Ahoy, fellow adventurers! Imagine your family’s next road trip filled with tales of swashbuckling pirates and legendary seafarers as you embark on an unforgettable journey along the Eastern United States’ most captivating coastal destinations. From the historic haunts of Blackbeard in North Carolina to the charming pirate-themed towns of Florida, this road trip will transport you to a world of daring escapades and hidden treasures. Get ready to immerse your children in stories that spark their imagination while exploring scenic seaside locales and vibrant maritime history. So, buckle up and set sail with us on an adventure that promises excitement, wonder, and cherished memories for the whole family. Arrr, mateys, let’s make waves and create lasting bonds on this extraordinary voyage!
Pirate History and Legends
- Delve into the stories of famous pirates like Blackbeard, Anne Bonny, and Calico Jack, who once roamed the Eastern Seaboard.
- Highlight historical events, pirate battles, and notorious hideouts that families can visit.
As you prepare for your trip, let’s make the journey even more exciting. Before you set sail, assign each family member the persona of a famous pirate—perhaps Dad can channel the fearsome Blackbeard, Mom can embody the daring Anne Bonny, while the kids take on the roles of Calico Jack or Mary Read. Throughout your adventure, bring out your inner pirate by completing fun tasks and games that capture the essence of these legendary figures. Create treasure maps for scavenger hunts, practice your best pirate lingo, and engage in playful pirate battles. With each stop, immerse yourselves in the rich maritime history and local pirate lore, sparking the imagination and excitement of the entire family.

Must-Visit Pirate Destinations
This charted course takes us from the Outer Banks to Coastal Florida. I’ll admit Ocracoke is a stretch, but it is one of the coolest pirate outposts on the list. If you have 10 days, consider it with some extra time in the Outer Banks. Each stop is rich in history and pirate lore, offering unique experiences and adventures for the whole family.
Ocracoke, North Carolina: Explore Blackbeard’s Legacy
Start your journey in Ocracoke, where the notorious Blackbeard met his dramatic end. Spend 2 nights exploring this historic island and its pirate past. Visit the Ocracoke Preservation Society Museum to learn about Blackbeard’s final battle. Don’t miss the opportunity to take a boat tour around the island and imagine the pirates navigating these waters. Be sure to visit the historic Ocracoke Lighthouse and enjoy the scenic views.
Myrtle Beach, South Carolina: Pirate Fantasy Comes to Life
Next, head to Myrtle Beach, South Carolina, for a mix of pirate fantasy and family fun. Stay for 2 nights and immerse yourselves in the Pirates Voyage Dinner Show, where you’ll be entertained by swashbuckling stunts, acrobatics, and pirate battles. This lively show is a hit with kids and adults alike, making it a memorable stop on your road trip. Visit the nearby Pirate Adventures of Myrtle Beach, where kids can dress up as pirates and go on a treasure hunt aboard a real pirate ship. Play a round of mini-golf at one of the many pirate-themed courses or spend some time relaxing on the beach. (234 miles, ferry, 7-hour drive from Ocracoke Island)
Charleston, South Carolina: Dive into Maritime History
Charleston, South Carolina, is a treasure trove of maritime history and pirate tales. Spend a day visiting the Old Exchange and Provost Dungeon, where infamous pirates were imprisoned and held trial. The dungeon’s dark, eerie atmosphere will transport you back to the 18th century, giving you a glimpse into the lives of pirates who once roamed these streets. Take a guided walking tour to learn more about Charleston’s pirate past and explore the historic waterfront. (100 miles, 2-hour drive from Myrtle Beach)
Savanah, GA: Inspiration for A Pirate Literary Legend
Make a memorable lunchtime stop in Savannah, Georgia, at the renowned Pirates’ House Restaurant. Established around 1753, this historic property originally served as an inn for visiting sailors, offering them a place to rest and share tales of the high seas. The inn’s storied past includes rumors of being a favored haunt for pirates, adding an air of mystery and adventure to your visit. Legend has it that the famous author Robert Louis Stevenson drew inspiration from his stay at the inn to pen his classic novel, “Treasure Island.”
St. Augustine, Florida: The Heart of Pirate Adventure
Finally, journey to St. Augustine, Florida, the oldest city in the United States. Discover the St. Augustine Pirate & Treasure Museum, home to one of the world’s largest collections of authentic pirate artifacts. Kids will love the interactive exhibits, including a real pirate ship and a treasure chest filled with gold coins. Just a short walk away is the Castillo de San Marcos, a historic fortress that once defended the city from pirate attacks. Wander through the ancient stone walls and imagine the battles fought to protect this coastal gem. (283 miles, 4.5-hour drive from Charleston)
Festivals and Events
If you time your travels right, you might catch one of several nautical events found at your ports of call.
Outer Banks, North Carolina
- Wind & Waves Sailing Maritime Festival: Held annually in June, this festival celebrates maritime culture with sailing races, boat displays, and maritime-themed activities. It takes place at Camp Hatteras KOA Resort in Rodanthe.
- Dare Day Festival: This two-day celebration in early June features live music, local food vendors, crafts, and family-friendly activities.
Charleston, South Carolina
- Charleston HarborFest: This maritime festival includes boat displays, sailing races, and pirate-themed activities. It’s a great event for families to enjoy.
