Florida Roadtrip November’26

Question

We are heading to Barbados next November for our friend’s 50th birthday, so I thought since we have to fly in and out of Miami to get there, we might as well make the most of it and add a 4 week road trip of Florida and some of the Southern States to the itinerary.

I am thinking of starting a week before we fly to Barbados, starting 31st October. I have had a go at putting an itinerary together and I was just wondering what you all think…

Fly into MIA from LAX 5am Sat 31st Oct, pick up hire car.

Islamorada- 1 night

Key West- 3 nights

Miami South Beach 3 nights

Sat 7th Nov, drop off hire car, head to Barbados, returning MIA Wed, 18th Nov. pick up hire car before continuing road trip

Homestead - 1 night (as Gateway to Everglades)

Naples - 2 Nights (after spending day 1 in Everglades NP)

St. Petersburg or Tampa - 2 nights (need suggestions as which would be best)

Tallahassee - 2 Nights

Montgomery AL - 2 nights (this stop mainly just to break the drive to Atlanta)

Atlanta GA - 3 nights

Charleston SC - 3 nights

Savannah GA - 2 nights

St. Augustine - 2 nights

Orlando - 5 nights

Sat 12th Dec head home to Perth, Australia.

How does this first attempt look? Any suggestions, changes, recommendations?

Answer

Your proposed Florida and Southern States road trip looks ambitious and exciting! You’ve included a nice mix of Florida Keys, Miami, the Gulf Coast, and Southern cities. Here’s some detailed feedback and suggestions to help refine your itinerary and make the most of your trip.

Initial thoughts on your schedule:

Florida Keys & Miami (31 Oct – 7 Nov): Your plan to spend 1 night in Islamorada and 3 nights in Key West is reasonable. Key West is small but vibrant, so three nights allows for relaxation, sightseeing, and maybe a day trip to Dry Tortugas National Park. South Beach for 3 nights is also ideal to enjoy the beach, art deco architecture, nightlife, and Wynwood area. Make sure to account for traffic along US-1 during weekends, especially when entering or leaving Key West.
Homestead & Everglades: 1 night in Homestead works as a gateway for a day in Everglades National Park. Consider early arrival in the park to do Shark Valley tram tour or Anhinga Trail hike. Naples for 2 nights after Everglades is good for relaxing along the Gulf Coast beaches and exploring nearby nature preserves.
St. Petersburg vs Tampa: Both are good options. If you want a vibrant arts and downtown waterfront scene, St. Petersburg is great with the Dali Museum and St. Pete Pier. Tampa offers Busch Gardens, Gasparilla, and a larger downtown area. Given your plan, 2 nights is tight for either, so pick based on interests—arts & relaxation (St. Pete) or theme parks & city vibe (Tampa).

Southern States leg:

Tallahassee – 2 nights: Works as a logical stop driving north from Tampa/St. Pete. Check out the Capitol, museums, and local dining.
Montgomery, AL – 2 nights: Good stop to break the long drive to Atlanta. Consider visiting Civil Rights Memorial, Rosa Parks Museum, and some historical sites.
Atlanta – 3 nights: Plenty to see: Georgia Aquarium, World of Coca-Cola, Atlanta Botanical Garden, and historic neighborhoods.
Charleston, SC – 3 nights: Ideal for strolling historic streets, waterfront, and plantations. Three nights is good to enjoy both city and nearby beaches or tours.
Savannah, GA – 2 nights: Enough to explore squares, riverfront, and Forsyth Park. Could also consider combining Charleston & Savannah with 2 nights each if you want a slightly faster pace.
St. Augustine – 2 nights: Works well for exploring historic Florida and the Castillo de San Marcos.

Orlando leg:

Orlando – 5 nights: Perfect for theme parks (Disney, Universal, etc.) and some relaxation. Gives flexibility for park hopping, rest days, or exploring areas like Winter Park or ICON Park.

General suggestions:

Consider travel fatigue: Some drives are long, especially Montgomery → Atlanta → Charleston. You might want to split or add shorter stops.
Book accommodations early, especially in Key West and Miami, as your travel is near peak season.
Factor in holiday traffic, particularly in Florida during early November and around Thanksgiving week.
Prioritize must-see attractions in each city to avoid feeling rushed; your pace is ambitious but manageable if planned well.
Consider leaving buffer time in case of delays or spontaneous activities, especially along Florida Keys and historic Southern towns.

Summary:

This itinerary gives a fantastic mix of beach, city, culture, and history. A few tweaks—like deciding between St. Pete and Tampa, considering shorter drives in the Southern states, and ensuring key activities are booked—will make your 4-week trip comfortable and enjoyable while still covering a lot of interesting destinations.

Florida Roadtrip November’26

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