Day 1 & 2
Washington D.C.
Fly into Washington D.C. and take the Silver Line metro straight from the airport - just $6 for a quick ride into downtown! It’s one of the easiest and most affordable ways to get into the city. Washington D.C. offers a perfect mix of classic landmarks, free attractions, and cutting-edge cultural experiences. Explore the world-class Smithsonian museums, or check out the latest additions like the National Museum of African American History and Culture. Enjoy the thriving culinary scene with top-notch restaurants, craft cocktail bars, and rooftop lounges. Whether you’re strolling through vibrant neighbourhoods like Shaw or Georgetown, hitting up local boutiques, or soaking in the city's lively nightlife.
Overnight: The Churchill Hotel or upgrade to Dupont Circle Hotel or similar
Day 3
Washington D.C. - Charlottesville, VA (115 miles)
Pick up your rental car near the Washington Hilton to skip the hassle of heading back to the airport. From there, hit the road towards the Blue Ridge Parkway, where you'll climb over 3,000 feet to take in breathtaking views of Skyline Drive through the scenic Shenandoah National Park. Afterward, make your way to Charlottesville, the historic hometown of Thomas Jefferson. Today, Charlottesville is a lively college town with a mix of unique shops, cozy cafes, trendy restaurants, and charming tea rooms. Whether you're wandering around the University of Virginia campus or exploring the local art scene, this town offers a perfect blend of history and modern charm.
Overnight: Home2 Suites by Hilton Charlottesville Downtown or upgrade to Omni Charlottesville or similar
Day 4 & 5
Charlottesville, VA - Richmond, VA (73 miles)
Before heading to Richmond, visit Thomas Jefferson’s Monticello, one of America’s most beautiful homes. Tour the house and gardens, immersing yourself in the history of this iconic landmark. Afterward, continue to Richmond, the capital of the Confederacy, which remains one of the most charming cities in the South. Once industrial waterfront warehouses have been converted into trendy shops, and areas like Shockoe Bottom and Shockoe Slip are full of vibrant restaurants, entertainment, and boutiques.
Richmond also boasts rich historical attractions, including the Museum & White House of the Confederacy and the Edgar Allan Poe Museum. Drive along Monument Avenue to see its iconic statues or explore Maymont, a stunning plantation-style estate with picturesque gardens. With its mix of history, culture, and modern flair, Richmond offers a captivating experience that blends southern tradition with a progressive vibe.
Overnight: Hilton Richmond Downtown or upgrade to Omni Richmond Hotel or similar
Day 6
Richmond, VA - Williamsburg, VA (52 miles)
Today, explore Colonial Williamsburg, the most meticulously restored 18th-century town in the U.S. The immersive restoration makes it feel as though you’ve stepped back in time, experiencing life in a colonial crown colony over 300 years ago. Wander the cobblestone streets, visit historic homes, and interact with costumed interpreters to truly transport yourself to the past.
Overnight: Homewood Suites by Hilton Williamsburg or similar
Day 7 & 8
Williamsburg, VA - Virginia Beach, VA (60 miles)
Leave Williamsburg and head to Jamestown, the first permanent English settlement in America, founded in 1607. Step back in time as you explore this historic site, where the early struggles of settlers paved the way for the nation’s future. Next, visit Yorktown, where the decisive battle of the American Revolution led to the birth of the United States.
Afterwards, continue to Virginia Beach, home to the world’s longest pleasure beach. Enjoy the sun, sand, and ocean views, and dine at Waterman’s Beachwood Grill, known for its excellent seafood and oceanfront setting. As the day winds down, the beachfront comes alive with energy, offering the perfect spot for cocktails on the boardwalk while watching the stunning sunset over the Atlantic. Whether you're soaking in history or enjoying coastal relaxation, this part of Virginia provides the perfect mix of heritage, natural beauty, and seaside fun.
Overnight: Boardwalk Resort and Villas or upgrade to The Historic Cavalier Hotel and Beach Club or similar
Day 9
Virginia Beach, VA - Annapolis, MD (241 miles)
Head to Annapolis, the "Yachting Capital" of the Chesapeake, where the relaxed vibe and breathtaking views await. Explore the Maryland State House, completed in 1779, offering views of the town's historic baroque streets. Wander through narrow streets lined with charming homes and buildings, and enjoy the lively waterfront, perfect for ship-watching. The Market House, with its bustling cafes and shops, provides a great spot to unwind. With its rich history, coastal beauty, and local flavors, Annapolis offers a perfect blend of relaxation and exploration in the heart of the Chesapeake Bay.
Overnight: Hilton Garden Inn Annapolis Downtown or upgrade to Graduate by Hilton Annapolis or similar
Day 10
Annapolis, MD - Baltimore, MD (31 miles)
Drive to “Charm City” – Baltimore, where shopping is a treat, offering everything from upscale malls to trendy designer boutiques. The city is also known for its vibrant food scene, with fantastic restaurants and the lively Fells Point district, where historic bars and pubs have been beautifully restored. Be sure to try Baltimore's famous crab dishes, a local specialty. Explore the bustling Inner Harbor, home to the renowned National Aquarium, one of the best in the country. With its mix of history, great food, and lively atmosphere, Baltimore offers something for everyone.
Overnight: Hampton Inn & Suites Baltimore Inner Harbor or upgrade to Hotel Monaco Baltimore or similar
Day 11
Baltimore, MD - Washington D.C. (41 miles)
On your way back to Washington D.C., make a stop at Mount Vernon, the historic home of George Washington. Explore the beautifully preserved estate, including the mansion, gardens, and fascinating exhibits that provide insight into the life of America’s first president. After soaking in the history, continue your journey to the airport for your flight home, reflecting on the unforgettable experiences and landmarks you've encountered during your trip.
