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&Bs. 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.
2026 Valentine's Day specials and events will be added below as they are announced.
Valentine's Events in Annapolis
Downtown Annapolis Chocolate Crawl
Thursday, Feb 12, from 3 pm to 7 pm, sip bubbly, taste delicious chocolate bites, and get 10% off your purchases when you mention the Annapolis Chocolate Crawl at Seasons Olive Oil, Spice and Tea Exchange, Woodcraft Artisans, Local Coast, Lucky Knott, Kim Hovel, The Cottage, Zachary's, and Brightside Boutique. Bring your friends, Valentine's shopping never tasted so good.
With Quill and Voice: A Valentine of Verse and Song from the Literary Salons of 17th-Century England Feb 14
Maryland Hall for the Performing Arts
Momentum: A Mixed Bill. Celebrate Valentine’s Day weekend with tickets to the ballet! This exciting live performance offers a magical night out as audience members enjoy a bouquet of world-premiering works. Feb 13 and 14
Candlelight: Valentine’s Day Special Feb 15
Dan Tyminski Band Feb 13
Vanessa Collier Feb 14
Emmaline: Be My Valentine Tour Feb 15
Romantic Hotels in Annapolis
Their Love on the Harbor package includes overnight accommodations, breakfast for two, and a bottle of sparkling wine.
Ask about their romance package, which includes champagne, cheese & charcuterie, chocolate-covered strawberries, and so much more! Call 410-268-5555 for details.
Enjoy a romantic getaway in a historic home. This B&B is in the heart of the historic district.
Valentine's Dining in Annapolis
A gift card to a restaurant participating in Annapolis Restaurant Week makes a great gift!
A special Valentine's dinner. Make reservations for dine-in or carry-out on Feb 14
Enjoy a Galentines High Tea from February 13 to 15, RSVP: https://tr.ee/qjt197s8kZ
Shopping in Annapolis for Valentine's Day
A gift card to a restaurant participating in Annapolis Restaurant Week makes a great gift!
Now taking reservations for Valentine's Day flowers.
Now making custom Valentine's Gift Baskets. Reserve yours by Feb 11.
Additional featured items and specials will be available soon!
Top traditional Valentine's Day gifts are all available in downtown Annapolis at
Valentine Flower Bouquets in Annapolis
Shop at the flower stand on Church Circle or Bloom Luxury Box
Chocolate in Annapolis
Shop at Kilwins and Uncle Bob's Fudge Kitchen
Gift baskets in Annapolis
Shop at Annebeth's,
Wine Shops in annapolis
Shop at Annebeth's, Mills Wine, Main Street Mini Market, and Gritz Liquor
Jewelry Stores in Annapolis
Shop from Zachary's Jewelers, Ron George Jewelers, Tilghman Company, and Blanca Flor Silver Jewelry.
Handcrafted Gifts in Annapolis
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.