Vintage image of a sailboat mast
Vintage image of a sailboat mast
Vintage image of a sailboat mast
Vintage image of The Mandalay sailing at sea
Vintage image of The Mandalay sailing at sea
Vintage image of The Mandalay sailing at sea

the Story behind

our old Sails

The Story Behind Our Old Sails

We specialize in intimate voyages aboard classic ships. Our CEO Charles Kropke grew up dreaming of bringing people to the Caribbean after falling in love with old sailing ads. Decades later, that idea became The Windjammer Way.

Whether it’s sharing a beachside rum with old and new friends or stargazing off the deck of a 102-year-old schooner, Windjammer cruises are about connection. And they’re only getting started.

What We Sail By

Human Connection

Doing good business starts with doing the right thing. When we invest in real relationships — with our guests, our crew, and our island partners — the rest follows. Integrity drives loyalty. Loyalty drives value.

Meaningful Voyages

We’re not here to build the biggest fleet or serve the most people at once. We’re here to create unforgettable voyages — ones that feel human, intimate, and full of meaning. Core memories. That’s the sweet spot.

Conscious Cruising

We don’t just sail through the Caribbean. We celebrate it. That means honoring its cultures, supporting its communities, and building something that contributes more than it consumes.

The Mandalay sailing in the Caribbean

The Mandalay’s History

The Mandalay’s History

Mermaid illustration
Mermaid illustration
Vintage image of a man steering a sailboat
Vintage image of a man steering a sailboat
Vintage image of a man steering a sailboat

Own a piece of maritime history — and the company behind it.

By investing in The Windjammer Way, you’re not only helping to restore the Mandalay — you’re becoming part-owner of a company reshaping the future of boutique cruising.

Coral illustration
Coral illustration
Coral illustration

Meet Our Team

From the helm to the galley, this team knows hospitality, heritage, and how to mix a damn good rum swizzle.

Charles Kropke headshot
Charles Kropke headshot
Charles Kropke headshot

Charles Kropke

Founder & CEO

Zack headshot
Zack headshot
Zack headshot

Zack Luttrell

President & COO

Julian Peterson headshot
Julian Peterson headshot
Julian Peterson headshot

Julian Peterson

Captain of the Mandalay

Taylor Bradley headshot
Taylor Bradley headshot
Taylor Bradley headshot

Taylor Bradley

Director of Marketing

Boston Brown headshot
Boston Brown headshot
Boston Brown headshot

Boston Brown

Executive Chef

Mashup Thompson headshot
Mashup Thompson headshot
Mashup Thompson headshot

Mashup Thompson

Head Bartender

Reflection of two people in a porthol window
Sunset view through sailboat silhouettes

faqs

Or as we call them, good questions.

When will the Mandalay be ready to sail?
When will the Mandalay be ready to sail?
When will the Mandalay be ready to sail?
How does the investment opportunity work?
How does the investment opportunity work?
How does the investment opportunity work?
What will it be like onboard?
What will it be like onboard?
What will it be like onboard?
Can I book a voyage yet?
Can I book a voyage yet?
Can I book a voyage yet?
How are you approaching sustainability?
How are you approaching sustainability?
How are you approaching sustainability?
Will you be adding more ships?
Will you be adding more ships?
Will you be adding more ships?
Starfish illustration
Starfish illustration
Starfish illustration
Join our mailing list
Join our mailing list
Join our mailing list