What to Do
Most of Thomas Jefferson's extraordinary home is open only for tours, but you can linger in his 1,000-foot-long terraced vegetable garden, eight acres of fruit orchards and vineyards. Sangiovese wine made from Monticello grapes is occasionally available in the gift shop (931 Jefferson Pkwy.; 434-984-9822 or monticello.org).
University of Virginia Tours
The University Guide Service offers tours of the stunning Jefferson-designed Lawn and Rotunda (Pavilion VIII; 434-924-3239). Afterward, stop for a beer and a burger at the 80-year-old Virginian (1521 University Ave.; 434-984-4667).
Winemaker Luca Paschina makes exceptional wines from Italian grape varieties. Go for a tour and tasting, and stay for a meal at the winery's northern Italian Palladio Restaurant (17655 Winery Rd., Barboursville; 540-832-3824).
There are no tours yet of Kluge's property, but the Farm Shop serves as a tasting room and sells estate-canned jams and topiary from the greenhouses (100 Grand Cru Dr.; 434-977-3895 or klugeestatteonline.com). There are 18 other wineries in the Charlottesville area; for more information, see monticellowinetrail.org.
Where to Eat
Keswick Hall at Monticello
Set near the foothills of the Blue Ridge Mountains, this 600-acre English country manor has 48 antiques-filled rooms, formal gardens, an infinity-edged swimming pool and an 18-hole golf course designed by Arnold Palmer. Chef John Brand's modern American menu includes terrific dishes like pumpkin seed-crusted duck breast. After dinner, there's brandy and snooker in the billiards room (doubles from $310; 701 Club Dr.; 800-274-5391 or keswick.com).
200 South Street Inn
Two blocks from the excellent book and antiques stores along downtown's old Main Street, 200 South Street consists of two beautifully restored 19th-century houses (one was formerly a girls' finishing school and then a brothel). Many of the rooms are outfitted with canopy beds and fireplaces (doubles from $125; 200 South St.; 800-964-7008 or southstreetinn.com).
Willow Grove Inn
Half an hour outside Charlottesville, this 225-year-old renovated plantation house is the ideal place to stay while visiting nearby vineyards. The distinguished kitchen serves Southern dishes like pecan-and-peanut-crusted rack of local lamb. On Saturday nights, a piano-and-bass duo plays hits from the '30s and '40s while guests dance (doubles from $295; 14079 Plantation Way, Orange; 800-949-1778 or willowgroveinn.com).
Where to Eat
This downtown diner gets packed at lunchtime with University of Virginia faculty. The retro interior features red-leather booths and vintage movie posters. There's roasted chicken and grilled rib eye, but Bizou's specialty is its succulent homemade meat loaf with chipotle ketchup (119 W. Main St.; 434-977-1818).
At Patricia Kluge's new combination gas-station-restaurant-convenience-store, you can refuel your car and order an egg-salad sandwich. Fuel's dining room offers French-accented dishes like grits with duck confit; the wine list includes more than two dozen by-the-glass selections (901 E. Market St.; 434-220-0864).
Located in Charlottesville's trendy Belmont section, Mas offers authentic and moderately priced Spanish tapas, like spicy potatoes with aioli and tender grilled squid with romesco. A concrete bar runs the length of the chic industrial space; seats there look into the open kitchen (501 Monticello Rd.; 434-979-0990).