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Historic Chesapeake Bay Hotels

If their walls could talk, what astonishing tales they'd tell

Elnicki Wade

The historic Chesapeake Bay hotels are a time traveler's dream. For more than 300 years, luxurious lodgings have risen along the shoreline and now offer today's guests a glimpse into America's past. Behind modern amenities like flat-screen TVs and high-speed internet are walls that withstood the test of time from colonial rebellions to industrial revolutions.

These remarkable hotels have harbored sailors who were shipped off to maritime battles, celebrated marriages of society's elite and showed European royalty high times on this side of the pond. You find them in unlikely places --- quaint seaside villages, rolling farmlands and urban areas nestled among steely skyscrapers. Several boast of resident ghosts. All of them have stories to tell.

As you cruise around the Bay this summer, take a journey back in time by adding vintage charm to your accommodations in the region's historic hotels.

Colonial Dames with Revolutionary Style

During the early 1700s, the Chesapeake Bay was a vibrant hub of Colonial America, where fortunes were made and homes were built to accommodate the lifestyles of a growing upper class. British monarchs doled out thousands of acres of fertile soil in land grants to friends and farmers who produced tobacco, grain, livestock and lumber. With slaves and indentured servants as cheap labor, the Bay's landed gentry filled their pockets by selling raw materials to Europe. And the booming trade industry bolstered a class of wealthy sea merchants who raked in riches by shipping goods across the Atlantic.

Before long, grand estates and elegant mansions graced the Bay's shores. Today, many of those homes have become hotels that invite guests to sleep in beds where tobacco plantation owners once pulled quilts over their shoulders or gaze through windows where sea captain's wives watched for their husband's ship to return.

The Inn at Warner Hall in Gloucester, Va., offers a splendid retro experience. The plantation was established in 1642 by Augustine Warner who received a land grant from England's queen. His descendents include George Washington and Robert E. Lee. The restored Colonial Revival mansion rests on 38 gorgeous acres near the Severn River not far from Williamsburg and Yorktown. Centuries- old trees, plush gardens and green pastures surround refurbished brick stables, smokehouse, dairy farm and family cemetery. Rooms furnished with period pieces overlook a serene riverfront view.

To witness the life of a prosperous merchant, head to the Robert Morris Inn at Oxford, Md. Its thick timber beams, red brick and paneled walls, and slate floors are a testament to fine 18th-century craftsmanship. The formal dining room features stunning tapestries, window valances and chandeliers. Above the fireplace in the tavern hangs the family coat of arms for Robert Morris, a sea-trade industry titan whose son is known as the Financier of the American Revolution. The younger Morris used his wealth from the shipping biz to leverage capital and provisions for the Continental Army, including $10,000 of his own coin to aid soldiers at the Battle of Trenton.

George Washington often visited Morris' Oxford home --- when he wasn't scampering around the East Coast stirring up trouble for the King of England. Our first president and his band of American insurgents were notorious for gathering in Chesapeake pubs and inns to lay the groundwork for our new nation.

If you want to contemplate the Constitution or just enjoy lavish lodgings where our founding fathers conspired against the British Crown, visit the Historic Inns of Annapolis. Three beautiful buildings dating back to the mid-1700s comprise the location that overlooks Maryland's capital and lively port. Each room shares a story of famous guests including statesmen, governors, Revolutionary War heroes and signers of the Declaration of Independence. Recent renovations discretely integrate modern amenities into the historic ambience.

From Social Turmoil to Seaside Heyday

The 1800s were a time of great change along the Chesapeake, as the century rolled in with back-to-back military conflicts and ended in an era of economic growth. During the War of 1812, America's fledgling Navy wrestled back control of the Atlantic seaboard from the British and cemented a strong maritime tradition in the Bay. Decades later, divided allegiances to the North and South tore the region apart during the Civil War.

Despite these social upheavals, the Bay flourished. Ports buzzed with commerce, shipbuilding boomed, and steamboats carried passengers and cargo from cities to seaside towns creating an energetic pulse of expansion. Once-isolated towns finally gained access to urban culture and architectural trends. Bay residents could order from or travel to Boston, New York or Philadelphia for fabrics, furnishing and design ideas that gave antebellum plantation houses a dose of Victorian pizzazz.

