Summer is the perfect time to explore all that the Chesapeake Bay has to offer, and in one weekend trip you can hit several unique destinations. We set out from Baltimore and head east across the bay toward Kent County, Maryland, stopping first in Fairlee Creek, a lovely anchorage spot that's a favorite of many Eastern Shore boaters. The marina in Fairlee is an excellent place for a family getaway, with many kid-focused features, plus beach parties and live entertainment on the weekends for adults. From Fairlee Creek, it's a scenic cruise to historic Georgetown, where the marinas have terrific amenities, including restaurants that are destinations in their own right.
Day 1 - Fairlee Creek, Maryland (approximately 25 miles)
After cruising to Fairlee Creek, dock at Mears Great Oak Landing, recently voted Best of the Bay by Chesapeake Bay Magazine readers. The 350-slip, full-service facility has top-notch amenities, including a fuel dock, WiFi, and a well-stocked ship's store, and it provides loads of recreational opportunities. Kids will love the basketball, tennis, and volleyball courts, not to mention the swimming pool, bouncy castle, waterslides, and weekend movie nights. There's also a private, sandy 180-foot-long beach along the creek.For grown ups, there's a hot tub overlooking the bay, as well as the popular Jellyfish Joel's Tiki Bar. The casual, tropical-themed watering hole hosts live bands on the weekends (R&B, classic rock, reggae), and during the summer there's a Hawaiian-style luau party every Friday night. Don't miss trying one of the bar's infamous frozen drinks: the Painkiller, the Rum Runner, and the Pain n'de Ass.
Day 2 - Georgetown, Maryland (approximately 25 miles)
From Fairlee Creek, cruise along the Sassafras River to Georgetown. The Sassafras is one of the true treasures of the Chesapeake region, and is considered by many to be one of the prettiest rivers in the upper bay. At the end of the eight-mile-long river there are several marina options or a peaceful anchorage. The 300-slip, family-owned Georgetown Yacht Basin offers a variety of complementary services, including a water taxi, the Two Toots, that will shuttle guests anywhere in the area. There are also kayaks, paddleboats, and bicycles for visiting boaters to use. The quaint town of Galena is an easy pedal away and has boutiques, curiosity shops, and cafes. There are several restaurants within a short walk of the marina, and many are pet friendly and offer outdoor dining. The owners of the Georgetown Yacht Basin also own the Kitty Knight Inn & Restaurant, which sits on a hill overlooking the marina. The property is named for local patriot and hero Kitty Knight, who persuaded the invading British not to destroy part of the town during the War of 1812, and who was rumored to have been one of George Washington's dance partners. The restaurant is open daily and offers both casual and fine dining, as well as drinks on the outdoor deck, which has stunning bay views. Don't be surprised if you spot an osprey or eagle soaring through the sky.
The full-service Sassafras Harbor Marina has 200 slips and can accommodate boats to 120 ft. Relax by the pool or stroll along the beautifully landscaped boardwalk. There are horseshoe pits, pool tables, and ping-pong tables when you're ready to take a break from simply enjoying the scenery, plus a fun on-site gift shop. Harbor Café, located on the marina grounds, is laid back and inviting, with dishes such as crab chowder, oyster stew, flatbread pizzas, and house-made cannolis. Order a box of the ricotta-cream-filled treats to go, and continue to savor the weekend's adventures even after you've returned to your home port.
Day 3 - Chestertown, MD
If you have access to a car and are interested in doing a little more exploring, the burg of Chestertown is an easy drive from both Fairlee Creek and Georgetown, and well worth a visit. The historic town dates back to 1668 and sits along the beautiful Chester River. It is home to many boutiques and antiques shops; Washington College, founded in 1782 and one of the country's leading liberal arts institutions; and the Imperial Hotel, with its excellent restaurant. (208 High Street, 410-778-5000). Walk the streets and admire the many Colonial-era homes, some of which were built in the 17th century. It's also possible to visit Chestertown by boat -- the Chestertown Marina offers dockage for boats up to 100 feet.
