As far as I know, each "romance" can be done in any order. Certain parts of each mission can be interspersed within others, but for ease of following this guide (as opposed to speed), I will focus entirely on one at a time.

TIP: Many point-and-click games include this feature but in case you did not know, double-click when your pointer is a hand (indicating to leave for another scene) so you do not have to wait for Duke's slow walk to reach the appropriate point.

Watch the credits in the beginning to get some backstory (which will be revealed throughout the game anyway, but it is still a nice touch).

You will miss out on a lot of the fun by simply following this guide, so I would recommend only reviewing in the unlikely event you are stuck. In the end, to each their own! I hope this is useful to at least someone out there!

Talk to Slewface

To Plunder Cove (top center)

To Jail Plaza (center)

To Dockside Jail (center left)

Talk to Lady Aziza, accept the mission

On a Boat!
Not a big deal for pirates, actually.


Push Ogu Raider Galleon

Examine Cargo Crane

Talk to Lady Aziza > I want to know about 'ye > how'd you get us here so fast > you know machines...

Asked for help!
Not that painful!


End conversation and use Lady Aziza's skill with the cargo crane

Throw them zombies

To Crater Fort (right)

Take a tree > take a fallen tree

Use tree trunk on cannon tower

Grand Slam
Just doin' my job.


Take cannon ball with chain (left) | take cannon (center right)

Open portcullis > use Lady Aziza's skill with portcullis

To the Temple

Use cannon ball with chain on cannon | take zipline (top left) > use zipline with cannon-more-or-less loaded

Use Lady Aziza's skill with Ogu Raider's Temple > use zipline-ready-to-go on Ogu Raider's Temple

Incoming!
We be swashbuckling now!


Me First Romance!
Kinda fun, who knew?

Punch Guard Monkeys

Monkeys!
Ooh, I hates 'em.


To Firehouse (center left)

Examine paw prints (center left)

To Plunder Cove

To the Inn (top center)

Talk to the Mysterious Lady (bottom right if you really had a hard time finding her) > accept mission

To the Fruit Stand (right) > To the Old Stone Pier (right)

Utilize Captain Starling's skills on Murial, the Gov's fiancée (front row red-head)

Use Captain Starling's tiara on administrator (lady sitting at desk)

Take fight card from desk

Talk to assistant (just left of Queenie the gorilla) > what's her secret > ask about fruit (he will notice the fruit is gone and go for a refill)

Use Fight Card on Barker

Sobering Loss
Ow.


Use Ferocious Jaguar on Guard Monkeys > Take undefended garbage

Use fizzy fruit on Queenie's food crate

To the Old Stone Pier

Jump into ring

Two Romances!
And much merriment!

To Jail Plaza

Push Aft Supports (bottom left of boat)

Push Wooden Supports (right/front of boat)

Done time!
I got me a dangerous past.


Talk to Bob the Bouncer (center of the stone bridge, exhaust dialog)

To Firehouse (right)

Talk to Fire Chief (right of "pig") > "How do I get into that ship..." > "That tavern sounds dangerous..."

To Jail Plaza > Examine Saltwater Reeds (right side of bridge near the water)

Push Load-Bearing Supports (under bridge, if you did not trigger the correct dialog this will still say "beams")

Arrrrsonist
Where there's smoke, there's...


To Firehouse

Talk to Coconut Tree Lady (center near tree)

A Manly Fight
Socially acceptable male contact.


"No Comment, Sheriff"

To Jail Plaza > To Dockside Jail > Talk to Elegant Prisoner (completely)

To Jail Plaza > To Plunder Cove > To the Inn > Talk to Quarrelin' Larry / Disputatious Dave (x5)

To the Fruit Stand > To Jail Plaza > To Dockside Jail > Take Evidence Folder (right folder)

To Jail Plaza > To Plunder Cove > To the Old Stone Pier > Use Naughty Governor Letter on Governor Derrick (front row)

Diplomacy!
Is different than killing everyone!


Talk to LL Sweet T > "Give me magic words..." > "Help me..."

To the Fruit Stand > Examine Driftwood Flowers (center in front of small sail boat)

To Firehouse > Talk to Coconut Tree Lady (completely)

Ice Be Broken!
SUCH ELEGANCE!


Talk to Coconut Tree Lady/Maeva (completely)

Last Romance!
Time to go.


The End!
The Brazen Blade has a new captain.


Let the credits roll for a bonus cut scene...