For private groups
Every signature Keys experience has an exclusive-use version. We assemble them into one seamless week.
Design This TripThe Keys are built for buy-outs. Charter a full sunset or reef boat out of Key West with Sunset Watersports, book private sportfishing boats from Bud N' Mary's in Islamorada, and for the ultimate centerpiece, take over Little Palm Island, a private island off Little Torch Key. Every signature experience has an exclusive-use version.
Lodging anchors well around Islamorada at Cheeca Lodge for the Upper Keys, or at the gated Ocean Reef Club near the top of the chain with two golf courses and its own marina and airport. A private dinner at Pierre's gives the group a shared evening centerpiece, and the linear island chain keeps boats, tables, and tee times within an easy drive.
We coordinate the manifest across boats, charters, and tables, stage the group dinners, and keep a single point of contact for the whole party.
What’s inside
A sample rhythm
Gather
A villa estate or private-club base, a relaxed first group dinner.
Sea day
A full-boat reef or sunset charter for the whole party.
Split & choose
Private sportfishing, golf, and spa in parallel.
Centerpiece
A private island or oceanfront dinner to close the week.
The The Florida Keyswe’d build in
Where to stay
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.
Little Torch Key
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.
Visit official siteIslamorada
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.
Visit official siteKey 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.
Visit official siteMarathon
A 24-acre Marathon resort wrapping the largest private beach in the Keys, with five pools and sweeping views toward the Seven Mile Bridge.
Visit official siteNorth Key Largo
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.
Visit official siteDuck Key
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.
Visit official siteOn the water
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.
Key West
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.
Visit official siteKey West
Small-group dolphin and snorkel trips aboard SQUID, an all-electric custom catamaran, the quietest and most sustainable way onto the water.
Visit official siteIslamorada
The Islamorada institution for tarpon feeding off the docks, boat rentals, and backcountry eco tours into the flats and islands of the bay.
Visit official siteKey West
Full-boat private charters, the popular sandbar excursions, and champagne sunset sails along the Key West waterfront.
Visit official siteFlats & bluewater
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.
Islamorada
The legendary Islamorada marina operating since 1944, home to one of the largest fleets of backcountry flats guides and offshore charter captains anywhere.
Visit official siteIslamorada
Light-tackle and fly guides poling the skinny water of Florida Bay for bonefish, permit, redfish, and the prized Islamorada tarpon.
Visit official siteIslamorada
On-property guides and the long private pier make the storied Islamorada resort an easy base for both backcountry and offshore days.
Visit official siteKey West
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.
The table
The Keys table runs from Islamorada fish houses to courtyard tables hidden in Old Town Key West. We hold the hard reservations.
Islamorada
A colonial-plantation-style oceanfront landmark at Morada Bay, long regarded as Islamorada's most romantic and refined dining room.
Visit official siteKey Largo
The Key Largo institution for just-off-the-boat local fish, prepared Matecumbe-style or simply grilled, a benchmark for fresh Keys seafood.
Visit official siteSunset Key
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.
Visit official siteKey West
The famously bohemian Bahama Village courtyard in Old Town Key West, with roaming roosters, live music, and a legendary breakfast.
Visit official siteIslamorada
A long-running bayfront Islamorada room with toes-in-the-sand tables and one of the Upper Keys' best sunset settings.
Visit official siteKey West
A historic Key West home turned fine-dining institution, its oceanfront deck a perennial pick for the island's special-occasion dinner.
Visit official siteLand & landmarks
Between the dives and the dinners, the Keys are a drive worth slowing for: a former railroad bridge over open ocean, a state-park beach, and the historic streets at the end of the road.
Marathon to Bahia Honda
The signature span of the Overseas Highway, soaring nearly seven miles over open water, with the old Flagler railroad bridge running alongside for walkers and cyclists.
Big Pine Key
Routinely named one of America's best beaches, a Lower Keys state park of pale sand and clear water with the old bridge as its backdrop.
Visit official siteKey West
The walkable heart of the island: Duval Street, the Hemingway Home, Mallory Square's sunset celebration, and the southernmost point of the continental US.
Off Key West
Reached by ferry or seaplane from Key West, a remote cluster of islands built around 19th-century Fort Jefferson, ringed by some of the clearest water in the Keys.
Visit official siteIslamorada
Galleries, the Florida Keys History & Discovery Center, and the Hurricane Monument trace the Upper Keys' artists, wreckers, and railroad past.
Islamorada
A quiet Islamorada beach and boardwalk over the shallows, a low-key stop to wade the flats between the bigger destinations.
Or another way
Private group retreat
Share what you can already picture. A concierge fills in everything still open and sends back a plan, not a quote.