St. Augustine, Florida
- Old City Pirate Fest: Held annually in February, this event features a Thieves Market, pirate-themed activities, and live entertainment. It’s a full day of fun for the whole family.
- Searle’s Sack and Encampment: This event commemorates the 1668 pirate raid on St. Augustine with living history encampments, militia drills, and a thrilling pirate battle reenactment.
Scenic Coastal Routes
Prepare for a scenic journey along the Eastern coast, where picturesque drives, charming coastal towns, and beautiful beaches await your discovery. Each route offers stunning vistas, unique attractions, and memorable experiences that will captivate the whole family.
The Outer Banks Scenic Byway
Begin your adventure with the Outer Banks Scenic Byway in North Carolina. This 138-mile stretch of road traverses barrier islands, offering breathtaking views of the Atlantic Ocean and Pamlico Sound. Pass through charming towns like Rodanthe, Avon, and Buxton, where you can explore historic lighthouses, pristine beaches, and wildlife refuges. Don’t miss the Cape Hatteras National Seashore, where you can climb the iconic lighthouse and enjoy a day of beachcombing and picnicking.
Tips:
- Take a ferry ride from Hatteras to Ocracoke Island for a unique experience.
- Stop at the Pea Island National Wildlife Refuge for birdwatching and nature trails.
Coastal Highway 17
Continue your journey south along Coastal Highway 17, which takes you through some of the most scenic and historic areas of the Eastern coast. This route winds through North and South Carolina, offering glimpses of picturesque marshlands, coastal forests, and charming small towns.
Tips:
- Visit the charming town of Beaufort, North Carolina, known for its historic homes, waterfront dining, and maritime museum.
- Explore the charming streets of Georgetown, South Carolina, with its historic district, waterfront park, and boutique shops.
Charleston to Savannah Scenic Route
The drive from Charleston, South Carolina, to Savannah, Georgia, is a journey through history and natural beauty. This route, approximately 108 miles, takes you past stunning coastal landscapes, moss-draped oaks, and historic plantations.
Tips:
- Stop at the Angel Oak Tree on Johns Island, a magnificent Southern live oak estimated to be over 400 years old.
- Visit the charming town of Beaufort, South Carolina, known for its antebellum architecture and scenic waterfront park.
Family Travel Tips
Taking a family road trip is an exciting adventure, but it comes with its own set of challenges, especially when traveling with children. Be sure to check out my favorite Travel Tips to ensure you have a memorable trip.
Educational and Fun Facts
Throughout your pirate-themed road trip, enrich the journey with fascinating facts and trivia about pirates and maritime history. These tidbits will captivate both kids and adults, adding an element of discovery and wonder to your adventure.
Pirate Facts and Trivia
- Blackbeard’s Fearsome Appearance: Blackbeard, whose real name was Edward Teach, was known for his intimidating presence. He would weave slow-burning fuses into his long beard and light them during battles, creating a fearsome, smoky aura around his head to intimidate his enemies.
- The Pirate Code: Pirates often operated under a set of rules known as the “Pirate Code.” These codes varied from ship to ship but commonly included rules about dividing plunder, maintaining discipline, and ensuring fair treatment of all crew members. Violators faced severe punishments, such as marooning or death.
- Pirate Flags: The iconic Jolly Roger flag, featuring a skull and crossbones, was used by pirates to signal their intent to attack. Different pirate captains had unique versions of the flag, often incorporating symbols like hourglasses, swords, or skeletons to strike fear into the hearts of their victims.
- Golden Age of Piracy: The period from the late 17th century to the early 18th century is known as the Golden Age of Piracy. During this time, piracy flourished in the Caribbean, the Americas, and the West African coast, with notorious pirates like Blackbeard, Calico Jack, and Anne Bonny making their mark on history.
- Pirate Ships: Pirates preferred fast, agile ships like sloops and schooners, which allowed them to outrun naval vessels and quickly navigate through shallow waters. These ships were often heavily armed and modified for speed and maneuverability.
Maritime History and Legends
- The Bermuda Triangle: The Bermuda Triangle, a region in the western part of the North Atlantic Ocean, is infamous for the mysterious disappearance of ships and airplanes. Some believe that the area is cursed or plagued by supernatural forces, while others attribute the phenomena to natural causes.
- Whale Hunting: In the 19th century, the whaling industry was a significant part of maritime history. Whalers ventured into treacherous waters to hunt whales for their oil, which was used to fuel lamps and make soap. The practice of whale hunting has since declined due to conservation efforts.
- Lighthouses: Lighthouses have guided sailors safely to shore for centuries. The oldest existing lighthouse in the United States is the Sandy Hook Lighthouse in New Jersey, which was first lit in 1764 and still stands today.
Encouraging Exploration
Embark on this pirate-themed road trip with a sense of adventure and curiosity. Each stop offers new discoveries and exciting opportunities for family bonding. Encourage your kids to ask questions, seek out stories, and imagine themselves as pirates on a quest for glory. Beyond the excitement, this trip is an opportunity to create lasting family memories. Shared experiences, laughter, and wonder will strengthen your bonds and leave a lasting impact.
Set sail with adventure, enjoy each other’s company, and create memories to cherish for a lifetime. Happy travels, mateys! 🏴☠️