# The Overseas Highway A 3-day, ~210-mile Southern road trip from Miami. It chains The Overseas Highway. - **Days:** 3 - **Distance:** ~210 mi - **Starts in:** Miami - **Themes:** Outdoors, Food, History - **Routes chained:** [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) US 1 to the end of the road: forty-two bridges over turquoise water to Key West, with a hurricane monument, a rescued movie boat, tiny key deer and the last mile marker in America. The interstate ends where the fun starts. ## Why this itinerary works Starting in Miami, this 3-day itinerary connects The Overseas Highway. It suits travellers interested in parks, coast, mountains & water; barbecue, boudin, oysters & tamales; battlefields, the movement & the past. The day-by-day bases let you split roughly 210 miles into a sequence of visits rather than trying to cover every linked route end to end. Use the daily highlights to decide which places deserve your longest stops. ## Day by day ### Day 1: Miami → Islamorada Card Sound Road for a beer at Alabama Jack's, the African Queen still afloat in Key Largo, snorkel the reef at Pennekamp, then the 1935 Hurricane Monument at Islamorada — dinner and a sunset dock at the fishing capital. Make the reef outing the day's anchor and reserve it before filling the morning with roadside stops. Wind and sea conditions can change a boat plan; keep a land-based Key Largo visit as the alternative. The driver should skip the beer. Islamorada is the first-night base, giving the Middle Keys their own day rather than trying to reach Key West in one run. Highlights to consider: - **Alabama Jack's** (Card Sound) — An open-air conch shack on the old smugglers' road, serving conch fritters to bikers and boaters since the 1950s. The correct way to enter the Keys. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) - **The African Queen** (Key Largo) — The actual 1912 steam launch from the Bogart-Hepburn film, rescued and running canal cruises. Bogie never came to Key Largo for the movie; the boat did, eventually. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) - **1935 Hurricane Monument** (Islamorada) — A WPA crypt holding victims of the Labor Day storm, the most intense US landfall on record. It killed hundreds of WWI veteran bonus-army workers and finished Flagler's railroad for good. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) ### Day 2: Islamorada → Big Pine Key The Turtle Hospital in Marathon, walk Pigeon Key beneath the Old Seven Mile Bridge, swim the deep cut at Bahia Honda, then key deer at dusk and a slice at the No Name Pub. Overnight Big Pine. Highlights to consider: - **The Turtle Hospital** (Marathon) — A working sea-turtle hospital in a converted motel, running rescue, surgery and release since 1986. Book the tour; you will meet the patients. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) - **Pigeon Key & the Old Seven** (Marathon) — The railroad workers' island village sits under the original Seven Mile Bridge; the restored old span is now a two-mile walk over open ocean. Golden hour here beats any postcard. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) - **Bahia Honda State Park** (Big Pine Key) — The Keys' best natural beach beside the dramatic broken arch of Flagler's Bahia Honda bridge. Swim where the ocean and the Gulf trade water. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) - **No Name Pub & the Key Deer** (Big Pine Key) — A dollar-bill-papered pub hiding down a back road since the 1930s, in the middle of the National Key Deer Refuge. The knee-high deer own the right of way at dusk. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) ### Day 3: Big Pine → Key West The last stretch of blue to Mile Marker 0: Hemingway's six-toed cats, the Southernmost Point line, and a green flash from Mallory Square. Drive back or fly out of the little island airport. Highlights to consider: - **Mile Marker 0** (Key West) — The end of US 1 at Whitehead and Fleming. The sign gets stolen constantly, the photo line never shortens, and the atlas officially runs out of South here. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) - **Bahia Honda State Park** (Big Pine Key) — The Keys' best natural beach beside the dramatic broken arch of Flagler's Bahia Honda bridge. Swim where the ocean and the Gulf trade water. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) - **No Name Pub & the Key Deer** (Big Pine Key) — A dollar-bill-papered pub hiding down a back road since the 1930s, in the middle of the National Key Deer Refuge. The knee-high deer own the right of way at dusk. [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy) ## Practical planning Budget an average of about 70 miles per day across the whole trip, or roughly 1.6–2.3 hours behind the wheel at an assumed 30–45 mph back-roads pace. This is a planning estimate, not a measured time for each leg: transfer days can be longer and rest days shorter. Add meal stops, tours, ferries, traffic and hikes separately; use each day's navigation link for current driving estimates. ### Overnight bases - Day 1: Miami → Islamorada - Day 2: Big Pine - Day 3: Big Pine → Key West ### Best season & route notes - [The Overseas Highway](https://dixieroadtrip.com/routes/overseas-hwy): Leave Miami before 8am or after 7pm; the 18-Mile Stretch decides your whole day. ## Frequently asked questions ### How many days and miles is The Overseas Highway? The Overseas Highway is a 3-day trip of about 210 miles. ### Where does The Overseas Highway start? It starts in Miami. ### Which routes does The Overseas Highway chain together? It chains The Overseas Highway. ### Where are the overnight bases on The Overseas Highway? Day 1: Miami → Islamorada; Day 2: Big Pine; Day 3: Big Pine → Key West. ## Related itineraries - [A1A End to End: St. Augustine to Key West](https://dixieroadtrip.com/trips/a1a-end-to-end) — 6 days, ~520 mi --- Canonical URL: https://dixieroadtrip.com/trips/keys-overseas Publisher: Dixie Media (Dixie Road Trip, https://dixieroadtrip.com/) Last updated: 2026-10-04