Where to stay, eat, drink, shop, and what to do in Key West, Florida.
Key West is where Lily Frank Jewelry goes to remember that the most beautiful things were never meant to authentic.
Long before the brand had a name, the Florida Keys were shaping its visual language: weathered white conch houses, shell-pink sunsets, palms bending toward the ocean, luminous pearls, natural shells, and jewelry chosen for salt air and sun-warmed skin.
We return every year, and every Key West vacation gives us more ideas than we arrived with. The island is eccentric, authentic, a little untamed, and completely uninterested in becoming anywhere else.
Its history only adds to the allure. Cuban, Bahamian, maritime, and Old Florida influences exist side by side. Historic estates hide behind tropical gardens. Old hotels overlook the sea. Roosters cross the street beneath the palms while cocktails are poured in rooms that belong to another era.
Key West is polished in some places and wonderfully undone in others. That contrast has always felt very Lily Frank.
We set natural shells by hand, pair them with luminous pearls, and design statement jewelry that feels collected rather than conventional—pieces made to move from a swimsuit and bare feet to white linen, bias-cut silk, and dinner beneath the palms.
Our annual trips have become part of the creative rhythm behind every collection. We return home thinking about new shell silhouettes, ocean-washed blue, sun-faded pink, pearl against bronzed skin, and beauty shaped by time and tide.
Our Key West travel guide gathers the historic hotels, independent shops, restaurants, landmarks, cocktail bars, and island experiences that capture the Florida Keys at their most authentic.
Where to stay
The Marquesa
Three restored nineteenth-century houses a block off Duval, joined by courtyards and three small pools. It is the quietest luxury on the island and the one that feels least like a resort — the rooms are furnished rather than decorated, and the gardens do most of the talking. If you want Old Town on foot and silence at night, this is the address.
Casa Marina
Flagler’s 1920s resort at the southern edge of the island, with the only substantial private beach in Key West. Nearly a century of hospitality behind it, and the scale to prove it: long verandahs, a lawn running to the water, and the particular Old Florida grandeur that the guesthouses cannot offer. Book it for the beach and the architecture, not for walking distance.
The Gardens Hotel
A walled acre in the middle of Old Town, built around what was once a private botanical collection. Intimate, deeply shaded, and adults-only quiet. The kind of place where the garden is the reason you booked.
Ocean Key Resort
At the top of Duval on Mallory Square, so the sunset happens directly in front of you rather than somewhere you have to walk to. Harbour-view balconies and a spa. Livelier than the others here — choose it if you want to be in the middle of things.
Where to eat
Café Marquesa
Fifty seats, an open kitchen, and the most consistent cooking in Old Town. This is the dinner to book first and the one to keep if you have to cancel the others.
Latitudes
On Sunset Key, reachable only by the hotel launch from the Westin dock — the boat is the point. Tables sit on sand a few metres from the water, facing west. It appears on more “most romantic” and “most scenic” lists than anywhere else in the Keys, and the reservation is genuinely hard to get. Book it before you book flights.
Blue Heaven
The Bahama Village courtyard, under an almond tree, with roosters walking between the tables and string lights overhead. It is famous for brunch and it earns it. Nothing about it is polished, which is exactly the contrast Key West does well.
Little Pearl
A four-course menu set by the chef, dinner only, in a small Old Town room. The most serious food on the island and the right choice for one proper night out.
Café Solé
Off the tourist grid, French technique applied to whatever came off the boat that morning. A locals’ restaurant that has stayed a locals’ restaurant.
Louie’s Backyard
A Victorian house on the Atlantic with a deck built out over the rocks. Go for lunch or for a drink at the Afterdeck bar downstairs, where the water is close enough to hear.
Where to drink
Green Parrot
Open since 1890 and the oldest continuously operating bar in Florida. No televisions worth mentioning, live music most nights, and a crowd that has not changed much in a century. The corner of Whitehead and Southard is the honest heart of the island.
The Chart Room
A tiny room inside the Pier House with a handful of stools and free popcorn. Jimmy Buffett played here for drinks in 1971, in front of treasure hunters and smugglers, before anyone knew who he was. It has been left alone since, which is the whole appeal.
Sloppy Joe’s
Opened on 5 December 1933 — the day Prohibition was repealed — by the rumrunner and charter captain Joe Russell, who was Hemingway’s fishing partner and closest friend on the island. It is loud and full of tourists now. Go once anyway, early, and stand where the bar has always been.
What to see
The Ernest Hemingway Home & Museum
907 Whitehead Street. He wrote a substantial part of his best work in the studio above the garden, and the house still holds the proportions and the light that made it possible — deep verandahs, tall shutters, ceilings built for heat before air conditioning existed. The six-toed cats are descendants of his. Of everything on this island, this is the one to give real time to rather than photograph and leave.
The conch houses of Old Town
The vernacular architecture is the reason the island looks the way it does: horizontal lapped siding painted white, full-width two-storey verandahs, operable louvered shutters, and a roof scuttle to vent the heat. Walk William, Fleming and Caroline Streets and read the houses rather than the shop windows. Many of the finest were built by Bahamian ship carpenters, which is why they are put together like boats.
Bahama Village
Petronia Street and the blocks around it — the Bahamian quarter, and still the least renovated part of Old Town. Independent galleries, small shops, and the roosters. This is where the island’s Cuban and Bahamian history is legible rather than commemorated.
The Historic Seaport
The working waterfront since the 1800s, and still working. Independent shops and galleries along Margaret Street, shrimp boats, and the boat that takes you to Sunset Key. Best at the end of the afternoon.
What to do
- Sunset from the water, not from Mallory Square. A schooner or a small charter out of the Historic Seaport gets you the same sun without the crowd and the buskers.
- The Key West Lighthouse. Eighty-eight steps, directly across from the Hemingway house, and the only place to see how small and how green the island actually is.
- The Petronia Street galleries. Slower and more interesting than the Duval Street shops.
- Snorkel the reef. The only living coral barrier reef in the continental United States sits six miles offshore.
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What we pack for Key West
Mother of pearl in direct sunlight: the Large Pearl Nautilus Shell Earrings for the evening, the Small Pearl for the boat, and for a bachelorette brunch, the Vintage Silver Palm Tree Ring with its two tiny jade coconuts.
The styling story is This and That: Key West Edition. Everything shell is in the Seashell Chic collection.