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.
Day 1: Bay St. Louis
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.
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.
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.
AS YOU AMBLE THE WHITE BEACHES of the Alabama Coast, you leave footprints on sands that once were the tops of the Appalachian Mountains. Transported south at the end of the last Ice Age, the sand is composed of pure white quartz crystals that create the legendary white sugar grains of Alabama beaches. A casual seaside village, an unspoiled natural island and a genteel cosmopolitan city thrive along the history-rich coastline.
Day 1: Orange Beach
A dynamic beach town surrounded by water in all directions, Orange Beach is a fishing wonderland nicknamed the “Red Snapper Capital of the World.” From the bayous to the reefs, and all the way out to the oil rigs, catches include several delicacies beside snapper. The abundance of fresh seafood dishes is found everywhere from shore shack to posh resort.
Unable to drag those toes away from the sand? Make tracks for The Gulf, a casual chic seaside hideaway with a unique shipping container design. Hang out at the bar or a communal table sipping and nibbling in the fragrant salty air.
For eclectic Southern and French-inspired dishes, head off the beaten path to Cosmo’s on Canal Road. Live music on the wooden deck makes Cosmo’s a happy hour favorite. Their Banana Leaf Wrapped Fish is on Alabama tourism’s list of “100 Dishes to Eat Before You Die.” Leave room for Soul Lovin’ Puddin’ or Peanut Butter Pie to finish.
Work off some of those Puddin’ calories on one of the 15 trails at Hugh S. Branyon Back Country Trail Complex. The hiking path winds among six distinct ecosystems within its 6,180 acres. For a more leisurely day, soak up the sunshine on one of the many public beaches.
Orange Beach Marina offers two retail stores and two award-winning restaurants. In a fully protected harbor off Terry Cove just minutes from the Gulf at Perdido Pass and the ICW, it accommodates yachts to 130 feet. Nearby Saunders Yachtworks is family-owned and offers a full-service boatyard.
As a barrier island, Dauphin is part of a complex estuarine environment that includes sandy beaches, tidal marshes and shallow lagoons rich in sea life. Attractions on the east end of the island include historic Fort Gaines, the Dauphin Island Sea Lab, Indian Shell Mound Park and Audubon Bird Sanctuary. On the west end are beautiful shimmering beaches, public golf courses and parks shaded by ancient oaks.
Dauphin Island is among the top four spots in North America for viewing spring bird migrations. A wide variety of species rest and recuperate on the 137 acres of the Audubon sanctuary whose unique geographic features include forests, marshes and dunes.
For thousands of years, the abundance of food, fresh water and other essential resources made this area a popular seasonal settlement for indigenous people. Indian Shell Mound Park is one of the best-preserved archaeological sites in the south. The mounds are believed to be the remnants of seafood meals consumed by Native Americans between 1100 and 1550. Today, Southeastern tribes maintain an ancestral connection to the ancient mounds’ original occupants.
A few blocks from the park is Light- house Bakery. Housed in an historic home, the front porch is a perfect setting for breakfast or one of their infamous cinnamon rolls with pecans. From there, it’s a short walk to The Hippie Fish boutique for not-too-touristy shirts and jewelry.
Any time of day is perfect for a smoothie, a fresh fruit bowl, an amazing waffle or ice cream at Foxy’s Waffle Bar and Sugar Den. Their motto: ALL CHILL! NO FRILL!
The sunsets on Dauphin Island are totally spectacular. View them from one of the local eateries or pick up the highly rated steamer pot from Skinner’s Seafood on Bienville Boulevard and dine on board as the sun sets.
The 235-slip Dauphin Island Marina sits at the base of Dauphin Island Bridge between the ICW and Mobile Bay. The full-service marina amenities include fuel, maintenance and a restaurant.
Mobile is one of America’s oldest cities, well known for its miles of streets canopied by majestic oaks. The city’s oldest living resident, the massive 300-year-old Duffee Oak, is just one of the city’s many centenarian live oaks. Beneath the hanging branches, large homes with sweeping front porches are adorned with hanging plants, swings and rockers with colorful pillows, and often a huge cat curled around itself.
