Maximizing your paid time off doesn’t have to mean jet-setting to distant locations. With a bit of strategic planning, you can transform 15 PTO days into a year filled with memorable weekend adventures and extended holiday escapes—and Wilmington & the Brandywine Valley is the perfect place to test this theory. Here’s how you can do it. 

January: A New Year’s Refresh  

PTO Used: 1 Day 
Days Off: 4 days 

Make the most of the long Martin Luther King Jr. Day weekend by taking one PTO day for a rejuvenating four-day retreat. Begin your journey at the Hagley Museum & Library, where you can immerse yourself in stunning winter landscapes and engaging exhibitions. Enjoy a cozy evening at the Inn at Montchanin Village, paired with a delightful meal at Krazy Kat’s. We recommend taking advantage of their onsite spa too! Conclude your weekend with a refreshing hike through the picturesque trails of Brandywine Creek State Park, soaking in the unbeatable, scenic views. 

February: A Romantic Escape 

PTO Used: 1 Day 
Days Off: 3 Days 

Turn Valentine’s Day into an unforgettable long weekend by taking off on Friday for a romantic escape. Start your getaway with a happy hour wine tasting at Va La Vineyards, then indulge in an elegant Valentine’s Day dinner at the historic Le Cavalier at the Green Room. Spend the next day strolling through the inspiring galleries of the Delaware Art Museum, followed by a leisurely late lunch in Trolley Square. Choose to stay at the luxurious HOTEL DU PONT or the stylish Hyatt Wilmington Riverfront, perfectly situated for exploring Wilmington’s vibrant downtown and Riverfront neighborhoods. Cap off your weekend with a morning of fun and indulgence at Wilma’s, enjoying a decadent brunch and trying your hand at duckpin bowling—an ideal ending to your romantic retreat. 

March/April: Spring Awakens in the Brandywine Valley  

PTO Used: 1 Day 
Days Off: 3 Days 

As winter’s chill gives way to blossoming blooms, March and April are ideal for a long weekend of outdoor adventures and indulgent dining. Begin your springtime exploration at Lums Pond State Park, where the Go Ape Treetop Adventure Course offers exhilarating zip lines and obstacle challenges among the budding canopies. Whether you’re soaring through the trees or paddling across the tranquil waters of the pond, Lums Pond is a must-visit spring destination. After an adrenaline-packed morning, recharge with lunch at Del Pez Gastropub, celebrated for its relaxed vibe and creative twists on classic pub and Tex-Mex cuisine. 

Next, immerse yourself in the rich history and breathtaking gardens of the Winterthur Museum, Garden and Library, where blooming landscapes provide the perfect backdrop for learning about the du Pont family’s legacy and art collections. Pair this cultural outing with a stop at Brandywine Brewing Company for a refreshing craft beer experience. 

Spring also ushers in special events like Mt. Cuba Center's Wildflower Celebration and City Restaurant Week, offering opportunities to savor seasonal delights and explore local flavors. With longer days and warmer weather, March and April showcase Wilmington and the Brandywine Valley as its vibrant blooms come back to life.  

May: Memorial Day Fun 

PTO Used: 1 Day 
Days Off: 4 Days  

Stretch your Memorial Day weekend with a Friday off and enjoy four days of local delights. Begin with a visit to Longwood Gardens, where spring blooms are at their peak, and their iconic Festival of Fountains event creates dazzling displays of color with water set to classic and popular music. When you’ve had your fill of beautiful sights, take a break with lunch at Buckley’s Tavern, the historic tavern known to fill stomachs with delicious food and classic charm to all who cross its path.  

If you’re more of a history buff, explore the New Castle Courthouse Museum and the beautiful views of the Read House and Gardens in the colonial town of Historic New Castle, followed by a delightful meal at Jessop’s Tavern, a charming spot known for its colonial-era ambiance and hearty fare. For a little adventure, grab your helmets for a bike ride along the scenic JAM Trail (Jack A. Markell Trail), a picturesque route connecting Historic New Castle to Wilmington’s Riverfront neighborhood. Pedal past marshlands, waterways, and charming neighborhoods, rounding out a perfect weekend of outdoor adventure and local discovery. 

*Forgot your bike at home? Head to Wilmington’s Riverfront to rent one from FIN Bike rentals.  

If Memorial Day Weekend calls for beachside relaxation, consider arriving early in May to Greater Wilmington to kick off the festivities with one of its signature annual events. Iconic gatherings like A Day in Old New Castle offer a glimpse into history with charming tours and activities, while the Wilmington Grand Prix race brings exhilarating action as amateur and professional cyclists navigate exclusive paths through stunning estate properties typically closed to the public. These unique experiences combine world-class sportsmanship and picturesque views, setting the tone for a memorable long weekend in Wilmington and the Brandywine Valley. 

June: Celebrate Freedom and History 

PTO Used: 1 Day  
Days Off: 4 Days 

June is a month to honor the past and embrace the future, as Wilmington comes alive with vibrant Juneteenth celebrations. Extend your weekend with a PTO day and begin your journey at the Delaware History Museum, where exhibitions illuminate the rich tapestry of African American history in the First State. Within the museum, the Mitchell Center for African American Heritage tells compelling stories of resilience, achievement, and the enduring fight for equality—perfect for reflecting on this historic occasion. 

Next, head to Tubman-Garrett Riverfront Park, named in honor of Harriet Tubman and Thomas Garrett, two icons of freedom. During Wilmington’s annual Juneteenth celebrations, the park transforms into a lively hub of activity, featuring live music, cultural performances, and local vendors offering unique art, food, and crafts. Relax by the Christina River, soak in the festive atmosphere, and join the community in commemorating emancipation and celebrating cultural heritage.  

Round out your weekend with a meal at African American-owned establishments like Green Box Kitchen or Oath 84, where you'll find incredible options to suit all palates. Take time to explore Wilmington's vibrant network of Black-owned businesses, including LaFate Gallery, Town & Shore Handcrafted, and Morgan’s of Delaware. Wilmington in June offers a meaningful and enriching experience to honor history and support the future of its thriving communities. 

July: Celebrate Independence Day 

PTO Used: 1 Day 
Days Off: 4 Days 

Extend your Fourth of July weekend with an extra day off to turn it into a memorable holiday retreat. Begin your festivities with an evening concert at The Grand Opera House or The Queen Wilmington, both iconic venues in downtown Wilmington. Afterward, savor dinner at one of Market Street’s culinary gems—indulge in innovative dishes at Bardea Food & Drink, enjoy the sophisticated ambiance of The Quoin Restaurant, or opt for the laid-back charm of Chelsea Tavern for a casual yet flavorful meal. 

For a touch of history, hop on the ferry to Pea Patch Island and explore Fort Delaware. This Civil War-era fortress offers a fascinating glimpse into the past, showcasing its role in protecting Delaware and Philadelphia during the war. The scenic ferry ride across the Delaware River adds to the experience, making it a must for history buffs and families alike. 

Cap off your holiday weekend with a visit to Nemours Estate, where you’ll be transported to a world of elegance and grandeur. Explore the stunning formal gardens inspired by Versailles and take a tour of the grand du Pont mansion, a perfect way to spend a leisurely summer day. This extended Fourth of July getaway blends entertainment, history, and beauty for a well-rounded celebration.