By You do not have to drive to the mountains or the coast to disappear with someone you love. The Triad packs vineyard hills, candlelit Southern dining, four-diamond hotels, and 18th-century cobblestone streets into a compact triangle, which means a romantic weekend here is long on charm and short on windshield time. Here is how to put together two unhurried days for two across Greensboro, Winston-Salem, and the Yadkin Valley.
Where To Stay: Romantic Hotels And Inns
Lodging sets the tone for the whole weekend, and the Triad has a short list of genuinely special properties that you can book directly or through travel sites like Expedia.
Greensboro: Proximity Hotel And The O.Henry
The Proximity Hotel is a AAA Four Diamond property and was one of the first hotels in America to earn LEED Platinum certification. The loft-style rooms have soaring windows, custom furnishings, and original commissioned artwork, and the on-site Print Works Bistro serves European-leaning plates and craft cocktails along the creek. Guests can borrow complimentary bicycles to explore the city greenways. It sits at 704 Green Valley Road, Greensboro, NC 27408 (336-379-8200).
Its sister property, the O.Henry Hotel, leans into old-world romance with daily afternoon tea in the Social Lobby and live jazz on Thursday evenings and select Saturdays (no cover charge). The hotel offers dedicated romance packages, and the adjoining Green Valley Grill does Mediterranean plates with al fresco courtyard seating, cozy blankets included on cool nights. Find it at 624 Green Valley Road, Greensboro, NC 27408 (336-854-2000).
Winston-Salem: Kimpton Cardinal And Historic Inns
For a downtown stay, the Kimpton Cardinal Hotel occupies the historic R.J. Reynolds Building, the Art Deco tower that inspired the Empire State Building. The lobby and its restaurant, The Katharine Brasserie and Bar, blend Parisian polish with Southern hospitality, and the playful indoor recreation rooms make it easy to never leave. The hotel is at 51 East 4th Street, Winston-Salem, NC 27101 (877-216-3448).
If you prefer historic charm over high-rise glamour, Winston-Salem also has a cluster of restored downtown inns and bed-and-breakfasts within walking distance of restaurants and Old Salem. Booking a room with a fireplace or a garden view is an easy upgrade to the mood.
Day One: Slow Mornings, Gardens, And A Memorable Dinner
Start With A Garden Walk
Ease into the weekend with a stroll somewhere green. In Greensboro, the adjacent Tanger Family Bicentennial Garden (1105 Hobbs Road) and the Bog Garden (1101 Hobbs Road) are both free, open daily from 8 a.m. weather permitting, and connected by elevated boardwalks and a waterfall. The Tanger garden is especially photogenic in spring when the roses and fragrance garden are in bloom.
Over in Winston-Salem, Reynolda Gardens (100 Reynolda Village) offers formal garden paths, a conservatory, and rolling woodland trails, all free of admission and open daily from dawn to dusk. The Welcome Center and Conservatory keep shorter hours (Tuesday through Saturday 9:30 a.m. to 4:30 p.m., Sunday 1:30 to 4:30 p.m., closed Monday); you can reach the gardens at 336-758-5593.
Wander Historic Old Salem
For an afternoon that feels like stepping into another century, tour Old Salem Museums and Gardens, the restored 1766 Moravian congregation town in the heart of Winston-Salem. Costumed interpreters work the trade shops, and the on-site bakery turns out famous Moravian sugar cake and ginger cookies that make a sweet shared snack. The visitor center is at 900 Old Salem Road, Winston-Salem, NC 27101 (336-721-7350). Old Salem is generally open Tuesday through Saturday 9:30 a.m. to 4:30 p.m. and Sunday afternoons, closed Monday. Two-stop tickets run about $22 per adult and $12 per student in the standard February-to-November season, with higher all-access and holiday rates; children three and under are free. Confirm current pricing and seasonal hours before you go, since rates change with the calendar.
Dinner For Two
Reserve a candlelit table to anchor the evening. In Winston-Salem, The Katharine Brasserie and Bar inside the Kimpton Cardinal pairs French brasserie classics with regional ingredients and works equally well for casual nibbling at the bar or a multi-course celebration. In Greensboro, the Green Valley Grill and Print Works Bistro (at the O.Henry and Proximity respectively) both deliver the kind of attentive, special-occasion service that suits an anniversary. Whichever city you choose, book ahead on weekends.
Day Two: Yadkin Valley Wine Country
The single best move for a romantic Triad weekend is a day trip into the Yadkin Valley, North Carolina’s first federally recognized wine region and home to more than 40 vineyards within easy reach of Winston-Salem. Rolling hills, Blue Ridge views, and Tuscan-style tasting rooms make it feel far more remote than the short drive suggests.
A Standout Stop: Raffaldini Vineyards
If you only visit one winery, make it Raffaldini Vineyards and Winery, whose hilltop Villa and Piazza overlook vines planted with Italian varietals like Vermentino, Sangiovese, and Montepulciano. The view alone earns the trip, and a tasting on the terrace is the kind of unhurried hour that defines a getaway. It is located at 450 Groce Road, Ronda, NC 28670 (336-835-9463), and is generally open daily except Tuesday, roughly 11 a.m. to 5 p.m. (Sunday from noon). Reservations are strongly recommended, especially on weekends, and tastings are booked through the winery’s online system. Bring a picnic, settle in, and let the afternoon stretch.
Make A Tasting Trail Of It
Because so many wineries sit within a few miles of one another, couples often link two or three into a relaxed afternoon. A good rhythm is one tasting before lunch, a long lunch, and a final golden-hour stop. Use one of these guides to map your route:
- Plan the region: Visit North Carolina’s Greensboro and Winston-Salem guide covers the Yadkin Valley and surrounding towns.
- Pace yourselves: designate a driver or hire a small-group wine tour so both of you can taste freely.
- Pack a cooler: bottles you fall for travel home best on ice, and several wineries welcome picnics on the grounds.
Romantic Extras Worth Building In
- Afternoon tea: the O.Henry serves housemade scones, finger sandwiches, and sweets daily in its Social Lobby, a low-key treat between activities.
- Live jazz: time a Thursday or Saturday evening around the O.Henry Trio’s free sets in the lobby.
- A spa afternoon: Greensboro’s resort spas are an easy add-on if rain scratches the vineyard plan.
- Greenway cycling: borrow the Proximity’s complimentary bikes and ride a stretch of Greensboro’s connected trail network together.
Plan Your Visit
- Proximity Hotel: 704 Green Valley Road, Greensboro, NC 27408; 336-379-8200; proximityhotel.com
- O.Henry Hotel: 624 Green Valley Road, Greensboro, NC 27408; 336-854-2000; ohenryhotel.com
- Kimpton Cardinal Hotel: 51 East 4th Street, Winston-Salem, NC 27101; 877-216-3448; thecardinalhotel.com
- Old Salem Museums and Gardens: 900 Old Salem Road, Winston-Salem, NC 27101; 336-721-7350; open Tue-Sat and Sun afternoon, closed Mon; tickets from about $22 adult (verify current rates); oldsalem.org
- Reynolda Gardens: 100 Reynolda Village, Winston-Salem, NC 27106; 336-758-5593; free, dawn to dusk daily; reynolda.org
- Raffaldini Vineyards: 450 Groce Road, Ronda, NC 28670; 336-835-9463; open daily except Tuesday, reservations recommended; raffaldini.com
Planning tip: book your dinner reservation and your winery tasting slot first, then build the rest of the weekend around those two fixed points. Weekends fill quickly in spring and fall, and the gardens and Old Salem are flexible enough to slot in wherever the day leaves room.