Top Maryland Sightseeing Tours in 2026

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!

Explore Virginia’s Great Falls Park with this app-based self-guided hiking tour. Discover top highlights and hidden gems, including views of hidden waterfalls, the best rock climbing and rappelling spots, a route through the canals, and an abandoned colonial-era city. The app audio plays automatically using your smartphone’s GPS, making for a seamless way to explore. Note that park entry and parking fees are not included.

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.

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.

Baltimore's sassy seaside town played a critical role in defeating the British Navy (twice!) and has become our go-to neighborhood for live music, vintage shopping, and great eating. Meet sailors and sinners, Frederick Douglass and the woman who took over the town, the hotel that Under Armour built and the oldest house in Baltimore. Hear insider stories from a born and raise Baltimorean who loves Charm City. Fells Point history is as engaging as its architecture is charming. Crazy stone streets alert: wear sensible shoes!

Cruising through the calm waters of Baltimore's Inner Harbor, this 60-minute sunset sightseeing cruise offers a unique opportunity to witness the spectacular sunset and city lights reflecting off the water while admiring the natural beauty of the surrounding harbor. With a curated playlist of background music enhancing the ambiance, guests can relax with refreshing beverages and snacks available for purchase from the onboard full bar. Perfect for families and couples alike, this cashless cruise ensures a smooth experience as travelers take in the vibrant views of Baltimore.

From the National Aquarium to one of the wildest Super Bowls ever played, a mayor who swam in a seal pond to the only Outsider Art Museum in the country, the Civil War to a sinking hill Baltimore's Inner Harbor riches to rags to riches story has something for everyone. Starting at The Civil War Museum this walking tour ends at The American Visionary Art Museum, whose gift shop John Waters says is the best anywhere. Chock-a-block full of all-ages history and things to see and do and eat

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!

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.

Put a ghoulish twist on your night out with a haunted pub crawl through historic Annapolis. Visit three bars over the course of the night, each with a ghost story behind it that will scare you sober. Drinks available at your own purchase.

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.

Step aboard a classic vessel for a scenic Chesapeake Bay Bridge cruise. As you depart the dock in downtown Annapolis, you will pass along the seawall of the United States Naval Academy and out into open water. As you approach the Bay Bridge, keep an eye out for local wildlife, including osprey, eagles, rays, and even the occasional dolphin, while enjoying great outdoors sightseeing. Then, marvel at the twin spans of the bridge, one of the largest over-water structures in the world. Sit back and relax with a soft drink, beer, or wine available for purchase, and enjoy the sights on this 90-minute journey.

Cruise Baltimore and learn all about its rich history from the comfort of your own car with this self-guided audio driving tour. This app-based tour works with your smartphone to send you on a sightseeing route, aided by a live GPS map. Drive past sites like the USS Constellation, Fells Point, and Baltimore City Hall while listening to riveting tales of Baltimoreans such as Frederick Douglass and Edgar Allen Poe.

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.

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

Our Baltimore Cultural tour allow you to get a personal perspective of why Baltimore is called "Charm City".

See the highlights of Washington DC without having to rent a car or rely on public transportation by opting for a private tour of the city. Your driver will pick you up at your hotel, the airport, or Union Station and take you out to see sights such as the exterior of the U.S. Capitol building, the White House, the Martin Luther King, Jr. Memorial, and the Lincoln Memorial.

Get the most out of your trip to the East Coast on this 3-day sightseeing tour from Washington DC. At Niagara Falls State Park, admire the world-famous falls and upgrade to visit the Cave of the Winds, ride the Maid of the Mist, and more. Then, head to New York City, where you can explore the best of the Big Apple (and upgrade to add a Statue of Liberty cruise and other top experiences).

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.

Walk through Harpers Ferry's haunted history with this self-guided ghost tour. Explore eerie sites, including St. Peter’s Roman Catholic Church, the infamous John Brown’s Fort, and the mysterious Hog Alley. Listen to captivating audio narration that shares chilling tales of the town's dark past, local legends, and reported paranormal sightings. Perfect for history enthusiasts and those curious about the supernatural, this tour lets you uncover the secrets of Harpers Ferry at your own pace. Experience the thrill of the unknown while wandering through historic streets and sites steeped in mystery. - Self-guided audio tour with GPS navigation for easy exploration - Discover haunted sites like John Brown's Fort and Harpers Cemetery - Flexible timing: start when you’re ready and pause whenever you want - Recommended for history lovers and those interested in local legends

Enjoy a relaxing trip out on the Chesapeake Bay with this intimate, small-group sailing tour. Pick from several convenient start times, meet your captain and crew at the dock, and hop aboard your vessel—the Eternal Hope, a 42-foot (13-meter) sailing yacht. Then, sit back and take in the views, spot wildlife, and soak up the sea breezes as you head out on the water.

Enjoy a comfortable, one-of-a-kind way to explore the nation's capital on this private limousine tour. Meet your guide at your preferred Washington DC, Virginia, or Maryland address, and hop aboard your luxury vehicle. In the space of just half a day, you'll see dozens of Washington DC's top landmarks, from the White House and Jefferson Memorial to the Supreme Court, Library of Congress, and much more.

Experience a quieter, more intimate cherry blossom viewing on this half-day tour to Kenwood, one of the region’s most exclusive spring destinations. Skip the crowded Tidal Basin and wander through residential streets lined with hundreds of mature cherry trees, creating a canopy of pink blooms overhead. This tour offers time for photos, peaceful walks, and insights into the Kenwood community’s history and tradition of cherry planting. Perfect for travelers seeking a relaxed, beautiful seasonal escape right outside Washington. Reserved Air and Space Museum Ticket Included for a self-guided visit the next day (gift item provided by the tour operator and customer will not get extra charged)