Florida Keys Road Trip: 5 Days From Miami to Key West

A fish sandwich beside the water is a perfectly respectable reason to stop driving, especially when the next island can wait until tomorrow.

I would give Miami to Key West five days, move south slowly, and finish with the car parked while the island streets, food, and waterfront take over.

Table of Contents

The Five-Day Florida Keys Route

Day 1: Miami to Key Largo
Day 2: Key Largo to Islamorada
Day 3: Islamorada to Marathon and Bahia Honda
Day 4: Lower Keys to Key West
Day 5: Key West

The Overseas Highway is an All-American Road and the only road connection through most of the Keys. That makes the route wonderfully simple and occasionally very slow, especially when crashes, construction, holiday traffic, or weather affect U.S. 1.

If you are pairing this with a cruise, my Florida road trips before a cruise guide can help. For a standalone Keys vacation, I would avoid putting a ship departure immediately after a long drive back from Key West.

Day 1: Miami to Key Largo

Leave Miami after the worst commuter traffic if your schedule allows and treat Key Largo as the first destination rather than the place you pass while thinking about Key West. The drive changes character once you leave the mainland and begin crossing into the island chain.

Choose your water activity

Key Largo is the place I would prioritize snorkeling, diving, paddling, or a glass-bottom boat depending on your comfort level. Book with an established operator and remember that wind and sea conditions can alter trips.

If diving is the reason for the vacation, give Key Largo an extra night. One afternoon does not need to carry the entire underwater part of your trip.

Stay for dinner

Eat seafood somewhere casual and waterfront if that is the mood you came for, then get a good night’s sleep. Tomorrow’s drive is short enough that there is no advantage to squeezing another island into the first day.

Day 2: Key Largo to Islamorada

Drive south to Islamorada and let the day revolve around the water, art, food, or fishing rather than mileage. The islands begin feeling less like an extension of Miami and more like their own rhythm here.

Stop by mile marker, not by town border

Addresses throughout the Keys often use mile markers as useful geographic references. I keep an eye on them because they make it much easier to understand whether a restaurant or stop is actually on the way.

Eat local seafood

Islamorada is a good place for fish, conch, stone crab in season, and whatever local catch is available. Ask what is fresh rather than ordering one supposedly mandatory Keys dish at every restaurant.

Stay in Islamorada or continue only if you want fewer hotels

I like one night here because sunset and dinner become the day’s finale. If moving hotels annoys you, use Marathon for two nights instead and make Islamorada a long stop on the way.

Day 3: Marathon and Bahia Honda

Continue through the Middle Keys toward Marathon, where the route begins opening into some of its best bridge-and-water scenery. This is the day I would keep flexible enough for a beach, wildlife center, or boat activity.

Seven Mile Bridge area

The famous bridge is part of the drive rather than an attraction you need to conquer. Keep your attention on traffic and save photos for legal parking areas rather than slowing unpredictably on U.S. 1.

Bahia Honda State Park

Bahia Honda is one of the beach stops I would genuinely plan around. Florida State Parks currently opens the park from 8 a.m. to sunset and warns that popular day-use areas can temporarily close when they reach capacity.

Arrive early on weekends and holidays, especially if beach time is a priority. Check the Bahia Honda State Park page for current capacity notices, fees, snorkeling, kayak, and marina information.

Sleep in Marathon or the Lower Keys

Marathon gives you a wider selection of everyday services, while a Lower Keys stay can feel quieter and put you closer to Key West tomorrow. Choose based on whether you want convenience or atmosphere.

Day 4: Lower Keys to Key West

Do not rush this morning simply because Key West is famous. The Lower Keys offer quieter scenery and a chance to enjoy the road before the trip becomes a walkable city break.

Watch for Key deer responsibly

Big Pine Key and surrounding islands are habitat for the endangered Key deer. Drive carefully, obey speed limits, and never feed or approach wildlife.

Reach Key West and park the car

Once you check in, I would avoid driving unless your lodging location truly requires it. The Florida Keys tourism office notes that visitors can park in Old Town and do much of Key West on foot, which is much more pleasant than circling narrow streets for another space.

