Fresh off its win as one of the New York Times “52 Must-See Places in 2024,” Baltimore is once again reclaiming its reputation as the “Charm City” after building new cultural venues and revitalizing its urban waterways and ports of call. As the birthplace of the American clipper ship, Baltimore has held a prominent role in the seafaring history of the United States for centuries, with its waterfront Fells Point neighborhood renowned as a hub of maritime activity and shipbuilding since the 1760s. Shipbuilding ceased after the Civil War but the 18th and 19th century buildings that catered to mariners, wayfarers and shipbuilders remain, bars, brothels and boarding houses among them stalwartly lining its cobblestone streets with a nautical nod to their storied past and repurposed for a new future. Today Fells Point welcomes with taverns, pubs, award-winning restaurants, luxury boutique hotels, and family-owned cafés housed in the old historic haunts, tempting tourists and locals alike with pleasures, past and present.
We sail to Fells Point aboard a restored 1955-era army tugboat, the Stony Point, from our marina across the harbor, docking within walking distance of two of our favorite restaurants. Quintessential hole-in-the-wall gems that speak volumes about the city’s colorful neighborhoods, they include a former biker bar turned eclectic eatery that has garnered continuous praise as one of Baltimore’s best for years, Peter’s Inn.
Housed in an 1850s rowhouse, Peter’s Inn is only open three nights a week with limited, always coveted, seating secured by email, (no phone here) and sold out quickly. The food is inventive, inviting and unconventionally ingenious, spelled out on a handwritten chalkboard menu that changes weekly and bids diners to “Be Well, Feel Well, Tip Well and Fare Well! Floss Daily.” In addition to upscale entrees like Mushroom Toast with Wagyu Beef Croutons, Gorgonzola and Marsala; Pasta al Limone with Shrimp, Pistachio and Chili Threads; One Bite Scallop with Maine Lobster Ravioli; Lobster Bisque and Spinach; and buttery prime cut steaks you can cut like butter, the owners make some of the best garlic bread we’ve ever had and a signature salad with a secret dressing impossible to replicate. We top it all off with a dangerously decadent chocolate pot au crème that defies comparison, dreamed up and delivered by the husband and wife chef-duo who have been dishing out food, drink and fellowship here for 30 years, building their business on word-of-mouth accolades only from die-hard fans like us and tall wagging neighborhood dogs who stop by for bacon.
Around the corner, you’ll find Little Donna’s, a cozy quirky gem named among the top 50 restaurants in the North America by the New York Times, and the first Maryland restaurant to break the proverbial kitchen ceiling with national acclaim. Tavern pie, a la Chicago’s famous pizza, is on their menu of must haves. But the perogis, palacinka, sausages and stuffed schnitzels inspired by little Donna, the owner’s Serbian grandmother who cooked like the Polish do, get us every time. Opened in 2023, this small neighborhood newcomer has made itself at home in a 120-year-old row house, cooking up elevated comfort food that is making its Le Cordon Bleu trained chef, who honed his skills at Michelin star and James Beard award-winning restaurants, one of the hottest names on the city’s culinary scene today. Be forewarned, reservations are hard to come by but walk-ins who walk in early like we do, before the dinner hour, can usually find a seat at the bar and a story with every meal.
Photo courtesy Little Donna’s
If the light is on, we’ll stop in at one of Baltimore’s often signless corner dive bars for an after-dinner drink – nothing fancy, cheap beer, whisky and shots are staples in these iconic haunts. Corner bars have a long history in this city of neighborhoods, and ones like Mary’s Tavern are old school drinking holes where their longtime owners live on site and tend bar for the locals and merry-makers who happen by, cash only please. Ensconced in the front parlor of a corner rowhome, Mary’s is a throwback to the past, looking much the same as it did when the current owner’s parents opened it in 1959, even down to the retro jukebox that’s a hidden treasure. Once open on just about every street corner, there are not many places like this left in Baltimore, where you can drink in the local life without any pretenses so we go when we can.
Just past Baltimore’s Key Bridge, named in honor of Francis Scott Key, author of the Star Spangled Banner who lived nearby, is the entrance to the Patapsco River. The mouth of the Patapsco forms Baltimore Harbor, with the rest of this 39-mile-long waterway ultimately flowing into the Chesapeake. Branching off the river four miles from the harbor on the northern shores of the river is Bear Creek inlet, where a hidden gem of a crab shack marina restaurant, Hard Yacht Café, evokes the ambiance of a Key West tiki bar.
Navigating the shallow waters and low bridges to get here is no easy feat for a tugboat with a nine-foot draft. It calls for a fearless captain, an accurate depth finder and an advance call to the keeper of the Bear Creek drawbridge to stop traffic and raise the road to let us tug through. But what waits on the other side – pickle shots, fresh orange crushes, grilled tuna bites, seaweed salad, live music and loyal locals – makes the trip all the more worthwhile.
