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Sample Florida Keys Itinerary  


Day 1:  Meet Catatonic 500 at Stock Island

Separated from Key West by the narrow Cow Key Channel, this off-the-beaten-path island is not just an extension of its famous neighbor to the south but also a destination.

Home to boatyards, artist studios and the area’s last working waterfront, Stock Island has a quiet, laid-back charm. 

Day 2: Boca Grande Key


This uninhabited island is part of the Key West National Wildlife Refuge and lies 14 miles west of Key West. Filled with mature mangroves and an inner salt pond, much of the island is home to several species of aquatic birds that are on the federally endangered and threatened list.


Past the sandbar and up towards Mullet Banks, there is a partially exposed wreck that offers some fun snorkeling and free diving options at deeper depths. The partially exposed wreck is usually lined with camera ready Cormorants perched just above the waterline, a variety of smaller colorful fish swimming about the wreck and an occasional stingray or turtle in this area.


Day 3: Marquesas Keys


The Marquesas Keys form an uninhabited island group about 20 miles (32 km) west of Key West, four miles (6 km) in diameter, and largely covered by mangrove forest.

The central lagoon is called Mooney Harbor. The northernmost key is the largest and has a strip of sandy beach free of mangrove. In the past it was known as "Entrance Key". It surrounds the lagoon in the north and east. Adjoining in the south are smaller keys such as Gull Keys, Mooney Harbor Key, and finally about four unnamed keys in the southwest corner of the group. Older charts show that two of these keys once were named "Button Island" and "Round Island".


Day 4: Sand Key Lighthouse 


Sand Key Light has stood sentinel over a treacherous reef for hundreds of years, part of that time as a manned lighthouse with a long list of light keepers, some of whom gave their own lives to warn mariners away from the hazardous shoals.  Today, no evidence of human habitation remains on the island. The historic lighthouse remains standing but over the years has fallen into a state of disrepair.  Sand Key’s defining light characteristic of two flashes every fifteen seconds is now displayed from a nearby structure at a height of just forty feet.  Some of the best snorkeling to be had in the Keys can be found here.

From this point we can decide whether to proceed North or South, depending on conditions and the preference of the guests:




Day 5: Jewfish Basin -  just north of Key West on the Gulf side is a gorgeous, secluded anchorage. 


Day 6: Marvin Key 


Marvin key has been called “Best Sandbar in the Keys.”  Once you get there and walk around, you can't tell you’re not somewhere out in the Bahamas Out Islands!  The large flats/shoal to gulfside is very shallow (less than ankle deep). Small pockets of water in the sand around the Island are at Spa-like temperatures in the tropical sun. Lie down in the Sand and have a therapeutic Spa treatment. 


Locals keep this area very clean so you can take off your water shoes and walk around in the deep sand.  Snipe point is just to the West of Marvin Keys. 



Day 7 - Content Keys


The Content Keys are a boating and fishing paradise located about 10 miles northwest of Big Pine Key.  The Content Keys are a pair of islands that mark the entrance to Content Passage in the Lower Florida Keys.  They are unspoiled, tropical islands with patches of white, sandy beaches and sandbars and the water that flows through them is crystal-clear.




Day 5: Looe Key


Looe Key National Marine Sanctuary, one of Big Pine’s groove and spur reefs, is essential. This reef got its name from the HMS Looe which supposedly ran aground there in 1744 while towing a captured French ship, the Snow. While crossing the reef, the HMS Looe hit hard in only 25 feet of water and quickly burned to the waterline, taking the accompanying ship with her. Recent archeological studies say that the ship that went down with the Looe was named Billander Betty and that ballast stones located at the eastern end of the reef are from those two ships. With a rich history and its unique shape and varying depths, Looe Key is an excellent SCUBA and snorkeling site for people of all skill levels who are keen on visiting Florida Keys Parks. Water clarity is mostly excellent and sea conditions are generally moderate.



Day 6:  Bahia Honda Key


The 2.5-mile (4.0 km) natural, white sand beach was rated the #1 beach in the United States by "Dr. Beach" Stephen Leatherman (the first Florida beach to be so honored), making it popular for swimming. A nature trail near the park's oceanside beach skirts a tidal lagoon before passing through a coastal hardwood hammock. The Sand and Sea Nature Center features displays about local sea and shore life, including corals, shells, crabs, sea urchins, drift seeds, sea sponges and sea turtles.

Kayaking and snorkeling is excellent here.  The park is also a part of the Great Florida Birding Trail.


Day 7:  Key West – 


Walk or take a bike ride around this iconic town and visit the old Cemetery for a walk through Keys history.  Explore the bars and restaurants on Duval Street, too.


Some of our favorite local restaurants are: Louie’s Backyard, Hot Tin Roof, Firefly, Flaming Buoy. 


Day eight: Key West - Say farewell and start planning your next trip aboard Yacht Catatonic

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