Sometimes, a girl’s gotta get out of dodge. And in my case, it’s just a convenient hop, skip and jump from DC back to my parent’s house in nearby Annapolis, Maryland. In case the waterfront town, home to eighteenth century buildings, the world’s “sailing capital” and of course, the attractive men of the United States Naval Academy weren’t enough of a draw, the town has amassed quite the shopping scene since I officially moved away six years ago.
In the past two years, this sleepy waterfront town has transformed from a tourist destination to a shopping mecca rivaling the boutiques of nearby Georgetown and Bethesda.
I thought I’d give you a tour of just a few of my faves… in case you’re in the market for an escape as well. Each of the town’s three areas is completely walk-able and offers a unique flavor.
MAIN STREET — As you might expect, this is the town’s main drag, sloping gently upwards from the water. It’s where you’ll find most of the restaurants, plus lots of shopping.

Chesapeake Trading Co. CTC is a must-visit for both out-of-towners and locals alike, as this wood-floored storefront packs clothing, books, gift items and home goods into one all-around favorite storefront. Travelers will find a limited selection of Annapolis merch, mostly with a more generic “Chesapeake” theme, but will be delighted with the selection of Lacoste polos, tasteful windbreakers, or printed Wellies in the winter.

The Pink Crab If you’re looking for Lily, search no further. Annapolis’ first Lily Pulitzer signature store, the Pink Crab, provides just the right touch of preppy to a town known primarily for their polo wearing, yacht driving citizens.

Zachary’s Fine Jewelers: Anapolitans in search of beautiful baubles should make a beeline for longtime jewelry staple Zachary’s, the family owned and operated business that maintains the distinction of being the number one supplier of engagement rings to Naval Academy grads and personnel in Annapolis.

Madison: Madison owner Catharine Incaprera has been a Costume Supervisor and Star Dresser for celebs like Kate Hudson, Nicole Kidman, Colin Farrell, Daniel Craig, Christian Bale, Gary Oldman, and Jamie Fox. Madison was designed to fill what Incaprera saw as a missing niche in the Annapolis fashion scene - West Coast style at an affordable price.

Diva: Don’t miss this stylish shop, which stocks casual and going-out wear by names like Walter, Alice + Olivia and Bailey 44. Service is exceptional, and the well-edited selection of merch is loved by locals and celebs alike.
Paradigm: While over half of the merchandise in this self-dubbed “stylish yet smart” boutique costs less than $100, the vibe here is anything but cheap: The modern 4,000 square foot space, glittering chandeliers, and floor-to-ceiling windows are befitting of Soho’s best, as is the service, which is never less than top-notch.
WEST STREET — This up-and-coming area is just off Church Circle and an easy walk from Main Street. You’ll find coffeehouses, art galleries, and a few trendy boutiques that are not to be missed.

Horse: The first boutique to populate the now cooler than thou West Street Corridor, Horse mixes the best of big box selection with the top-notch customer service fitting its small size. You’ll find an attractive array of casual, work-appropriate, and nighttime wear by names like T-Bags, Karta and Rebecca Taylor.

Saucy Shoes: Styles range from casual to going-out worthy, and brands are chic (Kate Spade, Tibi, Hollywould) but won’t break the bank. Oh, and don’t forget to say hello to the resident shop dog, the owner’s large but friendly pooch named Diesel.

Laura Bevilacqua: The modern vibe of the store (accented by an over-the-counter glowing sign and sleek, white interior) matches the well-edited clothing selection. Only a few of each item are present, and tailored pants by names like Paige Black Label pair equally well with statement tops by names like Valentino RED or classic totes by handbag label BUI by Barbara Bui.
MARYLAND AVENUE– Annapolis’ haven for art galleries and interior design shops, this small side street has St. John’s College on one end and the gates of the Naval Academy on the other.

Sitting Pretty: “Ladies, let’s shop!” The motto of this Maryland Avenue fave is perfectly apropos. This stylish yet sophisticated outpost for Anapolitans is full of feminine yet not frilly merchandise by names like Tibi, Kay Unger, Kate Spade, Tory Burch, White + Warren and Nannette Lepore.

Mary and Blanche: At this tiny gift boutique, you’ll find a selection of totchkes sure to tickle your fancy. It’s the perfect spot to find that out-of-the-ordinary hostess gift (beer bottle bands) or hilarious birthday card.

Bailey’s Maryland Avenue: In a town world famous for its sailing street cred, it’s a wonder that prepster apparel haven Bailey’s didn’t emerge until nearly three years ago. Owner Pamela Brown’s shop isn’t a stuffy shop where only the likes of Bitsy and Muffy would be caught shopping, but a classic yet stylish boutique with a preppy twist.