Day One: Jefferson’s Vision & Vineyard Views

Morning: A Mountaintop Beginning

Start with breakfast at Arcady, then head just 2.5 miles away to Monticello. Take a guided house tour, wander Jefferson’s gardens, and pause on the West Lawn for sweeping Blue Ridge views. Give yourself time here—Monticello is best experienced slowly.

Lunch: Local Favorite

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: Presidential Perspective

Continue to James Monroe’s Highland, a quieter and more pastoral presidential home. The landscape and exhibits offer a thoughtful contrast to Monticello.

Late Afternoon: Wine with a View

Unwind at nearby Jefferson Vineyards or Keswick Vineyards, both just minutes from Arcady. Enjoy a relaxed tasting and linger over vineyard views.

Evening: Downtown Elegance

Reserve dinner at C & O Restaurant. Housed in an early 20th‑century railway station building, the C&O blends its history with a cozy, refined dinner experience

Day Two: Architecture, Legacy & The Monticello Wine Trail

Morning: Jefferson’s University

After breakfast at Arcady, 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

Enjoy a relaxed lunch at Simeon Market,  just 1.5 miles from Arcady, perfect for a handcrafted sandwich and local flavor.

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, the Tasting Room features two copper bars in a lofted interior, lawns overlook the vineyards.

• Barboursville Vineyards for Old World ambiance and historic ruins

Take your time—this is Virginia wine country at its best.

Evening: Relaxed & Memorable

Choose an intimate dinner at The Alley Light, known for its cozy atmosphere and exceptional cocktails. Be sure to gps their address as they’re easy to miss!

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