14 day itinerary
Roadtrip Chicago To Sea Island
Itinerary
A road trip from Chicago to Sea Island sounds like a fantastic adventure, especially with family in tow. Let’s create a relaxed, family-friendly itinerary that includes parks, green spaces, and plenty of opportunities to enjoy the journey. Buckle up, and let’s hit the road!
Day 1: Chicago, IL
Morning: Start your trip with a leisurely breakfast at a local café. Afterward, head to . It’s free and has beautiful gardens and a playground for the kids.
Afternoon: Explore further, perhaps with a picnic lunch. You can stroll along the lakefront or visit the if you’re up for it.
Evening: Enjoy dinner at a family-friendly restaurant in the area, like Portillo’s for some classic Chicago-style hot dogs.
Day 2: Chicago, IL to Indianapolis, IN (Approx. 3 hours)
Morning: Depart Chicago after breakfast. Stop at for a quick stretch and a visit to the if there’s an event happening.
Afternoon: Arrive in Indianapolis and have lunch at The Eagle. Afterward, head to . You can rent bikes or just enjoy a leisurely walk.
Evening: Check into your hotel and have dinner at Shapiro’s Delicatessen for some hearty family fare.
Day 3: Indianapolis, IN to Louisville, KY (Approx. 2 hours)
Morning: After breakfast, visit the —it’s a hit with families!
Afternoon: Drive to Louisville and have lunch at Mellow Mushroom. Spend the afternoon at , where the kids can run around and you can enjoy the views of the Ohio River.
Evening: Dinner at Bourbon Bistro for a taste of local cuisine.
Day 4: Louisville, KY to Nashville, TN (Approx. 3 hours)
Morning: Depart for Nashville after breakfast. Stop at for a short hike and some fresh air.
Afternoon: Arrive in Nashville and have lunch at Hattie B’s Hot Chicken. Spend the afternoon at , where you can see the Parthenon replica and let the kids play.
Evening: Enjoy a family-friendly dinner at The Pancake Pantry.
Day 5: Nashville, TN
Morning: Visit the Nashville Zoo at Grassmere. It’s a great way to spend the morning!
Afternoon: Have lunch at The Pharmacy Burger Parlor & Beer Garden. Afterward, explore for some easy hiking and wildlife spotting.
Evening: Dinner at Puckett’s Grocery & Restaurant for some Southern comfort food.
Day 6: Nashville, TN to Chattanooga, TN (Approx. 2 hours)
Morning: Depart for Chattanooga after breakfast. Stop at for stunning views and a visit to .
Afternoon: Arrive in Chattanooga and have lunch at The Blue Plate. Spend the afternoon at , where there’s a carousel and plenty of green space.
Evening: Dinner at Tony’s Pasta Shop & Trattoria.
Day 7: Chattanooga, TN to Atlanta, GA (Approx. 2 hours)
Morning: After breakfast, visit the before heading out.
Afternoon: Arrive in Atlanta and have lunch at The Varsity. Spend the afternoon at , where you can relax and let the kids play.
Evening: Dinner at Mary Mac’s Tea Room for a taste of Southern hospitality.
Day 8: Atlanta, GA
Morning: Visit the —it’s one of the largest in the world!
Afternoon: Have lunch at Ponce City Market and explore the shops. Afterward, head to for some beautiful scenery.
Evening: Dinner at The Cheesecake Factory for a family-friendly option.
Day 9: Atlanta, GA to Savannah, GA (Approx. 3.5 hours)
Morning: Depart for Savannah after breakfast. Stop at for a quick history lesson and some outdoor time.
Afternoon: Arrive in Savannah and have lunch at Mrs. Wilkes’ Dining Room. Spend the afternoon exploring , where the kids can play and you can enjoy the beautiful fountain.
Evening: Dinner at The Pirate’s House for a fun, themed experience.
Day 10: Savannah, GA
Morning: Take a leisurely stroll through the historic district and visit .
Afternoon: Have lunch at The Collins Quarter. Spend the afternoon at for some hiking and nature exploration.
Evening: Dinner at The Grey, a family-friendly spot with a unique twist.
Day 11: Savannah, GA to Hilton Head Island, SC (Approx. 1 hour)
Morning: Depart for Hilton Head after breakfast. Spend the morning at .
Afternoon: Have lunch at The Sea Shack. Spend the afternoon biking around the island or visiting .
Evening: Dinner at Harbour Town with a view of the lighthouse.
Day 12: Hilton Head Island, SC
Morning: Enjoy a beach day! Build sandcastles and relax.
Afternoon: Have lunch at The Dunes House. Spend the afternoon at for some outdoor fun.
Evening: Dinner at The Salty Dog Café for a casual family meal.
Day 13: Hilton Head Island, SC to Sea Island, GA (Approx. 1.5 hours)
Morning: Depart for Sea Island after breakfast. Arrive and check into your accommodation.
Afternoon: Have lunch at the resort or a nearby café. Spend the afternoon at .
Evening: Enjoy a family dinner at .
Day 14: Sea Island, GA
Morning: Relax and enjoy the amenities at Sea Island. Perhaps a family bike ride or a visit to the .
Afternoon: Have lunch at The Beach Club. Spend the afternoon at the beach or pool.
Evening: For your last dinner, enjoy a special meal at (make reservations in advance).
Final Thoughts
This itinerary balances travel time with plenty of opportunities to explore parks, green spaces, and family-friendly activities. Remember to take your time, enjoy the scenery, and make some wonderful memories along the way! Safe travels! 🌟