Coming Fall 2026!Downtown Largo · Across from City Hall
A cozy wine bar with speakeasy charm, right in the heart of downtown Largo.
Come as you are. Stay as long as you like.
What's Happening
No pretense, no pressure. Jessica and Nikki lead an intimate, beginner-friendly intro to wine: how to taste it, talk about it, and love it. Limited seats keep it personal.
Ticketed · Per PersonSolo and duo acts fill the room with the kind of music that makes a glass of wine taste better. No cover. Just good music and good company.
Free EntryWe bring in one of our favorite small-production winemakers or local artisans to share their story. Cross-promotion, good wine, and real conversation.
Ticketed · Per PersonDuring select events, every glass helps support a rotating local charity. Because great wine is even better when it gives back!
Free EntryWant to know when these go live?
Your Special Occasion
From birthdays and bachelorettes to corporate nights out and everything worth celebrating, Vintage Sister's speakeasy vibe makes every private event feel like a night you'll want to repeat. Jessica and Nikki handle the details so you can enjoy the moment.
Meet Jessica & Nikki
"Two sisters bringing one shared dream to life… a cozy spot for incredible bottles, great stories, and even better company."
Vintage Sister is a sister-owned wine bar in downtown Largo, Florida, right across from City Hall. We built it on a simple belief: wine should feel like a love story. Our list is full of wines with character, heart, and stories worth sharing.
Jessica brings 15+ years in wine sales, hospitality, and tasting room management, including two and a half years at Cooper's Hawk Winery & Restaurant, where she lived and breathed wine and earned her Level 1 Sommelier certification. Nikki brings an MBA and 15+ years in client relations and event management with the Jacksonville Jaguars and Tampa Bay Buccaneers, alongside a deep personal passion for wine and connection.
Together, we created the place we always wished existed: warm, welcoming, a little unexpected, and built for everyone from the seasoned sipper to the curious first-timer. Whether you stop in for a quick glass after work or settle in for the whole evening, this is your corner.
We'd love to see you when we open.
Get on the ListOpen every day of the week.
Yes, even Mondays.
Exact hours coming soon.
Be the first to know about new wines, upcoming events, and when we open the doors. No spam, just the good stuff.
You're on the list. We'll be in touch. 🍷