A Winter Holiday

Discover the magic of Virginia's winter charm. Traverse spectacular landscapes to uncover exceptional experiences, five-star resorts, soothing spas, and one-of-a-kind luxury. Your unforgettable escape begins here.

Wind down your day with a magical walk along King Street where cobblestone streets are lined with boutique shops, antique stores, and eclectic galleries, offering a delightful array of one-of-a-kind treasures. Return to the Morrison House for a nightcap at The Study where you can enjoy a cleverly crafted cocktail or an inviting glass of wine to sip at your leisure in a cozy setting.

DAY TWO

Your journey then leads you to Charlottesville, a historic city sitting at the foothills of the Blue Ridge Mountains. Discover why it has been awarded Wine Enthusiast’s “Wine Region of the Year” as you begin your day with a chauffeur-driven excursion along the Monticello Wine Trail, indulging in a private tour and tasting at wineries like Pippin Hill Farm & Vineyards, renowned for its sweeping views of the surrounding mountains and their farm-to-table culinary delicacies.

Experience the iconic Thomas Jefferson’s Monticello in a whole new light during the winter season as you delve into the rich history and architectural splendor of this historical gem in a serene atmosphere. Afterward, explore Charlottesville’s Historic Downtown Mall, where you will find yourself surrounded by historic buildings offering distinctive shopping experiences, and boutiques, galleries, and cafes provide warm respites amidst the winter chill.

Check into The Clifton, an historic estate with ties to Jefferson. Set on 100 acres of rolling hills, this boutique property blends Southern charm with modern elegance to create a tranquil retreat for those seeking a relaxing getaway in the heart of Virginia's wine country. Here, savor a private dinner at The Clifton’s 1799 Restaurant, where Michelin-starred Chef Matthew Bousquet serves up food inspired by the land and the 18th-century ambiance, providing the perfect resolution to your day.

DAY THREE

Fulfill your sense of adventure with a morning hot air balloon ride over the scenic Shenandoah, offering a breathtaking aerial perspective of the wintry landscapes. Transition to Wintergreen Resort for an exclusive winter sports experience that offers varying difficulty levels of slopes to accommodate both seasoned professionals and beginners alike.

DAY FIVE

Take an excursion to Virginia Beach for an unforgettable winter whale-watching trip. Only an hour’s drive from Williamsburg the Atlantic Ocean awaits, where the winter months bring a fascinating display of marine life, including humpback whales and playful dolphins.

Then pamper yourself at The Spa of Colonial Williamsburg, or take a leisurely stroll through Merchants Square, adorned with winter decorations, creating a picturesque backdrop for a shopping excursion.

Your trip comes to a culmination with dinner at the Rockefeller Room, the crown jewel of the Williamsburg Inn, where exquisite flavors combine with timeless charm to create memories that will linger long after your visit.