Planning a fall winery trip? Friend, there’s nothing better. The air is crisp. The leaves are golden. The grapes smell sweet on the breeze. And that first swirl of something deep red in your glass? Pure heaven.

But let’s be honest. Wine tasting can feel intimidating. Do I swirl? Do I spit? Do I nod knowingly when someone says “oaky with notes of leather”? And if you’re not careful, you can go from classy sips to “oops, tipsy before noon” way too fast.

That’s why I’m pouring you my favorite tips for sipping smarter, laughing louder, and making the most of your winery adventures this fall.

Why Fall Is the Best Time to Go

Autumn and wineries are a love story. Cool air, glowing vines, cozy sweaters, and boots crunching through leaves. The grapes are at their peak, new vintages are being released, and every glass feels like it was made for the season. It is winery magic at its best.

Pick Your Winery Vibe

Do you want big and glamorous with chandeliers, polished bars, and sparkling flights? Or small and cozy with family-owned spots, cheese boards, and the winemaker behind the counter? I lean boutique. More charm. More sparkle. Less fuss.

Make it a Moment

Flights are fun, with tiny pours lined up like a wine fashion show. But my favorite is grabbing a glass and heading outside. Sitting under the vines, golden sun overhead, autumn air swirling around you. Suddenly you are inside a postcard.

And of course, I bring my Lolita Wine Glass. It is my sparkle, my signature, my instant souvenir. This year, my go-to is the Wine Not? Wine Glass. Cheeky, chic, and always good for a smile. Because honestly… wine not have one more pour?

Other favorites from my Wine-Themed Collection are Wine Squad for girlfriend getaways and Life Is Better With Wine when you are keeping it classic.

Lolita’s Tips for Tasting Like a Pro

1. Plan transportation. Uber, Lyft, or a DD. Worth it.
2. Eat first. Empty stomach equals rookie mistake.
3. Taste in order. Whites, then rosés, then reds, then dessert wines.
4. Skip perfume. Let the wine shine.
5. Hold by the stem. Chic and practical.
6. Swirl, sniff, sip. Wake it up, smell it, savor it.
7. Use the dump bucket. Normal, not rude.
8. Ask questions. Winemakers love sharing.
9. Hydrate. Alternate with water.
10. Take notes or pics. Pour number five will erase your memory.
11. Pace yourself. SIP. Do not slam.

Bonus: Bring Your Own Glass

Make it extra fun. Have each friend bring their own Lolita Wine Glass. It makes every pour personal, every photo fabulous, and it doubles as a souvenir. Some wineries even let you use it for tastings. Sparkle guaranteed.

Where to Go

Wine country is everywhere. Napa and Sonoma are iconic. The Finger Lakes in New York glow in the fall. Oregon and Virginia are gorgeous too. And do not forget the small local gems near home. Pure magic.

Final Sip

A winery trip does not have to be fussy. Plan your ride. Pack your cutest sweater. Bring your sparkle, also known as your Lolita Wine Glass, and sip like you own the vineyard.

Because the best part of wine tasting is not just the wine. It is the laughter, the discoveries, and the memories you will toast to again and again

XOXO,
Lolita