Thomas Harbin Photography
Located in Chesapeake Bay at the mouth of the Severn River some 20 nautical miles from the Key Bridge is Annapolis, home to the Naval Academy and renowned as the sailing capital of the eastern shoreboard. Here the battle-scarred tug confidently tucks in alongside elite Beneteau, grand Grand Banks, classic Hinkleys, high-perfomance Hanse’s, sloop-rigged Catalinas, avant-garde Wallys and the crème de la creme of mega yachts. A thriving shipping industry brought great wealth to Annapolis, reflected in the quality of life still showcased here still.
Chick and Ruth’s is our go-to-place in town for breakfast, a landmark deli-style café where the Pledge of Allegiance is recited every morning and the crab cakes – all jumbo lump crab – are so good that they’re shipped across the US to people who can’t get enough of them. When the day is done, it’s a race to Davis’ Pub, opened as a general store in the 1920s, reimagined into a lounge for watermen in the 1940s, and transformed in 1986 to the neighborhood roadhouse we frequent now. Featured on Guy Fieri’s “Diners, Dives and Drive-Ins,” its signature Crab Pretzel gets rave reviews. Wash it down with a Natty Bo and feel like a local when you go.
Forty two rivers crisscross Maryland, feeding into the Chesapeake Bay and luring us to places of pastoral beauty rich with waterfront estates, storybook towns and maritime history. Follow the meandering Miles River to the resort town of St. Michaels with dolphins frolicking in your wake. Founded in 1677, St. Michaels thrived in the 1800s when shipbuilding was its main industry, and oyster and crab harvests produced small fortunes for local fishermen and merchants.
Weekenders flock to St. Michaels from Memorial Day to late fall to partake in anything crab, view the historic vessels on display at the Chesapeake Bay Maritime Museum, and enjoy the many festivals this small town hosts. As a member of the museum and often mistaken for one of its fleet of preserved ships – crab dredgers, Chesapeake log canoes, a replica of a colonial-era tall ship and more – Stony Point docks at the end of the property when we’re in town. It’s not all that uncommon to wake up to inquisitive visitors strolling her decks to take the opportunity to explore an actual tug. But that’s part of the fun of boating, meeting like-minded folks eager to discover and share similar passions, including getting their personal take on restaurants they recommend.
Eateries are plentiful in St. Michaels, from crab shacks to high end restaurants. Experience the height of fine dining at the award-winning Inn at Perry Cabin. Savor seasonally inspired fare at Bistro St. Michaels, housed in a historic two-story home with kitchen-view bar seating we can’t resist. And dig into the all-day comfort food, crab balls, burgers and tipsy chicken, on offer at the Carpenter Saloon, dating back to 1887 and the place where the locals go to close out the night.
Photo courtesy of Inn at Perry Cabin, St. Michaels, MD
Steeped in history and country charm, the Chester River flows through the Delmarva Peninsula providing deepwater cruising tailor-made for the tug. Delmarva is agricultural in nature and many small coves nestle against rolling fields or stands of wind-blocking trees where manicured mega-acred estates owned by legacy landowners indulge in its scenic splendors. Quiet anchorages line the river and small local marinas pop up here and there, including family-owned Rolph’s Marina. Located just outside of Chestertown, Rolph’s entices passing boaters with live music and cold beer from a beached boat that has been reimagined into a sand bar.
Founded in 1706, Chestertown is one of those places where generations of families have put down roots for centuries, moving away maybe but always ready to return at the hint of a hometown affair like the annual Sultana Downrigging weekend we tugged to in late October. The schooner Sultana calls Chestertown home. A full scale reproduction of a 1767 vessel used by the British Royal Navy to enforce the notorious “Tea Taxes” in the years preceding the American Revolution, she sails as a floating classroom from April to November. The town’s Downrigging festival marks the end of its sailing season, attracting a fleet of historic ships and modern-day boaters to this riverside town to celebrate the event.
When we pulled into town, a fleet of eight tall ships and wooden boats lined the docks, including the restored oyster dredging schooner, AJ Meerwald; the 17th century trading ship St. Mary’s Maryland Dove; a replica of the Lynx, orginally built in Fells Point in 1812; a reproduction of the Swedish Kalmar Nyckel, constructed in 1625; and the Pride of Baltimore II, a reproduction of a War of 1812-era topsail clipper ship that sails out of Baltimore. Tall ships like these celebrate a legacy of maritime history and never fail to draw an admiring crowd.
