Historic Trails and Coastal Escapes

Upon arrival in Washington, DC, you will make your way to your hotel for a three-night stay, either by taxi or via the convenient Silver Line on the Metro. To make the most of your time in the nation’s capital, you’ll have two-day access to a Hop-on, Hop-off sightseeing bus, allowing you to explore the city’s most famous landmarks at your own pace. From the majestic U.S. Capitol and the iconic White House to the towering Washington Monument and the reflective Lincoln Memorial, this tour ensures you experience all the highlights of the National Mall and beyond. Along the way, you can hop off to visit some of the city’s incredible free museums, including the Smithsonian National Air and Space Museum, where you can see historic aircraft and space artifacts, and the National Museum of African American History and Culture, which offers a powerful journey through centuries of history, culture, and achievements. In addition to sightseeing, you may choose to explore charming Georgetown, take a scenic stroll along the Tidal Basin, or enjoy the vibrant dining scene in neighbourhoods like Dupont Circle or The Wharf.

This morning, you will collect your car and depart Washington, D.C. as you make your way south to Virginia Beach, a coastal gem known for its sandy shores and lively oceanfront. Upon arrival, check in to your hotel and begin exploring this vibrant beachside destination. Take a stroll or rent a bike to ride along the famous three-mile-long Virginia Beach Boardwalk, lined with oceanfront cafés, shops, and entertainment. The beach itself offers plenty of opportunities to relax on the golden sand, swim in the Atlantic, or try out water activities like kayaking, paddleboarding, or even dolphin-watching tours. If you’re feeling adventurous, head to First Landing State Park for scenic nature trails or visit the Virginia Aquarium & Marine Science Center to learn about the region’s marine life. As evening falls, dine at one of the many seafood restaurants overlooking the water, where you can enjoy freshly caught oysters and other coastal specialties.

On Day 6, you will leave the coastal charm of Virginia Beach behind and travel inland to Williamsburg, a historic gem that takes you back to the days of colonial America. To enhance your experience, we have included a Colonial Williamsburg pass, offering you the opportunity to learn about life in colonial America and the events leading up to the American Revolution. Stroll through the beautifully preserved 18th-century streets, tour government buildings and family homes, and witness skilled tradespeople such as blacksmiths, printers, and milliners using traditional 1700s techniques. Historical reenactments bring the past to life as expert interpreters recreate moments from America’s early history, providing a fascinating and interactive experience.

If you’re looking for more adventure, nearby Jamestown and Yorktown provide additional historical sites that played crucial roles in the birth of the nation. In the evenings, enjoy a meal at one of Williamsburg’s charming taverns, where you can dine on authentic colonial-inspired cuisine by candlelight.

Journey west into the breathtaking landscapes of Shenandoah National Park for a two-night stay at Skyland Lodge, a peaceful retreat nestled within the park (subject to availability). Along the way, consider making a stop at Monticello, the magnificent home of former President Thomas Jefferson. This UNESCO World Heritage Site offers a fascinating insight into Jefferson’s life, his contributions to American history, and the architectural brilliance of his estate. Tour the grand house, stroll through the beautifully landscaped gardens, and learn about the daily life on this historic plantation before continuing your scenic drive into the Blue Ridge Mountains.

Once inside Shenandoah National Park, prepare to be captivated by its stunning natural beauty. Skyland Lodge, perched along the famous Skyline Drive, offers sweeping mountain views and easy access to some of the park’s best hiking trails. Spend your time here exploring miles of scenic trails, from leisurely walks to more challenging hikes like the Stony Man Trail, which rewards you with breathtaking panoramic views. Wildlife enthusiasts may spot deer, black bears, and a variety of bird species, while those looking for a more relaxed experience can simply soak in the tranquility of the mountains from one of the scenic overlooks. Consider taking a horseback riding tour through the forest or enjoying a peaceful drive along Skyline Drive, stopping at viewpoints to admire the rolling hills and valleys stretching into the distance. In the evenings, unwind at Skyland Lodge’s restaurant, where you can enjoy hearty Appalachian-inspired cuisine with a view of the sun setting over the mountains.

Leave the serene beauty of Shenandoah National Park behind and travel north to Frederick, Maryland, a charming city rich in history and culture. En route, consider stopping at Luray Caverns, one of the most spectacular cave systems in the United States. Located in the Shenandoah Valley, these underground caverns are famous for their towering stalactites and stalagmites, shimmering pools, and cathedral-sized chambers. One of the highlights is the Great Stalacpipe Organ, an incredible natural instrument that produces musical tones by striking the rock formations. A guided tour will lead you through this otherworldly landscape, offering a fascinating glimpse into the geological wonders formed over millions of years.

