Personal Concierge · Key West, FL
Every Stay The Keys guest gets Chasity Williams — a real person on the island who books the reef trip, holds the golf cart, finds the table at 8, and tells you which beach is actually worth the walk. No app, no call center, no guessing from reviews written by someone who visited in 2019.
How It Works
Chasity has spent years on this island watching which captains show up on time, which kitchens hold a table, and which rental fleets keep their carts charged. She builds the plan around your group, not around whoever paid for the top of a search page.
Ages, mobility, how early anyone is willing to wake up, and what nobody wants to do twice.
Day by day, with times, walking distances, and what to wear on the boat. Swap anything you don't like.
Charters, carts, tee times, tables, tickets. Deposits handled, confirmations in one message thread.
A squall kills the reef trip at 9am? She has the rainy-day version ready before you've finished coffee.
A Sample Week
This is the skeleton Chasity starts from, then bends around your group. Water days go early, history goes when the sun is high, and nothing is scheduled against sunset.
Getting Around
The island of Key West runs about four miles end to end and one to two miles across — roughly four square miles of land — and it is flat as a table. A car is the worst way to see it and the hardest thing to park. Chasity reserves whichever of these fits your group before the fleets sell out — and they do sell out in season.
Roughly $175–$300 a day in season
Roughly $15–$30 a day, cheaper by the week
Roughly $45–$85 a day
Free
Also free
Metered, scarce, and slow
Rates above are typical high-season ballparks and move with the calendar. Chasity confirms live pricing and availability when she books, and holds carts and bikes early for Fantasy Fest, spring break and the winter holidays.
On The Water
Key West sits beside the only living coral barrier reef in the continental United States. Almost everything worth doing here happens on the water, and almost all of it is better before noon.
Catamaran six miles offshore to the barrier reef. Gear, instruction and usually a drink on the way back. The single best thing a first-timer can do here.
Catamaran or schooner out of the Historic Seaport with beer, wine and something to eat while the sun goes down over the Gulf. Quieter than the Mallory Square crowd.
A guided loop right around the island with a stop or two. You cover water most visitors never see, including the Atlantic side and the back country flats.
Shallow backcountry channels toward Geiger and Sugarloaf. Rays, small sharks, wading birds, and no engine noise. The best thing to do on a windy day.
A few hundred feet above the water on a winch boat. Ten minutes airborne, dry the whole time unless you ask otherwise. Kids love it and it photographs well.
Skiff with a guide poling for tarpon, permit and bonefish. Two anglers, technical casting, and the most serious fishing in the Keys.
Mahi, tuna and wahoo offshore; snapper and grouper on the reef. Party boats run four-hour trips that suit kids and budgets; private charters go all day.
Ferry 70 miles west to Fort Jefferson — a Civil War fort in open water with snorkeling straight off the beach. Breakfast, lunch and gear included on the boat.
Your own captain, your own cooler, and an afternoon anchored in waist-deep water. The right call for a family group or a celebration.
Reef dives for the newly certified, and a 520-foot ship sunk as an artificial reef for everyone else. Refresher dives available if it has been a few years.
The reef without getting wet, which matters if someone in the group won't swim or can't. Runs day and sunset trips from the Seaport.
On Land
What to do when the water is rough, the sun is directly overhead, or somebody in the group has had enough salt for one week.
Eighteen holes on Stock Island, the only course in the Lower Keys, threaded through mangroves. The par-three third plays over the mangrove itself. Book early tee times — afternoons are hot and buggy.
A Civil War fort, the best shore snorkeling on the island, and the west-facing beach locals use for sunset. Bring water shoes; the beach is rock, not sand.
A glass dome full of free-flying butterflies and two flamingos. Air conditioned, twenty minutes, and it rescues a rained-out afternoon with children.
The lanes between Duval and White Street, plus the cemetery with its above-ground vaults. Best in the hour before sunset when the light hits the gingerbread trim.
Whitehead Street, the writing studio above the garden, and about fifty six-toed cats descended from his. Take the guided tour, not the self-guided loop.
Harry Truman's winter White House, preserved down to the poker table. The most genuinely interesting hour of history on the island.
Gold, emeralds and silver bars off the Atocha, plus the salvage story behind them. You can lift a real gold bar in the front room.
Eighty-eight steps to the best view in Old Town; the red brick Custom House for art and island history; and the Eco-Discovery Center at Truman Waterfront, which is free and explains the reef you just swam over.
The hop-on trolley or Conch Train is the fastest way to make sense of the island on a first morning. Ghost and pub walks after dark are better than they sound.
Where To Go
Key West is a coral island, so the beaches are small and man-made. Anyone expecting Clearwater will be disappointed — but each of these is worth an afternoon if you know what it is.
The best one. Deep water close in, actual snorkeling, shade under the pines, and the sunset side of the island. State park entry fee, and bring water shoes — the beach is coral rock, not sand.
Best overallFree, walkable from Old Town, with a pier, a garden club inside an old fort, volleyball, a dog beach and a café on the sand. The most useful beach for a mixed group.
Free & easyThe long one on South Roosevelt — half a mile of imported sand with kayak, chair and watersports rentals right on it. The closest thing here to a resort beach.
Longest sandTiny, harbor side, faces east. Not for a day out — for a coffee at sunrise while the shrimp boats come in and nobody else on the island is awake.
About 45 minutes up the highway, and the beach in every Florida Keys photograph you've seen. Pair it with the Key deer on Big Pine at MM 30 and make a day of the drive. Arrive before 10am.
Two pocket beaches beside Higgs. Dog Beach is a single sandy corner next to Louie's Backyard where dogs swim off-lead; Rest Beach is the quiet strip locals read on.
Said plainly: on a hot July afternoon, the pool at the house beats every beach on this list. Chasity will happily plan a day that consists of nothing else.
Eat & Drink
Key West has roughly four hundred places to eat and about thirty worth your holiday. These are the ones she books, grouped by when you'll want them.
In January through April and over any holiday, the good rooms are full a week out and the great ones a month out. Send Chasity your dates and she'll hold the tables before you land — including the ones that don't take online reservations.
Send Her My DatesWhen To Come
Every month here has a personality. Knowing which one you're walking into is most of the trick.
Dry, breezy, mid-seventies. Everything is open and everything is full. Book carts, charters and tables far ahead; expect March spring break energy on Duval.
Water warms up, crowds thin, rates soften. The Conch Republic celebration lands in late April and the Songwriters Festival fills the bars in May.
Flat mornings and excellent visibility on the reef. Hemingway Days in July, lobster mini-season at the end of it. Plan water for mornings and shade for afternoons.
Lowest rates, shortest lines, and the heart of hurricane season. Worth it if you watch the forecast and buy the travel insurance.
Ten days of parades, costumes and street parties at the end of the month. Extraordinary, and not a quiet family week. Accommodation goes months in advance.
Powerboat races in November, the lighted boat parade in December, and a New Year's Eve where a conch shell and a drag queen in a red shoe both come down at midnight.
Local Rules
Concierge Request
Send your dates and your group, and she'll come back with a plan you can change — plus everything worth booking before you arrive. There's no charge for Stay The Keys guests, and no obligation if you'd rather wing it.
