Iconic
Islamorada
Pierre's
A colonial-plantation-style oceanfront landmark at Morada Bay, long regarded as Islamorada's most romantic and refined dining room.
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For the food-led
Stone crab, fresh catch, and a chef in your kitchen.
The Keys table is built on what comes off the boat. We build the trip around it.
Design This TripThe Fish House in Key Largo sets the standard for just-off-the-boat local fish, prepared Matecumbe-style, while Pierre's on Morada Bay and Latitudes on Sunset Key deliver the chain's most refined oceanfront tables. In Key West, the bohemian Bahama Village courtyard at Blue Heaven anchors the Old Town food crawl.
Source the catch, then cook it in
Time the trip to the local catch: stone crab in season, hogfish and yellowtail snapper off the reef, and Key lime pie everywhere it is made well. A private chef brought to the villa, building dinner from the day's catch, is the ideal luxury-food spine, with the oceanfront icons reserved around it.
We hold the hard reservations, arrange the launch to Sunset Key, and pair a private-chef villa night with the island's best fish houses and courtyard tables.
What’s inside
- Islamorada fish houses and Key West classics
- A launch-ride dinner on Sunset Key
- Private-chef villa nights from the day's catch
- Local sourcing: stone crab, snapper, Key lime pie
- The oceanfront icons, reserved
A sample rhythm
- 01
Reef to dock
A morning on the water to see where the catch comes from.
- 02
Chef nights
Private-chef dinners in the villa, built from fresh local seafood.
- 03
Icons
Sunset tables at the oceanfront classics, reserved.
- 04
Key West crawl
A courtyard dinner and an Old Town food evening.
The The Florida Keyswe’d build in
The pieces that fit this trip.
The table
Stone crab, conch, and Key West classics.
The Keys table runs from Islamorada fish houses to courtyard tables hidden in Old Town Key West. We hold the hard reservations.
Award-winning
Key Largo
The Fish House
The Key Largo institution for just-off-the-boat local fish, prepared Matecumbe-style or simply grilled, a benchmark for fresh Keys seafood.
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Sunset Key
Latitudes
Reached by a short launch ride to Sunset Key, a beachfront table set for the Gulf sunset, the most scenic dinner in the Key West orbit.
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Key West
Blue Heaven
The famously bohemian Bahama Village courtyard in Old Town Key West, with roaming roosters, live music, and a legendary breakfast.
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Islamorada
Marker 88
A long-running bayfront Islamorada room with toes-in-the-sand tables and one of the Upper Keys' best sunset settings.
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Key West
Louie's Backyard
A historic Key West home turned fine-dining institution, its oceanfront deck a perennial pick for the island's special-occasion dinner.
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Island resorts strung along the Overseas Highway.
From an Islamorada institution to an adults-only private island off Little Torch Key, these are the stays a Florida Keys trip is built around.
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Little Torch Key
Little Palm Island Resort & Spa
An adults-only private island reached only by boat or seaplane, with thatched-roof bungalow suites, no televisions, and a barefoot-luxury seclusion found nowhere else in the Keys.
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Islamorada
Cheeca Lodge & Spa
The storied 27-acre Islamorada resort with a private fishing pier, oceanfront pools, and a tennis and watersports program that has anchored the Upper Keys for generations.
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Key Largo
Bungalows Key Largo
An all-inclusive, adults-only retreat of waterfront bungalows on a private 12-acre peninsula, with two pools, a marina, and a tranquility spa.
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Marathon
Isla Bella Beach Resort
A 24-acre Marathon resort wrapping the largest private beach in the Keys, with five pools and sweeping views toward the Seven Mile Bridge.
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North Key Largo
Ocean Reef Club
A gated 2,500-acre private community at the top of the Keys, with two championship golf courses, a 175-slip marina, and a private airport for members and guests.
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Duck Key
Hawks Cay Resort
A 60-acre island resort on Duck Key with a saltwater lagoon, villa rentals, five pools, and a full marina midway down the island chain.
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Sandbars, sunset sails, and a backcountry only reachable by boat.
The Keys reveal themselves from the water: sunset sails out of Key West, sandbar afternoons, and skinny-water runs into the backcountry. Private full-boat charters are the luxury way to do it.
Top rated
Key West
Danger Charters
Key West's signature sail-snorkel-kayak day and the wind-and-wine sunset sail aboard classic shallow-draft schooners that slip into the backcountry.
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Key West
Honest Eco
Small-group dolphin and snorkel trips aboard SQUID, an all-electric custom catamaran, the quietest and most sustainable way onto the water.
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Islamorada
Robbie's of Islamorada
The Islamorada institution for tarpon feeding off the docks, boat rentals, and backcountry eco tours into the flats and islands of the bay.
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Key West
Sunset Watersports Key West
Full-boat private charters, the popular sandbar excursions, and champagne sunset sails along the Key West waterfront.
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The sportfishing capital of the world.
Islamorada is the self-styled sportfishing capital of the world. Private charters run year-round: bonefish and tarpon on the backcountry flats, sailfish and mahi offshore in the Gulf Stream.
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Islamorada
Bud N' Mary's Marina
The legendary Islamorada marina operating since 1944, home to one of the largest fleets of backcountry flats guides and offshore charter captains anywhere.
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Islamorada
Robbie's Backcountry Charters
Light-tackle and fly guides poling the skinny water of Florida Bay for bonefish, permit, redfish, and the prized Islamorada tarpon.
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Islamorada
Cheeca Lodge fishing pier
On-property guides and the long private pier make the storied Islamorada resort an easy base for both backcountry and offshore days.
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Key West
Key West offshore charters
Out of the Key West Historic Seaport, full-day private boats run the deep edge of the Gulf Stream for sailfish, mahi-mahi, tuna, and wahoo.
Or another way
More ways to experience The Florida Keys.
Food & chef experience
Let’s design it around you.
Share what you can already picture. A concierge fills in everything still open and sends back a plan, not a quote.