For the whole group
Calm swimming water, multi-bedroom villas with real kitchens, and resort programming when you want it.
Design This TripIsla Bella Beach Resort in Marathon is a strong family base, wrapping the largest private beach in the Keys with five pools and easy views toward the Seven Mile Bridge. Hawks Cay Resort on Duck Key adds villa rentals around a saltwater lagoon and a full marina, ideal for a group that wants space and its own front door.
Fill days with a beginner snorkel trip from John Pennekamp, a behind-the-scenes tour of the Turtle Hospital in Marathon, and a sandbar afternoon by boat. A villa with a full kitchen plus a private chef for one night means dinner with tired kids never becomes a logistics problem.
We arrange the cribs, the car seats, the grocery pre-stock, and the activities that flex around nap time, then build in the resort's pools and kids' programming for the in-between hours.
What’s inside
A sample rhythm
Settle in
Villa check-in, a grocery pre-stock waiting, an easy first beach afternoon.
Active mornings
Snorkeling, the Turtle Hospital, or the pool complex, paced around the youngest.
Slow afternoons
Naps and shade, then a sandbar swim by boat.
Dinners in
A private chef in the villa, one big night out at an island fish house.
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 siteReef & dive
The reef tract runs the length of the Keys a few miles offshore. John Pennekamp Coral Reef State Park is the gateway, and dive boats reach the wrecks and shallow gardens beyond.
Reef conditions are best in calm summer seas; winter fronts can blow out visibility for a day or two.
Key Largo
The first undersea park in the United States, the gateway to the reef, with daily snorkel and dive boats out to Molasses Reef and the Christ of the Abyss statue.
Visit official siteBig Pine Key
A spur-and-groove reef in the Lower Keys sanctuary, considered some of the finest shallow snorkeling and diving in the chain.
Visit official siteMarathon
A protected sanctuary preservation area off Marathon marked by a historic lighthouse, with vibrant coral heads in easy snorkeling depth.
Key Largo
A long-running Key Largo dive operation running the reef and the famous Spiegel Grove and Duane shipwrecks for certified divers.
Visit official siteMarathon
Marathon-based snorkel and dive trips to Sombrero Reef and the wrecks, well suited to first-timers and families.
Visit official siteSignature days
The one-of-a-kind days: a seaplane out to Fort Jefferson, kayaking the mangrove tunnels, and a turtle hospital and tiny-deer refuge found only in the Keys.
Key West
A low, scenic flight to Dry Tortugas National Park, landing beside Fort Jefferson with the reef and shipwrecks visible the whole way out.
Visit official siteMarathon
A working sea-turtle rescue and rehabilitation center in Marathon offering guided behind-the-scenes tours of its patients and hospital.
Visit official siteBig Pine Key
A Lower Keys refuge protecting the endangered, miniature Key deer, with quiet trails and the spring-fed Blue Hole overlook.
Visit official siteIslandwide
A paved cycling and walking path running much of the island chain, including the historic Old Seven Mile Bridge segment.
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 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 siteOr another way
Private family villa
Share what you can already picture. A concierge fills in everything still open and sends back a plan, not a quote.
