Key West

Chris and Lori at the Southernmost Point buoy with the turquoise Atlantic behind them

The Southernmost Point buoy — Key West's most iconic landmark, 90 miles from Cuba

Chris up close at the Southernmost Point marker — the Conch Republic's most famous photo op

Chris and Lori at the beach near the Southernmost Point — the water is impossibly blue

Chris and Lori outside Mi Casa es su Casa restaurant — waterfront dining at its best

Chris and Lori at the orchid garden — Key West's botanical side surprises every visitor

A wild rooster on a stone post — Key West's free-roaming chickens are protected by city law

Chris at the helm at sunset — sailing out of Key West on a classic wooden schooner

On deck under full sail — Key West's sailing culture is as old as the island itself

Chris and Lori kayaking the mangrove channels — one of the best free activities in the Keys

Chris with US Navy personnel at a Key West waterfront restaurant — the island has a proud military history

Chris at the Key West Bight Marina — home to some of the best sportfishing boats in the country

A brown pelican on the dock — Key West wildlife operates entirely on its own schedule

Under the palms in Key West — the light here is different from anywhere else in Florida

Chris and Lori in front of the Greetings from Key West mural — the first photo op of every trip

The iconic Key West welcome mural — a rite of passage for every first-time visitor to the Conch Republic

Chris boarding the Conch Air turboprop at Key West International — the smallest commercial airport in Florida

Chris at the Key West International Airport sign — the gateway to the southernmost city in the continental US

Oysters and calamari at a Key West waterfront restaurant — the seafood here is as fresh as it gets

The Key West Key Lime Shoppe — a mandatory stop for anyone who takes pie seriously

Chris and Lori at the famous Key West signpost — pointing to everywhere from Cuba to Tokyo

Lori at the Key West directional signpost — every distance on this post feels both impossibly far and completely reachable

The Key West Bight boardwalk — lined with restaurants, dive shops, and charter boats heading out to the reef

A Jimmy Buffett tribute in Key West — the man who turned this island into a state of mind

The Conch Republic Seafood Company on a busy evening — one of the best outdoor bars on the waterfront

Mel Fisher Days in Key West — the annual event celebrating the treasure hunter who found $450 million in Spanish gold

The sticker-covered building on the Key West boardwalk — every layer tells a story of someone who passed through

Chris at the sticker wall — Key West has a tradition of leaving your mark, and this wall has been collecting them for decades

The sponge man at the waterfront shops — Key West's sponge diving history is older than most people realize

A Key West rooster on the Captains Corner sign — the dive center behind him has been sending people to the reef for years

Chris at NYAH hotel in Key West — one of the more interesting boutique stays on the island

Chris at the Key West harbor with a classic fishing trawler — the working boats here are as much a part of the scenery as the sunsets

Chris at the Mile 0 marker on US Route 1 — the official start of the road, right in Key West

Chris outside Harpoon Harry's on Caroline Street — one of the best casual seafood spots in Old Town

Chris at the World Famous Key West Conch Fritter Stand — mandatory stop on any visit

Chris at the waterfront farmers market — fresh tropical fruit and a view of the marina

Vibrant tropical fruit market in Key West — rambutan, papayas, and local citrus

Fresh produce at the Key West market — tomatoes, peppers, mushrooms from local growers

A vibrant market stall filled with fresh tropical fruits — the Keys grow things you can't find elsewhere

Fresh grilled fish with fries — the kind of straightforward seafood plate Key West does right

Chris in front of a US Coast Guard cutter — Key West has a serious maritime history

On deck of a historic vessel in the Key West harbor — the water here is a different shade of blue

A naval gun on the deck of a historic ship — Key West's military history runs deep

Chris at the Florida Keys Eco-Discovery Center — free admission and worth the stop

The brick walls and courtyard of Fort Zachary Taylor — Civil War history with ocean views

Key West's famous free-roaming chickens — protected by local ordinance and completely unbothered

The ornate white church in Old Town — Key West's architecture tells a story beyond the bars

The Mile 0 sign stack for US Route 1 — the start of the Florida Keys Scenic Highway

The Celebrity Constellation docked in Key West — the island welcomes hundreds of ships a year

A brown pelican perched on a boat in the marina — wildlife is everywhere in the Keys

A Key West church at night, stained glass glowing — Old Town has layers beyond the bars

Bronze busts along a brick walkway — Key West honors its history at every turn

Key West street scene — the energy of Old Town captured in motion

Key West waterfront — the harbor, the boats, and the light that makes this place unlike anywhere else

Traveling with your dog?

Key West is one of Split's approved destinations. Our Travel With Pets guide covers the best dog-friendly restaurants, hotels, and parks here — all places we've actually visited or vetted.