5-Day Romantic Getaway in Winston-Salem

Fall in love all over again in Winston-Salem, the city of arts, culture, and charm.

22 April 2023

Located in North Carolina, Winston-Salem offers a charming destination for couples looking for a romantic getaway. Discover the city's rich history through a visit to the restored Old Salem Museum & Gardens. Savor the area's vibrant cuisine and world-class wines at local restaurants and wineries.

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Travel plan

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Day 1

Arriving in Winston-Salem

  • Check into the luxurious Graylyn Estate, a stunning chateau-style hotel with 55 acres of lush gardens
  • Take a stroll through the thriving arts district of Downtown Winston-Salem
  • Learn about the founding of the city at the Old Salem Museums & Gardens
  • Enjoy a delicious dinner at the locally-sourced farm-to-table restaurant, Spring House Restaurant, Kitchen & Bar
Day 2

Savoring Winston-Salem's Culture and History

  • Start the day with breakfast at the grits-loving Mary's Gourmet Diner
  • Visit Reynolda House Museum of American Art, featuring works by Grant Wood, Edward Hopper, and Georgia O'Keeffe
  • Take a tour of the historic and beautiful Graylyn Estate, former home of Bowman Gray, the president of the R.J. Reynolds Tobacco Company
  • Dine at Mozelle's Fresh Southern Bistro, serving up classic southern dishes with a unique twist
Day 3

Exploring the Outdoors

  • Start the day with a leisurely walk through Tanglewood Park, home to a beautiful arboretum, golf courses, and horse trails
  • Take a relaxing paddleboat ride on the tranquil waters of Salem Lake
  • Hike to the top of Pilot Mountain State Park for breathtaking views of the surrounding countryside
  • Wrap up the day with dinner at the stylish and hip Quanto Basta Italian Eatery & Wine Bar
Day 4

Wandering Winston-Salem's Neighborhoods

  • Start your morning on Reynolda Village where you can find handmade crafts, exquisite antiques, and unique gifts
  • Visit the historic Bethabara Park, the original 1753 Moravian settlement
  • Take a scenic drive through the Buena Vista neighborhood and discover its stately homes and tree-lined streets
  • Experience the unique taste of Ethiopian cuisine at Foothills Brewing Downtown Brewpub
Day 5

Wining and Dinning

  • Start the day with a coffee from the quirky and cheerful Krankies Coffee
  • Take a tour of the excellent Childress Vineyards Winery and indulge in some of their famous tastings
  • Satisfy your cravings with delicious cuisine at the farm-to-fork restaurant, Canteen Market and Bistro
  • End the day with a visit to the award-winning breweries in the downtown area including Foothills Brewing and Small Batch Beer Co.

Length of stay

1 day 2 days 3 days 4 days 5 days

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

How to get there

Plane

The easiest way to get to Winston-Salem by air is to fly into Piedmont Triad International Airport (GSO) located approximately 30 minutes outside of the city. Major airlines such as American, Delta, and United fly into GSO from various destinations across the United States.

Car

Driving is also a popular way to get to Winston-Salem. If you're coming from the north or south, simply take Interstate 77 to Interstate 40 West. If you're coming from the east or west, take Interstate 40 to Winston-Salem. Parking can be found in various locations throughout the city, including parking garages and street parking.

Train

While there is no direct train service to Winston-Salem, you can take Amtrak to the nearby city of Greensboro, located approximately 30 minutes away. From Greensboro, you can then take a Greyhound bus or rent a car to complete your journey to Winston-Salem.

Boat

There is no direct water transportation to Winston-Salem as it is not located on a major body of water. However, if you have a boat, you can potentially access the city via the Yadkin River or nearby lakes such as High Rock Lake or Belews Lake, which are all within driving distance of Winston-Salem.

Bus

Greyhound offers bus service to Winston-Salem from various locations across the United States, including nearby cities such as Greensboro and Charlotte. The Greyhound bus station is located in downtown Winston-Salem, making it a convenient option for those staying in the city center.

Destination

Winston-Salem

Winston-Salem, the city that sounds like the lovechild of a British prime minister and a tobacco plant. But don't let the name fool you, there's more to this place than just smoke and politics.

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Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

Get Romantic in Winston-Salem: A 4-Day Adventure

A romantic trip to Winston-Salem, United States takes couples on a journey through picturesque landscapes and charming neighborhoods. Explore the art galleries, vintage shops, and cafes along the cobblestone streets, as well as the historic sites that showcase the city's rich cultural heritage. Dine on delectable Southern cuisine and sample locally produced wines, all while basking in the city's serene ambiance.

3-Day Arts, Food & History Trip to Winston-Salem

Discover the charm and history of Winston-Salem on a romantic getaway. Stroll through the gardens of Reynolda Village and share a romantic meal at one of the city's renowned restaurants. Enjoy a stay in a luxurious hotel and take in the beauty of this southern gem.

Winston-Salem: A Fun Day Out on a Budget

Winston-Salem is a charming city located in the foothills of North Carolina, offering both historical attractions and stunning natural landscapes. Travelling on a limited budget, visitors can explore the Old Salem Historic District, Reynolda House Museum of American Art, and Tanglewood Park. For affordable accommodation, budget-friendly hotels and motels are available in the city, while local markets and eateries offer delicious cuisine at reasonable prices.

Winning in Winston-Salem: History, Art & Bites

Winston-Salem, located in North Carolina, is a city that offers a blend of history, art, and modern amenities. As a tourist, one can explore the historic district of Old Salem, where the Moravians settled in the 18th century. The Reynolda House Museum of American Art offers visitors an opportunity to see a vast collection of American art and artifacts.