The title of this article may make this sound like a long trip. In actuality it's only about a mile from Amelia Island, the northern most island in Florida, to Cumberland Island, the southern most island in Georgia.
While the trip is relatively short, it's not an easy paddle. The St. Mary's River, Amelia River, and Atlantic Ocean all meet in this spot. There is a confluence of currents, tides, and winds that can make for rough water. It is recommended that you have open water kayak experience to take this route. Despite the conditions, the views and destination are worth the trip.
Several outfitters can set you up with guided tours that leave from Fort Clinch State Park on the north end of Amelia Island. This island is home to several high end resorts and golf courses. The small city of Fernandina Beach sits on the west side of the island. The south end of the island is more natural with typical Florida wetlands. The sunrise facing beach is 13 miles long beach. There are only two bridges to get you on and off the island.
Cumberland Island is quite the contrast. Part of the Cumberland Island National Seashore, it can only be reached by boat. It is a bit larger than it's southern neighbor, with 18 miles of undeveloped oceanfront. There are a few private homes, but most of the island is set aside as wilderness. A favorite activity after kayaking over is to go seashell hunting in the tidal pools along the coast. It's also possible to see wild horses, pelicans, and sea turtles.
Speaking of wildlife, while kayaking back to Florida you may see dolphins or something larger under the water. The King's Bay Naval Submarine Base is just a few miles to the north. Imagine coming face to face with a submarine as you are kayaking to a wilderness island.