With its historic harbor, cobblestone streets, and a steady breeze off the Chesapeake Bay, Annapolis is the ultimate summer destination for coastal lovers. The town’s signature blend of classic prep and nautical charm isn’t just a vibe—it’s a lifestyle. Whether you’re setting sail, sipping cocktails, or strolling Main Street, here’s your ultimate style and city guide to looking (and feeling) right at home.

Where to Sail

There’s no better way to see Annapolis than from the water. Book a private charter through Chesapeake Classic Yacht Charters, or take the helm yourself with a lesson from Annapolis Sailing School. For a more relaxed route, hop on a narrated historic tour with Watermark Cruises.

Style Tip:

For Her: Casual chino shorts, lightweight sweater, and flip flops keep things practical yet polished. Add a sunhat, aviators, and a nautical tote for extra flair.

For Him: A performance polo, solid colored swim trunks (yes, they double as shorts!), and a zip-up pullover keep him cool, crisp, and ready for a captain’s photo op.

Layer with:

• Quarter-zips

• Cable-knit sweaters
  

• Lightweight windbreakers

• Or get the best of all three, with a Holebrook sweater! 

Where to Eat

From dockside oysters to elegant candlelit dinners, Annapolis delivers on the food front. Head to Choptank for a laid-back lunch with local flavor—Maryland crab cakes are a must. For dinner, try Luna Blu for Italian or Chart House for waterfront views and fresh seafood.

Style Tip:

For a casual daytime bite, she’ll love a breezy sundress. He can’t go wrong with a fresh polo and crisp white shorts! 

For dinner, elevate the look:

It’s all about looking effortless—but intentional.

Where to Shop

Annapolis has no shortage of charming boutiques, but The Lucky Knot is a standout for those who love timeless, coastal fashion with a modern twist. Step inside and you’ll find racks of embroidered dresses, preppy polos, breezy knits, and plenty of accessories to take you from boat to brunch. Also check out our Brand New Mens Shop, across the street from The Lucky Knot! 

Also worth a browse:

•  3 Sisters – contemporary fashion with a girly edge

• The Cottage – cozy, giftable finds with a nautical flair

• Penny Post – chic stationery and thoughtful gifts

Style Tip:

Looking for souvenirs? Skip the tourist tees and opt for a signature accessory: a beaded bracelet stack, a classic rope belt, or a lightweight scarf in a bold stripe. A chic token of your trip! 

Style Recap: Annapolis Essentials

• Stripes, white denim, and navy everything

• Boat shoes or flip flops

• A great day-to-night dress

• Layers for changing weather

• Sunhat + sunglasses = non-negotiable

Annapolis is where tradition meets trend. Whether you’re catching the wind on a sailboat, enjoying crab cakes dockside, or discovering your new favorite dress on Main Street, one thing’s for sure: this town was made for style moments.