Tipsy Teacher Wine Club
Founding Members · Class of 2026
Wine that sells out, delivered before it does.
Four seasonal boxes a year. Free shipping. Every box helps fund a real classroom.
Our first 50 members get a numbered Founding Member card. Join by Sunday, October 18.
Gold: 6 bottles plus a complimentary gift valued at $29.99 or more, $178.02 a box.
Nothing charged until your box ships. Love your first box or your money back.
As featured by
Baltimore Magazine · CBS
Your first box is the Fall Box.
Led by reds, built for sweater weather. Ships the first week of November, and nothing is charged until it does.
Ships first week of November
Led by Extra Credit Cab.
Our medium dry Cabernet anchors the Fall Box, with Berry'd In Papers alongside it. Members get every seasonal release before it goes public, and our small batches do sell out.
Prefer sweeter wines, a white, or a rosé? Swap any bottle until October 25.
Nothing charged until your box ships the first week of November. Club boxes ship free.
What's in the Gold box
Six bottles plus a complimentary gift valued at $29.99 or more, shipped free. Every bottle is swappable until October 25.
×2Extra Credit CabMedium dry red
×2Berry'd In PapersSemi sweet red
×1Early DismissalSemi sweet white
×1Summer VacationSemi sweet rosé
This shipment's gift: the Tipsy Teacher beanie, a knit beanie with an engraved leather patch. Gold and Platinum members get a new gift with every shipment.
Silver box: 1 Extra Credit Cab, 1 Berry'd In Papers, 1 Early Dismissal. Platinum box: 4 Extra Credit Cab, 4 Berry'd In Papers, 2 Early Dismissal, 2 Summer Vacation.
Swap any bottle for another wine in the lineup until October 25.
Pick your box size
Gold is our recommended starting point. You're only charged when a box ships.
Silver
For trying the club or sending a smaller seasonal gift
3 bottles per box, 4 boxes a year
$99.99 per box
$33.33 per bottle
Free shipping, every box
Fall Box: 1 Extra Credit Cab, 1 Berry'd In Papers, 1 Early Dismissal
- First access to seasonal releases
- Swap bottles or skip a season
- Physical membership card in your first box
- Founding Member card if you join by Oct 18
- $3 to this month's teacher every box
Gold
Our recommendation for most members
6 bottles per box, 4 boxes a year
$178.02 per box
$29.67 per bottle
Free shipping, every box
Fall Box: 2 Extra Credit Cab, 2 Berry'd In Papers, 1 Early Dismissal, 1 Summer Vacation. That's $219.94 of wine plus a gift valued at $29.99 or more for $178.02.
- Everything in Silver
- Best balance of value, variety, and gifting
- A complimentary gift valued at $29.99 or more with every shipment
- $6 to this month's teacher every box
Platinum
For stocking up, gifting, and the biggest classroom giveback
12 bottles per box, 4 boxes a year
$315.00 per box
$26.25 per bottle
Free shipping, every box
Fall Box: 4 Extra Credit Cab, 4 Berry'd In Papers, 2 Early Dismissal, 2 Summer Vacation
- Everything in Gold, including the gift with every shipment
- First pick of every release, before Silver and Gold
- Best price per bottle of any tier
- $12 to this month's teacher every box
| Silver | Gold | Platinum | |
|---|---|---|---|
| Bottles per box | 3 | 6 | 12 |
| Price per box | $99.99 | $178.02 | $315.00 |
| Price per bottle | $33.33 | $29.67 | $26.25 |
| Boxes per year | 4 | 4 | 4 |
| Free shipping | ✓ | ✓ | ✓ |
| Gift valued at $29.99+ with every shipment | — | ✓ | ✓ |
| Physical membership card | ✓ | ✓ | ✓ |
| Founding Member card (join by Oct 18) | ✓ | ✓ | ✓ |
| Release access | Early | Early | First pick |
| Event perks | ✓ | ✓ | ✓ |
| To this month's teacher | $3 a box | $6 a box | $12 a box |
Club boxes always ship free, every tier.
Not ready to join? Shop bottles one at a time.
Become a Founding Member.
Join by Sunday, October 18 and you're one of our first 50 members, the Wine Club Class of 2026. Gold gives you 6 bottles and a complimentary gift valued at $29.99 or more with every shipment, free shipping, first access to releases that sell out, and a box that helps support teachers.
Your Fall Box funds Ms. James
“Every child deserves to feel valued and heard. As a school counselor, I want to offer students a safe space for them to express their feelings and concerns.”
Ms. James, school counselor, Magnolia Middle School, Joppa, MD
She’s raising $200 for sensory tools, fidgets, and games that help her 250 students talk about their feelings. $1 from every club bottle goes to her goal.
