12-Hour Private Monticello and Charlottesville Tour with Virginia Wine

12 Hours Round trip from Charlottesville Easy pace

The Rotunda on the Grounds of the University of Virginia

The journey

Trip highlights

01 Private full-day excursion from Washington, D.C. through Virginia's Piedmont countryside
02 In-depth visit to Monticello, including its architecture, gardens, and estate history
03 Thoughtful perspective on Jefferson's legacy, including the history of enslaved people at Monticello
04 Explore Charlottesville and the University of Virginia's renowned Academical Village
05 Optional stop at a carefully selected Virginia winery near the Blue Ridge Mountains

Step into the world of Thomas Jefferson on a private full-day journey from Washington, D.C. through Virginia's scenic Piedmont countryside to Charlottesville and the mountaintop estate of Monticello. Explore the places and landscapes that shaped Jefferson's ideas - his home, his vision for education, and the agricultural setting of the Virginia Piedmont. Discover Monticello's architecture, gardens, and working estate while engaging with Jefferson's political ideals and complex legacy, including the lives and labor of the enslaved people who lived and worked there. Continue to Charlottesville and the University of Virginia's influential Academical Village, with the option to end the day at a carefully selected winery in the Blue Ridge foothills, where tastings may be purchased directly from the winery.

At a glance

What this trip includes

Duration 12 Hours

Tour type Private

Activity level Easy

Accommodation Not included

Transport Included

Wheelchair access Yes

Cities Washington D.C., Charlottesville

Languages English

Day by day

The itinerary

Day 01

Monticello, Charlottesville, and Virginia Wine Country

Explore the world of Thomas Jefferson on a private full-day journey from Washington, D.C. through Virginia's beautiful Piedmont countryside to Charlottesville and Monticello.

This experience connects three important parts of Jefferson's world: his mountaintop home at Monticello, the University of Virginia and its Academical Village, and the agricultural landscape of the Virginia Piedmont. At Monticello, explore Jefferson's architecture, gardens, household, agricultural experiments, political ideas, and complex legacy, including the lives and labor of the enslaved people who lived and worked on the estate.

Continue to Charlottesville and the University of Virginia, where Jefferson translated many of his architectural and educational ideals into one of the most influential university landscapes in the United States.

The day can conclude with a visit to a carefully selected Virginia winery in the foothills of the Blue Ridge Mountains. Guests who wish to participate in a tasting may purchase one directly from the winery. This is a private journey and can be adjusted according to your interests, available time, site reservations, weather, and preferred pace.

The fine print

Trip details

What's Included

Professional guide throughout the day
Private SUV or van transportation
Admission to Monticello
Guided visit to the University of Virginia grounds
Bottled water and light snacks
Flexible itinerary tailored to guest interests
Hotel pickup and drop-off within the Washington metropolitan area

What's Not Included

Meals and refreshments
Winery tasting fees, paid directly to the wineries
Gratuities for the guide and driver
Personal purchases and souvenirs
Optional specialty tours at Monticello not included in standard admission
Additional admissions not specifically listed as included in the tour description

What to bring

Comfortable walking shoes
Weather-appropriate clothing
Hat, sunglasses, and sunscreen during warmer months
Camera or smartphone for photographs
Personal medications if needed
Valid identification for guests participating in wine tastings
Curiosity and questions - Jefferson's world offers plenty to discuss!

Know before you go

This is a full-day excursion of approximately 11-12 hours, including travel time.
Monticello and the University of Virginia require moderate walking on paved paths, brick walkways, and gently sloping terrain.
Winery visits may be adjusted based on operating hours, seasonal availability, and guest preferences.
The itinerary can be customized to emphasize Jefferson's architecture, political career, agricultural innovations, the history of slavery at Monticello, the University of Virginia, or Virginia wine country.
Summer temperatures can be warm and humid. Comfortable clothing is recommended.
Advance reservations are strongly recommended during peak travel seasons.
Private transportation and flexible pacing are provided throughout the day.
This tour combines history, architecture, agriculture, wine, and beautiful scenery into a memorable exploration of central Virginia.