The story of America’s independence flows through Chesapeake, Portsmouth, and Suffolk—three cities connected by waterways, landscapes, and centuries of history. In three days, step into the past, savor local flavors, and explore the places and people that helped shape a nation.

Day 1: Chesapeake — Revolutionary! A Turning Point in Virginia

Located in Battlefield Park, adjacent to the museum, is an interpretive pathway that echoes the diverse people connected to this pivotal moment in history. Markers recognize British forces, Patriot leaders and militia, free and enslaved Black men, and the Indigenous community. The stories reflect a true cultural blend - perspectives that shaped the events at Great Bridge and the path of early America. In the heart of Great Bridge, you will drive on Battlefield Boulevard, a central roadway named in honor of the battle.

For lunch, there are multiple ways to enjoy a taste of Chesapeake. Explore Summit Pointe – an easy walk at the city’s hub for a variety of locally owned restaurants, from casual to upscale. Relax at Woody’s Raw Bar & Grill and soak in a waterfront view that feels like stepping back into an 18th-century waterside village. Lockside Bar & Grill proudly supports local farmers and fishermen, serving up great food with views of the historic Intracoastal Waterway.

For your shopping pleasure, browse a few Chesapeake boutiques. 3 Little Black Birds is filled with artisan and hand-crafted treasures, while Vintage Vibe Home offers antiques, décor, and unique collectibles across two buildings. Stop by the Chesapeake Visitor Center for souvenirs, Virginia is for Lovers merchandise, items made in Chesapeake, books by local authors, and more.

For a relaxing end to your first day, unwind along the Chesapeake Ale Trail, where award-winning breweries pour bold flavors ranging from German traditions to baseball-themed craft brews. Pair your tasting with dinner—decadent pizza, bratwurst, food-truck bites, and more. Every stop along the trail is packed with flavor and fun.

Day 2: Portsmouth — Virginia’s Historic Seaport®

Wake up ready to explore Portsmouth, a small seaport city brimming with more than 300 years of history. Fuel your morning in Olde Towne with breakfast at Yoolk’s on US, known for its fresh-squeezed mimosas, or grab a coffee at the former headquarters of Benedict Arnold’s Virginia Campaign.

Near the waterfront, enjoy a scenic lunch at Fish & Slips at Tidewater Yacht Marina. Here, overlooking the Elizabeth River, you stand on the very shoreline where battles from the Revolutionary War through the Civil War played out—and where British troops last lingered before departing for Yorktown and eventual surrender.

Spend your afternoon along The Portsmouth Seawall, visiting unique attractions like the Lightship Portsmouth Museum, the Portsmouth Naval Shipyard Museum, and the only Fresnel Lens on display outside a museum setting. Explore shops, galleries, and six additional museums along High Street, each offering its own window into Portsmouth’s vibrant character.

As dusk settles, enjoy dinner at one of Olde Towne’s quirky, locally owned restaurants. For a memorable night, catch a film at the beautifully restored Commodore Theatre, a 1945 Art Deco gem, or dine at The Bier Garden, a German-style restaurant with 23 taps, more than 400 beers, and a charming, illuminated garden.

Day 3: Suffolk — Historic Roots, Creative Spirit

On your final day, head to Suffolk, located just 15–30 minutes from Chesapeake and Portsmouth. Begin at the Suffolk Visitor Center, housed in the 1839 Roman Revival Nansemond County Courthouse. Explore exhibits on Suffolk’s history and the Great Dismal Swamp, gather travel materials, and browse the gift shop for local keepsakes.

Continue just steps away to Riddick’s Folly House Museum (c. 1837). This grand Greek-Revival mansion—once playfully dubbed “Riddick’s Folly”—now is proudly featured on the National Register of Historic Places. Tour all four floors, 21 rooms, and 16 fireplaces while learning about its role as Union Army headquarters during the Civil War.

Spend the afternoon immersed in the arts at the Suffolk Center for Cultural Arts and the Suffolk Art Gallery, where rotating exhibits spotlight regional and national talent. As you stroll downtown, enjoy the city’s vibrant public art—from outdoor murals to whimsically painted electrical boxes.

If shopping beckons, Suffolk’s local boutiques invite you to explore. Find unique apparel at Cecelia’s Boutique and Gifts, customized creations at Embroidery Etc., trendy finds at Darla’s Downtown, handmade soy candles at Flickerstix, and timeless treasures at Brandon House Vintage Market.

Snap a selfie with Suffolk’s most famous icon, Mr. Peanut®, by finding one of the cast-iron fence toppers around the city — each once part of the original factory grounds. Then stop by a longtime local favorite, the Planters Peanut Center, where freshly roasted peanuts have been sold since 1967 and the irresistible aroma still comes from a peanut roaster dating back to 1936.

If Mother Nature beckons, journey into the Great Dismal Swamp National Wildlife Refuge. Far from dismal, this breathtaking landscape offers hiking, biking, birdwatching, and a deep connection to American history. Suffolk Tourism also offers guided eco-tours throughout the year—check VisitSuffolkVa.com for schedules.

End your day at Nansemond Brewing Station, where live music, trivia nights, and creative local brews provide the perfect toast to three unforgettable days in Coastal Virginia.