Swashbuckling Options

[Afgncaap5]

tl;dr - What're your favorite ways to swashbuckle?

So, a friend of mine pulled out an Eberron adventure, Voyage of the Golden Dragon. I said "Great, when will you run it?" He said "But... you're the guy who runs Eberron games..." I said "Yeah, but I never get to PLAY them." Then he awkwardly agreed to run it. Yay!

So... now I'm paralyzed with several years' worth of story and character concepts. I want to play a gunslinger-style Cannith Wand Adept, a dinosaur riding private investigator, a runecarved Warforged, a dwarfish land owner, a power of purity gnome with elemental grafts, and a House Tharashk researcher who's haunted by the fellow half-orcs who were lost in the testing of the Earthquake Machine that was just meant to open fissures to find dragonmarks faster. Logically, none of these ideas are compatible. So I'm scaling it back: Eberron's about swashbuckling adventure, cinematic action, and high-stakes intrigue with a splash of dark fantasy, so I might as well focus on the most swashbuckle-y classes and character traits.

The Swashbuckler and Duelist are, naturally, conceptually in the right territory, though potentially not ideal. Fighter, Swordsage, and Rogue all have a lot of fun they can add. Even barbarian might fit for those times when I just want to bull-rush someone off of an airship instead of fighting directly. And, of course, there are skill tricks aplenty that can help to replicate the sorts of Errol Flynn-style shenanigans that I'm looking for. But I'm used to making sorcerer and wizards instead of melee fighters and skill monkeys, so I thought I should ask people if they have any good ideas for improving mobility, using environment to my advantage, fighting dirty, or other things that can help buckles to be swashed. Any ideas?

[sleepyphoenixx]

I'd definitely make it a martial adept because maneuvers rock. They help with the issues you're worried about (mobility, dirty tricks) and add some much needed variety to martials.
Whether you pick Warblade or Swordsage depends on if you want to be more of a fighter or more of a skillmonkey, and the PrCs you want to take.

For swashbuckling flavor you could look into Storm Sentry - pushing people off airships with their dragonmark powers is kind of what they do, among other things.
The PrC is also short enough not to impede your initiating too much and quite fun to play.
If your game goes to higher levels you could finish it off with Eternal Blade, since you're going to be a half-elf already anyway.

For a more skillmonkey-oriented character Windwright Captain is also a fun option. It's not exactly the strongest of classes but the flavor is great, you get enough skill points and your own airship that you can control at range.
The one really noteworthy feature the class has is that its ability to rebuke elementals is dependant on character level, not class level, so you can potentially gain 2 fun minions.

[Troacctid]

Swashbuckler is a giant trap, so we can take that one right off the table.

For me, the rogue-type classes are the big winners. Rogue is fine, but I am personally a bigger fan of psychic rogue! The addition of magic powers adds an extra layer to the class that makes it more dynamic and fun to play IMO. Scout, factotum, spellthief, bard, and swordsage are all fine choices as well, and while I'm not a huge fan of warblade as the base, since it's a bit lacking in panache, it's a fine multiclass.

[pi4t]

If Pathfinder content, and in particular Path of War Expanded (PoW is the Pathfinder equivalent of Tome of Battle), consider the Privateer. It's an initiating class (or more strictly a class template; a major alternate class feature which can be applied to multiple classes, if you will) which has abilities which fit the swashbuckler theme. You can find the playtest version here (https://docs.google.com/document/d/1hHsiSKoL2nR4oWgzPKQwXfqYENuNkDmBiX323SlTPfc/edit); the differences between that and the released version seem to be minimal. The two classes it can be applied to are here: warlord (http://www.d20pfsrd.com/path-of-war/classes/warlord), stalker (http://www.d20pfsrd.com/path-of-war/classes/stalker).

[mabriss lethe]

Swashbuckler is a giant trap, so we can take that one right off the table.

