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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, across the northern Virginia wine region to ending your taste of historytour at the home of the first President of the United States of America!


Spring, Summer and Fall
4 Days / 3 Nights



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. If Mr. Madison is receiving guests today hear the history, archaeology, and wine of James Madison’s Montpelier. Excavate side-by-side with Montpelier’s expert archaeology staff through the Piedmont clays that make the region’s archaeology (and wine!) internationally known.


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.


Board the coach for a short ride to 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. Spring is the perfect time to potteraround with an expert horticulturist around the Highland flowers, herbs, and vegetables. There may even be time for you to create your own potted garden!


It’s now time for an early evening check in for the next two nights at your Charlottesville area hotel.  

There will be time to relax and refresh before you gather for an included dinner at one of the charming restaurants the area has to offer.

UVA Rotunda in Spring - Photo Credit - Brantley Ussery (1).jpg


After a hearty breakfast at the hotel, board the motorcoach and travel to your first destination of the day. 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. 

Today the Monticello Wine Trail, all within 25 miles of Charlottesville are producing wines of national and international acclaim. Each winery owes homage to Thomas Jefferson’s vision of winemaking and are honored to help fulfill his dream.


This full morning will begin with a powerful 15-minute introductory film located at the visitor’s center which is built around a fountained courtyard. 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. 


Once you’ve had time to learn all about this unique man’s life and work it will be time to travel the short distance for an included lunch at the Historic Michie Tavern. Enjoy your hearty midday fare in a rustic tavern setting by servers dressed in period attire. While you’re 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 an 18th century traveler looking for a bit of refreshment and nourishment.


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 Virginia wine.


Return to the hotel for some time to refresh. Dinner is on your own this evening in downtown Charlottesville where you will find some of the best restaurants, cafes, and casual eateries in the area.

Monticello aerial - Thomas Jefferson Foundation.jpg

DAY 3 

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 drive north for the next thirty minutes. 


Arrive at the family-owned, 125-acre estate winery that welcomes 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. 


Imagine yourself nestled in the acreage of lush green vineyards launching your artistic side to create your very own masterpiece. Enjoy the beautiful breezes of the warmer summer days at the crisp, white linen cloth covered table, sipping on a glass of their finest wine and with every brush stroke you slowly take yourself back to a simpler time before, cars, airplanes, telephones, and computers overtook our world. 


For the next few hours following lunch we will proceed with our 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 our final tour and wine tasting event at a local vineyard who saw the potential to create wines which pulse with the distinctiveness and elegance of the rocky hills of Loudoun County. 

Soak up the ambience, and this beautiful setting, play a little competitive game of corn hole with your fellow travelers before departing for your overnight stay in the Leesburg, VA area.


After you have settled into your rooms, time to gather for dinner at a favorite restaurant that began as a grain mill in 1899. Almost 90 years later, the mill was restored, and is now this High – end, beautiful historic building serving American fare & Virginia’s fine wines in a refined dining room, rustic bar, or atrium.


Return to your hotel for the rest of evening.

Carter Mountain Pano.jpeg

DAY 4 

After breakfast at the hotel, check out of your room and board the coach. 

Today your travels will take you to George Washington’s home, Mount Vernon. One of the nation’s most beloved historic sites, Mount Vernon offers a glimpse into 18th - century plantation life through beautiful gardens and grounds, intriguing museum exhibits and immersive programs honoring George Washington, life, and legacy. Following a video that provides a brief overview of the property, embark on guided tour of George Washington’s home, and witness the vibrant colors, intricate architectural details, and elegant furnishings of this impressive 21 room mansion. 


After the tour, time will be given to explore on your own, and enjoy lunch located on site if you desire.  


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!


Happy Travels!


Your package includes:

  • 3 Nights accommodations

  • 3 Breakfasts

  • 3 Lunches (Includes wine pairing on day 1 & 3)

  • 2 Dinners 

  • ​Guided grounds tour of President James Madison’s home - Montpelier

  • 30-minute guided outdoor history walk of President James Monroe’s home – 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 Thomas Jefferson’s - Monticello 

  • Guided tour of The Academical Village/Rotunda

  • 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 Loudoun County Vineyard.

  • Guided tour of President George Washington’s - Mount Vernon home

  • Baggage handling for one piece of luggage per traveler

  • Accommodations, baggage service, admissions, and group meals for the coach driver

  • Taxes and Gratuities (Note: Gratuities for any local guides and coach driver are not included and are at your discretion based on service.)

Additional optional features - Select from the following:

  • Meeting with Mr. Madison

  • Excavate with expert archaeologist. 

  • “Pick ‘em”  – Seasonal

  • Make your own potted garden

  • Lawn Games 

  • Paint & Taste.

24/7 Personalized Service

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