Top Maryland Private Sightseeing Tours

Experience Ocean City, Maryland, like never before with our exhilarating beach helicopter tour! Departing from Ocean City Municipal Airport, just two miles south of the iconic boardwalk, this 15-mile aerial adventure offers spectacular views of the Atlantic Ocean, the bustling boardwalk, and the breathtaking beaches that make this coastal town a favorite destination. The Beach Tour is a fan favorite, boasting a 4.9-star rating from over 370 reviews. Whether you're a first-time flyer or a seasoned aviation enthusiast, this tour promises an unforgettable perspective of Ocean City's vibrant shoreline. With top-tier customer service and an unwavering commitment to safety—evidenced by a perfect zero-incident record—you can relax and enjoy the ride, knowing you're in expert hands. Don't miss out on this unique opportunity to see Ocean City from the skies. Book your beach helicopter tour today and create memories that will last a lifetime!

This tour is all about the real Baltimore, the one shaped by sports, industry, invention, authors and community. Along the way, you’ll see statues that celebrate hometown heroes, a clock tower that once guided the city’s time, a dental museum that’s more fascinating than it sounds, a historic market, and yes — Edgar Allan Poe’s grave. All not to be missed sites. And for this price? It's the best deal in town. This tour is on our walking tour app, it's location aware, smartphone guided, hands free, go at your own pace, not big groups, and go anytime.

Celebrate in style with MyFlight Tours' private Baltimore downtown helicopter tour! Perfect for birthdays, anniversaries, and special occasions, this unforgettable experience offers stunning views of the city’s iconic skyline as soon as you lift off from the pier. Soar over the Inner Harbor, marvel at the towering Transamerica Tower, and glide past M&T Bank Stadium and Baltimore’s vibrant neighborhoods. Make your next celebration one to remember from the skies!

Tick off the highlights of Washington D.C. during this private, half-day tour. Customize your own itinerary, selecting a range of local sights to visit. Optional stops include the White House, Arlington National Cemetery, Lincoln Memorial, or the National Museum of American History at the Smithsonian. Air-conditioned vehicle transfers with hotel pickup and drop-off are provided.

Winding through trails, town, and time, this self-guided audio tour explores the powerful stories and landscapes of Harpers Ferry. Over the course of 3 miles, you’ll journey from quiet riverbanks to dramatic ridgelines, past weathered ruins and historic landmarks that shaped the course of American history. This is no ordinary walk—it’s a deep dive into a place where freedom was fought for, ideas were tested, and the nation’s future often hung in the balance. From John Brown’s bold raid to the legacy of Storer College, each stop brings to life a new chapter of ambition, conflict, and change. With GPS-triggered audio guiding your way, you can explore at your own pace—pausing for a scenic view or reflecting at a historic site. Whether you’re a history lover, a curious traveler, or just here for the beauty, this tour offers a moving and memorable way to experience Harpers Ferry.

Your tour will take you through the historic downtown area known as Old Towne, where Victorian-style buildings and century-old businesses tell the incredible story of the "Petticoat Regime"—the pioneering women who owned and operated 30 out of 32 hotels by 1926. We'll start at the Ocean City Life-Saving Museum near the inlet and walk north along the Boardwalk and Baltimore Avenue, ending at the famous Thrasher's French Fries stand.You will hear stories about remarkable businesswomen like Zipporah "Zippy" Lewis, who lived in a house made from shipwreck wood and left her land to her daughters instead of her sons, and Ella Phillips Dennis, who along with other women, created one of America's most successful female-dominated business communities during an era when women weren't even allowed to vote. Go at your own pace, anytime. This tour is smartphone guided and never expires. It's all on your walking tour app.

The Battle of Antietam is the single most fatal battle in American military history. Over 23,000 soldiers were killed, wounded, or missing after this 12-hour conflict; this private self-guided audio tour uses a GPS-powered app to guide your drive through key landmarks. You’ll need a separate entry ticket to access the battlefield; lifetime access lets you replay the tour anytime.