Few Chesapeake Bay hotels pay higher homage to the Bay's maritime legacy than the Inn at Perry Cabin in St. Michaels, Md. The lodging along the Miles River was built in 1816 by Samuel Hambleton, a War of 1812 veteran and aide-de-camp to Commodore Oliver Hazard Perry. As a tribute to his commander's victorious campaign against the British in Lake Erie, Hambleton designed the inn to look like the cabin on Perry's flagship U.S.S. Niagara. Today, the luxury resort proudly carries Perry's name and encourages guests to join on-site sailing courses and relish the vintage nautical décor.

Also on Maryland's Eastern Shore, just a quick jaunt from the Bay Bridge, is Kent Manor, which epitomizes the evolution of a rural estate elevated to Victorian elegance. The farmhouse was built in 1820. In 1843, Alexander Thompson inherited the place and erected an addition with Italian marble fireplace mantels and other stylish features. A.T. was a man of the times --- rich, flamboyant, cigar smoking and fond of women and his prized white horse. To this day, nearby Thompson Creek beares his name, and some guests swear to smelling his tobacco fumes in nonsmoking rooms and seeing his spirit gallop around the grounds on a pallid steed.

Industrial Strength Glitz & Glamour

When the 20th century came roaring in, the Chesapeake region was poised and ready for action. Manufacturing plants from Baltimore to Norfolk were cranking out everything from tin cans and sugar cubes to steel beams that supported U.S. bridges, skyscrapers and military necessities for waging world wars.

Chesapeake oysters were an international rage, and Prohibition couldn't halt the flow of the Bay's popular brews and libations. Baltimore's industrial barons were ranked alongside the Rockefellers and Vanderbilts. Regional architecture reflected the bawdiness of the day, and hotels achieved new heights in grandeur.

Wharfs were rowdy places, and saloons and brothels were frequented by sailors and immigrants with paychecks burning holes in their pockets. The Admiral Fell Inn, now a lovely hotel in Baltimore's Fells Point neighborhood, was built to solve some of those social quandaries. In 1900, Port Mission opened a Christian boarding house and recreation center named The Anchorage. After a rigorous delousing, sailors could enjoy a safe night's sleep inside. The YMCA took over in 1929, expanding the place to 105 rooms, but the lodgings were so small that guests nicknamed it the Doghouse. In 1955, a vinegar factory occupied the space, but it closed in the 1970s. Fortunately in 1996, the location was purchased and turned into a boutique inn with vintage décor.

Baltimore's upper-crust visitors who were unscathed by the Depression required much swankier accommodations. Built in 1929, the Lord Baltimore Hotel is 23 stories high, holds 440 rooms and boasts 20,000 square feet of ballroom. Famed as the tallest hotel in Maryland at that time, the grand dame remains the preferred location for society events and debutant balls. Its stunning art deco lobby is adorned by elegant columns and brass accents.

The Bay's southern waters also had its share of opulence, but the most glamorous destination was The Cavalier in Virginia Beach. Construction began in 1926 and was completed in 13 months with manicured golf courses, an indoor pool and an elegant building designed to attract A-list stars. Limousines were stationed at steamer ship and railroad stations, and the hotel office had a photographer and stockbroker with a New York Stock Exchange ticker tape. Big band notables such as Benny Goodman, Cab Calloway and Glenn Miller captivated guests at the Beach Club. An impressive guest roster included F. Scott Fitzgerald, Frank Sinatra, Judy Garland, Elizabeth Taylor, Bing Crosby and presidents from FDR to JFK. Unfortunately in 1942 Uncle Sam was a party pooper and claimed the hotel for use as a radar training station. It reopened in 1976 and underwent extensive renovations in 2014, returning the hotel to its former glory with an on-site distillery brewing top-shelf bourbon, rye whiskey and vodka.


1. Inn at Warner Hall

Gloucester, Va.

2. Robert Morris Inn

Oxford, Md.

3. Historic Inns of Annapolis

Annapolis, Md.

4. Inn at Perry Cabin

St. Michaels, Md.

5. Kent Manor

Stevensville, Md.

6. Admiral Fell Inn

Baltimore, Md.

