GENTLE GULF BREEZES carry the echoes of long-ago battles won and lost, the soulful tunes of travelers on Mississippi Blues Trail, and the enticing aromas from the multicultural flavors of coastal cuisine. The rich history of the Mississippi Coast is best experienced by spending time in the small communities dotting the 62 miles of shoreline.
Bay St. Louis to Pass Christian — 5 NM
This quaint seaside city overlooking its namesake bay has blossomed into an eclectic artist community whose residents might include descendants of Native Americans, rapacious pirates or Confederate generals.
Old Town is perfect for strolling. Start at the Mockingbird Café housed in an 1868 building boasting a rare three-sided gallery. They serve breakfast, brunch and lunch daily. The Belfast Breakfast drink—a cold brew blended with Jameson and Irish cream topped with whipped cream and cinnamon—may be a jump start or a sudden end to the day!
Blues Hall, built in 1894, is one of the stops on the acclaimed Mississippi Blues Trail. Lucky visitors might catch an open mic evening held on a stage that hosted noted gospel, jazz and R&B artists such as Etta James, Irma Thomas and Professor Longhair.
A stop at the Daiquiri Shak for one (or two) frozen drinks with names like 190 Octane might provide the courage to join other brave souls in the marsh mist for a Ghost Boat Tour by TheMysticGhostRide Company. Both the boat tour and the Ghost Cemetery Walking Pub Crawl are filled with eerie legends of the Bay told like never before.
Where to Dock: Bay St. Louis Municipal Harbor
On the eastern side of Bay St. Louis lies the sleepy summer town of Pass Christian. Spend a few hours sunbathing on the softest, cleanest beach sand along the shoreline or biking the Pass Christian Scenic Drive Historic District. Majestic live oaks and historic dwellings, charming cottages and elegant mansions line the two-mile drive. Beach cottage eatery Sea Level serves burgers, dogs, seafood tacos and 45 snowball flavors at umbrella shaded picnic tables.
Where to Dock: Pass Christian Harbor (slips on east and west side of the harbor)
Pass Christian to Gulfport — 9 NM
Just a mild wind eastward is the tiny community of Long Beach whose colorful past includes pirate Captain Cleytus Pitcher who supposedly buried treasure near the border of Pass Christian in the early 1800s. According to local legend, his alcohol-fueled crew burned down his tree house with Pitcher still in it. Besides still-unearthed pirate riches, culinary treasures are discovered at Parrish’s Restaurant & Lounge. Menu choices from bouillabaisse to Wagyu tomahawk steaks and house made dessert creations are served against a spectacular sunset background.
Gulfport, the state’s second largest city and a working seaport since 1902, is now a world-class maritime terminal. A lively downtown amid ancient live oak trees and dignified old homes with sagging porch swings offers plenty of snacking, sipping and shopping options.
Irresistible aromas lure you into Coast Roast Coffee & Tea for a rich brew from beans perfected in their 100-year-old roasters. For steaks, short ribs and seafood, head over to Rack House Steaks & Spirits. Bar-side are 30 wines by the glass and more than 100 bourbons, ryes, whiskeys and scotches. Many restaurants serve the state’s signature dessert: Mississippi Mud Pie, a gooey chocolate glaze over melted marshmallows on a crusty brownie base.
Fishbone Alley, a funky little side lane, backs up to a cluster of pubs. Local artists adorn the alley walls with colorful murals celebrating Gulfport’s thriving arts scene. To work off some of those earlier treats, wrestle with a one-arm bandit on Casino Row and stay for one of the many shows.
Where to Dock: Gulfport Municipal Marina/Bert Jones Yacht Harbor
Gulfport to Biloxi — 11 NM
Much of the city’s return to its pre- hurricane(s) glitz and glamour is due to the gaming houses that range from backwater barges to deluxe resort- entertainment complexes. The Casino Hopper Trolley stops at blackjack tables, city attractions, restaurants and beaches.
Kick off your morning with Crawfish Étouffée-N-Grits with a biscuit and homemade strawberry jam at Fill-Up with Billups before heading out to the many museums.
The ceramics of George E. Ohr, self-proclaimed “mad potter of Biloxi,” and other innovative ceramic artists are displayed at the Ohr-O’Keefe Museum of Art. The small but colorfully engaging Mardi Gras Museum is housed in an historic antebellum building. The Maritime & Seafood Industry Museum’s extraordinary photographs chronicle the first Native American settlements through generations of immigrants, all part of the region’s melting pot culture.
For a genuine waterman experience and a real shrimping expedition, The Biloxi Shrimping Trip highlights the fascinating world of sea creatures including catching, cooking and eating local shrimp.
Atlantic bottlenose dolphins like to race boats 12 miles south to the six barrier islands notoriously used by pirates, privateers and smugglers throughout most of their history. Hidden booty has been unearthed as recently as the 1980s. Cat, Horn, Petit Bois and Ship Islands are included in the Gulf Islands National Seashore. Cat Island contains bayous and marshes, home to several species of birds and alligators. USA Today named Ship Island "the hidden gem of Mississippi” for its spectacular beaches. All facilities, including the storied Civil War era Fort Massachusetts, are open to boaters.
The largest, Horn Island, was a creative source and favorite subject of famed Gulf artist Walter Anderson. It’s worth an overnight on the hook to listen to the song of the cicadas and reflect on the enduring mystique of the Mississippi Coast.