This private walking tour offers a calm and comfortable introduction to historic Annapolis at an easy pace. You explore the city as residents once did, along flat streets and quiet waterfront paths shaped by daily life and civic tradition. Clear storytelling brings forward the voices of merchants, lawmakers, families, and sailors who defined early Annapolis. Your walk begins near the harbor where trade and community met. The route continues through peaceful public spaces with time to pause, sit, and enjoy the surroundings. Stories focus on early American governance, maritime heritage, and local customs explained in a relaxed and engaging way. This experience suits travelers aged 50+ who value culture, history, and thoughtful narration without rushing. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Discover the highlights of Washington D.C. during this four-hour private tour. Follow a customizable itinerary with a seasoned guide and long-time local resident. Understand the history and significance of iconic landmarks like the White House, Supreme Court, Lincoln Memorial, and more—with plenty of get-down photo stops along the way. Enjoy complimentary bottled water and door-to-door transfers from the airport or your DC Metro Area hotel.

Rarely are guests able to relive history in a relaxed, conversational atmosphere with guides who are local to the area and want to share what makes their home special to them. Along with the 300+ year history of the region, your private driver will share with you stories, show you other points of interest, fill you in on the best restaurants or other attractions that only the locals know. This is a chance to experience Harpers Ferry and Jefferson County not just in times long past but as a thriving and diverse region. Many of the guests are looking for authentic interactions on a personal level that are more real than just a history tour. With facts about how George Washington and his family shaped the area and the country is to where the best ice cream shop is along the way, we strive to make your journey with us is like traveling with a friend through the centuries!

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in the picturesque views of St. Michaels, MD. Your journey includes gliding through the harbor and possibly spotting wildlife like osprey and dolphins. Enjoy a friendly crew that shares captivating stories about the area and sailing. Whether you’re looking for a fun family outing or a peaceful escape, this sailing experience is perfect for all ages. - Duration: 2 hours, with daily availability - Max capacity of 13 guests, ensuring a personalized experience - Beer and wine tasting available for adults, with complimentary water - Departing from Harbour Inn, 101 N Harbor Road, St. Michaels, MD

Explore the best that the United States capital has to offer when you book this half-day, private sightseeing tour by mini-bus. Tours can accommodate up to 30 people, great for company events or large parties, and itineraries are completely customizable. Choose to see top monuments like the White House, Lincoln Memorial, and National Mall, or make stops at any location of your choosing in the district.

Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor and US Naval Academy. We'll see the Georgian mansions, the iconic Maryland State House, and much more as you learn the fascinating story of the town. We'll see where the Treaty of Paris was signed (bringing to a conclusion the Revolutionary War) and where General Washington resigned as general, thus becoming the "greatest man in the world" and the "American Cincinnatus. " We'll explore the campuses of two institutes of learning that have shaped American culture. We'll walk along the city dock, harbor, and see the view to the Chesapeake Bay and wider world. I'll also share personal and family stories along the way, to add a personal dimension to the tour. I welcome all questions and special interests for our tour!

Discover the charm of Bethesda on this engaging two-hour tour that blends shopping and food at one of the area's most upscale shopping and dining districts, Bethesda Row! We’ll explore this lively, walkable district, popping into key shops you love while also sampling some of the area’s foodie highlights. Along the way, I’ll introduce you to some of my favorite local shops —think artisan gelato makers, talented bakers, specialty coffee roasters, and neighborhood chefs. Enjoy curated samples and warm welcomes from the people behind these beloved businesses, offering a more personal and insider experience than you’d typically find on your own. This experience is ideal for travelers looking to experience the local lifestyle and venture beyond the typical tourist attractions, this immersive tour offers a fun and flavorful introduction to Bethesda Row’s vibrant shopping, dining, and culinary scene.

Looking for Washington DC private tours? Explore DC with World’s Five Star Limo Service. This Mercedes Van Tour is for up to 14 people. We provide pick up and drop off at any desired place in Washington DC, Virginia and Maryland. Distinguish customer service, modified limos and reliability shape our Tour Quality. Capture yourself in front of most of the historical buildings in the shortest possible time.

