Gary Jobson is editor-at-large of Sailing World and Cruising World magazines. In 1977 he won the America’s Cup with Ted Turner, and in 2003 he was inducted into the America’s Cup Hall of Fame.
The place I go to sit is up on the hill by the Maryland State House (100 State Cir.). It’s a very soothing spot. Of course, there’s no substitute for being out on a boat. There’s a great sense of freedom I feel anytime I’m out on the Chesapeake Bay.
McGarvey’s (8 Market Space; 410-263-5700) is one of my favorite places to have a beer. It’s always welcoming, and you’re more than likely to bump into some sailing type.
When I want to have breakfast and pretend I’m still in college, I go to 49 West (49 West St.; 410-626-9796). They make great waffles.
Four or five times a year, we’ll go to the Rams Head Tavern (33 West St.; 410-268-4545) to catch a live music act.
Joe Gross was a sportswriter and editor at the Annapolis Capital for 35 years. He’s working on a book about William McCool, pilot of the doomed Columbia space shuttle.
There are a couple of restaurants in Annapolis that only locals go to. Chris’ Charcoal Pit (1946 West St.; 410-266-5200) is one of the most popular. It’s mostly Greek, some Italian. Their gyros are the best—my wife’s favorite is the Athenian chicken.
Another place that’s sort of a secret is Las Delicias (626-G Admiral Dr.; 410-573-0500). You don’t go for the atmosphere; you go for the food. It’s a combination of French and Salvadoran cuisine.
There’s a bookstore called the Hard Bean Coffee & BookSellers (36 Market Space; 410-263-8770). It’s one of the few small bookstores left. They have wireless Internet and great coffee.
Navy football games are great to watch. I also love watching the Navy women’s soccer team. The coach is a former member of the United States national team.
Judy Jordan is an artist whose work, mostly figurative textiles and fabrics, has been shown in Washington and New York.
There’s a little place I love called Echoes & Accents (224 Chinquapin Round Rd.; 410-280-8800). They have new and gently used furniture, china, and home decor. It’s a fun place.
One of my favorite stores is Art Things (2 Annapolis St.; 410-268-3520). It sells all kinds of art materials. Right next door is a place called Cottonseed Glory (4 Annapolis St.; 410-263-3897), which has every imaginable fabric for quilting.
The best park is Quiet Waters Park (600 Quiet Waters Park Rd.; 410-222-1777). It has trails for biking and walking, small-boat rentals, two dog parks, and an ice rink in the winter. The visitors’ center puts on art shows.
Dick Franyo was an investment banker for 30 years before opening Boatyard Bar & Grill, named one of the top 12 bars in the world by Sail magazine.
The Maritime Museum (723 Second St.; 410-295-0104) has some neat things, and they do great trips in the summer out to Thomas Point Shoal Lighthouse—that’s the old lighthouse that you see in all the pictures. The Chesapeake Bay Foundation (6 Herndon Ave.; 410-268-8816) is also a great trip. You can tour the building (call ahead for times), which is one of the greenest buildings in the country.
A great store is Tastings Gourmet Market (1410 Forest Dr., Suite 2; 410-263-1324). The woman who runs it is a fromagère, and she’s probably the area’s foremost expert on cheese.
If you want to learn to sail, J World (213 Eastern Ave.; 800-966-2038) and Annapolis Sailing School (7001 Bembe Beach Rd.; 410-267-7205) have courses during the week and on weekends.
Katie Moose is an author of regional cookbooks and guidebooks covering Annapolis and the Chesapeake area.
My favorite place in Annapolis is probably the Hammond-Harwood House (19 Maryland Ave.; 410-263-4683). It’s historic and has a wonderful garden and one of the most beautiful doorways in America.
I also love the US Naval Academy Museum (118 Maryland Ave.; 410-293-2108). Every time we have guests, I make sure they visit. It has wonderful ship models and uniforms.
Another very special place is Caroline’s Cakes (1580 Whitehall Rd.; 888-801-2253). Caroline started baking more than 25 years ago for friends, but now she ships her cakes all over the country.
Jason Stearns is an opera singer who has performed with the National Symphony Orchestra and the Metropolitan Opera.
A cheap way to see Annapolis is to go down to the city dock and take a ride on the water taxi (visit watermarkcruises.com for schedules and locations). It takes you all around the creeks and rivers of Annapolis.
If you want more of a sailing experience, the Woodwind and the Woodwind II (docked at the Annapolis Marriott Waterfront, 80 Compromise St.; 410-263-7837) are 74-foot schooners that take people out on the Chesapeake Bay.
You also have to go to Storm Bros. (130 Dock St.; 410-263-3376), a little ice-cream place. They have about 50 selections, and they pile it on pretty good. The butter pecan is my favorite.
My wife and I love the Middleton Tavern (2 Market Space; 410-263-3323). I took her there on a trip for our anniversary in 1983, and she said, “Do you think we could live here?” That was how we ended up in Annapolis. In the wintertime, there are nice fires going. It’s a wonderful place to spend an afternoon, and George Washington ate there, which you can’t say about many places.