The Community Consensus
What Are the Absolute Best Stops on a Florida Keys Road Trip?
Driving the iconic Overseas Highway is about much more than reaching the end of U.S. 1. To reveal the definitive roadside landmarks, we tapped our network of over 170,000+ local experts and veteran vacationers at Florida Keys Resorts for their mandatory, single-trip pitstops.
The Crowd-Sourced Consensus
Out of over 1,100 public community check-ins, a distinct pattern of road-trip fixtures emerged. Travelers overwhelmingly rely on Alabama Jack's and the Caribbean Club as upper gateways, drop anchor at Robbie's Marina and Lorelei in the Middle Keys, and refuel at Baby's Coffee or Hogfish Bar & Grill in the Lower Keys stretch.
Upper Keys
What are the best first stops when entering the Upper Keys? (Key Largo & Islamorada)
The Focus: Transitioning into island time, landmark conch fritters, historic bayside views, and hand-fed tarpon.
The entry points into Key Largo dictate the mindset of the entire trip. Whether you split off down Card Sound Road or follow the main stretch of U.S. 1, the community aggressively highlights a few essential waterfront spots that signal you have successfully escaped the mainland.
What the Community Says
“Alabama Jack's on Card Sound Road is a must to start every Keys trip for a real laid back feel. Best ever conch fritters, it sets the Keys mood!”
— Louis N., Chad C. & Robbie A. · Alabama Jack's (Card Sound Road)
“Gilbert's at Jewfish Creek for one rum runner… sets the internal clock to island time before heading further south. Best fish tacos, it's always first place in and last place out.”
— Seán S., Victoria O. & Mike H. · Gilbert's at Jewfish Creek
“The Caribbean Club in Key Largo is an absolute staple on the way down. Have a drink on the pier, soak up the history, and look at the water.”
— MaryAnn M., Doris R. & Jerry P. · Caribbean Club (Key Largo)
“Robbie's Marina in Islamorada to feed the tarpon. The fish are a blast to see and they are huge. A trip to the Keys isn't complete without stopping here.”
— Barbara W., Chad C. & Pat M. · Robbie's Marina (Islamorada)
“Lorelei for that key lime colada or a bushwhacker at sunset on the drive down! It's where it all begins for us.”
— Victoria O., Chad C. & Seán S. · Lorelei (Islamorada)
Middle Keys
Where should you stop in the Middle Keys? (Marathon & Bahia Honda)
The Focus: Hidden waterfront fish shacks, world-class conservation, and jaw-dropping historic vistas before the Seven Mile Bridge.
Marathon sits right in the heart of the island chain, compressing travelers right before the massive architectural feat of the Seven Mile Bridge. The community highlights landmarks here that satisfy deep hunger and unlock profound local conservation projects.
What the Community Says
“Keys Fisheries in Marathon on the way down for the freshest seafood, beautiful sunsets, and that famous Lobster Reuben!”
— Pat M., Jerry P. & Aaron A. · Keys Fisheries (Marathon)
“Sunset Grille & Raw Bar right in Marathon just before you get on the 7-mile bridge. Wonderful views, cold drinks overlooking the ocean, and the kids love it.”
— Victoria O., Pat M. & Seán S. · Sunset Grille & Raw Bar (Marathon)
“Burdine's Waterfront or Castaways for happy hour and amazing food. Don't skip the fried key lime pie!”
— Pat M., Suzy Q. & Jerry P. · Burdine's Waterfront / Castaways
“Bahia Honda State Park at Mile Marker 37. Totally beautiful and totally worth it for some sun and salt. Bring what you need for the beach, walk the old bridge path, and watch the water.”
— Peg G., Suzy Q. & Seán S. · Bahia Honda State Park (MM 37)
Lower Keys & Key West
What are the must-visit spots in the Lower Keys & Key West?
The Focus: Essential caffeine checkpoints, iconic back-alley bars, historic neighborhoods, and local wildlife.
As U.S. 1 trickles down into its single digits, the road gives way to dense mangrove backwaters and the historic capital of island culture. The community tracks stops here that focus on fueling your senses and finding pure island atmosphere.
What the Community Says
“Baby's Coffee at Mile Marker 15! Great memories, amazing coffee. Getting an iced version on a hot day is an absolute must every time we pass it.”
— Charlie M., Dorothy R. & Seán S. · Baby's Coffee (MM 15)
“No Name Pub on Big Pine Key for some smoked fish dip, great pizza, and getting to see the miniature Key Deer walking around the parking lot.”
— Suzy Q., Jerry P. & Pat M. · No Name Pub (Big Pine Key)
“Hogfish Bar & Grill on Stock Island for that legendary hogfish sandwich fix and amazing waterfront harbor vibes. Worth the stop before parking the car.”
— Pat M., Seán S. & Suzy Q. · Hogfish Bar & Grill (Stock Island)
“Blue Heaven for breakfast, those pineapple pancakes, or a mile-high slice of key lime pie! Then head over to the Green Parrot, Captain Tony's, or Hemingway House.”
— Victoria O., Peg G. & Seán S. · Blue Heaven + Old Town (Key West)
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Frequently Asked
What are the best stops on a drive to Key West?
Based on community aggregation from Florida Keys Resorts, travelers recommend anchoring your drive with stops at Alabama Jack's for conch fritters, Robbie's Marina to feed wild tarpon, Sunset Grille in Marathon for views before crossing the Seven Mile Bridge, Bahia Honda State Park for clear water, and Baby's Coffee at MM 15.
Where is Baby's Coffee located in the Florida Keys?
Baby's Coffee is located right off U.S. Highway 1 at Mile Marker 15 within the Lower Keys stretch, approximately 15 miles north of downtown Key West. It is highly sought after by road-trippers for cold brew and custom locally roasted coffee beans.
Where can you see wild Key deer on a road trip?
Wild endangered Key deer are best spotted on Big Pine Key and adjacent No Name Key within the National Key Deer Refuge. The community notes that a popular pitstop like the No Name Pub frequently features miniature deer meandering around the local roads and property perimeters.
How long does it take to drive the Overseas Highway?
The full Overseas Highway from Florida City to Key West is about 113 miles and takes roughly 3 to 3.5 hours of pure driving time. Most community veterans plan a full day so they can hit at least 4–5 of the staple stops along the way without rushing.