Road Trip Itinerary: East Islip, NY → Winter Haven, FL

Day 1: East Islip → Richmond, VA

Morning: Depart East Islip and cruise north on I-95, stopping at a Shell station in New Brunswick, NJ for a quick fuel top‑up and coffee break. Continue past the Delaware Memorial Bridge, using EZ‑Pass for a smooth toll experience.

Afternoon: After crossing the Chesapeake Bay Bridge‑Tunnel, enjoy a scenic lunch in Virginia Beach and stretch your legs on the boardwalk before heading inland toward Richmond. The drive includes a short toll at the Richmond Turnpike (EZ‑Pass).

Evening: Arrive in Richmond and explore the historic Virginia State Capitol area before checking into a downtown hotel. Dine at a local restaurant and rest up for the next day’s drive.

Day 2: Richmond → Savannah, GA

Morning: Leave Richmond early, stopping at a BP station in Fayetteville, NC for fuel and a snack. Cruise past the Cape Fear River and enjoy the rolling countryside of the Carolinas.

Afternoon: Arrive in Charleston, SC for a brief visit to the Historic District and a quick bite at a waterfront café. Continue south, paying SunPass tolls at the Florida Turnpike entry as you cross into Florida.

Evening: Reach Savannah and wander the Riverfront with its iconic oak‑lined squares. Check into a boutique inn and enjoy dinner at a historic tavern.

Day 3: Savannah → Winter Haven, FL

Morning: Depart Savannah after a hearty Southern breakfast, refueling at a Chevron station in Jacksonville, FL. Take a short detour to view the St. Johns River from the downtown waterfront.

Afternoon: Cruise along I-75 “Alligator Alley,” stopping at a Shell station near Naples for a quick refuel and to stretch. Continue north, passing the SunPass toll plaza at the I-75/FL‑44 interchange.

Evening: Arrive in Winter Haven, FL and settle into your accommodation. Unwind with a walk around the scenic Chain of Lakes before concluding your road trip.

Time and Cost Estimates

• Shell station – New Brunswick, NJ: 15 min, $45 fuel
• Delaware Memorial Bridge toll: 5 min, $6
• Shell station – Fayetteville, NC: 15 min, $48 fuel
• Charleston Historic District: 2 hr, $0 (free walk)
• SunPass toll – Florida Turnpike entry: 5 min, $8
• BP station – Richmond, VA: 15 min, $45 fuel
• Chevron station – Jacksonville, FL: 15 min, $50 fuel
• Shell station – Naples, FL: 15 min, $55 fuel
• SunPass toll – I‑75/FL‑44 interchange: 5 min, $7
• Chain of Lakes walk: 1 hr, $0
• Accommodation (3 nights): 3 nights, $540
• Meals (approx.): 3 days, $180
• Total Estimated Cost: $934

Tips

To extend the adventure, add a day in the Blue Ridge Parkway for scenic mountain drives, or linger longer in Charleston and Savannah to soak up their historic charm. If you need to shorten the trip, combine the Day 1 and Day 2 drives into a single long day and skip the Charleston stop, but be prepared for a longer stretch behind the wheel and plan additional fuel breaks accordingly.