Islamorada or Marathon

Question

Hi we are driving down from Miami area on our way to Key West we would like to break the drive up by staying in Islamorada or Marathon. We would like to go kayaking and have a walk around maybe snorkeling [if I'm brave enough 😄] in the daytime. In the evening we like to have a stroll around a few bars making use of any happy hours followed by a meal. Which would be your recommendaction?

Answer

Both Islamorada and Marathon are excellent stops on the way to Key West, but they each have a slightly different vibe and offerings that may influence your choice depending on what you want from your stay.

Islamorada:

Known as the “Sportfishing Capital of the World,” Islamorada is ideal if you enjoy kayaking in calm waters, paddleboarding, and exploring mangroves.
There are great snorkeling spots nearby, such as the Florida Keys National Marine Sanctuary, so if you’re feeling adventurous, it’s a perfect place to try.
The village area has a few local bars and restaurants where you can stroll in the evening. Places like Lorelei Restaurant & Cabana Bar or Islander Resort offer sunset views and casual happy hours.
Islamorada has a slightly more upscale and laid-back feel, with boutique shops, galleries, and small local attractions.

Marathon:

Marathon is more central in the Keys and offers easier access to family-friendly beaches and parks, such as Sombrero Beach and Curry Hammock State Park, which is great for kayaking and short hikes.
The snorkeling around Marathon is also good, especially at the nearby coral reefs, though it might feel a bit busier than Islamorada.
Evening options include waterfront bars and casual dining spots. While the nightlife is quieter than Key West, there are still a handful of spots with happy hours and live music, like the Island Fish Company or Keys Fisheries.
Marathon tends to be more practical for families or groups looking for easy access to activities and amenities.

In summary, if you prefer a slightly more scenic and boutique feel with kayaking, snorkeling, and casual evening strolls, Islamorada is likely your best choice. If convenience, family-friendly beaches, and central access to the middle Keys are more important, Marathon would work well.

Tip: Regardless of which you choose, both towns are only a short drive apart, so you could also plan a mix—one night in each—if your schedule allows.