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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.

If eating huge plates of pork, deciphering local slang, and snowshoeing through the woods of Québec can’t bring two siblings together, what can?

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.

The Shockoe Slip in Richmond, Virginia has many quaint shops, good restaurants, and several upscale hotels. One of those hotels is the Berkeley Hotel. This boutique hotel is beautifully furnished. The rooms and bathrooms are richly decorated. Breakfast, lunch, and dinner are offered in the hotel restaurant. Access to the Jamestown Center fitness club is included for guests. The attentive staff will be happy to assist you in any way they can. Nearby you will find the Richmond City Hall, the Virginia State Capital, the James River, and many other historic sites. A stroll down Cary Street is fun whether you are going to a restaurant or shopping or sightseeing. I have stayed at the Berkeley several times and have never been anything but pleased with the service and the hotel.

Nicknamed “the chic boutique,” New To You has been a popular Northern Virginia consignment shop for the stylistic fashionista seeking a savvy bargain for a second-hand Armani, Anthroplogie, Carolina Herrera, Chanel, Hermes, Prada, or another high-end name. Gently worn designer, vintage, and good-as-new clothing, business wear, gowns, shoes, boots, scarves, purses, and jewelry constitute many of the items carefully screened and selected by owner Christine Novak. Strong emphasis on quality, cleanliness, and fit.

For visitors, Carytown, located near the downtown hotels and the Museum District, is the preferred place to shop. This several-block stretch of West Cary Street is full of independently owned shops and restaurants, as well as the historic Byrd Theatre, a 1920s movie palace showing recent and classic films at bargain prices. A few notable shops are Mongrel, an all-occasion gift shop with a great selection of Richmond- and Virginia-themed items, World of Mirth, a colorful, kitschy toy store that’s fun for all ages, and Eurotrash, featuring fashion-forward European women’s clothing for all styles and budgets.

Seafood is the star at Rappahannock Restaurant in downtown Richmond. This is the third venture of the Croxton family, which has played a major role in the Chesapeake Bay oyster resurgence. The restaurant’s raw bar features four oyster varieties, clams, and caviar; Virginia fish and meat round out the menu. Cocktails are given similar reverence and made with fresh, seasonal ingredients to complement the food. Should you wish to go straight to the source, the Merroir tasting room is an hour from Richmond and overlooks the Rappahannock River where the oysters are grown.

Since 1970, owner and Virginia native Joel Cohen and his family have been offering trendy business, casual, and evening clothing to women of various ages and sizes as well as jewelry, handbags, purses, belts, and other accessories. Popular brands include Angel, Crystal Boutique, Finley, Zelda, Stizzoli, and Joseph Ribkoff. To define your colors and style, staff act as your personal shoppers allowing for a comfortable shopping experience.

Hudson Trail Outfitters is a local chain that caters to outdoor enthusiasts in the Washington, D.C. area. The first store opened in 1971 with the goal of selling the highest-quality specialized gear and apparel and providing top-notch customer service. The strategy worked: The shop became a huge success, and four more have since opened in Maryland, Virginia, and D.C. Part of what makes the company special is its focus on the community. It holds weekly events that include yoga, hiking, biking, paddling, and boot camp meet-ups. This is a must-stop for information on the area’s best trails and natural highlights.

“The menu at this authentic Japanese restaurant changes constantly. This place is legit authentic Japanese, they even make you take off your shoes and wear their slippers … Men have to wear a button-down collared shirt, so be ready. You can order from their menu a la carte, but the thing to do is make reservations and get their tasting menu. This is what we do every time and it never disappoints. The tasting menu is about seven to eight dishes depending on what the chef decides to send. The meal is unforgettable. In signature Japanese style, the dishes are small, but compact with tons of awesome flavors.” —Kevin Diedrich, a bar manager and consultant who grew up in Northern Virginia.

The most exclusive lodge in New Zealand, having hosted everyone from Queen Elizabeth II to the late Robin Williams, Huka Lodge feels like a refined country getaway set on the banks of the Waikato River near the North Island resort town of Taupo. Founded in 1924 by a charismatic Irishman named Alan Pye, the property was later reimagined by entrepreneur Alex van Heeren with the help of interiors specialist Virginia Fisher and famed New Zealand landscape designer Suzanne Turley. The surrounding grounds are ranked as a ‘Garden of National Significance’ by the New Zealand Gardens Trust. Whether staying in the lodge suites—which feature French doors that open up to a wooden terrace just steps from the river—or the lofty private cottages, guests will feel like royalty here.

The Jefferson Hotel has been the gold standard for discerning visitors to Richmond (including 13 U.S. presidents) since 1895. Not content to rest on their laurels, the hotel completed a renovation in 2016, restoring its landmarked public areas and refreshing and expanding the guest rooms and suites. The new rooms feel more like posh apartments, with doorbells, foyers to the sitting and dressing areas, and luxury touches like soaking tubs, walk-in showers, and in-mirror televisions. The alligator drawer pulls are a nod to the creatures who used to live in the lobby fountains in the early 20th century. The Rotunda and Palm Court lobbies, with their Tiffany stained glass ceilings, have overlooked many power meetings and celebrations, and provide a magnificent backdrop for decadent afternoon tea or the popular champagne Sunday brunch. The four-star Lemaire restaurant serves a New American menu of Virginia ingredients in their distinctive dining rooms, while the more relaxed TJ’s bistro is open for hearty breakfasts and classic lunch fare. Guests of the Jefferson may work off all that locally sourced food at the 3,000-square-foot gym or in the indoor pool with skylights and an outdoor pool deck.

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.

Better known as MOHAI, this collection dives deep into local history, from the region’s maritime history to its tradition of technological innovation. Highlights include Boeing’s first commercial plane, the 1856 Petticoat Flag sewn by women during the Battle of Seattle, and the original Rainier Brewing Company neon R sign. Behind the stunning building—overlooking Lake Union—bob National Historic Landmark vessels: most notably the star of the 1934 MGM movie Tugboat Annie and the 1921 Virginia V, a steamer that opens its decks for balls, excursions, and trivia nights. The Center for Wooden Boats has displays and rents vessels on the neighboring docks (cwb.org).

Chef Patrick O’Connell opened his country restaurant out of a former gas station in 1978 and rave word-of-mouth reviews soon made it “destination dining.” He opened rooms in 1984 and a few years later, it became a member of the prestigious Relais & Chateau hotel association. Today, it remains one of a handful of country hotels worth the trip for the meal as well as the stay, and it continues to rack up stars and top lists for dining and accommodations.

Two dozen opulent rooms reflect the style of a whimsical English country manor (as interpreted by O’Connell and London stage designer Joyce Conwy Evans), setting the tone for an over-the-top dinner with an exacting attention to detail. Be sure to visit the kitchen after your meal to see culinary magic in action. Little Washington (the first town named by George himself) is a bit over an hour from its capital namesake, and the Inn’s campus of guest rooms, shops, and gardens are spread over the colonial town; take the Perimeter Path walk to visit all of the farm operations and the newest guest quarters: a Little Bug Inn for pollinating and beneficial insects.