Mobile celebrated the first Mardi Gras in the New World in 1703, long before the party began in New Orleans. Here it’s a family-oriented festival where Moon Pies are thrown along the parade route. Whether or not you’re in town for Mardi Gras, the Mobile Carnival Museum provides not only an excellent look into the history of one of the country’s oldest festivals, but also the design of the colorful costumes and the elaborate floats.
Beyond the usual must-see tourist stops—the blooms at Bellingrath Gardens, the retired battleship USS Alabama or the comprehensive GulfQuest National Maritime Museum— Mobile offers several unique adventures.
Treasure hunters and bargain chasers flock to the 800 booths spread over 30 acres at the daily Mobile Flea Market. For genuine treasures, the Mobile Museum of Art houses more than 6,400 pieces of American, European and Asian decorative items ranging from contemporary artwork to classical antiquity.
Three centuries of ghosts, hauntings and dark secrets are woven into Mobile’s history. Hear tales of darkness, death and dismemberment on a Dark Secrets Tour of antebellum mansions, overgrown gardens and a church with a mysterious past. The historic Church Street Graveyard is considered one of Alabama’s most haunted cemeteries.
With so much cultural and ethnic diversity in its past and present, Mobile is an excellent place to gain an under- standing of life in the South during the Civil War era. Begin with a narrated tour of the Bragg-Mitchell Mansion, built in 1855. Then take the time to explore more than 40 stops along the Dora Franklin Finley African American Heritage Trail. The historical stories highlighted include early Creoles of color and survivors from the Clotilda, the last African slave ship to enter America in 1860.
Need a break from all the shopping, history and culture? Braided River Brewing Company offers a range of seasonal brews and limited releases. Or, spend the day along the miles of shimmering sand on Mobile Bay accompanied by a colorful beach umbrella and the latest mystery penned by a local author.
The downtown district’s historic buildings, fronted with lacy cast-iron balconies, surround shaded city squares. Art galleries, boutiques and eateries serving traditional Southern cuisine with a sophisticated twist are concentrated along Dauphin Street.
Tuck into A Spot of Tea for daily breakfast, lunch and brunch. While known for its Bananas Foster French toast, (another on one of the state tourism’s “Top 100” lists), the chicken salad is equally notable.
Just down the street is The Noble South, an airy eatery with whitewash walls and orange metal chairs. The brunch menu has irrestibles like Fig Crepes with maple syrup, lemon anglaise and honey roasted pecans.
NoJa, an inviting Mediterranian restaurant housed in an 1840s townhouse, offers seasonal dishes and scrumptious desserts including a Ginger Donut crowned with popcorn ice cream and caramel sauce.
For classic seafood such as shrimp etouffee and gumbo, try Wintzell’s Oyster House which began as a six-stool oyster bar in 1938 and is now a Gulf Coast tradition. Get in the spirit with their signature Dragon Drink, inspired by Vernadean, a beloved fire-breathing Mardi Gras float.
They come in all shapes and sizes, lengths and locations, ages and angles. For boaters, America’s coastal bridges are a fairly common sight, one that often goes unappreciated and undervalued, especially when most of us only get to see them up close from underneath — a unique perspective not often enjoyed by the general public.
Here are the stories of nine of our country’s famous bridges that span America’s frequently traveled waterways, along with fascinating facts that you can share as you sail under or drive over them.
Perhaps the world’s most recognized span, this 139-year-old granddaddy of bridges took about 13 years to construct, linking Manhattan to Brooklyn and comprising the East River’s first fixed crossing. As the longest suspension bridge in the world when it opened in 1883, its main span measures 1,595 feet and deck rises 127 feet above the river’s surface.
