Annapolis Shop Local Valentine's Day Guide 2025

Peaceful Petals 💐‍

554 Baltimore Annapolis Blvd., Severna Park, MD 21146

JoJo, a lovable flower truck, launched Peaceful Petals by popping up on weekends. Over time, JoJo blossomed into a full-time flower shop in Severna Park. Their fresh flower bar will brighten anyone’s day.

Pop into the shop to create your own bouquet of gorgeous wildflowers. Need help? The friendly sales staff are pros at bouquet-building. You can also order ahead for Valentine’s Day (or Galentine’s Day) delivery. For the true lucky ones, gift them a monthly flower delivery subscription!

Zachary's Jewelers 💎

‍100 Main St, Annapolis, MD 21401

Jewelry is always a good idea. Family-owned Zachary’s Jewelers offers fine designer lines and custom jewelry. Choosing the perfect piece can feel overwhelming, but Zachary’s simplifies the process with their guide to Five Timeless Jewelry Pieces Every Woman Should Own:

Studs: Diamonds are forever and pearls are classic. You can’t go wrong with either.
Signature Pendant: Meant for everyday wear, often with personal meaning, like initials or symbols.
Elevated Chain: Consider a sprinkle of diamonds.
Second-skin bracelet: You don’t have to play tennis to know the tennis bracelet is iconic.
Signature Ring: A ring that has zero to do with your marital status. Possibly a birth stone, etc.

The Sugar Shoppe 🍭

‍4a Riggs Ave, Severna Park, MD 21146

At The Sugar Shoppe, we’re all kids in a candy store. All ages will enjoy a smorgasbord of their favorite chocolates, gummies, sours, and more. As someone who regularly calls the “Wegmans candy bins” her favorite food, I don’t say this lightly: their candy is top-notch and dare I say fresh?! Go ahead—spoil the little (or big) Valentine’s in your life.

Mills Fine Wine and Spirits 🍻

‍87 Main St Annapolis, MD 21401

PSA: Men deserve quality Valentine’s gifts too. Mills Fine Wine and Spirits’ build-your-own six-packs are just that. Mills has a fabulous beer (plus wine and liquor) selection. They offer delivery and curbside pickup for the upmost convenience. Cheers to that!

Lolli & Pops 🍭

‍2002 Annapolis Mall Rd, Annapolis, MD 21401

If you haven’t walked the Annapolis Mall in a while, these frigid temps are the perfect excuse. Lolli & Pops offers a wide selection of candy, gummies, chocolate, international snacks, and gifts for every occasion. Their Chocolate Gummy Bears are my absolute favorite. Oh, and check out their Valentine’s Day lineup of Heart Gummy Kabobs, Boozy Bears, Champagne Truffles, and more!

Bloomstone Jewelers 💎

‍2548 Solomons Island Rd, Annapolis, MD 21401

Let’s repeat it for the boys in the back: “Jewelry is always a good idea.” Yet, the price tags can scare some away . . . Luckily, Annapolis’ only lab grown diamond retailer, Bloomstone Jewelers has good news for your wallet. Lab-grown diamonds are priced based on growth conditions, allowing for incremental price increases. In simpler terms, the bigger the diamond, the more savings. And they’re chemically, physically, and optically the same as mined diamonds. Thinking of popping the question? Check out Bloomstone’s loose diamonds for custom engagement rings.

The Cottage 💌

‍149 Main St, Annapolis, MD 214015

62B Ritchie Hwy, Severna Park, MD 21146

This charming boutique has a Valentine’s Day Shop—filled with adorable PJs, jewelry, and clothing like this adorable Lilly Pulitzer sweater set—to fit all price ranges.

These Scratch-Off Valentine Cards have such retro feels too!

If needed, ask The Cottage’s staff to help pick out a thoughtful gift for your main squeeze. And when in doubt, remember: gift cards never go out of style.

Speaking of gift cards . . . some more sweet gift card ideas:

Our dinner picks

Acqua al 2

A fantastic Italian spot with loads of charm. As far as Annapolis restaurants, Acqua is about as sexy as it gets. And they have a special, prix fixe menu for Valentine's Day. You can reserve a table with live music or without. Here's the menu.

The Choptank

Sure, the Choptank is best in the spring, summer, and fall. Most waterfront restaurants are. But it's still a classy joint with great food that's an A-plus date spot.

Make a reservation

This goes without saying but you should definitely call ahead and make a reservation. Osteria 177, Naptown Scoop's all-time favorite restaurant in Annapolis, was fully booked a month before Valentine's!