Start your day with a hearty breakfast at Brookfield Village Diner, then fill up and hit I-95 S by 8:00 AM to avoid early congestion. Mid-morning, stretch your legs with a quick scenic stop at Sherwood Island State Park for a coastal walk and coffee from the park kiosk before resuming the long southbound drive through Connecticut and into New York.
After the Sherwood Island stop, plan a leisurely lunch break at Norman Rockwell Museum Café (a slight detour if you want art with your sandwich) or grab fresh seafood at Captain's Cove Seaport for waterfront views before hitting the road again. Mid-afternoon, stretch your legs with a brisk walk on the boardwalk at Silver Sands State Park or a quick photo stop at The Pequonnock River Overlook, then refill snacks and fuel at a large highway service plaza before the long evening drive toward your motel stop.
After a long day on the highway, unwind with dinner at Cracker Barrel Old Country Store near your chosen interstate exit for homestyle comfort food and a browse through their country shop, then check into a well-reviewed budget motel like Hampton Inn or Best Western Plus for a reliable night's rest. If you have energy left, take a short post-dinner stroll at Riverside Park (or a nearby municipal green) to stretch your legs and enjoy the sunset before turning in early to recharge for the final drive to Fort Myers.
Finish the final stretch south with an early arrival plan that includes a refreshing break at Paynes Creek Historic State Park for a short boardwalk walk through wetlands and a chance to spot wading birds before the afternoon heat. Time your approach into Fort Myers to pull off at Edison & Ford Winter Estates for a self-guided tour of the historic homes and fragrant botanical gardens-the perfect mellow way to transition from the road to your coastal arrival.
After checking into your accommodation, take a relaxed, sun-soaked afternoon exploring Lakes Regional Park, where you can rent a paddleboat, stroll the shaded trails, and visit the butterfly garden for a calm transition off the highway. Follow that with a late-afternoon wander through the vibrant streets of Downtown Fort Myers (Edison District)-browse art galleries, grab a fresh citrus smoothie at a local café, and stake out a table at Fort Myers River District waterfront spots to watch the sunset over the Caloosahatchee River.
Once you've settled in, savor a relaxed dinner at The Veranda, an elegant historic restaurant with Southern-inspired dishes and a lovely garden patio that feels like a proper reward after the drive. After dinner, take a gentle post-meal stroll along the lit riverfront at Centennial Park to enjoy live music or local performers (often frequent in the evenings), then stop by The Sidney & Berne Davis Art Center for a nightcap at their gallery café or to catch an evening concert if one is scheduled.