Fine Wine, Patsy Cline, & Jefferson Design

Embark on a journey through Northern Virginia's picturesque vineyards, indulging in the finest wines amidst the backdrop of historic mansions. Delight your palate with farm-fresh delicacies as you wander through the rolling landscapes.

Experience the enchanting beauty of the Shenandoah Valley and explore the hometown of the legendary Patsy Cline. Immerse yourself in the rich tapestry of American history as you marvel at the architectural masterpieces crafted by the visionary Thomas Jefferson.

Join us for a leisurely excursion from Winchester to Charlottesville, Virginia, and let the essence of Virginia's heritage captivate your senses.

3 Days /2 Nights

Group size

Estimated Tour Pricing Inclusions: 3 nights’ accommodation, 3 breakfasts, 1 lunch, 2 dinners, admissions, entrance, and guide fees as stated in the itinerary, including taxes, and gratuity (excluding gratuity for guides and driver, unless requested).
Highlights Include:
  • Patsy Cline's Historic House
  • Skyline Drive
  • Monticello
  • Thomas Jefferson's World
  • Historic Michie Tavern
  • Vineyards
  • Downtown Charlottesville
  • Rotunda
  • Tasting Tour
  • James Madison's Montpelier

Sample Itinerary:  

  Day One - Patsy Cline & Skyline Drive
  • Arrive in Virginia, depart for Patsy Cline’s Historic House, and take a tour of Patsy Cline’s hometown. She began her radio career at Winchester Radio Station WINC in 1946 at age 14. We will see her home, Radio Station WINC, and pay a visit to her gravesite. Many seniors in the area still recall when Patsy played at area clubs in her early career.
  • Tour the Patsy Cline Historic House. Keeping true with one of Patsy Cline’s signature songs, “Come on in and sit right down and make yourself at home”, we’ll visit The Patsy Cline Historic House, a historic property on the National Register of Historic Places and the Virginia Landmarks Register. Patsy resided here from 1948-53, longer than at any other house associated with her in the Winchester and Nashville areas, and she returned to it intermittently until her singing career began in 1957.
  • Enjoy lunch on own along the Pedestrian Mall of Downtown Winchester.  Discover charming shops, delicious restaurants, centuries-old architecture, numerous historical landmarks, and museums. Old Town Winchester offers convenience, charm, and a warm welcome to all.
  • Drive along Skyline Drive and check-in to your Charlottesville hotel.
  • Enjoy dinner included at a casual eatery offering an American buffet with carving stations, fresh-baked bread, & more. Return to hotel.

  Day Two - Jefferson Design & Fine Wine
  • Enjoy breakfast at the hotel.
  • Depart and arrive at Monticello and catch the shuttle to the house. The Monticello is the mountaintop home of Thomas Jefferson. The house is a remarkable integration of classical architecture and modern innovation designed by Jefferson and built on the mountain top where he had played as a boy. Mr. Jefferson named his home Monticello, meaning Little Mountain and always used the Italian pronunciation of Monticello (mon-ti-chel-oh).
    • Visit the spectacular Gardens and Mulberry Row, the plantation “street” along which Monticello slaves lived and labored.
    • See Thomas Jefferson's World, in the Carl and Hunter Smith Education Center a 14-minute introductory film that dramatically present Jefferson’s ideals and accomplishments and illustrate Monticello’s central importance to his life and work. The film is shown on a 16-by-9-foot screen in a 2,400-square-foot theater with 125 seats.
    • Tour new Robert H. and Clarice Smith Gallery: The Words of Thomas Jefferson, an innovative exhibition in which quotations by and about Jefferson are projected in light. Thomas Jefferson and ‘the boisterous Sea of Liberty,’ an exhibition tracing the development and ongoing influence of Jefferson’s ideas about liberty through an interactive presentation on a wall of high-definition screens.
    • Monticello as Experiment: ‘To Try All Things,’ an exhibition that explores Jefferson’s use of Monticello as a laboratory for his belief that “useful knowledge” could make life more efficient and convenient. Making Monticello: Jefferson’s ‘Essay in Architecture,’ an exhibition covering the architectural origins, construction, and 40-year evolution of the iconic Monticello house.
  • Enjoy lunch included today at Historic Michie Tavern. This is one of the oldest homesteads remaining in Virginia. The Tavern and its outbuildings offer a glimpse of 18th-century life. Hearty, typical colonial fare is served in “The Ordinary.”
  • Depart and visit Ash Lawn-Highland, the home of Jefferson’s good friend and fellow President James Monroe is a 535-acre estate where visitors can find the atmosphere of an early 19th-century working plantation. Monroe held more major offices than any other President.
  • Depart and visit a local winery along the Monticello Wine Trail, the Birthplace of American Wine. Enjoy a wine tasting with a tour of the vineyard.
  • Enjoy dinner on own along Charlottesville’s pedestrian downtown mall. Return to the hotel after dinner for the evening.

Day Three - The Rotunda, Montpeliier, & Bristown Manor
  • Enjoy breakfast at the hotel prior to checking out.
  • Visit the Academic Village at The University of Virginia with photo opportunity at The Rotunda. The Rotunda was designed by Thomas Jefferson as the architectural and academic heart of the University’s community of scholars. He named the University’s original buildings the “Academical Village.” As the phrase suggests, the Academical Village is based on the Jeffersonian principle that learning is a lifelong process, and that interaction between faculty and students is vital to the pursuit of knowledge. Jefferson modeled the Rotunda after the Pantheon, a second-century temple in Rome.
  • Next, visit James Madison’s Montpelier, home of the 4th President of the United States and Father of the Constitution, James and Dolley Madison. This 1-hour tour of the mansion includes information on Madison the man, The Constitution & Bill of Rights, Slavery – Madison’s big regret, and his wife, Dolley – America’s first ‘First Lady’.
  • Enjoy a farewell dinner in the stunning Bristow Manor. An 1800s southern style manor house set in the picturesque rolling countryside of Virginia; the grounds offer a serene atmosphere for guests to enjoy. Depart for home.

Day Four - Say Goodby to Virginia
  • After breakfasting at your hotel, depart for home.


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