The crew wakes up in jail.

No one is entirely sure how bad the charges are, how long they’re staying, or whether the local authorities are competent enough to notice an escape. As tempers cool and confidence spikes, a risky plan begins to form. It involves social engineering, misplaced trust, and a surprising amount of baked goods.

Outside the cell, power dynamics are stranger than expected. Inside it, old memories resurface, new creations take shape, and one very important family connection comes to light.

Freedom is possible. Legality is questionable. Heroism is… negotiable.

The Sailing Sales sets out on its very first journey across the Endless Isles with a simple plan: arrive somewhere profitable and cause minimal trouble.

That plan does not survive contact with reality.

A missing map, a suspiciously helpful island, and a deeply committed bureaucracy stand between the crew and their first successful day as traveling merchants. As paperwork piles up and heroic instincts kick in at the worst possible moments, things spiral in ways no one fully intended.

By the end of the day, questions remain unanswered, authorities are concerned, and at least one situation has gone very, very wrong.

Welcome to the Endless Isles. Roll initiative.

Before the adventure kicks off, we take a little time to introduce ourselves, our characters, and the world we’ll be playing in.

This episode is a relaxed, get-to-know-us conversation. We talk backstories, vibes, worldbuilding, and how we like to play, before the dice start rolling and things inevitably go off the rails.

If you’re ready to jump straight into the campaign, Episode 1 is where it all begins. If you’re curious who’s behind the voices and the chaos, this is a good place to start.

Adventure is coming. Chaos is inevitable.

Can We Level Up Yet is a new actual-play D&D podcast built around collaborative storytelling, bad decisions, and a world full of drifting islands, strange factions, and even stranger heroes.

Join a washed-up wizard, a boy hero with a prophecy problem, and a traumatized tabaxi artificer searching for his wife as they set sail across the Endless Isles.

Launching February 8th, everywhere podcasts are found.