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 New Jersey Turnpike service area for a quick coffee and a fuel top‑up. Continue through Pennsylvania, enjoying a brief view of the historic Philadelphia Museum of Art steps from the highway.

Afternoon: After crossing the Delaware Memorial Bridge (E‑ZPass toll), drive into Maryland and pause at a Harrisburg Rest Stop for lunch and another gas fill‑up. The route then takes you through the scenic Chesapeake Bay Bridge‑Tunnel (toll included) before reaching Virginia.

Evening: Arrive in Richmond and explore the Historic Shockoe Bottom district for dinner, then settle into a downtown hotel for a restful night.

Day 2: Richmond → Savannah, GA

Morning: Leave Richmond and head south on I‑95, making a quick stop at a Fredericksburg, VA gas station for fuel and snacks. Pass the Washington, D.C. National Mall skyline as you zip through the capital (E‑ZPass tolls on the D.C. Capitol Tunnel).

Afternoon: Continue through North Carolina, refueling at a Raleigh service plaza and enjoying a short walk at the North Carolina Museum of Natural Sciences. Cross into South Carolina, where a brief stop at a Charleston fuel stop lets you stretch your legs.

Evening: Arrive in Savannah; wander the cobblestone streets of the Savannah Historic District and dine along the riverfront before checking into a boutique inn.

Day 3: Savannah → Winter Haven, FL

Morning: Depart Savannah, refuel at a St. Augustine gas station, and admire the historic Castillo de San Marcos from the roadside viewpoint. Continue south, entering Florida and switching to SunPass for upcoming tolls.

Afternoon: Cruise along I‑95, stopping at a Orlando service area for a quick lunch and fuel top‑up. Take a brief detour to the Lake Eola Park for a scenic walk before re‑joining the highway.

Evening: Arrive in Winter Haven, explore the charming downtown and the nearby Chain of Lakes for sunset views, then settle into your final accommodation.

Time and Cost Estimates

• Fuel Stops (7 total) – Approx. 1 hour total – $220
• E‑ZPass tolls (NY, NJ, PA, MD, DC, VA) – Approx. 45 minutes – $30
• SunPass tolls (FL) – Approx. 30 minutes – $25
• Philadelphia Museum of Art view – 15 minutes – Free
• Chesapeake Bay Bridge‑Tunnel – 30 minutes – $20
• Washington, D.C. National Mall skyline – 20 minutes – Free
• Historic Shockoe Bottom (Richmond) – 2 hours – $20 (dinner)
• Savannah Historic District – 3 hours – $15 (parking & snacks)
• Castillo de San Marcos viewpoint – 20 minutes – $10 (parking)
• Lake Eola Park (Orlando) – 30 minutes – Free
• Chain of Lakes (Winter Haven) – 1 hour – Free
• Total Estimated Cost – $340

Tips

If you have extra time, add a day to explore the Washington, D.C. monuments or the Orlando theme parks. To shorten the trip, combine Day 1 and Day 2 by pushing further to Savannah on the first day, but be prepared for a longer driving stretch (over 12 hours) and ensure you have ample rest stops.