7. Lord Baltimore Hotel

Baltimore, Md.

8. The Cavalier

Virginia Beach, Va.

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Florida's Fall Calendar of Events 2022

From the Gulf to the Atlantic and every bay in between, boaters and their families have plenty to look forward to on the Florida coasts this fall. Start the season with a couple of pints at Oktoberfest and spooks at a haunted ghost tour, throw in a boating event or two, and round it out with a lighted boat parade.


Black trolley with "Ghosts and Gravestones" logo on the side
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St. Augustine


Learn about the haunted history in the oldest city in the United States through the lens of the undead. Get tickets for haunted pub crawls, trolly tours and walking tours. You’ll get in the Halloween spirit and learn the stories behind St. Augustine’s most spirited locations from professional storytellers with just the right amount of spook. Kids are welcome on trolly and walking tours, and pets are allowed on walking tours! Check out Ghost Tours of St. Augustine or Ghosts & Gravestones.

Where to Dock: Camachee Cove Yacht Harbor

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Oktoberfest | Credit Pixabay


Jacksonville Beach, Tampa

October 7-9

Kick off the fall season with Oktoberfest on the Atlantic or Gulf Coast with Beaches Oktoberfest and Oktoberfest Tampa. With Tampa’s event ranking in the top five in the country and Jacksonville Beach’s being the largest in the state, you’re sure to find the brew for you!

Where to Dock: Fort George Island Marina (Jacksonville), Westshore Yacht Club (Tampa)


Apollo Beach

October 20-23

Just across the Bay from Tampa and St. Pete, Apollo Beach is teeming with wildlife on land and on the water. At this four-day festival, you’ll find a free expo with nature organizations and artwork, daily field and boat trips to sites not accessible to the public, and expert wildlife and conservation seminars. Nature aficionados won’t want to miss this opportunity at the Florida Fish and Wildlife Conservation Commission’s Suncoast Youth Conservation Center.

Where to Dock: Apollo Beach Marina


West Palm Beach

October 22

Has your dog always wanted to be an (un)professional racer? Now is Fido’s time to shine! Register your pup for a day full of zoomies, Doggie Costume Contest, and plenty of BBQ and entertainment for the whole family. Proceeds benefit Furry Friends Adoption, Clinic & Ranch.

Where to Dock: Palm Harbor Marina

Jazz band on stage under bright lights playing instruments



October 14-16

No matter your music taste, you’re sure to find something to jam out to at this three-day festival, from smooth jazz and blues to funk and zydeco. You’ll find plenty of vendors at the festival, and Tampa’s Ybor City neighborhood offers old-school charm and Latin American eateries. St. Petersburg offers hip breweries, coffee shops and more.

Where to Dock: Clearwater Beach Municipal Marina



October 22

Join in a celebration of life at the Water Lantern Festival this fall. Start the day with food trucks, music and family- friendly fun, and end by releasing your personalized lantern on the water at sunset.

Where to Dock: Marina Jack

Two dark grey mega-yachts docked at the boat show
Fort Lauderdale International Boat Show | Credit Informa Markets


Fort Lauderdale

October 26-30

The largest in-water boat show in the world offers viewings and demos of everything from superyachts to kayaks and fishing gear. Stop by the Superyacht Village to sip a cocktail on one of the most luxurious boats in the world, the Convention Center for watersport and innovative boating gear demos, and take the family to a kid-friendly fishing seminar.

Where to Dock: 17th Street Yacht Basin, Hilton Fort Lauderdale Marina, Pier 66 Hotel & Marina



October 28-30

Join the Old Naples Waterfront Association in the historic center to kick off stone crab season! Eat stone crab to your heart’s content in a prime harvesting location of the tasty crustacean and enjoy plenty of entertainment, from live music to local galleries and craft vendors. florida-seafood-festivals-calendar

Where to Dock: Naples Bay Resort & Marina


close up view of a seafood platter with vegetables, salmon, scallops, and shrimp
Florida Seafood Festival | Source VISIT FLORIDA



November 4-5

Cruise to the charming Apalachicola, tucked away among expansive wildlife reserves and just a bay away from the Gulf. Along with some of the best oysters and seafood you can eat, the whole family will enjoy a parade, carnival, Blessing of the Fleet, hours of live music every day, and competitions such as the oyster shucking contest and blue crab races.  