Gold is preselected. Swap, skip, or cancel after your first box. Nothing is charged until your first box ships the first week of November.
The last classroom stocked
Mrs. Johnson's classroom, Delmar Elementary
$300 in supplies delivered, 100% of her goal: book bins, markers, index cards, and cardstock for 24 kids.
Funded by Tipsy Teacher orders. Your club box helps stock the next classroom.
Founding Member card
Your membership travels with you.
- Member discount at every Tipsy Teacher event
- A Members' XL Tasting Pour at every event, included with your membership
- Members' fast lane at our tastings. Look for the member sign and come straight to the front.
- Early access to every new release
- A vote in the Teachers' Lounge, our members' community
Every member, in every tier, gets a physical membership card with their first shipment. Our first 50 members get the numbered Founding Member card, Wine Club Class of 2026. One XL Tasting Pour per member per event. 21+.
You are not just buying wine. You are funding a classroom.
Kenny made it through school because teachers quietly covered the supplies his family couldn't afford. Brittany is a teacher who still spends her own money to make her classroom a better place to learn. Together they built Tipsy Teacher Wines to return the favor: every club box helps fund classroom supplies for the Maryland teacher we feature that month.
Kenny & Brittany, founders. Bottled in Maryland. Made to give back. See how the giveback works
Loved by teachers, gift givers, and wine lovers
★★★★★ 4.9 stars from 107+ reviews
"Summer Vacation is one of the best and most refreshing wines I've had in a long time."
"I bought 3 bottles and friends loved it so much I had to order more. Such a fun gift too."
"The perfect way to relax after teaching, knowing I'm helping another teacher fund their classroom."
Questions, answered
How often do boxes come?
Four seasonal boxes a year, on the first week of November, February, May, and August. We email you before every box ships with time to swap bottles or skip the season.
What's in the first box?
The Fall Box, shipping the first week of November. Gold members get 2 Extra Credit Cab, 2 Berry'd In Papers, 1 Early Dismissal, and 1 Summer Vacation. Silver and Platinum get the same lineup scaled to their box size, and you can swap any bottle before it ships.
What do Gold and Platinum members get with each box?
A complimentary gift valued at $29.99 or more with every shipment. This shipment's gift: the Tipsy Teacher beanie. Silver boxes don't include the gift.
Do I get a membership card?
Yes. Every member, in every tier, gets a physical membership card with their first shipment. Our first 50 members get the numbered Founding Member card.
What is a Founding Member?
Our first 50 members, the Wine Club Class of 2026. Founding Members get a numbered plastic Founding Member card and keep their member number for life. Enrollment closes Sunday, October 18, or when spot 50 fills.
What if I join after October 18?
You can still join. Founding Member enrollment closes Sunday, October 18, so your first box is the Winter Box, shipping the first week of February.
Can I swap bottles?
Yes. Before each seasonal box ships, we email you a link to customize it. Or just email contact@tipsyteacher.com and we'll swap it for you. For the Fall Box the deadline is October 25.
Can I skip a season?
Yes. You can skip any season before your box ships. Just email us and it's done.
Can I cancel?
Yes, anytime after your first box. Email contact@tipsyteacher.com and we'll take care of it. No contract.
When am I charged?
You are not charged until your first box ships the first week of November. After that you are charged when each seasonal box ships, the first week of February, May, and August. Sales tax, where it applies, is added at that time. Before every shipment we email you with time to swap bottles, skip the season, or make changes.
Do I get free shipping?
Yes. Every wine club box ships free, on all three tiers, including Silver's 3 bottle box. The sitewide 6+ bottle offer applies to one-time orders only.
Do I need to be home to sign?
Yes. Wine shipments require an adult 21 or older to sign at delivery. Not going to be home? Skip the season or adjust delivery before your box ships.
What if I don't like my first box?
You're covered by the Teacher's Promise: love your first box or your money back, every penny.
What do I get at Tipsy Teacher events?
Show your member card at Tipsy Teacher events for your member discount, one Members' XL Tasting Pour (a generous pour of your choice, included with your membership), and the members' fast lane at our tastings: look for the member sign and come straight to the front. One XL Tasting Pour per member per event. Members must be 21 or older.
Where do you ship?
Most states where the law allows wine shipping. Add your state on the signup form and it will tell you right away.
Join the Class of 2026
Founding Member enrollment closes Sunday, October 18, or when spot 50 fills. Your Fall Box ships free the first week of November, and nothing is charged until it ships.
Cancel anytime after your first box. You must be 21 or older to join. We ship where the law allows. $1 from every bottle goes to the teacher we fund that month.
Limited to 50 membersJoin now
