7-Day Relaxing Driving Itinerary: Virginia Beach → Richmond → Washington DC → Clemmons (Winston‑Salem) → Nashville → Jackson (MS) → New Orleans → Houston
Viewed by 86 travelers
Day 1: Coastal start
Virginia Beach, VA → Richmond, VA on September 8, 2025
Classic local breakfast spot with Southern-style breakfasts and coffee; great way to fuel up before the drive. Check hours (typically open from early morning around 7:00am).
Comfort-food deli in Richmond with creative sandwiches and Jewish-deli classics; good midday refuel and walkable from downtown sights (typically open mornings–afternoons).
A large, free-to-enter museum with encyclopedic collections and a peaceful sculpture garden; museum hours typically start at 10:00am and close around 5:00pm — perfect for an afternoon visit.
Historic estate and gardens with walking paths and a small animal exhibit; open daylight hours (frequently 9:00am–5:00pm), a relaxing way to unwind before dinner.
Popular Richmond restaurant offering elevated Southern plates in a comfortable setting; usually opens for dinner around 5:00pm — reservations recommended for a relaxed evening.
Pick 1–2 Smithsonian museums (American History, Natural History, or National Museum of African American History & Culture); Smithsonian museums are free and generally open 10:00am–5:30pm — plan visits and reserve timed entry if required.
Historic Washington grille near the White House with classic American fare; a convenient and atmospheric spot for lunch (open throughout the day, but expect a line at peak times).
Farm-to-table restaurant with a broad menu and good cocktails, comfortable for couples; typically open evenings from early dinner hours (reservations recommended).
Historic house museum and five-acre formal garden with walking paths and a calming atmosphere; Reynolda Gardens and museum hours typically run from mid-morning to late afternoon (check seasonal hours).
Upscale-casual Southern dining in downtown Winston‑Salem, ideal for a relaxed, romantic dinner; usually opens for dinner around 5:00pm — reservations recommended.
Long driving day (~7–8 hours). Plan one or two scenic breaks to stretch; I-40 is the main route most of the way, so allow for rest and gas stops for a relaxed pace.
Pancake Pantry is a Nashville institution for sweet and savory breakfast (expect a line) or choose Puckett’s for Southern breakfast in a more relaxed setting; most open early (7:00–8:00am).
Walk the Broadway strip and snap photos of the Ryman and live-music venues; shops and attractions are open during the day and make for a relaxed morning wandering.
Popular, comfortable spot serving elevated Southern-American food — ideal for a late dinner after arrival (check nightly hours and reserve if possible).
Take the St. Charles streetcar through the Garden District for a relaxed scenic ride and mansion-spotting; the streetcar runs most of the day into evening (fare applies).
Choose GW Fins for excellent seafood (happy to accommodate reservations) or Commander’s Palace for an elevated Creole experience (reservations recommended, check dress code and opening times).
Preservation Hall offers intimate traditional jazz performances (ticketed shows in the evening); Frenchmen Street has a cluster of live-music venues for a more informal night out — check show times and reserve tickets where possible.
If your timing allows, Space Center Houston is open roughly 10:00am–5:00pm and is a memorable stop for couples who enjoy science and history (check same-day hours and last-entry times).
Hugo’s offers refined Mexican cuisine in Montrose and makes an excellent final-night dinner (reservations recommended), or try any local BBQ or Tex-Mex spot to round out the trip.