Slow pre-Xmas Road trip from Chicago to Sarasota

Question

We’re planning a two-week (plus a few days) road trip from Chicago to Sarasota during the first half of December. A couple of years ago, we did a similar one-way trip around the same time, driving from Chicago to St. Augustine. We were lucky with the weather, and we reached our destination in 2 days

This time, we’d like to drive both ways, take our time, and see the Christmas season in small towns along the route. Below is the tentative plan I’ve put together, and I’d love your recommendations, precautions, and suggestions. Thank you in advance for your help!

Proposed Itinerary:

2 nights – French Lick, Indiana

1 night – Franklin or Nashville, Tennessee

1 night – Dahlonega, Georgia

1 night – Alachua, Florida (I couldn’t find a better or safer stop on the way to Sarasota—open to suggestions!)

2 nights – Crystal River, Florida

4–5 nights – Sarasota, Florida

1 night – Alachua (return trip, not sure yet)

1 night –Helen, Georgia

1 night – Franklin again (for the Dickens Christmas Festival)

1 night – Louisville, Kentucky

Thank you so much in advance for any tips or ideas, and safety advice!

Answer

Your proposed road trip from Chicago to Sarasota sounds wonderful and very manageable for a relaxed pre-Christmas journey. Driving shorter distances each day allows you to enjoy local attractions, small towns, and festive lights without feeling rushed.

Here are some thoughts and suggestions for your itinerary:

French Lick, Indiana (2 nights) – Great choice for a leisurely start. French Lick Resort has a beautiful historic hotel and during December the village and resort are usually decorated for the holidays. Consider exploring the small-town shops and perhaps the West Baden Springs Hotel nearby.
Franklin or Nashville, Tennessee (1 night) – Both are fine stops. Franklin offers a charming historic downtown with festive decorations, and if you prefer music and Southern charm, Nashville is bigger and livelier, but you may encounter more traffic. Choose based on whether you want a small-town vibe or a city stop.
Dahlonega, Georgia (1 night) – Perfect for a small-town Christmas feel. Known for its historic square, wine tasting, and holiday lights. Make sure to check if there are any local holiday events or craft fairs.
Alachua, Florida (1 night) – This is a convenient halfway stop to break up the drive, but if you want a slightly more charming town, consider Gainesville. It has more dining options, a vibrant local scene, and holiday decorations around the downtown area.
Crystal River, Florida (2 nights) – Excellent choice for a relaxing stay on the Gulf Coast. You can enjoy nature, including manatee tours if the season allows, and slow-paced waterfront dining.
Sarasota, Florida (4–5 nights) – Plenty of time to enjoy beaches, the Ringling Museum, local gardens, and Sarasota’s charming downtown. Consider day trips to Anna Maria Island and Siesta Key for a mix of walking, nature, and scenic views.
Return trip options:
- Alachua – again convenient for a mid-way stop; Gainesville is also an option if you prefer a more lively small city.
- Helen, Georgia – beautiful alpine-style town, very festive for Christmas. Arriving in the afternoon allows you to see the lights and enjoy a walk around the quaint streets.
- Franklin again – if the timing aligns with the Dickens Christmas Festival, it’s a great way to enjoy the holiday festivities.
- Louisville, Kentucky – convenient last stop before heading north, and you can enjoy city lights and a nice dinner before finishing your journey to Chicago.

Precautions and tips:

Check weather forecasts daily. December can bring unexpected cold fronts, especially in Tennessee and Georgia, so be prepared for potentially icy roads or rain.
Book accommodations ahead, especially in small towns with limited hotel options or seasonal holiday events.
Plan for daylight driving as much as possible—many towns are more enjoyable in daylight, especially for Christmas lights and scenic routes.
Keep an emergency kit, snacks, and water in the car. Even though you’re on major highways, winter weather and detours can occur.
Consider local events in each town—many small towns have Christmas markets, parades, or light displays that are worth checking online before your trip.

Overall, your itinerary balances driving with exploration and holiday experiences nicely. With these adjustments and precautions, you should have a relaxed and festive road trip to Sarasota and back.