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?
