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Resonance’s annual ranking considers factors such as a city’s diversity, variety of cultural attractions, outdoor activities, and nightlife to give a comprehensive view of what it’s like to visit and live in these places.

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In Charlottesville, the influence of Thomas Jefferson looms large. The University of Virginia, which he founded, and Monticello, the fascinating house he built and rebuilt over many years, are the city’s two must-see sites. It’s a sophisticated, intellectual city that appreciates the best of everything—food, music, art, design, and sport—and revels in its beautiful setting. The gorgeous surrounding countryside offers scenic drives and destination restaurants, wineries, farms, and inns.

A year ago I had dinner at the Clifton, then under the supervision of Tucker Yoder. Mr. Yoder was elsewhere that evening, but I spent several hours at the “chef’s counter” in the kitchen, watching executive sous-chef Jarad Adams work his own delicious magic. Naturally Mr. Adams was meticulous with his food prep, but he was also surprisingly generous with his time for me. Imagine my delight when I returned this year to find Mr. Adams had been promoted to Executive Chef. On this visit, Mr. Adams’s tasting menu showed the same attention to detail as I remembered, but with a greater sense of adventure — even whimsy. From the amuse bouche (a spoonful of polenta topped with pork belly, apple, and a sprig of fennel) all the way through to the sticky toffee pudding with candied pecans, dates, and caramel ice cream for dessert, I was enchanted. The tasting menu consists of four courses and varies by the season. My first course was a toss-up between the butternut squash and apple soup and the shaved winter vegetable salad with hazelnuts, black cocoa, and a buttermilk dressing. I had no regrets about my choice of the salad, especially as butternut squash was the foundation of my next course: the most perfectly seared sea scallop I can remember. From there it was onto monkfish with beluga lentils, with Brussels sprout leaves dancing on top. Mr. Adams knows what he’s doing in the kitchen, and the Clifton — and Charlottesville — is lucky to have him.

On a recent trip to Charlottesville, Virginia, the heart of Virginia’s wine growing region, we made a pilgrimage to the world famous King Family Vineyards. Located in Crozet, a quick drive from Charlottesville, King Family is a relative newcomer to the industry, but they have quickly earned their place amongst some of the best wineries in the country. Starting just in 2000, the winery has quickly grown from producing 500 cases a year to more than 5,000 and with it they have earned a variety of honors, including the coveted Virginia Governor’s Cup award for red wine.

A work in progress throughout his adult life, Monticello truly reflects Thomas Jefferson’s many passions: architecture, philosophy, science, music, literature, art, and food. Check out the excellent visitors’ center first and take a shuttle to the mountaintop mansion with its expansive views. A guide takes you through the main-floor rooms, including Jefferson’s bedroom/study/library. Then explore the cellars, terrace walks, kitchen, thousand-foot vegetable garden, and Mulberry Row, where ongoing reconstruction illuminates the important roles slaves played at this complex and innovative plantation. Order timed tickets online for your desired date. Hours vary by season.

The Iris Inn, a luxury Shenandoah bed and breakfast, is the perfect base to explore Virginia’s Blue Ridge mountains. Located 30 minutes from Charlottesville, the Inn is close to nearly 30 wineries and is within a few minutes drive to the southern entrance of Shenandoah National Park. Owners Dave and Heidi Lanford warmly welcome visitors to their cozy mountainside inn with gourmet breakfasts and a complimentary nightly happy hour. The eco-friendly B&B also offers an electric vehicle charging station.

The C&O has been a mainstay of Charlottesville fine dining for decades. The vegetable soup and Steak Chinoise are justifiably beloved, but you really can’t go wrong with anything on the French- and Southern-influenced menu. The historic building has exposed brick walls, creaky floorboards, and six dining areas, including a patio, to accommodate both special occasions and casual dinners.

Stretching for seven blocks along University Avenue and West Main Street, The Corner is home to Mincer’s, selling UVA sportswear and accessories, Paul Victorius, selling historic prints, and dozens of restaurants and nightspots including Bodo’s Bagels, The College Inn, Littlejohn’s New York Deli, the venerable Virginian, and the classic greasy spoon diner White Spot. The stylish Graduate hotel is conveniently close to campus.

Head five miles out of town for great scenery and a fun family outing. Pick your own seasonal fruits and vegetables (or buy them at the farm stand) and enjoy casual farm-to-table dining, Prince Michel, wines and Bold Rock hard cider—all with an impressive view. Thursday evenings until 9 p.m. from May through September feature dinner, live music, hayrides, and memorable sunsets. The Apple Harvest Celebration starts in September.

A bucolic resort in the Virginia Piedmont, the Boar’s Head Resort is as deeply rooted in Virginia as its owner and neighbor, the University of Virginia. The land has hosted travelers since 1759, with the original Birdwood mansion dating to 1830. A short drive from downtown Charlottesville, Boar’s Head has plenty to keep a visitor occupied without even leaving the property, including an 18-hole golf course, a full-service spa, a fitness center with squash and tennis courts, and three swimming pools. The resort has 175 rooms spread over 573 acres; suites feature a seating area and balcony or patio, and some have fireplaces. Dining options range from healthy café fare (necessary fuel for all those tennis matches), to a grill overlooking the golf green, to an elegant meal in the restored Old Mill Room. The Blue Ridge mountains are renowned for their fall foliage, but visit in summer for fewer crowds (and UVA students) and the English-inspired grounds and gardens in full bloom. Be sure to ask for details on arranging a hot-air balloon ride over the countryside to appreciate all of historic Virginia.