For me, the rogue-type classes are the big winners. Rogue is fine, but I am personally a bigger fan of psychic rogue! The addition of magic powers adds an extra layer to the class that makes it more dynamic and fun to play IMO. Scout, factotum, spellthief, bard, and swordsage are all fine choices as well, and while I'm not a huge fan of warblade as the base, since it's a bit lacking in panache, it's a fine multiclass.

While I agree for the most part, swashbuckler can be useful for dipping for rogue-ish builds.

[Troacctid]

While I agree for the most part, swashbuckler can be useful for dipping for rogue-ish builds.
Disagree—swashbuckler is a trap in rogue-ish builds as well.

[Afgncaap5]

Honestly, if I go Swashbuckler class... I don't think I will, but I'm not rulin' it out... it'll only be as a two-ish level dip, probably for Rogue synergies from Complete Scoundrel, along with the skill tricks.

[gorfnab]

Here are two Swashbuckler Handbooks that may help you out a little bit.
Class and Concept: The Swashbuckler (http://www.minmaxboards.com/index.php?PHPSESSID=r3s01gk3ie39hcdviajag7elb5&topic=10768)
Paradoxes of Fighting Defensively: A Swashbucklers' Handbook (http://www.giantitp.com/forums/showthread.php?399424-Paradoxes-of-Fighting-Defensively-A-Swashbucklers-Handbook)

Here is a Swashbuckler build that I made some time ago.

Human or Strongheart Halfling
1. Swashbuckler - Deadly Defense (CS), Combat Expertise, B: Weapon Finesse
2. Cobra Strike (UA) Decisive Strike (PHBII) Monk - B: Dodge
3. Cobra Strike (UA) Monk - Carmendine Monk (CoV), B: Mobility
4. Swashbuckler
5. Swashbuckler
6. Thief Acrobat - Combat Reflexes
7. Thief Acrobat
8. Thief Acrobat
9. Thief Acrobat - Einhander (PHBII)
10. Thief Acrobat or Warblade
11. Warblade or Duelist
12. Warblade or Duelist - Ironheart Aura (ToB)
13. Duelist
14. Duelist
15. Duelist - Robilar's Gambit (PHBII)
16. Duelist
17. Duelist
18. Duelist - Stormgaurd Warrior (ToB)
19. Duelist
20. Duelist

Levels 10 through 12 can be rearranged depending on your needs. The current setup gives you Improved Evasion and Uncanny Dodge at these levels. However if you don't need Improved Evasion take one less level of Thief Acrobat and move the first level of Warblade to level 10. If you don't need Uncanny Dodge don't take the 2nd level of Warblade and instead go into Duelist a level early. If you don't need either abilities take Warblade at level 10 and enter Duelist at level 11.

If flaws are available pick up EWP: Broadblade Shortsword (CAdv, pre-errata version if possible) or Versatile Unarmed Strike (PHBII) and Snap Kick (ToB) (may need to rearrange later feats). If traits are available pick up Cautious (UA).

Items:
Vest of Defense (MIC)
Bracers of Blocking (Dragon 322)
Broadblade Shortsword (CAdv) (pre-errata version if possible) or Rapier with the Defensive Surge (MIC) enhancement.

[AslanCross]

Seconding Path of War (Warlord) if it's available. If not, go for a Swordsage.

[Diovid]

You could always go with something like this:

Race: Desert Half-Orc
Build: Fighter 5 / Half-Orc Paragon 1 / Fighter +4 / Scarlet Corsair 10
Fighter variants (yes, all of them should be combinable): Dead levels, zhentarim substitution levels, sneak attack fighter, skilled city dweller and either thug or hit-and-run fighter (DotU).

Other beneficial things you might want to pick up for this build: the Never Outnumbered skill trick (Complete Scoundrel), the Craven feat (Champions of Ruin), the Dreaful Wrath feat* (Races of Destiny), the Imperious Command feat (DotU) and the Menacing Demeanor feat (Races of Destiny).

*Dreaful Wrath requires you to use the Half-Human Half-Orc variant (Races of Destiny p. 150) or to take the Human Heritage feat (Races of Destiny).

It has a focus on bluffing, feiting, intimidation and sneak attacks. What more could you want?