A Local's Guide to Annapolis
Thank you to SAS Shoes for sponsoring this post. All opinions are my own.
SIMPLIFY LOAFER
As much as I love to explore new and unfamiliar cities, I’m loyal to the cobblestone streets of my hometown, Annapolis. I have such a deep love for this nautical town on the Chesapeake Bay, and it’s about time that I share it with all of you!
So whether you’re staying for a long weekend or squeezing in a day trip, here’s how to experience Maryland’s capital city like a true Annapolitan.
BUT FIRST, GRAB COFFEE DOWNTOWN
We have some seriously cute coffee shops downtown Annapolis. Conveniently located, there are options wherever your adventures take you! Caffeinate at Brown Mustache Coffee inside Old Fox Books on Maryland Avenue, at City Dock Coffee right off Main Street, or at Light House Bistro on West Street.
BROWN MUSTACHE COFFEE | CITY DOCK COFFEE | LIGHT HOUSE BISTRO
BROWSE THE BOUTIQUES ON MAIN STREET
There are so many boutiques in Annapolis to browse, especially on Main Street. Most are small, woman-owned businesses that offer a unique selection clothing, jewelry, accessories + home decor. Trendy Millennials will love 3 Sisters, Brightside Boutique, Lilac Bijoux + Lou Lou, and preppy, Lilly lovers will fall in love with The Lucky Knot + The Pink Crab.
If you’re on the hunt for the perfect keepsake to commemorate your visit, check out HERE. a pop-up shop, Kokopelli and Local by Design. These boutiques have curated collections from Maryland designers and artists, including Aid Through Trade, Anchor Point Paper Co., Coastal Calligraphy, Kim Hovell, Maryland Mercantile, Sweet Mint Handmade + over 50 more.
3 SISTERS | BRIGHTSIDE BOUTIQUE | HERE. A POP UP SHOP | KOKOPELLI LILAC BIJOUX | LOCAL BY DESIGN | LOU LOU | THE LUCKY KNOT | THE PINK CRAB
JEANS / SIMPLY LOAFER / PURSE
With so much to see and do, comfortable walking shoes are an absolute must. These moccasin loafers from SAS Shoes are perfect for long days spent exploring, thanks to its shock-absorbing sole. If you’re looking for a solid travel shoe, definitely check it out!
TRY A TASTY, LOCAL RESTAURANT
ANNAPOLIS MARKET HOUSE
Locally sourced, made to order lunches and dinners in the heart of downtown Annapolis
My recommendation: BLT Caesar Bowl
IRON ROOSTER
A hip spot in Ego Alley known for all-day breakfast + American comfort food
My recommendation: Housemade Roostart, Chicken & Waffles, French Toast
MASON’s FAMOUS LOBSTER ROLLS
‘Famous’ for bringing fresh, Maine lobster to Main Street
My recommendation: Classic Lobster Roll
MISS SHIRLEY’S CAFE
Award winning, decadent brunch food featured by Food Network's Diners, Drive-Ins & Dives, The New York Times, Food Network Magazine + Zagat
My recommendation: Avocado Toast, Funky Monkey Bread, Coconut Cream Stuffed French Toast
SOFI’S CREPES
French-inspired sweet + savory crepes
My recommendation: Nutella with strawberries, Apple Crisp
THE BIG CHEESE
The local favorite for sandwiches, voted ‘Best In Annapolis’ year after year
My recommendation: St. Mary’s Slugger
VIDA TACO BAR
A trendy taco bar with a la carte tacos + freshly squeezed margaritas
My recommendation: Guacamole, Tinga Chicken taco, Chorizo taco, Purple Drank
SHARE AN ICE CREAM CONE BY THE WATER
One of my favorite pastimes is sitting by the water with an ice cream cone in hand, watching the boats sail by. I think Annapolitans would agree it’s one of the simple pleasures that makes living in Annapolis so special. Where to get ice cream, however, is more subjective.
My personal favorite is peanut butter pretzel ice cream from The Red Bean, but others feel strongly about Annapolis Ice Cream Company, Kilwins + Storm Bros. Ice Cream Factory.
ANNAPOLIS ICE CREAM COMPANY | KILWINS | STORM BROS. ICE CREAM FACTORY | THE RED BEAN
TAKE A STROLL THROUGH THE NAVAL ACADEMY
The Naval Academy is meticulously beautiful. To experience its beauty firsthand, enter campus through Gate 1, which has pedestrian entrances on Randall Street and Prince George Street.
Don’t forget that visitors 18 and older must show a photo ID.
Can’t miss landmarks: Armel-Leftwich Visitor Center, Bancroft Hall, Dahlgren Hall, Herndon Monument and The Naval Academy Chapel
Have you added Annapolis to your bucket list? Please let me know if you have any questions, or are looking for additional recommendations! XO.