Who's Afraid of Virginia Wine

This custom-designed, State of Virginia wine tour not only helps you discover why they say, “Virginia is for Lovers” but also, the “Birthplace of Wine”. Along the way you will begin to realize the reason so many Presidents wanted their homes here. Fall in love with the beautiful mountain top views to the rich, golden sunsets as you wined your way from Charlottesville, through the Shenandoah Valley, and ending your journey in the northern Virginia wine region.

Package includes:
  •  Motorcoach transportation with onboard refreshments
  •  2 Nights accommodations at The Holiday Inn Monticello
  •  2 Breakfasts, 3 Lunches (Includes wine pairing on day 2&3) & 1 Dinners
  • Guided grounds tour of President James Madison’s home - Montpelier
  • 30-minute guided outdoor history walk of  Ash Lawn Highland, includes the site of the recently discovered 1799 Main house. 
  • Self-guided tour of Ash lawn Highlands’s guest house and interior exhibits
  • Docent led tour of house and grounds  - Monticello
  • Guided tour of The Academical Village/Rotund
  • Visit a local orchard, to   include ¼ peck bag of pick your own, local refreshment and snack
  • Docent led tour of President Woodrow Wilson’s Manse  Self-guided tour of President Wilson’s Museum, Pierce-Arrow Limousine & WW1 trench exhibit. 
  • Tour & tasting at a Family Vineyards
  • Baggage handling



Day One: Wednesday, September 14, 2022
Depart for your first stop of the day - Ash Lawn Highland, the home of President James Monroe. On arrival you will be led for the next thirty minutes by an expert guide on an outdoor history walk, which includes the site of the recently discovered 1799 Main House. Learn the significance of Highland and its enslaved and free occupants, as well as how recent archaeological discoveries have upturned the understanding of this plantation. Proceeding this, venture inside for a self-guided tour of the 1818 Guesthouse and interior exhibit spaces. There will be time for independent exploration of the grounds and original outbuildings.
Depart for your included lunch at the Historic Michie Tavern. This Virginia landmark captures 18th-century life, enjoy your hearty midday fare in a rustic tavern setting by servers dressed in period attire. While your there you will have time to explore the general store and the 1784 Pub which is located in the
oldest section of the Tavern. Experience the sights and sounds of what it may have been like as a traveler looking for a bit of refreshment and nourishment.
Board the motorcoach and travel the short distance to. Monticello “Little Mountain”, the home of Thomas Jefferson, author of the Declaration of Independence, Statute of Virginia for Religious Freedom, third president of the United States, and founder of the University of Virginia. Built on the mountain top where he played as a boy this classic architectural masterpiece and modern innovation was rebuilt and revised throughout his long life on the estate. Jefferson dreamed of surrounding vineyards that would produce high quality wine that could rival the best Old-World wines. Your visit will begin with a powerful 15 minute introductory film located at the visitors center, built around a fountained courtyard before you take a short ride to the top of the hill for a fully guided house and ground tours to include Mulberry Row, the tree-lined road running alongside the main house, served as the industrial hub of the 5,000-acre Monticello plantation and where some of the slaves who worked on the plantation lived.
Depart for your hotel check in for the next two nights. Once you've had time to freshen up enjoy your buffet dinner at a local favorite restaurant. The  rest of the evening you will have time to relax at your hotel.
Day Two: Thursday, September 15, 2022
Enjoy a hearty breakfast at the hotel before departure.
Arrive for a morning, guided grounds tour of James Madison’s - Montpelier, the 4th president of the United States, Father of the Constitution, and America’s 1st First Lady Dolley Madison. This incredible home and grounds are beautiful unto themselves. Their home showcases their life after his presidency and the story of the enslaved that served them.
Following this two-hour visit, depart by motor coach for lunch at a local family-owned vineyard. The main house on the farm was built in the mid 1800’s and was known for welcoming the community to their home and property to make use of the dance pavilion, the first public pool and first movie theater in the region! Sit back, relax, and take in all that is enchanting about the beautiful state of Virginia.
Arrive for lunch at Merrie Mill Farms.
Board the motor coach and continue your travels after lunch to The Academical Village at The University of Virginia. The Rotunda was designed by Thomas Jefferson as the architectural and academic heart of the University’s community of scholars. 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. Construction began in 1822 and was completed in 1826, shortly after Jefferson’s death on July 4 of that year. Built at a cost of almost $60,000, it was the last structure to be finished on the Lawn.
Now it’s time to enjoy the fruits of Mother Nature’s labor by visiting a local orchard overlooking the dramatic vistas and acres of fruit trees and grapevines. Take a stroll through the orchard and nurseries, pick some fresh fruits and local veggies to take home, or just take in the gorgeous backdrop and unwind with a glass of wine.
Return to the hotel for some time to refresh. Dinner is on your own tonight in historic downtown Charlottesville or relax at the hotel and enjoy their on-site restaurant facilities.
Day Three: Friday, September 16, 2022
Rise and shine to the sun’s rays and enjoy a relaxing breakfast served at the hotel.
Time to check out, board the motor coach and travel west for the one-hour drive to Historic Staunton, VA.
Sitting atop the crest of a hill in downtown Staunton's Gospel Hill historic district is the birthplace of President Woodrow Wilson, our 28th President. Your tour includes a self-guided tour of the museum which included the Pierce-Arrow limousine and WWI trench exhibit, as well as a guided tour of the Manse/birthplace. The house is often referred to as a manse which is the term the Presbyterian Church uses to identify the residence of their minister.
A late morning departure from Staunton enables us to take in the stunning scenic views of the Shenandoah Valley as we driver north for the next thirty minutes.
Arrive at the family-owned, 125-acre, Vineyards located in Mt. Crawford, VA. They welcome every guest with a warm smile and award-winning wines. Enjoy your included gourmet lunch at the onsite Bistro located on their Tuscan-style villa estate which offer beautiful panoramic views of the Blue Ridge Mountains.
Depart by motorcoach for the next few hours and proceed with your wine trail north through the Blue Ridge Mountains of Virginia before arriving to the area they call the East Coast’s Napa Valley Region. With more than 40 wineries and tasting rooms on rolling hills and cliff edged slopes it isn’t a wonder why so many visit Loudoun County year after year.
Time to wind it up with your final wine tasting event in the rocky hills of Loudoun County. Soak up the ambience, and this beautiful setting before you depart for home.
Time to wine down the road and depart for home, take with you all the memories of your time in this beautiful state of Virginia known for romance and of course, lovers of wine!

TRIP # 2251A

Dates: Sept 14 - 16, 2022

Cost: $899pp

Deposit: $150pp

Balance due: 7/26/22

Single Supplement: +$187


Moderate walking Moderate Walking



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