Where to Dock: Apalachicola Marina


Fernandina Beach

November 5

Celebrate the annual return of the North Atlantic right whale to the coasts of Florida and Georgia to give birth and nurse their young in historic Fernandina Beach. Learn about threats and conservation efforts for these gentle giants, participate in a beach clean-up, and enjoy family fun at educational exhibits, athletic events, and food and craft vendors.

Where to Dock: Oasis Marinas at Fernandina Beach


Key West

November 6-13

Cruise to Key West for three days of epic racing and a full week of family-friendly fun. Don’t miss the World’s Fastest Boat Parade on the first Sunday, or any three of the races throughout the week: the Truman Waterfront Cup, Southernmost Continental Champion, and Championship. Use downtime to explore the Race Village at Truman Waterfront and try out local pubs, shops and restaurants.

Where to Dock: Conch Harbor Marina

crowd on the beach admiring a large sand sculpture
Credit JJS Photo



November 11-14

Visit Siesta Key Beach to watch sculptors from around the world turn piles of white sand into sculpted masterpieces. Professional competitors have 24 hours to build their pieces, and visitors have the chance to participate in amateur sand-sculpting competitions and see the masters at work.  

Where to Dock: Safe Harbor Siesta Key



November 19-20

Art connoisseurs and amateurs alike will love this boutique art competition and festival in the scenic cultural center of Sarasota. Masters of different media—ceramics, jewelry, graphic art, painting, and more—will put the best of their work on display for patrons to browse and buy to their hearts’ content.

Where to Dock: Marina Jack

Mansion at night-time with palm trees filled with warm white holiday lights
St. Augustine Night of Lights | Source Om Flickr


St. Augustine

November 19-January 31

Ready to get in the holiday spirit? Cruise back to St. Augustine as early as before Thanksgiving for a dazzling display of more than 3 million lights in the historic district. Gaze in awe at the twinkly lights and find photo ops at the Bridge of Lions and the Christmas tree at the center of Plaza de la Constitución. Enjoy the sounds of the All Star Orchestra on the first night and stroll to businesses open later than usual.

Where to Dock: St. Augustine Municipal Marina



Miami Beach

December 1-3

Since the 1970s, this annual art extravaganza brings works of contemporary and modern pieces by renowed and emerging artists from around the world to showcase in Miami. Held at the Miami Beach Convention Center, for three days the public can gaze upon unique masterpieces presented by leading galleries from five continents.

Where to Dock: Sunset Harbour Yacht Club


Key Largo, FL

December 1-4

This annual four-day event showcases classic antique yachts, automobiles and aircraft to celebrate those who restore vintage collections. Experience a full schedule of events kicking off with a welcome party and dinner buffet on Thursday, then a weekend packed with drive-bys, shows, dinners, cocktail receptions, a costume party and more.

Where to Dock: Ocean Reef Club


With so many spectacular lighted boat parades on the coasts of Florida, we couldn’t choose just one! Dock at any of these coastal towns on the first three Saturdays of December to ring in the season on the festive Florida waterfronts.

Palm trees lined with warm white holiday lights and a sunset with boats in the background
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Daytona Beach Christmas Boat Parade
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The Seminole Hard Rock Winter Boat Parade
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December 10

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Maritime Museums in the Caribbean

The Caribbean is well known for its clear blue tropical waters. But as rich as it is in beauty, the islands have an even greater wealth of his- tory. Luckily, museums are located across the region to share the stories and significant events that can provide glimpses of what maritime life was like throughout the years. Their exhibits, relics and archives will have you looking at the region in a whole new light.

Here are eight Maritime Museums: 

National Museum of Bermuda Flagpole


You can find this treasure trove of artifacts in the Atlantic Ocean 650 miles east of North Carolina, the nearest land mass to this collection of islands. The museum shows how maritime events shaped the history, people and culture of Bermuda. It is located at the historic Royal Naval Dockyard within Bermuda’s largest fort. Exhibits cover 500 years of the country’s history from how the German U-505 submarine was captured by the U.S. Navy and concealed in Bermuda to how sailing races from North America to Bermuda have influenced the development of ocean-worthy boats and blue water sailing. Be sure to experience the museum’s unique spaces by strolling through the two-story boat loft to catching a dolphin show at the Keep Pond Terrace to taking in the expansive ocean views at the flagpole.

