Less than 4 hours from New York City, Annapolis, Maryland and the Chesapeake Bay is a mecca for individuals who want to enjoy history and heritage in a quaint maritime village.

 Get out on the water with a 2-hour sailing cruise on the Schooner Woodwind. Check the calendar online for a sunset sail or a wine-tasting afternoon.

Take a guided walking tour of the Naval Academy with professional, certified guides. USNA admissions presentations are held Monday through Friday at 10 a.m. and 2 p.m., and on Saturdays at 9 a.m. and 11 a.m. Visit the Admissions site for more information.

Chick and Ruth’s has been a staple of Main St in Annapolis for decade. Either for breakfast (replete with a join-in Pledge of Allegience) or lunch (with sandwiches named after local politicians). A real bit of “local flavor” and excellent diner food, especially the pastrami, that can definitely rival those of NYC.

For a real Maryland crab feast, a 15 minute drive from the historic district, head to Jimmy Cantler’s Riverside Inn and claim a picnic table overlooking lazy Mill Creek.

Find your perfect gift at one of the boutiques and quirky general stores of the downtown shopping district, especially at the Spice & Tea Exchange and the Pink Crab. For lunch try a savory crepe from Sofi’s Crepes (1 Craig Street).

A lusher taste of the city’s past is on view at the William Paca House and Garden, where you can stop and smell the flowers in a sumptuous two-acre spread of trees and flowers that dates back to the 18th century.

The Marriot Annapolis Waterfront Hotel wins for best location across from the City Dock. The Annapolis Inn is a historic landmark townhouse majestically poised on prestigious Prince George Street in the heart of the Historic District of Annapolis. Your state or country flag will be flying from our front porch to greet you when you arrive at the Flag House Inn. It is located across the street from the pedestrian entrance to the US Naval Academy and one short block to the Annapolis waterfront.  

Join a Historic Ghost Walk of downtown Annapolis and hear about unexplained footsteps, the Gravedigger and the poor souls hung to save room in local jails. As the sun sets and darkness descends upon the streets of historic and haunted Annapolis, a spirited period dressed guide will lead you by candlelight on an Annapolis ghost tour to explore the city’s streets.

 Watermark Cruises offers dozens of excursions, from a 40-minute narrated cruise of Annapolis to a Day on the Bay trip to St. Michaels.

For a beer and waterfront dining, head to Pusser’s Landing (80 Coprimise Street). With delightful outdoor deck, they serve freshly prepared Caribbean cuisine, along with Annapolitan favorites.

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