Apologies for the alliterative headline, but ‘tis true: May is the official opening of a season marked by celebrations.  Think graduations, weddings, parties, proms, beach days, boat races – the list goes on.  Annapolis at this time of year is party central, with visitors coming from everywhere for Commissioning Week at the United States Naval Academy and restaurants gearing up for the occasion. If you find over-crowding is daunting in downtown Annapolis, consider exploring Eastport; a colorful neighborhood just over the Eastport Bridge.

From downtown, it is a short walk to this picturesque settlement known for its friendly vibe and casual charm.  After admiring the collection of sailboats visible from the Eastport Bridge, check out the trendy Blackwall Hitch (400 Sixth Street) at the first stoplight after the bridge. A favorite of local resident and county exec Steve Schuh, the upscale establishment is known for its well-stocked oyster bar, lively happy hours, live music at night, and popular rooftop deck.  Stop for a slurp and a sip before heading on to Restaurant Row, or make a late-night visit on your way home.

O’Leary’s Seafood Restaurant (310 Third Street) is a cottage tucked away in Eastport. It’s one of our town’s better seafood destinations.  Pleasantly unpretentious yet simply sophisticated, it reflects the personality of its new owner and longtime staffer Will Peterson and boasts an excellent wine list under the direction of a savvy sommelier.  Dinner daily except Monday. Half-price wine Tuesdays. Call 410-263-0884 for reservations.

Carrol’s Creek Café (410 Severn Avenue) has a well-earned reputation as our finest waterfront dining spot, with consistently good food and drink equal to the view of the Naval Academy on the opposite shore.  Family-owned for 30 years, Carrol’s Creek serves lunch and dinner daily, along with a Sunday brunch. Call 410-263-8102 for reservations.

Boatyard Bar & Grill (400 Fourth Street) is the place to go for a taste of Annapolis – sailboat culture, crab cakes, and laid-back hospitality.  Owner Dick Franyo keeps a close eye on this little gem. It’s great for breakfast, lunch, dinner, happy hour, or any time you’re hungry or thirsty. It’s also the place to be when Wednesday Night Sailboat Races are in season.  Call 410-410-216-6206 for reservations.

Chart House (300 Second Street) has had a presence in Annapolis for many years, serving dinner only and an excellent Sunday brunch.  Food, service, and a waterfront location combine to keep its tables full and its patrons happy. Call 410-268-7166 for reservations.

Lewnes’ Steakhouse (401 4th St) has a cult following among folks who remember the fine old days of formal dining.  For several generations, the same Lewnes family has continued a tradition that makes this place special. Quiet atmosphere not conducive to children.  Call 410-263-1617 for reservations.

Ruth’s Chris (301 Severn Avenue) has its own loyal following, beguiled by the curbside valet parking, rich cuisine, and luxurious outdoor dining porch on the ground floor.  This is a good place for groups of friends and families who appreciate the finest. Call 410-990-0033 for reservations.

Davis’ Pub (400 Chester Avenue) is a favorite of the local dog population, who appreciate the complimentary water bowls and occasional free hot dogs they get at this down-home bar.  Tables outside are coveted and on weekends always occupied. Casual fun!

Note:  Reservations at all restaurants mentioned here are highly recommended.  Most waterfront restaurants are accessible by water taxis that depart from City Dock.