Road trip

Question

Hi All, just after some advice on the following itinerary.

Adult and child (8).

Into sightseeing, swimming, animals, bit of history etc.

Time of trip will be late Nov/Dec.

Currently we have:

Key West 2 nights (flying into here from Overseas via NYC so using this as a jet lag recovery)

Miami 3 nights

Naples 2 nights

Orlando 7 nights

St Augustine 2 nights

Jacksonville 2 nights

We will be flying out of Jacksonville to NYC.

I am wondering:

Suggestions to above itinerary.

Should I stop somewhere further up on the keys before Miami?

Jacksonville doesn’t have to be the end of the trip. Open to suggestions of a fly out point.

Total amount of nights in total can’t change but open to suggestions of plans for the 18 days.

Thanks in advance.

Carly

Answer

Your proposed Florida itinerary looks well-balanced for both adults and an 8-year-old, with a mix of beach time, city exploration, nature, and history. Late November to December is a great time for mild weather and fewer crowds. Here’s some detailed feedback and suggestions to optimize your trip:

Florida Keys & Miami:

Key West – 2 nights: Perfect for recovering from jet lag. Enjoy Duval Street, Mallory Square for sunsets, and a visit to the Key West Butterfly & Nature Conservatory. The 2-night stay is sufficient for a relaxed pace.
Stop further up the Keys? Consider Islamorada or Marathon for 1 night between Key West and Miami. Islamorada is great for snorkeling, visiting the Theater of the Sea (marine animal shows), or just enjoying quieter beaches. This break reduces the long drive from Key West to Miami and adds variety to your Keys experience.
Miami – 3 nights: Ideal for South Beach, Wynwood Walls, Little Havana, and Biscayne Bay activities. For family fun, you can add Miami Seaquarium or Jungle Island. Staying 3 nights allows beach time and sightseeing without rushing.

Naples & Southwest Coast:

Naples – 2 nights: Good choice after Miami. Explore Naples Pier, local beaches, and consider a day trip into Everglades National Park for wildlife viewing (airboat tours or trails). The 2 nights is suitable for both relaxation and short excursions.

Orlando:

Orlando – 7 nights: Perfect for theme parks and other family activities. With an 8-year-old, you can focus on Disney World parks, Universal Studios, and perhaps LEGOLAND or SeaWorld if desired. Seven nights gives flexibility to spread out the parks, include rest days, and explore areas like Winter Park or ICON Park.

Northern Florida:

St. Augustine – 2 nights: Excellent for history and family-friendly attractions like Castillo de San Marcos, St. Augustine Pirate & Treasure Museum, and trolley tours. Two nights is sufficient for a thorough visit.
Jacksonville – 2 nights: Works as the northern Florida endpoint, but consider the following alternatives if you want a slightly different experience or shorter drive to the airport:
- Daytona Beach – Offers beach activities, Daytona International Speedway tours, and is closer to Orlando if you want a smoother transition.
- Tampa or St. Petersburg – If your flights allow, these cities offer Busch Gardens, Florida Aquarium, and family-friendly museums, plus a different Gulf Coast experience.

General suggestions:

Adjusting the Keys leg: Adding a stop in Islamorada or Marathon between Key West and Miami breaks up driving and allows for additional nature or water-based activities.
Consider your flights: Flying out of Jacksonville is fine, but make sure your accommodation in Jacksonville is convenient for the airport. Alternatively, Tampa or Orlando could serve as departure points depending on airline options.
Drive pacing: Ensure no days have excessively long drives for comfort with a child. The itinerary as proposed keeps driving manageable.
Booking: Late November to December is a popular season; book accommodations and any popular tours or parks in advance.

Summary:

The itinerary is solid, providing a good mix of beaches, city life, wildlife, history, and theme parks. Adding one stop in the middle Keys can break up the travel and enhance your Florida experience. Jacksonville works as a departure city, but you could consider Tampa or Daytona Beach if it better suits flights or interests. Overall, the plan balances sightseeing, relaxation, and family-friendly activities across your 18 nights.

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