Boaters who haven’t set a waypoint for Annapolis, Maryland, the past few years might be surprised by how much they find there.

“Annapolis, for years and years, was really traditional with what was downtown,” says Samantha Branham, regional director for Safe Harbor Marinas. “But the landscape has changed. They’ve built it up, and there are new restaurants right on the waterfront. It’s really cool.”

One of her newer favorites is The Choptank, billed as a classic fish and crab house. Its deck overlooks the boating action. “You’re sitting right over everything,” Branham says.

Another favorite of hers is Preserve, which is on Main Street. The menu shows a range of options from lamb ragu to vegan pot de creme, but Branham goes for the oysters, which she orders topped with creative accompaniments. “They’ll do things that are a little different, like a pickled onion mignonette,” she says, adding that she has also enjoyed the apple variation. “It was really sweet.”

To work off some of the calories, boaters can head back to Safe Harbor Annapolis, which has tennis and pickleball courts for member use. After that, maybe it’s a light nosh at The Fat Crab restaurant on-site, with a newly extended pavilion, before another walk around downtown.

“It’s the state capital, so there’s also a lot of history,” she says. “You can do walking tours. The Naval Academy is there. It can be romantic, or it can be good for a family with kids. It’s beautiful. I’m biased, but I think it’s the most beautiful place in the world.”

Local Delicacy

So many places serve crab in Annapolis that eateries regularly battle to make it onto Top 10 lists. Crab cakes, crab bisque, crab dip and soft-shell crabs are just some of the varieties.

Music Galore

A newer event in the city is the Annapolis Songwriters Festival, which takes place in September. It was created a few years ago and is modeled after the Key West Songwriters Festival, with dozens of free performances over the course of four days, as well as some ticketed concerts for highlighted acts. Shows performed at the City Dock are free for children 12 and younger, with additional venues typically including Maryland Hall and Rams Head On Stage. Some musicians also perform in the local parks, hotels and bars, with many of those concerts free for boaters who are having a walkabout downtown. The styles of music at this festival are wide-ranging, with a little bit of something for everyone.

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It was a breezy fall afternoon on Chesapeake Bay, a perfect day for a sail, and I felt fortunate to have been invited out for a spin on Gary Jobson’s C.W. Hood 32, Whirlwind. Jobson—an America’s Cup winner and a member of the National Sailing Hall of Fame—keeps his boat on a hoist near his backyard in Annapolis, Maryland. As the director of Cruising World magazine’s Boat of the Year contest, I was in town for the annual Annapolis Sailboat Show and a week of boat tests. I’ve spent a lot of time on the bay in recent years and have come to know and appreciate it.

My Annapolis pals, however, never fail to remind me that their waterfront city has been called “the sailing capital of the United States.” Which, not coincidentally, is the exact same moniker that’s been applied to my very own hometown of Newport, Rhode Island. As we raised Whirlwind’s sails, I pondered the question of which town deserved the title. Only one can wear the crown, right?

Both cities began their existence in the 17th century, largely as shipping ports. The US Naval Academy is located in Annapolis, while the Navy’s North Atlantic fleet called Newport home for several decades, and the naval base remains a major local fixture. Historically, you could make the argument either way, so we’ll call that a toss-up.

Geographically, when it comes to the adjacent waters, I have a strong bias toward Newport. The Chesapeake features some excellent nearby cruising grounds, particularly along the Eastern Shore. But for me, it doesn’t match up to the neighboring Elizabeth Islands of Martha’s Vineyard and Nantucket, with Maine just an overnight sail away. The Chesapeake is shallow and really doesn’t hold a candle to Narragansett Bay and the deep blue Atlantic lapping Newport’s shores. Advantage: Newport.

One thing you don’t get in Newport, however, is the abundance of rivers and creeks that you have in Annapolis to moor a boat, so many of them right along the waterfront. And there are certainly far more options when it comes to marinas and facilities. The nod goes to Annapolis here.

As a destination in and of itself, thanks to that deep water, Newport attracts huge numbers of amazing yachts, from modest cruisers to multimillion-dollar superyachts. The America’s Cup was contested there, and the town remains home to many of the classic old 12 Meters. But Annapolis is every bit as attractive as a tourist spot, and the sailboat show each fall is easily the country’s best. Flip a coin on this one.

As far as actual sailing, the southwesterly sea breeze that fills in off Newport nearly every summer day is steady, wonderful, and hard to beat. There’s plenty of sailboat racing; the New York Yacht Club’s Newport station is an amazing, iconic landmark, and there are plenty of dedicated sailors. But I have to admit, the Annapolis Yacht Club, rebuilt after a devastating fire, is every bit as dynamic as the NYYC. I don’t have hard numbers at my disposal, but my overall take on participation leans toward Annapolis. I see plenty of moored boats in Newport that never seem to go anywhere. The weekly yacht racing out of Annapolis blows Newport away on that front.

So where, exactly, does that leave us? As Jobson and I doused the sails on Whirlwind after a cracking great sail, my fondness for Annapolis was sealed. Sure, for its homegrown passion, let’s call it the sailing capital. But I think that we can still dub Newport the nation’s yachting capital, with the grandness that title suggests. And yes, I’m waffling. What’s that saying about having your cake and eating it too?  

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