The Florida Keys are undoubtedly in a world of their own. The Keys have always been known as a perfect escape and for sailors it is one of the ultimate paradises. With a different outlook on life, the islands provide peacefulness along with a strong reputation for its diversity and ability to have fun.
To get a better sense of what the Keys represent, we created a 7 day itinerary that will provide a diverse view of the wide array of offerings the islands present.
Day 1: Biscayne Bay
Biscayne Bay is the perfect departure point for your sailing voyage. As we always suggest, spend the first day on your boat and familiarize yourself with your new home for the week. Sail off to the Biscayne Bay and have a relaxing first night out.
Day 2: Elliott Key
Elliott Key is a stop that will be able to entertain the entire family. The island that was once looked at as a primary spot for pineapple farming has now turned into a calm, relaxing spot. When you stop at Elliott Key, you’ll be able to camp, take a hike on one of it’s trails, take a satisfying dip in the turquoise waters, or simply admire the wildlife. Located entirely on the Biscayne National Park, you’ll find the island entirely uninhabited except for the local campground. It is highly encouraged to snorkel and hike up to the rocky beaches.
Day 3: John Pennekamp Coral Reef State Park
The park located in Key Largo is one of the first underwater parks in the United States. Since the park holds some of the only coral reef in the country, it has been added to the National Register of Historic Places. Even though the park has several interesting points of interest, it is the coral formations that bring in the most visitors. Due to this, the most common activity will be to go scuba diving or snorkeling. Visit the shipwrecks or see the iconic Christ of the Abyss statue.
After a long day, you can head directly to Rodriguez Key and anchor there. Here you can easily access great seafood and experience the local culture by taking a dinghy to the pier at Rock Harbor.
Day 4: Windley Key
The next stop will be to sail a short distance to Windley Key. What is most noticeable about this part of the keys is the rich history it holds from the 20th century. The Flagler Railroad was built using the limestone from the quarry. To get to know the history, visitors can walk along the incredibly quarry walls and even see samples of the actual quarry machine that was used to build the railroad and the decorative pieces after.
Like several of the islands you’ll encounter on your journey, the Windley Key is very family friendly with great restaurants, endless water activities, a theater and if you’re willing to make the trip, a dolphin research facility. Spend the night at the marina and make sure to fully enjoy all of the offerings of Windley Key.
Day 5: Indian Key
After spending the day at Windley Key, make the small voyage to the must-see Indian Key. Arrive at the Indian Key Anchorage and pick up a mooring ball and get ready to explore. Indian Key is considered a hidden wonder due to its complex, but deep history. After being taken over by a man named Jacob Housemen to play a part in the wrecking monopoly, it was later bought by a doctor who was overrun by the native Indians that took over the island. Much of the allure of the city is now found in its ruins and stone foundations that remain from the 19th century. The island remains uninhabited and is an open-air museum.
Day 6: Boca Chita Key
On the second to last day, start heading north and pass through Angelfish Creek. After taking in the sights, head further north to Boca Chita Key to anchor for the night. This picturesque island will keep you entertained for your last night out at sea. As most people that have been here will verify, you never know what you will see in the waters. If you’re lucky enough, you’ll see a few dolphins perform a show for you, but if not, the landscape and nature will surely be enough. Take in some sun and have a cocktail at the small beach, which holds a beautiful lagoon. Be sure to be equipped though, there are no facilities on the island.
Day 7: Back to Biscayne bay
Sadly, day 7 means you’re going back to the marina. The good thing is that at this point, you’ve sampled local food and drinks, saw coral reefs, learned about the history of the Upper and Middle Keys, and went on an unforgettable journey. Return your boat and we’re sure you’ll start planning another trip to the Florida Keys very soon!