Experience the Best of Coastal Virginia in a Long Weekend
HOT TAKE: Working remotely doesn’t have to mean working from home, especially when you can work from a cozy, coastal destination and experience some of the best food, culture, and natural beauty that the region has to offer after clocking out. After a recent long weekend spent on the coast of Virginia, we found that a quick little workcation is the best cure for the inevitable spring cabin-fever feeling.
We’d like to thank the Coastal Virginia Tourism Alliance for hosting our most recent trip.
Just a few hours from Washington, DC, Coastal Virginia is one of the best long weekend getaways on the East Coast, and you can explore several unique cities in just 72 hours. So if you’re looking for the best way to experience the cities that line Virginia’s Coast, here’s the perfect 3-day itinerary.
From waterfront stays in Norfolk to historic streets in Williamsburg and quiet beaches in Cape Charles, this Coastal Virginia itinerary blends remote work, art, history, incredible food, and outdoor adventure into one perfectly balanced long weekend. So whether you’re a digital nomad, WFH-er, or long weekend warrior, following this guide will allow you to have some of the most unforgettable experiences that the region has to offer… without using more than a few hours of PTO.
Day 1 — Norfolk: Art, Dinner, and Broadway
Seth and I put in a few hours of work on a Thursday morning in February and arrived in Norfolk in the late afternoon, just in time to check into our room at The Glass Light Hotel. The drive from our home in Washington, D.C. took us about 3.5 hours, and we switched off halfway, so we could each get another solid hour of work in from the car. This meant that we only had to burn 4 hours of PTO on this little local getaway, which we found to be well worth it!
Check‑In & Work Reset in Norfolk, VA
As soon as we got into town, we checked into the stunning Glass Light Hotel and Gallery in downtown Norfolk. This boutique property proved to be the perfect home base for our adventures and provided an ideal atmosphere for our little workcation. On top of a beautiful gallery space and art everywhere you look, the property has great WiFi and tons of corners to cozy up in and get some work done.
Dinner and a Show in Downtown Norfolk
When quitting time rolled around, we walked a few blocks from the hotel to dinner. There are tons of options along Granby Street, but Codex’s bright red door drew us in. It’s a modern, creative restaurant that serves a variety of small plates. The vibe is cool, the food is thoughtful, and it’s the perfect way to transition from work mode to a night out and about.
After dinner, we took another little stroll over to Chrysler Hall for a Broadway show. We snagged tickets for Shucked! — a fun, high‑energy musical that was the perfect way to cap off our first night in town.
Day 2 — Portsmouth & Chesapeake
Work & Play in Norfolk and Portsmouth
Today started with a few focused hours of emails and meetings. Again, our goal was to maximize PTO, so we locked in until lunchtime. When hunger inevitably struck, we caught a $2 ferry from Norfolk to Portsmouth to grab lunch at Olde Towne Coffee. This local favorite offers cozy seating, creative coffee (and smoothies!), and a laid‑back work-friendly atmosphere — plus the opportunity to bop around Portsmouth’s charming Olde Towne neighborhood.
Dinner in Chesapeake
After clocking out, we made our way to Union Taco at Summit Pointe in Chesapeake. This urban taqueria combines flavors from South America, the Pan Pacific, as well as local cuisines and is a great spot to unwind on a Friday night. PSA: It would be tragic if you missed their happy hour (and their $6 margaritas), just saying.
If you find yourself in town on the Second Saturday of the month, you can shop the neighborhood’s flea/farmers market that hosts 100+ local vendors.
Day 3 — Art, History & Colonial Exploration
History & Small‑Town Charm in Smithfield
Start your day with a trip to Smithfield to explore the charming historic downtown area. Be sure not to miss the Isle of Wight County Museum, where you can see the world’s oldest ham and peanut!
Fine Arts in Newport News
Next, head to the Torggler Fine Arts Center in Newport News. Whether you’re an art lover or just enjoy beautiful architecture, this stop gives you a chance to reset creatively. We loved that their current exhibits seamlessly blended art with environmental and social science as they explored themes of sea level rise, coral reef bleaching, and how our “stuff” may likely become relics, or future fossils, in the centuries to come.
History With a View at Fort Monroe National Monument
From there, explore Fort Monroe in Hampton– a critically important historical site from the lens of Black History and emancipation, and a beautiful place to wander, learn, and enjoy the site’s sweeping waterfront views.