Its building was a true family affair, designed by John Roebling who died unexpectedly after an injury he sustained in the early stages of the bridge’s construction. He was succeeded by his son, Washington who suffered a paralyzing caseof caisson disease. Unable to supervise construction in person, he directed the work from his nearby apartment using a telescope overlooking the site, while his wife Emily delivered handwritten instruction notes to the engineers.
Located between Piers 4 & 5 in Brooklyn Bridge Park on the East River is the new ONE°15 Brooklyn Marina with 100 slips for vessels up to 300+ feet. Estuary, the marina’s flagship restaurant, features new American cuisine, and the park is home to numerous restaurants, shops and cafes.
Chesapeake Bay Bridge (aka the Bay Bridge)
Soaring above Chesapeake Bay, this dual-span bridge connects Maryland’s densely populated Western Shore with the more rural Eastern Shore, running between Annapolis and Stevensville. The original two-way span opened in 1952; a parallel span was added in 1973 to alleviate congestion. It was only marginally successful.
Especially in summer, the bridge is often referred to as “the world’s tallest traffic jam,” packed bumper-to-bumper nearly 200 feet above the Bay. Because of its height, narrow spans, low guardrails and frequent high winds, the Bay Bridge is cited by some as one of the scariest crossings in America. But to west-bound travels, the sun setting over its tall towers and curved steel girders is a spectacular sight.
Located at the eastern base of the bridge on Kent Island is Bay Bridge Marina, which accommodates boats up to 70 feet. Sandy Point State Park Marina awaits on the westside for day use and fueling. Several other marinas are nearby.
Chesapeake Bay Bridge-Tunnel (CBBT)
Hailed as one of the great engineering marvels in the world when it opened in 1964, the original CBBT required the construction of four artificial islands, two miles of causeway, nearly six miles of approach roads, two-mile-long tunnels, four high-level bridges and 12 miles of trestle. It crosses the Chesapeake Bay between Cape Charles on the Delmarva Peninsula and Virginia Beach on the mainland.
The CBBT crosses two key East Coast shipping lanes. High-level bridges were initially proposed to span these channels, but the U.S. Navy objected to a bridge over one of the channels, because a collapse could cut off the Norfolk Naval Station from the Atlantic.
Cape Charles Yacht Center and Cape Charles Harbor Marina on the west side of the Delmarva Peninsula put you in the middle of the quaint shoreside town of Cape Charles and its charming shops, restaurants and accommodations.
Florida Keys Seven Mile Bridge
Among the world’s longest bridges when it was built, Seven Mile Bridge connects Knight’s Key in the Middle Keys to Little Duck Key in the Lower Keys. Actually two bridges, the newer span is open to vehicular traffic; the older is only for pedestrians and cyclists.
The older bridge was constructed in the early 1900s as part of the Key West Extension of Henry Flagler’s Florida East Coast Railway. After the Keys section of the railroad was damaged by the Labor Day Hurricane of 1935, Flagler sold it to the U.S. government, which convert edit to automobile use. Unsupported sections were added in 1935 to widen it for vehicular traffic, and the railroad tracks were recycled, painted white and used as guardrails.
Near the center, the bridge rises, providing a 65-foot clearance for boat passage in Moser Channel on the ICW. The remainder of the bridge is considerably closer to the water’s surface. Several marinas are on the Marathon end of the bridge.
Golden Gate Bridge
Named one of the Wonders of the Modern World by American Society of Civil Engineers, the 1.7-mile bridge was the world’s longest and tallest suspension bridge when it opened in 1937. Originally designed by engineer Joseph Strauss in 1917, the final design was conceived by Leon Moisseiff, engineer of New York City’s Manhattan Bridge.
The relatively unknown residential architect Irving Morrow designed many of the bridge’s Art Deco features, but his most famous contribution was its unique color, international orange. Others preferred that it was painted aluminum, dull gray, and the U.S. Navy suggested black and yellow stripes to ensure visibility by passing ships.
