used to stop her (or find out from the windmill hags by bartering something?)
i. party can sneak around to find out she has to bathe in animal blood to survive; they can keep her from bathing by fighting her or kill / release all her animals to get her out of there
ii. find the gem while she's dead/gone
XII. old Tower (completely optional)
a. lots of traps; can find Rictavio and some treasure
XIII. Krezk (completely optional)
a. when they give them wine, they are allowed in
b. burgomaster is sad about dead son
c. lots of people talk about the Abbey
d. Abbey has crazy angel guy
i. PCs can decide to engage in conversation or explore or whatever but there's little reason for them to do anything here
ii. If they do converse, they can get the wedding dress quest, but that involves going into the burgomaster's house in Vallaki which may or may not be off limits; getting the dress allows the son to be raised (yay!) but he's insane (boo)
XIV. Just skip it
a. Werewolves - I can't think of a single reason that this ties into the story unless the Fortune of Ravenloft is there
b. Tsolenka Pass - same
c. Amber Temple - same
Wrap It Up
XV. Castle
a. hopefully they've found all the cool bits and bobs and leveled up so now the party receives a formal invitation to the castle
i. when they get to the crossroads near the castle the stagecoach shows up and takes them inside
b. explore the castle
i. find the dragon skull to finish that quest
ii. find Mad Mary's daughter
iii. find any other fortunes of Ravenloft
iv. try not to die
c. find Strahd in the final battle location foretold by the cards; kill him
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When you finally write it all down, it's kind of crazy how many areas are easy to skip and/or don't tie into the story unless you make them. The werewolves are something you could tie in at Krezk or something, but you kind of have to go out of your way. You could also tie it in from the guy in the castle, but by that point you're probably not wanting to traipse all over the countryside again just to complete some random side quest. Anyway, hope this helps!
Edit: Got it formatted, whee!
