First visit to keys - need suggestions 11/2025

Question

We are presently in Sarasota and considering extending our trip down to see the keys as we’ve never been. We will be driving, 2 mature adults and two small dogs.

We are spontaneous and love to explore. Not into drinking or party scenes. Enjoy nature walks, history, new sites, and beautiful places.

Is there much to see in the keys between Miami and KW? If so, where should we stop? Must sees?

We have 2-4 days to explore the area.

Headed down Sunday 11/9/25.

We don’t have lodging yet and probably will leave it till day of to see where we get to. We typically stay in Airbnb’s. I see several available. Worst case we can sleep in our van or tent.

Thank you for suggestions.

Answer

The Florida Keys are a wonderful destination for a first-time visit, especially if you enjoy scenic drives, nature, history, and spontaneous exploration. Traveling from Miami down to Key West offers plenty to see and do along the way, and November is a great time for comfortable temperatures and less humidity.

Here are some suggestions for stops and activities along the route:

Key Largo: Visit John Pennekamp Coral Reef State Park for walking trails, kayaking, or a glass-bottom boat tour. It’s very dog-friendly on the trails and provides a taste of Florida’s marine environment.
Islamorada: Check out the History of Diving Museum or the Robbie’s Marina for feeding tarpon. There are small beach areas and scenic spots to stretch your legs.
Marathon: Explore the Turtle Hospital to learn about sea turtle rehabilitation. Sombrero Beach is a quiet spot for a walk with dogs and a picnic.
Big Pine Key: Home to the National Key Deer Refuge. You can do short nature walks and see the tiny Key deer in their natural habitat. This is a peaceful stop away from tourist crowds.
Key West: Must-sees include the historic Old Town, Ernest Hemingway Home & Museum, and Mallory Square for the sunset celebration. Dogs are welcome in many outdoor areas, though some attractions inside may not allow pets.

Tips for your spontaneous trip:

Book Airbnbs or pet-friendly accommodations on the fly, especially in Key West where availability can be limited. Smaller keys like Marathon or Big Pine Key may have last-minute options.
Plan your daily stops with flexibility—there are many roadside parks and viewpoints perfect for a short walk or picnic.
Bring food and water for your dogs, as some stretches between keys have limited services.
Driving the Overseas Highway (US 1) is the main attraction in itself. Enjoy the scenic bridges and ocean views between islands.

With 2-4 days, you could either:

Take a leisurely drive, stopping overnight along the way, exploring a few keys in depth.
Focus on the upper keys for a nature-focused trip and then spend a day or two in Key West for historic and cultural experiences.

Overall, your itinerary can be as relaxed or adventurous as you like. The Keys are perfect for exploring at your own pace, enjoying outdoor activities, beautiful landscapes, and unique local treasures along the way.