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Conch Republic Recruits options

Apr 20 - 27, 2027

Your Advisor

Susan Robinson

Second Shift Adventures

susan@secondshiftadventures.ca

4037101982

SEE MORE ADVENTURES HERE

Full Itinerary Daily Overview Pricing

Overview

The Conch Republic Escape is a Key West–anchored cruise getaway built around sunshine, sea days, live music, beachy detours, and just enough island nonsense to make it memorable. The cruise is the main event, but Second Shift Adventures helps shape the full experience around it — flights, hotel nights, transfers, cabin choices, timing, extra nights, and the kind of pre- and post-cruise fun that turns a sailing into an actual trip.

This one is best for people who want an easygoing, social, warm-weather escape with personality: patio drinks, salt air, music, wandering, and a little “we know a place” energy. Less booking-site mayhem, more Key West story arc — planned well enough to work, loose enough to feel like vacation.

tour options

Half Day Boat Rental (Multiple Boat Options)

Highlights Experience a half-day boat tour in Key West by rental Pontoons, Center Consoles, and Deck Boats are available Description About Select the boat that best fits your needs. We have everything from pontoons with space to lounge to smaller ...

Key West Haunted Pub Crawl

Highlights Join Key West Haunted Pub Crawl Enjoy favorite drinking buddies through the island's most haunted pubs & restaurants Visit the most historic and haunted pubs and taverns on the island Get a great way to have fun out on the town while me...

Day 1 · Tue, Apr 20 · Fort Myers, FL, USA

New Flight

Key West Appropriate Ride

Apr 20

Apr 27

Naples / Ft. Myers area

We’ll ease in around the Naples / Ft. Myers area with Gulf Coast sunshine, beach walks, waterfront dinners, patio drinks, and a softer landing before the Key West chaos begins. This is the warm-up lap: pretty, relaxed, coastal, and just fancy enou...

Moderate Hotel — Great Location, Easy Access

Apr 20 - 22, 2027

Moderate Hotel — Great Location, Easy Access This trip is built around a well-located, comfortable 3-star-plus hotel style — the kind of place that keeps the budget reasonable without putting you out in the middle of nowhere. Think clean, practica...

Day 2 · Wed, Apr 21 · Fort Myers, FL, USA

Naples / Ft. Myers area

We’ll ease in around the Naples / Ft. Myers area with Gulf Coast sunshine, beach walks, waterfront dinners, patio drinks, and a softer landing before the Key West chaos begins. This is the warm-up lap: pretty, relaxed, coastal, and just fancy enou...

Day 3 · Thu, Apr 22 · Key West, FL, USA

Key West Area

Then we land in Key West for the main event: the legendary Conch Republic Independence Celebration — Key West’s annual tongue-in-cheek party honouring its “secession” from the U.S. Expect the kind of only-in-Key-West energy that may include parade...

Budget Hotel — Head-in-a-Bed, Good Enough to Get You Out There

Apr 22 - 25, 2027

Budget Hotel — Head-in-a-Bed, Good Enough to Get You Out There This option is built around a simple, budget-friendly hotel style — the kind of place that keeps costs down so more of the travel budget can go toward the actual trip: food, drinks, ac...

Day 4 · Fri, Apr 23 · Key West, FL, USA

Key West Area

Then we land in Key West for the main event: the legendary Conch Republic Independence Celebration — Key West’s annual tongue-in-cheek party honouring its “secession” from the U.S. Expect the kind of only-in-Key-West energy that may include parade...

Day 5 · Sat, Apr 24 · Key West, FL, USA

Key West Area

Then we land in Key West for the main event: the legendary Conch Republic Independence Celebration — Key West’s annual tongue-in-cheek party honouring its “secession” from the U.S. Expect the kind of only-in-Key-West energy that may include parade...

Day 6 · Sun, Apr 25 · Hollywood, FL, USA

Checkout

Hollywood, Florida

After Key West, we’ll point ourselves back toward the mainland with one more dose of Florida road trip energy — maybe a South Beach wander, a Miami pit stop, or at minimum a strong “look at us, still pretending this vacation isn’t almost over” mom...

Budget Hotel — Head-in-a-Bed, Good Enough to Get You Out There

Apr 25 - 27, 2027

Budget Hotel — Head-in-a-Bed, Good Enough to Get You Out There This option is built around a simple, budget-friendly hotel style — the kind of place that keeps costs down so more of the travel budget can go toward the actual trip: food, drinks, ac...

Day 7 · Mon, Apr 26 · Hollywood, FL, USA

Hollywood, Florida

After Key West, we’ll point ourselves back toward the mainland with one more dose of Florida road trip energy — maybe a South Beach wander, a Miami pit stop, or at minimum a strong “look at us, still pretending this vacation isn’t almost over” mom...

Day 8 · Tue, Apr 27 · FLL - YYC

Checkout