For two
Begin in the Upper Keys at Islamorada, end on a private island off Little Torch Key, and let someone else carry every reservation in between.
Design This TripA Keys honeymoon works best as two acts. Open in Islamorada at Cheeca Lodge & Spa, where a private pier and oceanfront pools set an easy pace, then move to adults-only Little Palm Island Resort & Spa, a thatched-bungalow private island off Little Torch Key reached only by boat or seaplane.
Build the trip around a sunset sail out of Key West with Danger Charters, a romantic dinner at Pierre's on Morada Bay, and a couples' treatment in a seaside cabana at Little Palm Island. A short launch ride to Latitudes on Sunset Key makes for one unforgettable Gulf-sunset evening.
We hold the hard reservations, sequence the two stays so the drive down the island chain works in your favor, and keep the days soft enough that the only decision left is where to watch the sun go down.
What’s inside
A sample rhythm
Arrive Upper Keys
Settle into Islamorada, a slow first evening and a quiet oceanfront dinner.
On the water
A sunset sail and a reef snorkel, paced for two.
Private island
Cross to Little Palm Island for barefoot seclusion.
Slow close
Seaside spa mornings, a Gulf sunset dinner, nothing rushed.
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 siteThe 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 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 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.
Restore
The Keys are built for the slow restore after a day on the water: oceanfront treatment rooms, marina-side pools, and the unhurried pace of island time.
Islamorada
Indonesian-inspired rituals in a serene spa within the 27-acre Islamorada resort, the Upper Keys' established wellness retreat.
Visit official siteLittle Torch Key
Open-air, seaside treatment cabanas on the private island, where the only soundtrack is the water, the most secluded spa in the Keys.
Visit official siteKey Largo
A waterfront spa within the all-inclusive adults-only resort, with treatments included and a calm dedicated to couples.
Visit official site
Luxury honeymoon
Share what you can already picture. A concierge fills in everything still open and sends back a plan, not a quote.
