Got a wild idea? We build for service members — not the brass, not shareholders. If it's good, it ships.
Suggest a Feature →Key West & the Lower Keys
The end of the road. 90 miles from Cuba and 1,500 miles from reality.
Coast Guard Sector Key West and Air Station Borinquen coordinate one of the most complex maritime and aviation operations in the US — counter-narcotics and migrant interdiction across the Florida Straits, the Yucatan Channel, and the Caribbean. The operational stakes are real and constant.
Key West is the southernmost city in the continental United States, sitting at the end of the Overseas Highway 130 miles southwest of Miami. It is a city unlike anywhere else in America — a former sponge-diving and cigar-manufacturing town that became a Navy base, a literary capital (Hemingway, Tennessee Williams, Elizabeth Bishop all lived here), and eventually the world's most famous LGBTQ+ resort destination.
The pace of Key West is the Florida Keys pace: slow, warm, ocean-focused, and indifferent to the urgency of mainland life. The water is clear enough to see the bottom in 20 feet. The reefs are accessible. The sunsets are operatic.
Must Eat
The spots worth eating at before you PCS out.
Blue Heaven
"Roosters, outdoor dining, and the best breakfast in the Keys."
An outdoor restaurant in Bahama Village where roosters wander freely between tables while diners eat banana pancakes, lobster benedict, and the house granola. The space is a converted alley behind a water tower that has been a boxing ring, a cockfighting arena, and a pool hall. Deeply Key West.
Go weekday morning to avoid the 90-minute weekend wait.
El Meson de Pepe
"The best Cuban food in Key West. Malecón style at 90 miles from Havana."
A Cuban restaurant in Mallory Square serving ropa vieja, picadillo, and rice-and-beans of the caliber you'd find in Little Havana. The Cuba-to-Key West cultural current has been running for 200 years — El Meson de Pepe is the best expression of it in food form.
Hogfish Bar & Grill
"A working marina bar. Fresh hogfish sandwich off the local boats."
On Stock Island (the working-class island adjacent to Key West), Hogfish is a marina bar with tables on the dock and a kitchen that serves whatever the local boats brought in — hogfish sandwich being the signature. Cold beer and Keys views without the Duval Street tourist tax.
Stock Island is where the real Key West lives. Hogfish is the best ambassador.
Outdoor
Get outside. The land around military installations is usually the best reason to be there.
Dry Tortugas National Park
"Fort Jefferson on a remote island. Ferry or seaplane only. Extraordinary."
Accessible only by the Yankee Freedom ferry (2.5 hours) or seaplane, Fort Jefferson is a massive 19th-century fort on Garden Key — the largest masonry structure in the Western Hemisphere. The snorkeling around the moat wall is spectacular. Camping on the island overnight is a bucket-list experience.
Florida Keys Reef Snorkeling
"The only living coral reef in the continental US. Accessible from shore and boat."
The Florida Keys National Marine Sanctuary encompasses the only living coral barrier reef in the continental United States. Charter dive boats and snorkel tours operate daily from Key West to the reef — 4-7 miles offshore. Looe Key, Sand Key, and the Sambos reefs have excellent coral and fish life.
Back-Country Kayaking
"Mangrove tunnels, backcountry bays, and a world with no land visible."
The backcountry north and east of Key West — the Great White Heron National Wildlife Refuge — is a vast maze of mangrove islands, turtle grass flats, and shallow bays. Kayaking into the backcountry at sunrise, with no traffic and no development visible, is the best version of the Keys.
Culture & History
Places with stories. Most military towns sit on deep history — dig in.
Hemingway Home & Museum
"Where Papa wrote. The 6-toed cats are still there."
Ernest Hemingway's Key West home from 1931 to 1939 — where he wrote For Whom the Bell Tolls and A Farewell to Arms. The guided tours are excellent, and the house is genuinely preserved rather than reconstructed. Approximately 50 polydactyl cats (descendants of Hemingway's original) have the run of the property.
The tour guides are exceptionally knowledgeable about Hemingway's time here — take the guided tour.
Mallory Square Sunset Celebration
"Every evening at sunset. The city gathers to watch the sun go down."
A daily tradition — street performers, vendors, and tourists gather at Mallory Square to watch the sunset over the Gulf of Mexico. Jugglers, escape artists, a trained cat circus (yes), and Key West's particular blend of celebration and eccentricity. Go once. It's genuinely joyful.
Family
Stuff to do with the kids. Rated by people who have brought actual children.
Key West Aquarium
"One of the oldest aquariums in the US. Touch the sharks."
Opened in 1934, the Key West Aquarium is small but genuinely excellent — the shark touch tank, the Atlantic shore exhibit, and the guided tours where staff hand you a live sea turtle make this among the most interactive aquarium experiences available at any scale.
Smathers Beach
"The best family beach in Key West. Calm, shallow, with water sports equipment."
The widest and longest public beach in Key West on the Atlantic side, with water sports rentals — kayaks, paddleboards, windsurfers — and shallow, calm water suitable for young children. A beach bonnet (shade structure) rental makes a full afternoon manageable.
Day Trips
When you need to remember there's a world outside the gate.
"The tiny Key deer, Looe Key reef, and the quieter side of the Keys."
Big Pine Key is home to the diminutive Key deer — an endangered subspecies of white-tailed deer the size of a large dog. The National Key Deer Refuge protects them. Looe Key National Marine Sanctuary is nearby and considered the best reef diving in the continental US.
"The Florida Keys' best state park beach. Stunning."
Bahia Honda State Park, 40 miles north, consistently ranks as one of the top beaches in the US — sand bars extending into gin-clear water, with the ruins of the old Flagler railroad bridge as a backdrop. Kayak rentals, camping, and snorkel trips available.
"The city. When you need a real city after island life."
Three hours north on US-1 and the Turnpike. Miami is the closest major metropolitan area and the reference point for everything from Costco runs to concerts to real hospital care. A practical overnight trip several times a year for most Key West families.
The island traffic is one way and frequently gridlocked. Bicycle or scooter for local movement — it's how Key West actually works. MWR rents bikes.
Everything in Key West is 10–20% more expensive than Miami for similar goods. Costco runs to Homestead (130 miles north) are a legitimate quarterly strategy for families.
The humidity from June through October is punishing — indoor mold is a real issue for sensitive gear. Electronics, optics, and leather all require attention.
The Keys have their own culture that pre-dates the resort economy by a century. Conch culture (5th-generation Keys residents call themselves Conchs) is real and worth respecting. Don't be the tourist in the military uniform.
Key West is expensive, small, and can feel claustrophobic after extended time on a 4-by-2-mile island. The tourism economy dominates Duval Street and pricing throughout the city. Families frequently cite the lack of space and activities for children compared to mainland assignments. The weather from June through October is hot, humid, and hurricane-active. But the operational mission is significant, the water access is extraordinary, and service members who lean into the marine environment leave with fishing and diving skills they use for the rest of their lives.
This guide is built by people who've been stationed here. If there's a spot we got wrong or a gem we missed, tell us.