"Snatching that elusive thrill of discovery away from wine snobs and putting it back in the glasses of the people, one customer at a time."

Hours & Location


Red Red Wine Bar Map


Sunday: 10am – Midnight
Monday: 11am – Midnight
Tuesday: 11am – Midnight
Wednesday: 11am – Midnight
Thursday: 11am – Midnight
Friday: 11am – 2am
Saturday: 11am – 2am


189B Main Street
Annapolis, MD 21401
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About us

The backstory.

Brian and Lisa BolterWith a simple Annapolis storefront in 2011 this husband-wife team threw open the doors to the first of their four Maryland restaurants.

Brian Bolter was a Washington, DC news anchor. Lisa Bolter spent years in television news and public relations. Together they created Red Red Wine Bar. A life altering decision to be the change they want to see in the wine world, giving a voice to the wine disenfranchised. As storytellers by trade, Brian and Lisa firmly believe the more you know about someone the more likely you are to embrace them. That’s especially true with wine. Their core mission is to connect you to the stories, quirks, the magic inside every bottle. Every single label at Red Red Wine Bar has its own unique, personalized tasting note. A way to “get” what’s inside without knowing one thing about the varietal, the region or even wine, period.

Brian is the Beverage Director. Lisa is your guide through this one stop gastronomical destination. The 35+ wines by the glass and 120+ bottles pair perfectly with her elevated gourmet menu. Think of it as Maryland coastal meets California gourmet with a touch of New Orleans gluttony. The Red Red Wine Bar philosophy is simple. Buy local, support local musicians, artists, style, innovation and the creative community.


CNN International Passion to Portfolio – Red Red Wine Bar

CNN Money
August 20, 2018
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What’s New in Ocean City for the 2018 Beach Season

Baltimore Sun
May 7, 2018
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Legislator’s Wining and Dining Choices

Capital Gazette
January 4, 2018
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Annapolis Restaurants Red Red Wine Bar, Dry 85 Meet ‘Pent Up Demand’ in Ocean City

Delmarva Now
December 7, 2017
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Annapolis Eateries Aim to Upscale OC Dining Experience

OC Today
November 24, 2017
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Red Red Wine Bar Goes Mobile

What’s Up? Annapolis
November 15, 2014
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New Ways for Pouring Wine

Baltimore Sun
July 9, 2014
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Kevin Spacey Comes to Red Red Wine Bar

Washington Post
March 20, 2014
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A Wine Bistro, Minus the Attitude

Baltimore Magazine
August 28, 2013
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A Serious Game Changer: Annapolis vs. Eastport Tug-o-War

Annapolis Patch
November 2, 2012
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Out of the Box Thinking – Keg Wine in the Cork Yard for Boat Show

Annapolis Patch
October 4, 2012
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Annapolis Mayor, Restaurants Push to Extend Late-Night Outdoor Dining Hours

WJZ-TV Channel 13
September 23, 2012
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Red Red Wine Bar: Pairing People and Wine

July 25, 2012
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Sounds Good, Annapolis

Bay Weekly
March 12, 2012
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There’s More Than Port To Portugal These Days!

October 27, 2011
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Dock Here: Discover Annapolis On and Off the Water

Washington Post
September 8, 2011
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Fox 5 anchor Brian Bolter, channeling the news and a new wine bar business

Washington Post
November 21, 2010
Read more »



Naptown Brass Band New Orleans Brunch!

December 9, 2018 10:00 am - 1:00 pm
Enjoy the sweet sounds of N'awlins while downing beignets and cafe au laits!

Guest Bartender Night with Keiffer Mitchell benefitting Sharp Dressed Man!

December 11, 2018 6:00 pm - 8:00 pm

Nightmare Before Christmas Party!

December 12, 2018 6:00 pm - 11:59 pm
Dress as your favorite character and enjoy drink specials all night!

Midnight Madness with Indie Folk/Rock Alex Peters!

December 13, 2018 9:30 pm - 12:30 am
Enjoy the spirit of the season with holiday shopping downtown. Then dine, drink and dance the night with us and Alex Peters!

Paint Wine Glasses with Bloody Mary and Mimosa Specials!

December 15, 2018 11:00 am - 1:00 pm
Sign up at: https://wineanddesign.com/calendars/event.php?id=136172&fbclid=IwAR0oviXJm3fwpVfAU0TajMYFuykdIEJLlquoBPcEh3v6FW8UaAfBIHtKEv0

Sip & Shop with Local Vendors!

December 16, 2018 11:00 am - 2:00 pm
Support local businesses and enjoy drink specials. Get those last minute gifts in comfort!

Christmas Carol Karaoke!

December 18, 2018 7:30 pm - 11:59 pm
Belt out those carols! Let it out! Let the season course through your vocal chords!

Guest Bartender Night with Jeremy Parks/Dan Haas benefitting MD Theater for Performing Arts!

December 19, 2018 6:00 pm - 8:00 pm
Come help raise money to build the Maryland Theater for Performing Arts here in Annapolis and enjoy the acoustic singer/songwriter sounds of Dan Haas!

11th Hour Shopping with Skribe!

December 20, 2018 9:30 pm - 12:30 am
Enjoy the last minute shopping deals downtown. Then dine, drink and dance the night away with Skribe's garage folk/rock!

DRY 85 Private Barrel Bourbon Tasting!

December 22, 2018 1:00 pm - 3:00 pm
Taste private bourbon barrels selected exclusively by DRY 85 85. Named one of the Top 40 Whisky Bars in America. Bottles for purchase. The best gift!

Closed for Christmas

December 25, 2018 10:00 am - 10:00 am

Open Early for Christmas Hangover Bloody Mary Bar!

December 26, 2018 10:30 am - 2:30 pm

Free Champagne Tasting!

December 29, 2018 1:00 pm - 3:00 pm

NYE with Pressing Strings!

December 31, 2018 10:00 pm - 2:00 am
Ring in 2019 with Indie Reggae/Rock from Pressing Strings! Complimentary Champagne toast at midnight. $10 cover after 10pm.