WE’RE BUILDING THIS ONE FOR A MAXIMUM OF 10 SOULS.

april 20-27, 2027

Big enough for poolside nonsense, shared dinners and someone always being up for the detour.

Small enough to pile into a couple of jeeps, change the plan without a committee meeting and actually travel like a crew.

It’s 8–10 people, a couple of jeeps and the Conch Republic. Things could happen.

THE IDEA

This is a seven-day South Florida escape with four solid nights in Key West at the centre of it.

We’ll start or finish in Hollywood, Florida for some vintage beach-town energy — old Florida, neon, boardwalk wandering and a little faded charm.

Key West is the main event.

Think sunshine, pool time, little jeeps, ridiculous local history, good food, tiki boats, live music and the kind of detours that usually become the story.

Because this is Florida, we’re also leaving room for the occasional moment that feels like it should begin:

“Florida Man arrested after…”

Our Key West home base is part of the fun: four cottages gathered around a pool.

Enough togetherness to feel like a crew.

Enough space to disappear for a nap.

SO… WHAT THE HELL IS THE CONCH REPUBLIC?

Back in 1982, a U.S. Border Patrol roadblock made life miserable for people entering and leaving the Florida Keys.

Key West responded in the most Key West way possible:

They seceded from the United States.

The mayor declared the Conch Republic independent, symbolically declared war, surrendered about a minute later and applied for foreign aid.

Naturally, Key West turned the whole thing into an annual Independence Celebration.

Today it’s days of parades, pirates, conch-shell salutes, parties, boats, oddball competitions and general “sovereign state of mind” nonsense.

That’s why we’re going.

Not just for Key West.

For Key West while it’s actively celebrating the time it rage-quit America.

THE TRIP RHYTHM

VINTAGE HOLLYWOOD

A throwback South Florida chapter before or after the Keys.

Boardwalk energy, beach-town character, retro charm and one good wander before the trip changes gears.

FOUR SOLID NIGHTS IN KEY WEST

This is the heart of it.

Pool mornings.

Jeep runs.

Boat nonsense.

Long lunches.

Live music.

Side Quests.

Detours.

And at least one plan that gets abandoned because something better showed up.

THE JEEP RUN

A couple of jeeps. One tiny island. An unreasonable number of possible detours.

Beaches, back roads, old forts, odd landmarks, neighbourhoods and whatever earns a pull-over.

The goal isn’t to see everything. It’s to find the stuff worth talking about later.

Ideally without inspiring:

“Florida Man claims rental Jeep was ‘part of the adventure.’”

THE TIKI SEA BATTLE

There needs to be at least one properly ridiculous boat day.

We’re imagining a private tiki-boat situation with enough mischief built in to justify calling it a sea battle.

A perfectly tasteful harbour cruise would feel like a missed opportunity.

WHAT WE’RE IMAGINING

Vintage Hollywood
Old-school Florida with boardwalk wandering and retro charm.

The Keys Road Run
The drive south becomes part of the story.

The Tiki Sea Battle
Warm water and behaviour we’ll describe as “spirited.”

Pool HQ
Four cottages. One shared pool.

Conch Republic History
Pirates, wreckers, smugglers and the time Key West decided it was its own country.

Florida Man Watch
Not an official activity. More of an observational sport.

Second Shift Detours
Dive bars, oddities, tiny museums and the inevitable “we have an hour — should we?” idea.

Nothing here is locked into a day-by-day itinerary yet.

Join early and help shape the adventure.

THIS TRIP IS PROBABLY FOR YOU IF…

You like travelling with a small crew but don’t need everyone attached at the hip.

You’re happier in a jeep than on a tour bus.

You like live music, strange history, good food and places with personality.

You appreciate a pool day almost as much as a good Side Quest.

And occasionally you’re willing to say: “Sure. Why the hell not?”

YOU MAY WANT TO SKIP THIS ONE IF…

You want every hour planned.

You hate heat, humidity, live music or a little chaos.

You want a quiet resort retreat.

Or the phrase “a couple of jeeps and a tiki boat” causes more anxiety than curiosity.

Nothing wrong with that. This just isn’t that trip.

BRING YOUR BOOKING BUDDY — OR COME SOLO

The starting estimate assumes two people sharing accommodations.

Bring your person, your travel buddy, your favourite accomplice, another couple — or come solo.

We won’t find you a roommate.

We’re not summer camp, and nobody needs that kind of surprise at our age.

If you want your own space, we’ll price it accordingly.

WHAT WILL IT COST?

Estimated from $2,750 CAD per person

Based on two people sharing accommodations and including estimated flights from Calgary.

Final pricing will depend on airfare, dates, accommodations and which shared experiences the crew chooses.

We’ll spell it all out before anybody commits. No mystery math.

WHY GO WITH SECOND SHIFT?

Because you could absolutely book Key West yourself.

That’s not the hard part.

We build the rhythm, sort the logistics, find the Side Quests, connect the interesting bits and leave enough room for the trip to surprise you.

You show up. The crew gathers. We see what happens.

INTERESTED?

This is the “tell me more before I start making questionable financial decisions” stage.

No booking.

No payment.

Tell us who’s interested, who your booking buddy might be, where you’re travelling from and anything we should know to figure out whether this trip fits.