Where to Dock: Kings Wharf or Heritage Wharf


Turks and Caicos National Museum opened in 1991 to store artifacts found in the excavation of the Molasses Reef shipwreck, an unknown Spanish ship that sunk in 1515 on the Caicos Bank. The museum spans two locations: the Guinep House on Grand Turk Island, believed to be more than 180 years old and named after the large guinep tree on its property, and the Village at Grace Bay on Providenciales, where visitors can tour the Heritage House, an historically correct rendition of a typical 1800s Caicos dwelling. In addition to showcasing shipwreck artifacts, visitors also learn about the evolution of The Grand Turk Lighthouse as well as the rise and fall of the island’s salt industry. On Museum Day, the first Saturday in November, visitors can tour the exhibits for free, and in May, the Village at Grace Bay holds a “Back in the Day” event with activities reflecting historical life on the island.

Where to Dock: Blue Haven Resort & Marina

Map of the driving routes on the Grand Cayman Heritage Trail
Grand Cayman Heritage Trail Driving Routes | GCHT


If you like to take in history outdoors, these exhibitions are for you. The trail consists of 36 stops across all three islands (Grand Cayman and the Sister Islands) and is best traveled via car. Each stop is marked by a road sign that shares a notable historic event or contribution related to the maritime industry. Learn how turtling shaped the islands’ early economy, how ships were cleaned and repaired before boat lifts by a process called “careening”, and hear stories of notable shipwrecks. If you prefer to learn Cayman Island history in one place, you can check out the Cayman Islands National Museum, housed in Cayman’s oldest surviving public building, which has a series of permanent and rotating exhibits.

Where to Dock: The Barcadere Marina


Completed 500 years after Christopher Columbus arrived on the island of La Hispaniola, the Faro a Colon (aka The Columbus Lighthouse) is one of the Dominican Republic’s most popular attractions. Constructed in the shape of a Latin cross spanning the width of two soccer fields, the lighthouse was created to recognize the first “encounter between two worlds.” It includes a mausoleum that houses Christopher Columbus’ remains as well as a museum displaying original and replica artifacts from the time of Columbus’ voyage. The lighthouse also has a library containing documents and maps displaying some of the earliest drawings of the Americas.

Where to Dock: Marina Zarpar

Boats in the water with green hills in the background
Nelson's Dockyard | Source Alexa Zizzi


The Antigua Naval Dockyard, now named Nelson’s Dockyard, was built in the mid-1700s to serve as a strategic post and support the Royal Navy battle against the French and protect trade routes in the region. The dockyard officially closed in 1889 and reopened in 1961 as an historic site. In addition to exploring the dockyard, take advantage of the park’s 12 miles of hiking trails, two forts, and tours such as the “Rum in the Ruins” where you can listen to stories of the dockyard while sipping on a cocktail. If traveling by boat, get the best view of the gorgeous English Harbour and snag a slip at nearby Nelson’s Dockyard Marina, the only continuously working Georgian Era dockyard in the world.

Where to Dock: Nelson’s Dockyard Marina


Opened in 2020, the Bequia Heritage Museum includes the Boat Museum and Annexe that display and educate visitors about the boatbuilding and whaling industries as well as artifacts dating back to the period of the island’s European settlement. Vessels on display at the museum include a traditional Amerindian dug-out canoe and the decommissioned boat, Rescue, that was originally used for whaling.

Where to Dock: Bequia Marina

Curaçao Maritime Museum | Credit CP Hoffman


Located in a mansion built in 1729 on the Waaigat inlet, the Curaçao Maritime Museum shares with visitors the story and events that influenced Curaçao’s involvement in the maritime industry. Learn how trade ebbed and flowed in and out of Curaçao’s ports, reflective of the events happening around the world to the arrival of the first cruise ship in 1901 from New York, sparking the cruise tourism industry until the 1970s when air travel took over as the primary way for tourists to visit the island. Visitors can explore the museum at their own pace or take a guided tour.

