Virginia’s Small Town Charm: From Mountains to Maritime

Discover a side of Virginia that’s off the beaten path and packed to the brim with charm. This journey winds from the scenic beauty of Harrisonburg and the storybook streets of Staunton, through the rolling landscapes and craft experiences of Nelson County, and onward to the rich maritime heritage of Newport News.

Along the way, guests will enjoy charming downtowns, local flavors, natural wonders, and memorable cultural experiences, all thoughtfully paced for a relaxed, immersive motorcoach adventure. It’s Virginia at its most genuine: welcoming, walkable, and full of hidden gems.&

Day 1

Your adventure into Virginia’s charming small towns begins in Harrisonburg. Known as “The Friendly City,” this charming town is home to James Madison University and offers beautiful architecture, historic sites, and unique museums.

Start your tour with lunch at Virginia’s first Culinary District in Harrisonburg, where a walkable downtown brings together an eclectic mix of locally owned restaurants, international flavors, and craft beverages. From globally inspired cuisine to farm-to-table favorites, it’s a place where the Shenandoah Valley’s agricultural roots meet a vibrant, creative food scene.

Next, explore downtown with a guided Mural Tour in the town’s Arts and Cultural District. From colorful alleyways to large-scale works by regional artists, these murals turn an everyday stroll into an open-air gallery experience.

Afterward, visit the neighboring Valley Turnpike Museum and Civil War Orientation Center to learn about the region’s importance as a settlement along Route 11 and its strategic role in the Civil War, followed by a stop at the Harrisonburg Fire Museum. Together, these sites offer a deeper look at how transportation, conflict, and community service have shaped Harrisonburg’s story over time.

End your day with a group dinner at Monty’s Restaurant - a favorite for comforting dishes with a contemporary twist.

Day 2

On Day 2 of your journey, travel to the Queen City of Staunton, Virginia - frequently cited as having one of America’s most beautiful main streets. Begin your day with a guided tour of Staunton’s six historic districts, featuring an array of architectural styles including Greek Revival, Neo-Classical, and Gothic Revival. Stop by the historic Trinity Episcopal Church, where you can bask in the glow of Tiffany stained glass windows and marvel at the church’s Taylor & Boody organ.

Next, enjoy lunch and boutique shopping downtown with an optional scavenger hunt. After free time, enjoy a docent-led tour of the Woodrow Wilson Presidential Library & Museum to learn about the life and times of the 28th president.

Afterward, test your sommelier skills with a guided wine tasting with an optional charcuterie building workshop at Accordia Wine Bar & Eatery, followed by a group dinner at Mill Street Grill, a local favorite for hearty American fare housed in the repurposed White Star Mills factory building.

Finish your exploration of Staunton with a performance at American Shakespeare Center’s Blackfriars Playhouse, the world’s first re-creation of Shakespeare’s indoor theatre. This intimate, candlelit setting brings audiences remarkably close to the action, offering a lively and immersive take on classic and contemporary works.

Day 3

On Day 3 of your excursion, indulge your senses in the sights and flavors of Nelson County, VA. Begin with a peek inside the historic Blue Ridge Tunnel. Carved through Afton Mountain in the 1850s under the direction of Claudius Crozet, the Blue Ridge Tunnel was once the longest railroad tunnel in North America and a remarkable feat of engineering for its time. Today, this restored passage invites visitors to walk or bike its mile-long route beneath the mountains, offering a cool, atmospheric journey through both history and landscape.

Next, head to The HEART of Nelson Local Artisan Market, a community hub featuring unique handmade goods and products, followed by lunch at one of Wintergreen Resort’s many restaurant options.

In the afternoon and early evening, explore Nelson County’s many breweries, wineries and distilleries. From whisky tasting at Virginia Distillery Co. to vineyard tours and tastings at Veritas Vineyards and Winery, to brews, views, and bites at Devil’s Backbone Brewing Company, the region has become a destination for laid back tasting opportunities in an idyllic setting.

Day 4

Arrive in Newport News, where the spirit of the sea meets centuries of American history. Begin your day at The Mariners’ Museum and Park, recognized by the US Congress as “America’s National Maritime Museum.” Explore captivating exhibits that span global seafaring history, including the renowned USS Monitor Center, where artifacts and stories from the famed Civil War ironclad bring innovation and resilience to life.

Afterward, enjoy a cup of exceptionally roasted coffee and a bite to eat at Column 15 (located in the museum), offering scenic views and a peaceful pause before the afternoon’s discoveries.

Continue to Historic Endview, a beautifully preserved 18th-century home that witnessed the Peninsula Campaign of the Civil War. Through guided interpretation, step into the lives of those who experienced this defining chapter in American history.

Later, take in the natural beauty of Newport News Park—Spanning nearly 8,000 acres, this is one of the largest municipal parks in the country—where wooded trails, tranquil waterways, and open spaces invite a moment to unwind and reconnect with nature.

End the day with a group dinner at Fin Seafood Restaurant, where fresh, coastal flavors and an inviting atmosphere offer the perfect close to a day of exploration.

>Day 5: Art, Innovation & A Fond Farewell Begin your morning with a visit to the Virginia Living Museum, where you can encounter more habitats, wildlife, and plant species than you would in a lifetime of outdoor adventures in Virginia. The museum showcases the state’s regions from the upland coves of the Appalachian Mountains to the salty offshore waters of the Atlantic Ocean, which features more than 245 animal species.

Next, explore the rich history of the Newport News Shipyard by visiting The Shipyard Experience. This museum-quality exhibit will take you on a historic exploration of the iconic Newport News Shipyard and its surrounding landmarks, curated to unveil the city's deep-rooted connections to the Shipyard and its founders, the Huntington family.>

Enjoy a leisurely farewell lunch at Indulge Bakery and Bistro, a local favorite known for its European-style bakery and Bistro nestled in the heart of Historic Hilton Village—an ideal setting to reflect on the journey.

Before departure, take time for a final stroll through Historic Hilton Village, where a unique shopping experience offers everything from fine clothing and quality furs to antiques and collectibles, artwork, consignment, jewelry, crafts, beads, and more.