You Earned
This Glass.

The only wine brand in America made by teachers, for teachers. Small-batch. Handcrafted. Gives back with every bottle.

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★★★★★ 2,400+ Happy Customers
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Why Tipsy Teacher?

Why People Come Back for More

Small-batch, fruit-forward wine crafted in California. Founded by a teacher, built for everyone who pours themselves into their work.

🍇

Premium Small-Batch

Hand-selected California grapes, crafted in small batches. Not a novelty wine — a genuinely great one.

🎓

Teacher-Founded

Started by a real teacher and built by educators. Our co-founder Brittany is still in the classroom today.

💫

Personality That's Real

Clever names, great taste, and a story worth sharing. Wine that makes you smile and makes you come back.

Simple as 1-2-3

How It Works

1

Pick Your Pour

Browse our small-batch collection and choose the bottles that speak to you.

2

We Ship, You Sip

Carefully packed and shipped straight to your door. Free shipping on The Trio!.

3

Taste the Difference

Enjoy wine with a name that makes people smile and a taste that makes them come back.

Get The Teacher's Grading Trio →
The Teacher's Grading Trio
FREE
GIFT!
Most Popular

The Teacher's Grading Trio

  • Summer Vacation (Rosé) strawberry watermelon rosé $34 $29
  • After School Snack (Blend) black cherry raspberry red $34 $29
  • Berry'd in Papers (Red) blueberry red blend $34 $29
  • Free Shipping $15 FREE
  • Free First Order Gift $15 FREE
TOTAL VALUE $117 $87
Get The Trio →
✓ Free shipping   ✓ Free first-order gift   ✓ 100% satisfaction guarantee
The Collection

Meet the Wines

Small-batch. Teacher-tested. Seriously good wine.
The Teacher’s Grading Trio
Bestseller

The Teacher’s Grading Trio

$87.00
🍾 Peek the cork for a hidden message
Berry'd In Papers

Berry'd In Papers

blueberry red blend
$29.00
🍾 Peek the cork for a hidden message
Summer Vacation

Summer Vacation

strawberry watermelon rosé
$29.00
🍾 Peek the cork for a hidden message
After School Snack

After School Snack

black cherry raspberry red
$29.00
🍾 Peek the cork for a hidden message
Kenny and Britt - Founders of Tipsy Teacher
Our Story

A Kid From a Trailer Park. A Teacher With a Wine Glass.

Kenny grew up in a trailer park outside Baltimore. His family didn't always have money for school supplies. But his teachers quietly spent their own money so he could have what he needed. Notebooks. Pencils. The stuff most kids take for granted.

He never forgot that.

Fast forward to 2020. His friend Brittany, a teacher in Baltimore, is venting about how much of her own paycheck goes to her classroom. Same story. Decades later.

That conversation lit a fire.

Kenny said, "Why don't we sell something teachers love and use the proceeds to help them with supplies?" Brittany looked at the glass of wine in her hand.

"What about wine? Teachers love wine."

Tipsy Teacher was born.

What People Are Saying

Straight From the Teachers' Lounge

★★★★★
"Finally a wine brand that GETS me. The names crack me up and the wine is genuinely delicious. After School Snack is my Friday go-to."
JM
Jessica M.
3rd Grade Teacher, TX
★★★★★
"Bought the welcome pack as a gift for my teacher wife. She LOVED it. The free gift was such a nice touch. Already reordering."
DB
David B.
Teacher's Husband
★★★★★
"We ordered 12 bottles for our end-of-year teacher appreciation dinner. HUGE hit. Everyone wanted to know where to get their own."
SP
Sarah P.
PTA President, CA

Selling Fast — Limited Batch

Each wine is crafted in small batches. Once they're gone, they're gone until the next release.

Only 23% of this batch remaining

Join the Class

Get $10 off your first order + first dibs on new releases and teacher exclusives.

Got Questions?

Where do you ship?
We ship to most states in the US through Vinoshipper. Due to wine shipping regulations, availability varies by state. Enter your zip code at checkout to confirm.
What does the wine taste like?
Our wines range from a crisp, refreshing rosé (Summer Vacation) to a smooth semi-sweet blend (After School Snack) to a rich demi-sec red (Berry'd in Papers). Something for every palate!
Is this a subscription?
Nope! All purchases are one-time unless you opt into our Wine Club. No commitments, no auto-ships — just wine when you want it.
Isn't wine shipping expensive?
Great news — shipping is FREE on The Teacher's Grading Trio! For other orders, we offer a $15 flat rate, and free shipping kicks in at $99.
Can I buy this as a gift?
Absolutely! Tipsy Teacher wines make the PERFECT teacher appreciation gift. We offer gift packaging and you can include a custom note at checkout.
What if I don't like it?
We stand behind our wine 100%. If you're not happy with your order, reach out and we'll make it right. Your satisfaction is our top priority.
Is this real wine or just novelty stuff?
100% real, premium California wine. Our names are fun but the wine is serious — craft-quality grapes, professional winemaking, and a 4.9-star Google rating from 107+ real reviews.
What's the free gift with my first order?
Every first-time 3-Pack order includes a free gift (a $15 value). It’s our way of saying welcome to the class!

The Teacher's Grading Trio

3 bottles of premium small-batch wine. Free shipping included.

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