Mobility-friendly
The island chain's best scenery, planned to minimize rough terrain and long transfers.
Design This TripA single resort base limits transfers: Isla Bella Beach Resort in Marathon and Cheeca Lodge in Islamorada both offer accessible rooms, elevators, and level, paved grounds beside calm water. Several Keys state parks, including Bahia Honda, provide beach wheelchairs to reach the shoreline.
For smooth-terrain sightseeing, the paved Florida Keys Overseas Heritage Trail and the Old Seven Mile Bridge segment deliver open-water views without rough ground, and several Key West and Islamorada boat operators offer boarding assistance for guests who can transfer.
We confirm room and bathroom layouts in advance, arrange equipment, and choose the experiences and routes that keep the trip grand and the ground smooth.
What’s inside
A sample rhythm
One base
A single accessible resort with elevators and level grounds.
Smooth scenery
The paved heritage trail and open-water bridge views.
Gentle water
A beach-wheelchair shoreline and a boat with boarding help.
Restore
Level spa grounds and an unhurried island evening to close.
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 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 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 siteOr another way
Accessible luxury
Share what you can already picture. A concierge fills in everything still open and sends back a plan, not a quote.