This private walking tour introduces historic ghost stories through the calm streets of Annapolis at a relaxed and comfortable pace. You explore the city where colonial history and long-shared legends quietly intersect. Storytelling focuses on documented events, respected local traditions, and the people who shaped early America. Beginning near the Maryland State House, you hear how politics, power, and personal lives left traces still discussed today. Around Church Circle, stories reflect faith, daily life, and the rhythm of an 18th-century town. Near the William Paca House, refined society and private lives reveal another layer of Annapolis history. The walk concludes by the City Dock, where maritime life and waterfront legends complete the experience. This tour is designed for travelers who value history, and storytelling without haste. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Patterson Park is a rare blend of natural beauty, history, and everyday neighborhood life, often called the city’s “Best Backyard.” On this self-guided walking tour, you’ll find out how the park – which stretches across more than 130 acres in the heart of East Baltimore – has served Baltimoreans for over two centuries. You’ll also hear how it began as farmland, then became a defensive stronghold during the War of 1812, and why today it remains one of Baltimore’s most cherished public spaces. You’ll pass the Monument honoring Revolutionary War hero Casimir Pulaski, and wind your way over Harris Creek, one of Baltimore’s “ghost rivers” that’s now hidden underground. You’ll see the mile-long earthworks built by residents to prevent the British from attacking the city. You’ll also walk where President Abraham Lincoln ordered troops to camp while keeping peace after pro-Confederate residents threatened more violence after the Pratt Street Riot of 1861.

Perfect for Individuals or Small Groups. We offer guided tours, concierge service and airport transfers throughout the Washington DC , Maryland and Northern Virginia areas.

Go on a discovery tour with our E-scavenger hunt in Baltimore. You go on a search for the city's treasures with your family or friends. Use GPS to get to the right locations. At those location you'll play fun assignments and get interesting facts about the location or the city. Will you set the top score in Baltimore? This E-scavenger hunt is a unique way to discover a city. It will give you a fantastic day in Baltimore. Decide for yourself when you start, pause and end. The E-scavenger hunt is fun to do and also teaches you about the city. No time limits or age limits! Instructions for starting the tour will be given after booking. You can do this tour whenever you choose.

Explore the Antietam National Battlefield, the site of the bloodiest single day in American military history. This self-guided driving tour traces the pivotal battle of September 1862, allowing you to discover key sites like Dunker Church and Burnside Bridge at your own pace. Utilize GPS-triggered narration that brings historical stories to life as you navigate through serene landscapes that witnessed fierce combat. Reflect on the sacrifices made here and understand how this battle influenced the Emancipation Proclamation and the future of the nation. - Self-guided driving tour with GPS-triggered narration - Visit historic sites including Miller Cornfield and Bloody Lane - Flexible exploration: take your time at various landmarks - Total tour duration of 2 to 4 hours, designed for easy stops along the route

Assateague Island is famous for its rustic, coastal scenery and wild horses—but also swarms of biting insects, making it tricky to visit by land. On this private hour-long cruise, take in the island’s stunning landscapes and watch horses graze along the marshy shorelines while relaxing comfortably on your own chartered, captain-driven skiff boat.

Enjoy a private, full-day historical adventure through West Virginia and Maryland with your own personal driver-guide. Visit the charming town of Harpers Ferry, the Bolivar Heights Battlefield, and the fascinating National Museum of Civil War Medicine. End your journey with a relaxing stroll along Carroll Creek Park in Frederick. Perfect for couples, families, or small groups who want a personalized, comfortable, and flexible travel experience filled with history, culture, and scenic beauty.

Your Private Sunset Cruise offers a truly unique and intimate experience on the Chesapeake Bay—the nation’s largest estuary. Unlike standard group tours, our cruise is completely private, giving you and your guests uninterrupted time to relax, celebrate, and soak in the stunning natural beauty around you. As the sun sets over the Bay, you’ll enjoy complimentary sparkling cider, light snacks, and refreshing sparkling water, creating an atmosphere that feels both luxurious and personal. Designed for couples, families, and friends, this experience blends comfort, exclusivity, and unmatched scenic views. With limited availability, our sunset cruise provides a rare opportunity to create unforgettable moments on the water—making your evening not just a tour, but a cherished memory.