Fort Monroe is the largest stone fort ever built in the United States. During the Civil War, it became known as “Freedom’s Fortress,” as this site served as a refuge for thousands of enslaved people escaping to freedom. Today, it’s managed by the National Park Service and is free for all to visit.
Farm to Table Lunch in Newport News
For lunch, stop at Farmer’s Table in Newport News. It’s a local favorite for farm‑to‑table eats and locally-made goods for purchase with a relaxed, welcoming vibe.
Colonial Charm in Williamsburg
Afterwards, head to Williamsburg, the northern point of Virginia’s Historic Triangle. Wander cobblestone streets, explore colonial‑era buildings, and if you’re into local beer, Precarious Beer Project in Merchant Square with pinball, pool, tacos, burgers, and of course, local craft brews, is a must-stop!
If you’re in town during the warmer months, we highly recommend taking a Scenic Sunset Sail with Yorktown Sailing Charters. We recently went out on their Tall Ship, the Schooner Alliance II, and during our two-hour sightseeing tour, we spotted some wildlife and experienced the ship’s colonial-era cannon fire. Sails run daily from April through November, and tickets cost $60. Chips and beverages (beer, wine, and soda) are available for purchase on board as well.
If you’d rather relax on land, book a salt therapy or float tank session at the Williamsburg Salt Spa. They offer services ranging from relaxing in a salt cave (inspired by the famous Wieliczka Salt Mine in Poland) to soaking in their float tanks to meditating in their infrared saunas. Regardless of the combination of therapies you choose, you’ll leave feeling so relaxed.
When you get hungry, enjoy dinner and unique drinks in an 80-year-old bank, aka DoG Street Pub. This upscale tavern serves craft beers and Brit-inspired comfort food, including some seriously delicious beer cheese!
Day 4 — Suffolk, Cape Charles & Chincoteague
Coastal Morning Calm
On Sunday, you’ll want to get an early(ish) start for breakfast at Café Davina in Suffolk. This restaurant is housed in The Pinner House, a historic bed and breakfast set on 1.5 acres and steeped in over 130 years of history. Once home to the founder of the widely successful Suffolk Peanut Company, the property now hosts events, overnight guests, and a mean breakfast/brunch. And while everything we ordered was delicious, a highlight of our meal was the affogato flight!
Eastern Shore Exploration
After breakfast, make your way across the Bay to Cape Charles — a coastal gem with boutique shops, waterfront views, and plenty of small‑town coastal charm. This public beach is situated on the Chesapeake Bay, and there are no entrance or parking fees. The shallow water is calm with no waves and is perfect for families with small children.
We browsed the local shops and grabbed a lunch to-go from AJ’s Bar & Grill before heading to Savage Neck Dunes Natural Area Preserve for a chilly picnic by the water. The preserve is both home to some of the highest sand dunes in Virginia and the largest population of the rare and threatened northeastern beach tiger beetle. It also protects several miles of coastline that’s only accessible at low tide. To access the shore, you’ll take a short walk along the flat and sandy trail. Just be sure to check the tide ahead of time, practice Leave No Trace, and refrain from digging/disturbing the sand in order to protect the tiger beetle’s fragile habitat.
Alternatively, you can make your way to Kiptopeke State Park. Boasting over five miles of trails for hiking and biking, campsites, and plenty of opportunities to hang out both by and on the water, this park is also home to the Concrete Fleet aka Kiptopeke Breakwater, a ghost fleet of nine concrete ships that were sank about a half mile off the shore to bring protection to the ferry terminal during severe weather.
While the terminal has since closed, the breakwater still protects the pier and Kiptopeke Beach and provides habitat for marine life, including fish, shellfish, and birds. If the weather allows, you can get a closer look at the ships via kayak. Note: The water does get pretty choppy, and we had to fight the current and wind, which was a bit challenging after a while.
As you make your way home, we highly recommend stopping by Chincoteague Island, a place known for being home to wild ponies. If you have time for nothing else, make your way to the National Preserve’s Wildlife Loop, a popular 3.5-mile trail that circles the refuge’s marshes, providing excellent opportunities to see birds, deer, and other wildlife– we spotted a fox the last time we were there! This paved loop is accessible via foot, bike, or car, and experiencing it really is the cherry on top of a day spend in nature.
Four days may seem like a short time, but Coastal Virginia delivers. You’ll find history, art, culture, Broadway stages and sandy dunes, and this itinerary proves you can have it all in just 72 hours. Whether you’re looking for your next workcation idea or simply want to explore somewhere new, Coastal Virginia should be at the top of your list.
