Day One: Jefferson’s Vision & Vineyard Views

Morning: A Mountaintop Beginning

Start with a delicious gourmet breakfast at Arcady Vineyard Bed & Breakfast, then head just 2.5 miles away to Monticello. The Declaration of Independence turns 250 in 2026 and Monticello is offering additional tours in honor of this celebration. Take a guided house tour, wander Jefferson’s botanical gardens, and pause on the West Lawn which features the “nickel view” of the house, for sweeping Blue Ridge views. Give yourself time here—Monticello is best experienced slowly.

Lunch: Local Favorite

If you’re looking for a lunch steeped in history, consider 1799 Restaurant at The Clifton. Named for the year the estate was built, the property was once home to Martha Jefferson Randolph and Thomas Mann Randolph. Today, it blends Charlottesville’s presidential-era roots with modern wine country dining, offering seasonal, locally sourced menus for both lunch and dinner.

If you prefer a more casual setting, enjoy a relaxed lunch at Simeon Market. With its mainly outdoor seating and being just 1.5 miles from Arcady Vineyard Bed and Breakfast, it’s a perfect setting for a handcrafted sandwich, local flavor and community charm.

Afternoon: Presidential Perspective

Continue to James Monroe’s Highland, a quieter and more pastoral presidential home. The landscape and exhibits of Highland offer a thoughtful contrast to Monticello. Highland invites you into a more intimate, reflective experience where winding paths, open meadows, and quiet woodlands set the tone.

Late Afternoon: Wine with some Roots

Few wineries can claim a direct link to Thomas Jefferson—Jefferson Vineyards can. Less than a 5 minute drive from Arcady Vineyard Bed & Breakfast, it sits on land where Jefferson and Italian viticulturist, Filippo Mazzei attempted to grow grapes in the 1700s. Sit indoors and take in the visually appealing bottle display or sit outside and enjoy the scenic vineyard views, you can’t go wrong either way.

Gabriele Rausse, widely regarded as the “father of modern Virginia wine,” arrived from Italy in 1976 when many doubted vinifera grapes could thrive here. His early work at Barboursville Vineyards proved otherwise, and he went on to help establish Jefferson Vineyards while advising wineries across the state—shaping Virginia’s wine industry as a whole. Today, tastings at Gabriele Rausse Winery are held mostly outdoors in a relaxed, woodsy setting.

Evening: Downtown Charlottesville Elegance

One of Charlottesville’s longest-running restaurants, the C&O Restaurant is set in a late-1920s former railway building once tied to the Chesapeake & Ohio Railway. Originally a humble diner serving railroad workers, it has evolved into a cozy, refined dinner destination that still carries its historic charm.

Day Two: Architecture, Legacy & The Monticello Wine Trail

Morning: Jefferson’s University

After eating a wonderfully prepared gourmet breakfast at Arcady Vineyard, take a 20 minute drive to the Lawn at the University of Virginia (UVA). Founded by Thomas Jefferson in 1819, UVA is known for its historic campus, academic excellence, and notable alumni, including several U.S. presidents! Visit the Rotunda and explore the Academical Village—especially beautiful in the morning light.

Lunch: Downtown Local

Founded in 1988, Bodo’s Bagels in Charlottesville is a beloved local spot, famous for its fresh, New York–style bagels and made-to-order sandwiches, from classic lox to hearty egg and veggie options. The casual, bustling atmosphere makes it perfect for a quick lunch or a coffee-and-bagel picnic. A favorite for both locals and visitors alike.

Afternoon: A Deeper Wine Experience

Spend the afternoon exploring the Monticello Wine Trail. In addition to yesterday’s stops, consider:

• Merrie Mill Farm & Vineyard, located in nearby Keswick just about 15 minutes northeast of Arcady Vineyard Bed & Breakfast, the Tasting Room features two copper bars in a lofted interior, lawns overlook the vineyards. The main house at Merrie Mill Farm was built in 1857.

• Barboursville Vineyards for Old World ambiance and historic ruins. Thomas Jefferson designed the Barboursville mansion for his friend James Barbour in the early 1800s. The mansion is just 30 minutes northeast of Arcady Vineyard Bed & Breakfast, in Orange County, was completed in 1822, and is now in ruins and is part of Barboursville Vineyards

No shortage of history or wineries. You’re in the heart of Virginia Wine Country. Give yourself permission to take your time —this is Virginia wine country at its best.

Evening: Relaxed, Elevated & Memorable

One of our guest favorites (and ours too!) is The Ivy Inn located in Ivy, VA located just 20 minutes from Arcady Vineyard. Known for their locally-inspired seasonal American cuisine, the restaurant is housed in a 19th-century farmhouse, giving it an instantly warm, lived-in feel. It was originally part of the Faulkner House estate, a historic property dating back to the mid-1800s. The property transitioned into a restaurant in 1973, marking the beginning of its life as a dining destination. In 1995, Angelo and Farrell Vangelopoulos took ownership—and that’s when The Ivy Inn truly became a Charlottesville institution.

Return to Arcady for a peaceful nightcap on the deck, under the many stars.