Traverse the route of the famous Overseas Highway and discover the laid-back qualities of the “Middle Keys.” Our launch site is Robbie’s Marina, a quaint establishment on Lower Matecumbe Key sprinkled with booths selling colorful locally-made treasures.

After boarding our kayaks, we glide across crystal-clear waters to Indian Key and explore the island on foot. Indian Key became the first county seat for all of South Florida in 1836; and, at that time, this tiny island was the site of a lucrative business: salvaging cargo from shipwrecks in the Florida Keys. During the 1830s, Jacob Housman advertised his hotel on Indian Key as a therapeutic retreat for the ailing. During his short tenure, Housman’s vast improvements to this 11-acre island increased the population to over 100 residents. Then, in a daring and bloody raid, the island was sieged by a coalition of Seminole Indians resulting in one of the most retold and tragic stories in Florida history.

The numerous foundation ruins and cultural landscapes of this historic community are still visible today; these remnants provide both guest and locals with a better understanding of South Florida history.

On your way back from the island, keep an eye open to spot a pod of dolphins or even a passing green turtle. Enjoy unforgettable hours of discovery as you learn the Middle Keys’ vital role for both South Florida’s ecology and human history.