Start the day with a hearty breakfast at The Daily Grind in downtown Leonardtown before hitting the road, then take a scenic detour through Chesapeake Beach for a short waterfront stroll to stretch your legs. Mid-morning, pause at St. Marys River Overlook for photos and a picnic-style snack, and if time allows explore the shady trails around Point Lookout State Park to break up the drive and enjoy coastal marsh views on your way south toward Savannah.
Mid-afternoon, roll into historic Savannah and wander the oak-lined squares beginning with Chippewa Square, then follow the riverfront toward River Street for waterfront views, street performers, and boutique shopping. As the sun lowers, enjoy a leisurely late-afternoon tasting at Savannah Distilling Company or a craft cocktail at The Olde Pink House (reservations recommended), then check into your hotel and relax before an evening stroll along the lit promenade by the Savannah River.
As twilight settles, savor Southern seafood and Lowcountry flavors at The Collins Quarter at Forsyth Park with an outdoor table overlooking the park for a relaxed dinner. Afterward, take a moonlit ghost tour from Ghost City Tours to glide through lantern-lit lanes and hear Savannah's spine-tingling stories, then end the night with live jazz and nightcaps at the cozy speakeasy The Grey Market & Bar before returning to your hotel.
Leave Savannah after a quick coffee and pastry at Foxy Loxy Café, then enjoy a relaxed morning drive with a scenic stretch-break at Gamble Rogers Memorial State Recreation Area for a short beach walk and tidal marsh views. Arrive in Orlando before midday and head straight to Disney Springs for a leisurely brunch at The Polite Pig and souvenir browsing at World of Disney before checking in at your Walt Disney World hotel.
After arriving in Orlando, head to Lake Eola Park for a relaxed paddleboat ride and people-watching amid the downtown skyline, then stroll the nearby East End Market to sample local bites like gourmet empanadas and craft coffee. Later, make a quick detour to Disney's BoardWalk to soak up carnival-style entertainment and street performers before checking into your Walt Disney World hotel and preparing for an evening at the parks.
After check-in, unwind with a sunset stroll and lakeside cocktails at The Boathouse at Disney Springs, then grab waterfront seats to watch the evening lights come up along the promenade. Later, treat yourself to playful tapas and craft cocktails at Enzo's on the Lake for a relaxed, grown-up dinner before capping the night with fireworks viewing from the hotel terrace or a short shuttle ride to Magic Kingdom's fireworks viewing area (reserve a spot early if possible).