After exploring Luray Caverns, continue your journey to Frederick, where a mix of historic charm and modern vibrancy awaits. Nestled at the crossroads of Civil War history and scenic landscapes, Frederick offers a variety of attractions to explore. Walk through the beautifully preserved Historic Downtown, where cobblestone streets are lined with independent boutiques, art galleries, and inviting cafés. History enthusiasts may want to visit the National Museum of Civil War Medicine, which provides a compelling look into medical advancements during the war. Another must-see is Monocacy National Battlefield, where you can learn about the pivotal battle fought here in 1864. If you prefer outdoor activities, take a relaxing stroll along Carroll Creek Park, a picturesque waterfront area with walkways, fountains, and public art displays. In the evening, enjoy a meal at one of Frederick’s many excellent restaurants, where farm-to-table dining and craft breweries offer a true taste of Maryland’s culinary scene.

Make your way east to Baltimore, a vibrant harbour city known for its rich maritime history, cultural attractions, and dynamic waterfront. Upon arrival, begin your exploration at the Inner Harbor, the heart of Baltimore’s attractions. Here, you can visit the historic USS Constellation, the last Civil War-era ship still afloat, or explore the fascinating exhibits at the National Aquarium, home to thousands of marine creatures, including sharks, sea turtles, and dolphins. For a deeper dive into the city’s seafaring past, stop by the Baltimore Museum of Industry, which showcases the city’s role in American innovation. Strolling along the harbour, you’ll find a variety of waterfront dining options where you can savour the city’s famous Maryland crab cakes.

Head to Fell’s Point, a historic waterfront district known for its cobblestone streets, colonial-era buildings, and lively pubs. This area is perfect for boutique shopping, people-watching, or enjoying a waterfront meal. If you’re an art enthusiast, visit The Walters Art Museum or the Baltimore Museum of Art, which houses an impressive collection, including works by Matisse and Picasso. Sports fans may want to tour Oriole Park at Camden Yards, one of the most iconic baseball stadiums in the country. Before leaving Baltimore, take a trip to Fort McHenry National Monument, the site that inspired Francis Scott Key to write The Star-Spangled Banner. This historic fort offers stunning harbor views and a fascinating look into America’s past. As your time in Baltimore comes to an end, you’ll leave with a deeper appreciation for this dynamic and history-rich city.

Leave the bustling city of Baltimore behind and travel to Annapolis, Maryland’s charming capital on the shores of the Chesapeake Bay. Known for its colonial history, maritime heritage, and picturesque waterfront, Annapolis offers a delightful blend of history, culture, and coastal beauty. Start your visit with a stroll through the Historic District, where you’ll find beautifully preserved 18th-century architecture, including the Maryland State House, the oldest state capitol still in continuous legislative use. Continue to the U.S. Naval Academy, one of the city's most iconic landmarks, where you can take a guided tour of the impressive campus and visit the Naval Academy Museum to learn about the history of the U.S. Navy. Afterward, head to City Dock, the heart of Annapolis’ waterfront, where you can watch boats sailing in and out of the harbour, browse quaint shops, or enjoy fresh seafood at one of the many waterfront restaurants.

During your time here, immerse yourself in Annapolis’ maritime culture with a scenic boat tour along the Chesapeake Bay, offering stunning views of the city’s coastline and historic lighthouses. If you prefer to stay on land, visit the Annapolis Maritime Museum to learn about the region’s deep connection to the sea. Outdoor enthusiasts can take a leisurely walk along the trails of Quiet Waters Park, a serene spot offering beautiful views of the South River. History buffs may want to visit the William Paca House and Garden, a beautifully restored 18th-century Georgian mansion once home to a signer of the Declaration of Independence. Before concluding your stay, explore Main Street, a lively area lined with boutique shops, art galleries, and cosy cafés, perfect for a final taste of Annapolis’ charm. As your time in Maryland’s capital comes to an end, you’ll leave with wonderful memories of its rich history, scenic waterfront, and warm hospitality.

Your tour ends when you return your rental car to the agreed drop-off point. Alternatively, speak with your Discover North America Travel Specialist about possible trip extensions.