Various · Buying Guide

The Best Wine Clubs for Adventurous Drinkers

Notes from Chris Berry · June 18, 2026

Chris Berry, founder of Wine Underdogs.Chris BerryFounder, Wine Underdogs — chasing the world’s overlooked grapes

Most wine clubs are a convenience dressed up as a discovery. They send you the same dependable Cabernet and buttery Chardonnay everyone already drinks, charge a premium for the cardboard, and call it a journey. If you came here for that, you don't need me.

This is for the other kind of drinker. The one who orders the bottle on the list they can't pronounce. The one who would rather be wrong about something interesting than right about something dull.

There are only a handful of clubs worth the standing order, and they earn it in different ways. Here's how I'd choose.

Firstleaf — the one that learns you

Firstleaf is the club for people who want the algorithm to do the homework. You rate what you're sent, it adjusts, and the boxes get sharper over time. The intro offer — usually six bottles for around $44.95 with free shipping — is the loss-leader that gets everyone in the door; the recurring boxes settle higher.

What makes it worth a look for an underdog drinker isn't the famous grapes — it's that a learning club will, if you train it honestly, start handing you the lesser-known bottles you keep rating well. Reward the obscure and it feeds you more of it.

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Naked Wines — the one that funds the winemakers

Naked Wines is less a club than a patronage scheme, and that's the appeal. Your monthly deposit becomes credit, and that credit funds independent winemakers to make wine sold only to members. You are, in a small way, a backer rather than a customer.

For anyone who roots for the underdog — and if you're reading this site, you do — that model is the whole point. Independent growers working unfashionable grapes are exactly the people the mainstream market starves. This is a way to feed them.

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Wine.com — the one with the deepest shelf

Wine.com isn't a club so much as the largest serious wine shop in the country with a membership bolted on. If your problem is selection — you want to actually find a bottle of Xinomavro or Sercial rather than hope a box contains one — this is where you go hunting.

Their StewardShip membership — about $69 a year for unlimited free shipping — pays for itself if you order with any regularity. It's the least romantic option on this list and the most useful one.

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How to actually choose

Three drinkers, three answers.

If you want to be taught — to hand over the wheel and let a club widen your palate — start with Firstleaf and rate everything honestly.

If you want your money to mean something — to back the small producers the market overlooks — Naked Wines is the one with a conscience.

If you want to hunt — to chase a specific obscure bottle and find it — Wine.com has the deepest shelf in the room.

There's a Churchillian line about democracy being the worst system except for all the others. Wine clubs are a little like that: every one of them is a compromise, and the trick is choosing the compromise that matches the drinker you actually are.

Whichever you pick, do one thing the boxes won't do for you: keep notes. Rate what you drink. The point of a club isn't the bottle that arrives Tuesday — it's the map of your own taste it draws over a year.

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