Drew Estate Freestyle Live 2025

Born in the chaos of COVID-19, Freestyle Live wasn’t just an idea—it was a necessity. The world was shut down, lounges were empty, and the cigar community needed a way to come together. So, we did what we do best: we said, “F**k it, let’s go live.”

What started as a way to kick back with our people became a full-blown movement. Now, a few times a year, we fire up the cameras, light up something special, and invite you into our world.

No scripts. No suits. No corporate B.S. Just Drew Estate in its purest form—loud, unapologetic, and real as hell.

This Ain’t Just Another Livestream

Cigars aren’t just something you smoke—they’re a lifestyle, a culture, a brotherhood and sisterhood built on fire, tobacco, and good company. That’s why Freestyle Live is more than a broadcast.

We smoke. You light up your favorite Drew Estate cigar, we light up ours, and we all experience it together.

We talk real. No canned speeches, no marketing fluff—just unfiltered conversations about cigars, culture, and what’s coming next.

We connect. Whether you’re in your backyard, your lounge, or your man cave, when you’re watching Freestyle Live, you’re part of the Drew Estate family.

What You Get When You Roll With Us

Big Reveals – We drop new cigars, mystery smokes, and legendary blends before anyone else gets a taste.

Raw Conversations – Chat with the Drew Estate crew, ask your questions, and get straight-up answers.

No Boring Sh*t – We bring the energy, the stories, and the madness—this is a party, not a presentation.

Inside Access – If you want the real scoop on what’s next in the cigar world, this is where you get it first.

How to Get in on the Action

Follow Us on Facebook & YouTube – That’s where the magic happens.

Mark Your Calendar – These events don’t happen every day, and trust us, you don’t wanna miss one.

Show Up, Smoke Up – Light your cigar, pour a drink, and jump into the action.

Freestyle Live is for the ones lighting up, speaking their mind, and riding with us in real time. If you’re there, you’re part of it — the crew, the culture, and the next big thing from Drew Estate unfolding right in front of you. The ones who know, show up. The rest just ask what happened.