Tall Ships in Chestertown, MD / Photo by Chris Cerino
We anchored out among the classic yachts, catamarans and sailboats who had come to enjoy the fun in town from the water, clearly floating in a class and era of our own. A group of curious Chestertown alumni dinghied by to check out our all-steel vessel, wondering what a tugboat like ours was doing in a place like this. Eager for answers, they invited us to dinner on their rafted-up, handsome boats that, unlike ours, looked right at home here.
Coming aboard, we learned that our hosts had ties to Chestertown and one another that went back decades, testimony to the life-long allure of this noble port. Chestertown is a historic gem wherever you look. A waterfront trade port for more than two centuries, its 18th-century docks once teemed with steamers and sailing ships that transported locally produced tobacco, oysters, fish, and wheat— along with boatloads of slaves—downriver to Baltimore and ports beyond. Today it is home to Washington College, established in 1782 and named for the general who donated 50 guineas toward its founding, stately brick Water Street mansions, a walkable downtown lined with colonial charms and dining venues that evoke a nostalgic taste for times past from a repurposed distillery, a 19th-century pharmacy, a Victorian-era Imperial hotel and a corner bakery that is making history with its artisan breads and pastries, all baked on site, including warm-from-the-oven-Sun Buns worth standing in line for.
Our Saturday supper onboard Island Girl turned out to be nothing short of sensational, with a pot of Chesapeake crab soup, locally pulled, handpicked and personally prepared just for this gathering, with home baked bread, garden-fresh salad and a selection of wine, spirits and conversation that were the stuff of stories that get better with the retelling. We learned about the town’s illustrious – and infamous –history, its Memorial Day Tea Party festival, the weekend Farmers Market that takes over the town, and what it was like growing up and sailing local. They shared tales about the “Barefootin” newspaper career of a resident journalist for the town’s Cape Gazette, the not-so-fleeting fifteen minutes of fame a self-professed Beatles groupie, now a Washington College professor, had when her front-page Washington Post feature story threatened to go Hollywood, and the extraordinary model boats that our Island Girl hosts 92-year-old father makes just for the love of it.
We made friendships and memories that night that reflected the treasures that await throughout the Chesapeake and that will definitely bring us back here again. Only next time, we will have our custom-crafted, replica perfect, model “Steele” tugboat onboard. ☐
Boat People
The inspiration for tug bites
The boat people who live and play in Baltimore harbor are an accomplished group with a litany of successful land ventures, who are equally smitten with life at sea, sharing tales, tips and culinary treats that welcome you aboard as old friends without a care in the world. There’s Tom and his heavenly tiramisu, whipped up on his boat of the same name and perfected during his years in Italy as a skilled gondola builder, and grocery royals Jim and Becky with their doodle Fisher (or does he answer to Chester?) from West Virginia, whose smokin’ pulled pork sliders and back country moonshine make their yacht, Oppe-tunity, the spot for happy hour. Salesman at work, outdoorsman at play and photographer extraordinaire (his photos are all over this article), Thomas specializes in steamed blue crabs that he traps in the Chesapeake, hauls in by hand and sails back to the marina aboard his dingy for a night of crab picking that keeps you hungering for more.
Thomas Harbin Photography
An accomplished IT pro at the helm of computers everywhere and aboard the sailboat, Tangerine, Bill’s asparagus and prosciutto spears, artfully arranged with Cojito cheese, olives and a fresh baguette a la the White House catering crew he worked with in his youth, are a virtual party on a plate. Jami’s layered banana pudding is as traditionally southern as you can get, sweetening dinners onboard her luxury cruiser with trademark Georgia sugar. When he’s not driving to area airports, you’ll find John, nattily attired, resurrecting his great grandfather’s once bootlegged egg nog on his live-aboard boat, turning nog-nay-sayers into die hard aficionados all year round. A research epidemiologist and professor of medicine at Johns Hopkins Medicine, Dr. Jack, a sailor of note, artisan furniture-maker at leisure and gourmet chef by reputation, makes easy work of his classic layered lasagna, blissfully baked aboard his pristine, mahagony-rich 46-foot sailboat, Emerald Trader. Steve and Carol, long-time Baltimoreans and motor yacht live aboards six months a year, have perfected one-pot recipes like curry-scented mulligatawny soup that never fails to lure hungry sailors to your boat for a bowl or two. And our Beneteau buddies, easy rider and business owner Clayton and his wife Megan, an educational media specialist, know every great neighborhood restaurant intimately, promising the best of Baltimore whenever you go out on the town with them. Together with the boaters you meet at the marina, like Ethel whose banana bread is without equal, and out on the bay, you are virtually guaranteed a homemade taste of local life on the Chesapeake that stays with you long after you return to shore.
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