Where to Dock: Seru Boca Marina


With a decent internet connection, you can visit the Grand Bahama Museum from the comforts of your remote anchorage or mooring. Bahamian history and culture are explored through digital exhibits ranging from the islands’ natural landscapes and the history of the port authority to the role the Bahamas played during the Golden Age of Piracy. Learn about the first recorded piece of mail sent from the Bahamas in 1761 and the evolution of mailboats. Or savor a dark and stormy while reading about the Bahamas’ role in the rum-running industry during U.S. Prohibition. The Grand Bahama Museum was originally housed at The Garden of the Groves but was unfortunately destroyed by weather and time. To reach a wider audience and share Bahamian history and culture, the museum decided to move to a digital platform.

Where to Dock: Grand Bahama Yacht Club or Flamingo Bay Hotel & Marina

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This or That: Beaufort vs. Fernandina Beach



Fernandina Beach | credit Patrick Farrell


Beaufort lies on an inlet leading south to the Atlantic and is considered part of North Carolina’s “Inner Banks” and the Crystal Coast. The Crystal Coast spans 85 miles of stunning coastline in southern North Carolina, including 56 miles of protected beach of the Cape Lookout National Seashore.


Located on historic Amelia Island, Fernandina Beach is the northernmost city on Florida’s Atlantic Coast. Visitors will find easy access to Jacksonville, the mouth of the St. Mary’s River, and coastal destinations in southern Georgia such as Cumberland Island.


Beaufort History | credit Dori Arrington


Established in 1709, Beaufort was originally known as Fishtown, having been a fishing village and port of safety since the late 1600s. In addition to fishing, Beaufort was a hub for whaling, lumber, shipbuilding and farming. The earliest settlers made their mark by building Bahamian and West Indian-style homes, and the Plan of Beaufort Towne can still be seen in a 12-block historic district.


First settled in 1562, this town on historic Amelia Island went through many transformations under eight flags before it became what it is today. After the Civil War, Fernandina Beach became a bustling seaport and popular destination, called “The Queen of Summer Resorts” by many Northerners. Today’s visitors find themselves surrounded by the town’s lovely relics of the past — an historic district, Civil War port and the first cross-state railroad remain.


Fernandina Beach | credit Deremer Studios LLC


Beaufort has a thriving scene for anglers. Cast your line off a dock downtown, book a charter or head north to Cedar Island Wildlife Refuge to catch flounder, trout and redfish. Boat tours and private charters are a popular way to experience the stunning views and wildlife of the Crystal Coast. See porpoises, dolphins and wild horses on the beach. Better yet, book with Cruisin’ Tikis Beaufort to imbibe while you observe. Dock at Beaufort Docks.


Pier fishing is huge on Amelia Island, and anglers should head to the George Crady Bridge, which spans one mile of Nassau Sound. Snag a variety of fish in the area, including redfish, whiting, seatrout, tarpon and flounder. Boaters can start aquatic excursions in either the Atlantic Ocean to the east or Amelia River to the west. Go on a solo adventure, or join a tour or charter by boat, kayak or watersport with the likes of Amelia River Tours, Amelia Adventures & Kayak or Riptide Watersports. Dock at Fernandina Harbor Marina.


Beaufort | credit Dori Arrington


History buffs will feel right at home in Beaufort. Visit the Beaufort Historic Site to learn the town’s story through nine preserved historic homes in the middle of town. Three different maritime museums, including the North Carolina Maritime Museum, and the Bonehenge Whale Center offer marine merriment for the whole family. And for a taste of Crystal Coast wildlife, head over to the Rachel Carson Reserve where wild horses and countless birds, reptiles and aquatic mammals roam free.


Fernandina Beach is known for its easy living. Amelia Island Welcome Center is a great place to revisit Fernandina’s history and plan your day. Make your way to Centre Street on the water to browse eclectic shops and bustling art galleries, taste wild-caught shrimp at a bistro, or grab a pint at the Palace Saloon, Florida’s oldest tavern. If you’re in town on a Friday, you might stumble upon Sounds on Centre, a local concert series.

Read More

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