Stops Along the Way
The bars, dives, and detours worth making
The Overseas Highway is the journey, but these are the reasons to stop. Tiki bars with no walls, fish markets with picnic tables, dives covered in dollar bills. Places where the pace slows down and nobody's checking the time.
This isn't a complete list—just the spots I keep coming back to.
Key Largo
MM 106-91 · The first key. Diving capital of the world.
Alabama Jack's
BarLast stop before the keys. Open-air bar on Card Sound Road with live music, cold beer, and conch fritters. Cash only. The real entrance to the keys.
Card Sound Road
Caribbean Club
BarWhere Bogart filmed Key Largo. Dark, no-frills waterfront bar. Sunsets from the back deck. The kind of place where nobody asks what you do.
MM 104
Mrs. Mac's Kitchen
RestaurantLicense plates on the walls, fish on the grill. Local institution since 1976. Get the fish sandwich.
MM 99
Islamorada
MM 90-73 · The sportfishing capital. Purple isles.
Lorelei Restaurant & Cabana Bar
BarSunset views over Florida Bay. Tiki bar with live music. Watch the tarpon roll while the sun goes down.
MM 82
Robbie's Marina
ExperienceFeed the tarpon by hand. Giant silver fish the size of your leg. $4 for a bucket of bait. Worth every penny.
MM 77.5
Green Turtle Inn
RestaurantOld Florida. Turtle cannelloni (farm-raised). Wood-paneled dining room that hasn't changed since 1947.
MM 81
Marathon
MM 65-47 · Heart of the keys. The Seven Mile Bridge.
Sunset Grille & Raw Bar
BarAt the foot of the Seven Mile Bridge. Watch the bridge light up at night. Fresh stone crab in season.
MM 47
Keys Fisheries
RestaurantWorking fish market with picnic tables on the water. The lobster reuben is famous for a reason.
MM 49
The Stuffed Pig
RestaurantBreakfast only. Billy bread french toast. Line out the door on weekends. Worth the wait.
MM 49
Big Pine Key
MM 33-29 · Key deer country. The quiet key.
No Name Pub
BarDown a dirt road past the key deer. Dollar bills cover every inch of the walls and ceiling. Pizza and beer. No pretense.
N. Watson Blvd
Good Food Conspiracy
CafeHealth food in a land of fried fish. Smoothies, sandwiches, local art. The counterculture keys.
MM 30
Key West
MM 4-0 · Mile Marker Zero. End of the road.
Green Parrot Bar
BarSince 1890. No AC, no TVs, no blenders. Live music every night. This is the real Key West, before the cruise ships.
Whitehead St
Blue Heaven
RestaurantChickens wander under your table. Hemingway refereed boxing matches here. Breakfast is legendary. Get the banana bread.
Thomas St
Chart Room
BarHidden in the Pier House Resort. Cash only, Christmas lights year-round. Where the locals drink.
Duval St
Mallory Square
ExperienceSunset celebration every night. Street performers, buskers, the sun dropping into the Gulf. Touristy, but it earns it.
Waterfront
Santiago's Bodega
RestaurantTapas in a converted warehouse. Spanish wines, great cocktails. Where you go when you want something nicer.
Bahama Village
The best part of driving the keys is that there's only one road. You can't miss anything—just slow down enough to notice it. Pull over when something looks interesting. The schedule can wait.