What is the best way to see Annapolis in one day?

Answers from Our Experts (1)

Hayley Bosch

Local families are proud of their deep Annapolis roots and welcome visitors to share in their heritage. Forbes Travel Guide editors discovered a way for you take advantage of the warm locals and get the essence of city in just one day.
Start the morning with eggs, delly potatoes and a giant milkshake at local favorite Chick and Ruth’s Delly. Check out the photos covering the walls — you may recognize some famous faces. Beware: If it’s a weekend, there will be a line out the door.
Annapolis is the self-proclaimed sailing capital of the world and visitors need to get out on Chesapeake Bay to really experience Annapolitan life. Hop aboard the Woodwind yacht for a two-hour narrated cruise, or arrange for a private charter on the Woodwind II. Once you’ve had your sailing fix, it’s time to eat some crabs. Head to local hotspot, Jimmy Cantler’s Riverside Inn for Chesapeake Bay blue crabs. Cantler’s overlooks a creek off the Magothy River and is a great outdoor spot to pick a few crabs. Locals will tell you the best way to eat ’em is with vinegar, Old Bay seasoning and a beer in hand.
After washing up, head to downtown Annapolis for a dose of history. Try an organized stroll with Annapolis Tours in which the guides are dressed in full colonial garb and usually speak with a British accent. The two-hour-plus Four Centuries walking tour from Watermark includes a visit to the Old Senate Chamber where George Washington resigned as commander in chief in 1783.
When your history lesson is over, head to McGarvey’s Saloon & Oyster Bar for some in-season oysters on the half shell — only in the months with an ‘r’ in them — and an Aviator Lager from the restaurant’s microbrewery. If you’re still hungry, order one of the juicy charbroiled burgers.

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