The water under the bridge is often turbulent, given the clash of the silt-heavy Bay waters and the cold Pacific Ocean currents. Consequently, recreational and commercial traffic are carefully monitored and regulated. Looking to dock and dine nearby? Try the north end of the bridge. Le Garage at Schoonmaker Point Marina in Sausalito serves innovative French cuisine, and at the casual eatery, Fish, place an order at the counter and sit at one of the picnic tables overlooking Clipper Yacht Harbor.
The engineering marvel often called “Mighty Mac” is the longest suspension bridge with two towers between anchorages in the Western Hemisphere, with a shoreline-to-shoreline length of five miles. Opened in 1957, it took three and a half years to build, because Michigan’s harsh winters limited construction to the summer months. Engineers faced daunting challenges. The Great Lakes freeze during the winter, causing large icebergs to place enormous stress on the bridge’s base.
The total length of wire in the main cables is an amazing 42,000 miles, enough to wrap around the Earth nearly twice. Painting the bridge takes seven years; when workers finish, they immediately start again. Locals note that the current in the Straits of Mackinac frequently changes direction, and when combined with wind-blown waves, churn from passing freighters and rebound off the bridge pilings, boating under and near the bridge can be challenging.
St. Ignace on the Upper Peninsula has a full-service public marina with 136 slips and is close to shops, cafes and restaurants, like the Mackinac Grille & Patio Bar.
Sunshine Skyway Bridge
One of Florida’s most iconic sights, the current Sunshine Skyway Bridge opened in 1987 and is the second bridge of that name on this site. The striking cable-stayed span connects the St. Petersburg peninsula to Terra Ceia, just north of Bradenton. The original bridge opened in 1954. A similar structure was built parallel and to the west of it in 1969 to make it a four-lane bridge.
In 1980, the freighter MV Summit Venture collided with one of the bridge’s supports during a storm, causing the southbound span to collapse and sending vehicles into Tampa Bay. After the disaster, the northbound span was converted to carry one lane in either direction until the current bridge opened.
If you’re headed into Tampa Bay, Terra Ceia Preserve State Park is on your starboard side, a 2,000-acre mangrove forest and wetlands offering kayaking, fishing and nine miles of hiking trails. At the St. Pete end of the bridge, check out O’Neill’s Marina near Maximo Park.
Tacoma Narrows Bridge
The name Tacoma Narrows Bridge has been given to three different incarnations of this span connecting the city of Tacoma with the Kitsap Peninsula to the west. The original bridge opened in 1940 and spectacularly collapsed just four months later due to design flaws that resulted in what was termed “aeroelastic flutter.” It was replaced by the second Tacoma Narrows Bridge in 1950, which is still used for westbound traffic. A third parallel span opened in 2007 to carry eastbound traffic.
The collapse of the original bridge — nicknamed Galloping Gertie — had a major impact on the field of bridge aerodynamics, which influenced the design of all the world’s long-span bridges built since 1940. The newsreel footage of the collapse can still be viewed on YouTube today.
Just south of the bridge you find Narrows Marina with transient docks that offer 375 linear feet of three-hour complimentary guest side ties and 13 overnight moorage slips. The Narrows Brewing Company and Boathouse 19 restaurant are steps away.
This massive suspension bridge connecting Brooklyn and Staten Island opened in 1964 after decades of on-again off-again planning and five years of construction. Each tower is made up of more than a million tons of metal, one million bolts and three million rivets. The four main suspension cables are 36 inches in diameter, and each is composed of 26,108 wires totaling 142,520 miles in length. Due to thermal expansion of the steel cables, the upper roadway’s height is 12 feet lower in summer than in winter.
The double-decker bridge carries 13 lanes of traffic, seven on the upper level and six on the lower level. Both the upper and lower roadways are supported by trusses that stiffen the bridge against vertical, torsional and lateral pressure — thanks to lessons learned from the Tacoma Narrows Bridge collapse in 1940.
Fort Wadsworth, at the Staten Island end of the bridge, is one of the oldest military installations in America, built in the early 1800s to protect the Narrows. In 1994, the U.S. Navy turned Fort Wadsworth over to the National Park Service.