Talk to Captain Benny on the Findale Docks

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Get your boat out using /boat, and follow the laterns in the ocean

If you are at the correct spot it will look like this, just move towards the cove for a cutscene

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Discover where these loud noises are coming from

Board the Pirate Ship using the ladders on the back

Fight Deck Cadet Lou

Deck Cadet Lou: Level cap 15

• Level 10 Pikachu
• Level 10 Dratini
• Level 10 Snorlax

Fight Engineer Jack on the lower deck

Engineer Jack: Level cap 20

• Level 15 Gligar
• Level 15 Larvitar
• Level 15 Houndour
• Level 15 Flaafy

Fight First Mate Diego

First Mate Diego: Level cap 25

• Level 20 Kirlia
• Level 20 Metang
• Level 20 Wailmer
• Level 20 Milotic
• Level 20 Lileep

Leave the ship and head towards Baywharf's Pokemart to fight Captain Annabelle

Captain Annabelle: Level cap 30

• Level 25 Anniversary Dragonite (Water/Electric)
• Level 25 Anniversary Houndoom (Water/Psychic)
• Level 25 Anniversary Slaking (Grass/Fighting)
• Level 25 Anniversary Infernape (Ice/Ground)
• Level 25 Anniversary Darmanitan (Poison/Dark)
• Level 25 Shadow Roserade (Shadow)