Valentine's Day
in Annapolis
Celebrate LOVE in Annapolis with these Valentine's Day specials and events!
Start planning now for great gifts, nights out on the town, or romantic nights at home. We have everything you need in downtown Annapolis. You can find all the traditional gifts like flowers, chocolate, greeting cards, and jewelry or explore the boutiques, shops, and galleries for something unique. Make the night extra special with reservations for dinner and an overnight stay at one of downtown Annapolis' Hotels, Inn's or B&B's. It's all within walking distance when you visit downtown Annapolis.
As seating and inventory may be limited we recommend checking in advance to see if advance orders or reservations are recommended.
Valentine's Day specials and events will be added below as they are announced.
Events
Valentine's Day Concert and Wine Reception - experience the sounds of courtship with a French-themed concert by artist-in-residence Empressa Ensemble. Friday, February 14 Wine reception inspired by the theme (included in the price) to precede the concert from 5-6 pm, and the concert starts at 6 pm.
Maryland Hall for the Performing Arts
Candlelight: Valentine’s Day Special - candlelight concerts bring the magic of a live, multi-sensory musical experience. February 14, 202,5 6:30 pm
Candlelight: Coldplay & Imagine Dragons - candlelight concerts bring the magic of a live, multi-sensory musical experience. February 14, 2025, 8:45 pm
A Donny Hathaway Experience February 13, 8 pm
Infamous Love Songs: An Over the Rhine Valentine's Concert February 14, 8 pm
Double Duran: The Ultimate Duran Duran Experience February 15, 8 pm
Emmaline: Be My Valentine Tour February 16, 7:30 pm
A Bloody Valentine’s Dinner: True Crime, Murder, and Twisted History
Delve into the chilling world of local true crime, sinister murder, and a tapestry of twisted tales from Annapolis’ long history. Tickets are $85 each, which includes a spooky welcome cocktail, dinner, non-alcoholic beverages, and entertainment. February 14 in The Lounge at Stan and Joe’s. Doors open at 6:30 pm, dinner and storytelling 7:00 pm - 8:30 pm
Hotels
Their Love on the Harbor package includes overnight accommodations, breakfast for two, and a bottle of sparkling wine.
Their Timeless Romance at the Inns package includes accommodations, valet parking, champagne and chocolates, and 2 pm late check-out.
Ask about their romance package which includes champagne, cheese & charcuterie, chocolate-covered strawberries, and so much more! Call 410-268-5555 for details.
Dining
Chocolate & Wine Paring February 8, 2 pm-4 pm
Italian Wine Dinner February 11 at 6:30 pm
4 courses with 4 wines for $85 per person Ask about vegetarian & gluten-free options
Valentine's Day Dinner (for dine-in or carry-out) February 14
4-course dinner for $68 per person Ask about vegetarian & gluten-free options
Valentine's Weekend Dinner 3 courses for $160 per couple or to go for $140 per couple February 13-16
Valentine's Weekend Dinner 3 courses for $75 per person February 14-16
Live music during Happy Hour with Dana B on February 14, 4 pm-7 pm
Live music with Ferro & Friends February 14, 9 pm-12 pm
Live music with Rick & The Revolving Doors February 15, 9 pm-12 am
Valentine's Weekend Dinner 3 courses for $85 per person February 14-15
Valentine's Weekend Dinner 3 courses for $75 per person February 14-16
Live music with Patrick Donovan February 14, 8 pm-11 pm
Galentine's Day Dinner 3 courses for $34 or 4 courses for $50 per person February 5
Thursdate 4-course dinner for two with decadent Sparkling Chocolate Fondue with rose petals and candles on your table for $54 per person. Space is limited.
Valentine's Weekend Dinner 5 courses for $89 per person February 14-15
Live music from Brendan Pelan February 16, 4 pm-8 pm
Pearl Restaurant and Ponche Tiki Bar
Karaoke (upstairs in the Tiki Bar) February 13, 7 pm-11 pm
O'Brien's Oyster Bar & Seafood Tavern
Late Nights with Live DJs and Dancing on February 14 and 15 starting at 10:30 pm
Valentine's Weekend Dinner February 14-16
Valentine's Weekend Dinner February 14-16
Shopping
Shop the online Virtual Valentine pop-up shop to order from their selection of Valentine's Day gifts.
Visit in person to order from their selection of Valentine's Day gifts or to special order a gift basket click here.
Visit their online store or visit in person to order from their selection of Valentine's Day treats.
Visit their online store or visit in person to order from their selection of Valentine's Day gifts.
Mangia Baby Tasty Italian Treats
Order online from their selection of Valentine's treats.
Visit their online store or visit in person to order from their selection of bouquets and Valentine's Day gifts.
A gift card to a restaurant participating in Annapolis Restaurant Week makes a great gift!
Top traditional Valentine's Day gifts are all available in downtown Annapolis
Valentine Flower Bouquets
Shop at the flower stand on Church Circle or Bloom Luxury Box
Chocolate
Shop at Kilwins and Uncle Bob's Fudge Kitchen
Gift baskets
Shop at Annebeth's,
Wine
Shop at Annebeth's, Mills Wine, Main Street Mini Market, and Gritz Liquor
Jewelry
Shop from Zachary's Jewelers, Ron George Jewelers, Tilghman Company and Blanca Flor Silver Jewelry.
Handcrafted Gifts
Shop at Local by Design, Mango & Main, Gallery 57 West, Annapolis Pottery, and Pearl Gallery
Visit dozens of great downtown shops where you can find a wide range of Valentine's Day gifts.
If you know a downtown Annapolis business with a special Valentine's offering send us a link so that we can add them to this list.
This is a joint marketing program with the Downtown Annapolis Partnership and the Annapolis Arts District