Day 01: Virginia beach, Virginia

Your five-day Virginia getaway begins in Virginia Beach. Whether you like tranquil and serene beaches, or a more cosmopolitan vibe, the Virginia Beach area will have a beach that is perfect for you. Not only are the beaches along the Atlantic Ocean and Chesapeake Bay pristine, with beautiful blue waters, Virginia Beach offers a variety of truly unique and unforgettable experiences. Try your hand at horseback riding on the beach, or for those who want to get more up close and personal with the water and the wildlife, kayaking with dolphins is sure to leave a lasting impression. Ride the gentle waves in sit-on-top ocean kayaks, while you take a guided tour and discover the fascinating and fun world of the bottlenose dolphins that call these waters home. Explore the ViBe Creative District, located conveniently within the oceanfront area of Virginia Beach. This cultural arts enclave is a local hotspot where creative businesses have come together to share their passion and love of the arts with visitors and locals alike. After getting in touch with your creativity and artsy vibes, visit the Military Aviation Museum, home to one of the largest private collections of World War I and World War II era military aircraft in the world. Enjoy the heritage and machinery of these inspiring aircraft, many of which are airworthy and flown at the museum during flight demonstrations and at air shows throughout the year – they even offer rides to the public! 

Day 02: Norfolk, Virginia

Begin your second day in Virginia by driving to nearby Norfolk and exploring the Hampton Roads Naval Museum, an official museum of the United States Navy, dedicated to the study of more than 240 years of naval history in the Hampton Roads region. Take a self-guided tour of the Battleship Wisconsin, one of the largest and last battleships ever built by the U.S. Navy, which rests in Norfolk’s waters. Now it’s time to explore the new and revitalized Waterside District, an area buzzing with trendy restaurants and entertainment. Dining options are plentiful and you can even indulge your sweet tooth at Carolina Cupcakery, an establishment recently featured on the Food Network’s hit television series Cupcake Wars.Spend your afternoon by enjoying a combination of the Norfolk area’s top attractions, including the Norfolk Botanical Garden (Virginia’s largest botanical garden), the Virginia Zoological Park, or the Chrysler Museum of Art. Space enthusiasts will love a trip to the Virginia Air & Space Center located in nearby Hampton, Virginia. Serving as the official visitor center of NASA Langley Research Center, the Virginia Air & Space Center features a variety of interactive STEM (science, technology, engineering, and mathematics) exhibits, more than 30 historic aircraft, a hands-on space gallery, and unique space flight artifacts. 

Day 03: Charlottesville, Virginia

Discover the rolling hills of Central Virginia, and the quaint, historic city of Charlottesville. Offering a superb taste of Virginia’s history and charm, Charlottesville is home to Thomas Jefferson’s Monticello and the University of Virginia (both UNESCO World Heritage sites), more than 30 wineries, and a charming pedestrian avenue filled with restaurants and boutique shops. Visit Thomas Jefferson’s Monticello to learn more about how the third President of the United States lived at his beloved mountaintop home. Explore the grounds, including Jefferson’s prized gardens, located adjacent to the home. If more history is what you crave, the home of President James Monroe (Highland) is located a short drive to the east, and the home of President James Madison (Montpelier) can be reached in approximately 30 minutes. Enjoy lunch at the historic Michie Tavern, known for its scrumptious Southern fare – the fried chicken is a must! Then take a short drive to the top of Carter Mountain where you will find an orchard ripe with apples and peaches depending on the season, plus panoramic views of Charlottesville and the surrounding Blue Ridge Mountains. If you look carefully, you will be able to see the prestigious University of Virginia, designed by Thomas Jefferson himself. 

Next up is a visit to Charlottesville wine country. With more than 30 vineyards and wineries located along the Monticello Wine Trail, the landscape is teeming with grapevines, just as Jefferson had envisioned several hundred years before. In addition to wineries, you can also sample offerings from several craft breweries, artisanal cideries, and distilleries. 

One of Charlottesville’s most popular attractions is the historic pedestrian Downtown Mall. This eight- block avenue paved with brick, runs through the heart of Charlottesville and serves as a culinary, shopping, and arts hub. You can shop at one of the locally-owned boutiques, then dine and grab a drink at one of the many unique, trendy, or upscale restaurants. Live music and performances also regularly take place at the historic Paramount Theater, The Jefferson Theater, the Southern Café & Music Hall, and the Sprint Pavilion, an outdoor amphitheater on the Downtown Mall.

Day 04: Charlottesville & Staunton, Virginia

Start day 4 with a breakfast from the legendary Bodo’s Bagels, an iconic Charlottesville establishment. This restaurant has gained national recognition over the years for the bagel bliss it consistently provides its loyal patrons. Spend your morning strolling the grounds of the prestigious University of Virginia, which Thomas Jefferson founded and designed. Before departing Charlottesville, visit the room once occupied by the melancholic writer Edgar Allan Poe, when he was a student at the University of Virginia, and then look across the street, where several panels of the Berlin Wall are on display. 

A short and scenic drive will take you up and over mountains and then finally back down into the Shenandoah Valley and the idyllic city of Staunton. Like Charlottesville, Staunton is a relatively small city, but it offers a wide array of activities and attractions. Start your afternoon in Stauton with a visit to the Frontier Culture Museum. This living-history museum is one of Staunton’s top attractions and tells the story of the people who migrated from the Old World to America and the lives that they created for themselves in the Shenandoah Valley. Stop by the Woodrow Wilson Presidential Library and Museum for another interesting dose of local Virginia history. Woodrow Wilson, the nation’s 28th President, was born in Staunton and served as the leader of the country from 1913 to 1921. Adjacent to this museum is Wilson’s actual birthplace, which is available for tours. 

Enjoy a delightful dinner at one of Staunton’s popular restaurants before settling in for a comfortable night at the Stonewall Jackson Hotel, located in the heart of downtown Staunton.

Day 05: Luray Caverns, then depart for North Virginia

Depart Staunton for Skyline Drive, a scenic highway that twists and turns through the Shenandoah National Park. A drive on this renowned roadway will present you with Virginia’s breathtaking beauty, at a slow, relaxed pace, while driving at several thousand feet above sea level, surrounded by majestic mountains. There are also scenic overlooks, hiking options, or you can get lunch at Skyland Lodge. As you drive north on this scenic route, make a detour to Luray Caverns, the largest caverns in the eastern United States. You will feel like you have descended into another world, with large stalactites and stalagmites protruding from every corner of these mammoth caves. This geological wonder is also home to the Great Stalacpipe Organ, the world’s largest musical instrument, which will serenade you with its uniquely unforgettable and haunting tones. Depart Luray Caverns for Dulles International Airport to begin your journey home. Before you catch your flight, spend some time at the impressive Steven F. Udvar-Hazy National Air & Space Museum or do some shopping at Leesburg Premium Corner Outlets to pick up a few souvenirs to bring back home, reminding you fondly of your visit to Virginia for many years to come.