In this patriotic town, don’t miss the crab cakes, sunset cruises, and history tours.
Key Takeaways
Annapolis, Maryland, is not a town to bragbut it could.
Thiscoastal gemexisted here over a century before 1776, and it can still celebrate with the best of them.
The Maryland State House provides a perfect overview of the town and Main Street.Credit: Tara Donne
Annapolis has its history down but doesn’t stop there.
With food, history, water adventures, and small-town cobblestone charm, Annapolis has mastered the wholeSouthern hospitalitything.
Here’s our guide to the best things to do on your trip to Annapolis, Maryland.
Credit: Tara Donne
Many of the 24 stained glass windows and the mosaic are more than 100 years old.
It was here that Gen. George Washington resigned as commander in chief of the Continental Army in 1783.
Visitors can take a self-guided tour of the historic building.
Schooner Woodwind Sailing Cruises calls on passengers to help raise the sails and take the helm of its two 74-foot-long boats.
That’s what any local will say to an out-of-towner.
First-timers will find no better way to be introduced to the Chesapeake Bay than a cruise with Capt.
Captain Jen maneuvers her boat in the shadow of the immense Chesapeake Bay Bridge.
Sailing trips offer plenty of hands-on participation.
With a half-turn of the wheel, the wind roars into the sails.
She warns that tickets sell out as early as January, so don’t miss out.
They also have lots of handy tips.
City Dock hosts year-round boat slips as well as the annual Annapolis Spring Sailboat Show.Credit: Tara Donne
You’ll immediately see the cracker-packed varieties for what they really are: posers.
Maryland crabs aren’t a dime a dozen, and the cocky little pinchers know it.
Almost every local can tell you where to go for the “best crab cakein town.”
Cruising the Chesapeake Bay is a long-held Annapolis tradition.
But where that is always depends on who’s talking.
spice and a cold longneck to wash it all down.
Get there early to get steamed crabs at Cantler’s Riverside Inn.
Kayak tours are a popular way to see the city from a whole new vantage point—the water.
From April to December, local fishermen pull up to their docks to unload their catch directly.
Order their specialties online to enjoy anywhere in the U.S.
The restaurant is dedicated to protecting the Chesapeake Bay by donating its oyster shells to Oyster Recovery Partnership.
Beer is often added to the water for crab boils.Credit: Tara Donne
Dine on upscale seafood dishes across the water from historic Annapolis and the U.S.
Pair the Maryland crab omelet with a Spicy Shirley, aBloody Marywith a green tomato and bourbon-infused pickled okra.
Specializing in pickling and fermented foods, pair rotating seasonal cocktails with Badger Flame Beets or Mushroom Confit.
Preserve cafe showcases a seasonal, locally sourced menu.
Word on the street says the Great Frogs team has a refined palatethe scruffy pups in particular.
The cool tasting room will make even a hotter-than-Sam-Hill summer afternoon feel breezy and bearable.
So will the wine flights and complimentarycharcuterie plate.
Preserve serves daily happy hour deals.
Now she’s speaking the truth.
Enjoy a relaxing stay with luxurious room amenities like a clawfoot tub, wet bar, and private balcony.
Located within walking distance of Main Street shops and restaurants, the inns feature period furnishings and modern amenities.
Credit: Tara Donne
historicinnsofannapolis.com, 58 State Circle, Annapolis, MD 21401
The Annapolis Waterfront Hotel is located just steps away from the dock where passengers board Schooner Woodwind cruises.Credit: Tara Donne
