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Floriday Keys Sample Itinerary

DAY ONE — Coffins Patch and Sombrero Key Reef

Welcome aboard. Our Florida Keys journey begins in Marathon, but the feeling of getting away starts the moment we leave the dock. The sails fill, the shoreline eases behind us, and conversation gives way to the sound of wind in the sails and water moving along the hull. There’s a special romance to traveling this way: no rush of traffic, just the breeze, the open horizon, and the freedom to follow the sea.

And life aboard the Cathouse includes something else worth looking forward to: the food. With the exception of a few special meals ashore, breakfast, lunch, and dinner are prepared and served aboard throughout the week. Fresh ingredients—many locally and naturally sourced—are hand-prepared into healthy, incredibly flavorful and satisfying meals, from fresh fruit and tropical breakfasts to seafood, vibrant salads, savory entrées, and fresh catch prepared right aboard the boat. It’s cuisine designed to be every bit as memorable as the places we visit.

Our first snorkel stop is Coffins Patch. Despite its dramatic name, these shallow reefs are full of life and movement. Slip into the water and watch fish move across coral growing on the remains of the wreck, where a sunken vessel has become the foundation for new marine life and a reef of its own.

Then we take a short sail toward Sombrero Key Reef, where the historic lighthouse rises above the water. Beneath it, reef ridges and sandy channels offer another world to explore. Back aboard, settle in for the evening. As the sun lowers, the sea catches every shade of gold and rose. We’ll share our first sunset from the boat—a moment that can make an ordinary day feel once-in-a-lifetime.

DAY TWO — Bahia Honda, Looe Key, Newfound Harbor and Kiki’s Sandbar

This morning brings us to Bahia Honda State Park. Walk its sandy shore, wade into the shallows, and take in one of the loveliest stretches of coastline in the Keys. We may also snorkel Looe Key Reef, floating above its reef formations and watching for the small surprises that appear when you slow down and look closely.

As we continue into the Lower Keys, the waters around Newfound Harbor turn shades of blue and green. There may be time for another snorkel near Newfound Harbor Key’s protected patch reef, giving us another opportunity to explore beneath the surface.

Dinner is at Kiki’s Sandbar on Little Torch Key. Come for the waterfront setting and fresh seafood; stay for the live music Kiki’s is known for. With a cool drink in hand and a band playing nearby, it’s easy to let the evening run a little longer.

DAY THREE — Sambo Reefs and Key West

We sail west with an opportunity to snorkel at a beautiful spot in the Sambo reef area, with your captain selecting a location that makes the most of the day and the experience you’re looking for. Then we make our way to Key West Bight, secure the boat, and step into an entirely different rhythm.

Before nightfall, visit the Mel Fisher Maritime Museum. Its shipwreck artifacts tell stories of voyages, discovery, and the people whose lives were tied to these waters. Then follow the music toward Duval Street. Restaurants glow, bands play behind open doorways, and the whole street seems to invite you to stay out.

Key West has long drawn writers, sailors, adventurers, and characters of every kind. Ernest Hemingway found inspiration here, and his presence is deeply woven into the island. Stop by legendary destinations like Sloppy Joe’s and Captain Tony’s Saloon, places connected to the stories, personalities, and colorful history that helped shape the mythology of old Key West.

Decades later, Jimmy Buffett helped give that same island spirit a soundtrack. Key West inspired some of his best-known songs, and his easygoing blend of storytelling, music, and Caribbean feeling still echoes through its nightlife.

Choose a place that sounds good, find your favorite song, and enjoy the night.

DAY FOUR — Boca Grande Key

Today we leave the bustle behind and sail west to Boca Grande Key. This uninhabited island offers pale sand, open water, and a wonderful sense of distance from everything. We’ll choose an ideal anchorage off Boca, enjoying the island and its protected surroundings with care.

Out here, you may spend hours without another boat in sight. The solitude makes the sea feel grander, the horizon wider, and the quiet more complete. Watch the light move across the shallows. Listen to the water against the hull. There’s no schedule to chase.

Stay on deck after dark and watch the stars come forward, filling the sky far from the brightest town lights. It’s a stargazer’s dream come true. It’s easy to imagine ancient sailors reading that same sky as they crossed these waters, and to feel, for a moment, connected to their sense of wonder.

DAY FIVE — Offshore Sail and Sunset Grille

We turn back toward Marathon on an offshore sail, letting the wind do its work. Keep an eye on the water, because we may put lines out as we travel.

The tropical and offshore fish of these waters can provide some of the most exciting and challenging catches anywhere. Mahi-mahi, tuna, and wahoo are among the fish we may bring right to the boat, and few meals compare with fresh-caught fish prepared aboard. But the meal is only part of it. Watching a line suddenly come alive, taking the rod, and fighting a powerful fish alongside the boat can become one of the most memorable moments of the entire trip.

This day has room to surprise us. We might return to a favorite reef for one more swim, discover a new stop, or simply enjoy more time under sail before continuing toward the Seven Mile Bridge.

Tonight, we head ashore for dinner at Sunset Grille in Marathon. Its waterside deck looks toward the bridge, and its relaxed, tiki-style setting makes it a fitting place to gather after a day at sea. Order seafood, look out across the water, and trade stories: the reef you loved most, the song you heard in Key West, the night sky off Boca. As the light fades, there’s nowhere else you need to be.

DAY SIX — Home to Marathon

After an easy morning aboard, we make the short final sail to our home dock in Marathon. The sails come down, but the feeling of the voyage stays with you: salt air, music, open water, and the people who shared it.

That’s the beauty of a week in the Florida Keys. The itinerary is yours to enjoy, with the freedom to explore favorite destinations, linger a little longer, discover something new, or shape the journey around the experiences that matter most to you.

The route may vary. The memories become your own.

Want to venture farther? Ask us about sailing to the Dry Tortugas. Beyond Key West lies one of Florida’s most remarkable destinations—a remote collection of islands surrounded by clear blue water, coral reefs and abundant marine life, with historic Fort Jefferson rising from the sea. It’s secluded, unforgettable, and the kind of destination that makes arriving by sailboat part of the magic.