Things to do while cruising the Florida Keys

We recently took a sailing trip to the Florida Keys. We left from Jupiter, Florida and it took us three days to get there (short relaxing sails). Our first stop was Lake Boca. It is a very protected anchorage right by the inlet. The next evening we stopped in Lake Sylvia in Fort Lauderdale. Lake Sylvia was a very protected anchorage but a little ways from the inlet with no close dinghy landing to stop and walk Jetty. Our final stop before making it to the keys was the Miami Marine Stadium. This anchorage is large, and has multiple little beaches to pull the dinghy up to and walk around. The next day we were sailing through the upper keys. We spent about a month island hopping and made it as far as the Dry Tortugas. Below is a list of our favorite things to do while cruising the Florida Keys (as well as a few things we still want to do).

Upper Keys

Key Biscayne National Park is filled with beautiful reefs. Fishing and lobstering are great activities to get yourself in the groove of Island living. (Make sure you are up to date on the Florida Spiny Lobster Regulations)

Lobstering in the Florida Keys

Boca Chita Key: This looked like a great spot to stop and explore while cruising through the first few uninhabited islands of the keys. Unfortunately, pets are not allowed so we had to keep on cruising. If your crew is only humans Boca Chita has a beautiful harbor you can tie up to for the night ($25 first come first serve), as well as a cute lighthouse with an observation deck, and a hiking trail.

John Pennekamp Coral Reef State Park: The park covers over 150 nautical square miles of coral reefs, seagrass beds, and mangrove swamps. There are multiple mooring buoys that mark great snorkeling spots.

Christ of the Abyss: located on a reef called dry rocks just adjacent to John Pennekamp Coral Reef State Park is the most photographed underwater site in all of the Florida Keys. Don’t leave the keys without getting your own photo with this legend (this is on the list of places to stop on our way back home).

Alligator Reef Lighthouse: This lighthouse is surrounded by beautiful turquoise water and thriving reefs. Multiple mooring balls are available to tie up to while you spend the day snorkeling.



Indian Key: A great place to anchor for the night. You can dinghy to the dock and walk the recreated streets to find out about the shipwreck salvage company that use to run the island. There are also tarpon, bonefish, monster mangrove snapper, and lobster that live in the water around the island.






Robbie’s Marina: Buy a bucket of bait and hand feed the massive tarpon. Do NOT forget your camera.

Middle Keys

We spent the majority of our time in the middle keys on Marathon. The Marathon City Marina had great rates for mooring balls which were the best place to be during these crazy windy winter days.


Sombrero Reef Lighthouse: Plenty of thriving reefs. We try to avoid crowds as much as possible and the day we headed out to the lighthouse was pretty crowded. We opted for a reef close by that was not as well-marked on charts. It was beautiful and filled with huge hogfish and monster grouper.

Dolphin Research Center: This place is amazing! They research many different areas including cognition, behavior, and husbandry. They have even proven that dolphins have the mathematical ability to compare quantities. When you visit for the day you can see first hand what kind of research they are conducting. You can also watch the dolphins and sea lions amazing ability to imitate their trainers. DRC is a not-for-profit and is largely reliant on the community to continue their research. If you are cruising through the area definitely stop by! (Dog-Friendly)

Things to do while cruising the Florida Keys

Dolphin Research Center

Florida Keys Aquarium Encounters: I have been to my fair share of aquariums and this is definitely one of the best. You can hand feed the stingrays, feed the tarpon, or come face to face with one of the many sharks.

Things to do while cruising the Florida Keys

Stingray Touch Tank


Crane Point Museum, Nature Center, and Historic Site: This place has miles of beautiful nature trails, a bird sanctuary, and mass information about the history of Marathon. (Dog Friendly:)


Lower Keys

Mallory Square: Check out musicians, flame throwers, balancing acts, and a killer sunset.

Mallory Square Musicians

Mallory Square Musicians

Dry Tortugas: If you want to escape for a few days, learn some history, and snorkel an awesome shipwreck this is your place. We spent about a week in the Dry Tortugas and had a blast. The fishing was awesome.. yes we actually caught dinner! We also saw some of the most lively reefs we have seen since the Exumas. About a two-mile dingy ride from the main anchorage awaits Loggerhead Key. It has white sand beaches, turquoise water, and a beautiful lighthouse. If any friends wish to visit while you are in the Dry Tortugas there are a few Seaplanes and a ferry that make daily trips from Key West.

Fort Jefferson

Fort Jefferson

Loggerhead Key Lighthouse

Loggerhead Key Lighthouse


I hope this gave you some ideas of things to do while cruising through the Florida Keys.


Thanks for reading.

Sierra 🙂