Make sunset a plan, not a race

Choose Mallory Square, a waterfront restaurant, a sunset sail, or another west-facing spot and arrive with time to enjoy it. Key West sunset is not improved by sprinting there after an overstuffed afternoon.

Day 5: Key West

Give Key West an entire day without a relocation drive. Walk Old Town, choose one or two historic attractions, have a long lunch, and leave room for the weird little details that make the city fun.

Pick your history

Hemingway history, maritime stories, architecture, presidential history, and local cultural sites all compete for attention. Choose what genuinely interests you instead of collecting houses because they appear on a map.

Eat beyond Duval Street

Duval is part of the experience, but Key West’s food scene is much broader than the busiest blocks. Look for Cuban influence, seafood, Caribbean flavors, and places where the menu feels more local than generic resort-town fare.

Finish with another evening on foot

One of my favorite things about spending two nights in Key West is that sunset does not signal the beginning of a long drive. Have dessert, hear live music, or simply walk back to the hotel.

How Long Does the Drive Really Take?

Miami to Key West may show as only a few hours in light traffic, but the Overseas Highway is not a route I would schedule tightly. One crash or lane closure can create substantial delays because there are few alternate roads.

Check FL511, Florida’s official real-time traffic source, before each longer driving day. It shows incidents, construction, closures, congestion, and travel conditions on major routes.

Where to Stay

Key Largo: best for water activities and an easy first night after Miami. Choose somewhere close to your booked boat operator if you have an early departure.

Islamorada: my favorite one-night stop for sunset, restaurants, and a more relaxed island feel. It works especially well for couples.

Marathon: practical for two nights if you want fewer hotel changes and easy access to the Middle and Lower Keys. It also has broader everyday services.

Key West: pay attention to walkability and parking when comparing hotel prices. A room that lets you leave the car parked can save time, parking fees, and irritation.

Best Time for a Florida Keys Road Trip

Winter

Winter offers warm weather when much of the country is cold and is also peak season. Expect higher hotel prices and make reservations early.

Spring

Spring can be beautiful before the hottest weather settles in. Holiday and spring-break periods still create heavy traffic.

Summer and fall

Heat, humidity, thunderstorms, and hurricane season become major planning factors. Tropical systems can close roads, airports, parks, and the entire island chain to visitors when emergency officials determine evacuation is necessary.

Hurricane Season Changes the Rules

If a tropical storm or hurricane threatens the Keys, follow Monroe County and state emergency instructions immediately. U.S. 1 is the main evacuation route, which is not the time to prioritize a hotel cancellation policy over official guidance.

Use FL511 before and after major storms for current road information. I would also build travel insurance and flexible bookings into any peak hurricane-season trip.

Do You Need a Rental Car in Key West?

You need the car for the road trip, but you may not want it once you reach Key West. Compare hotel parking costs and return logistics if your trip ends there.

If you are driving back to Miami, keep the car parked for your Key West stay and start north early on departure day. Do not make the return drive immediately before an international flight or cruise check-in with no margin.

What to Pack

Reef-safe sun protection where required or recommended
Swimsuit and quick-drying towel
Light rain layer
Reusable water bottle
Small cooler
Comfortable sandals and walking shoes
Motion-sickness medication if boat trips affect you

My road trip tips cover the normal driving-day basics. In the Keys, I would add sun protection, patience, and a willingness to let one perfect waterfront afternoon replace whatever else was on the list.

One More Safety Resource for the Keys

My road trip packing list covers the practical car and beach gear for this route. During hurricane season I also keep the Monroe County Emergency Management page handy because evacuation and island-access instructions matter more than preserving an itinerary.

My Favorite Five-Day Keys Trip

The five-day route uses four nights: one each in Key Largo, Islamorada, Marathon, and Key West. Add a second Key West night and a sixth day when you want another relaxed evening there and more time for the return drive.

The Keys are not far enough apart to require an aggressive schedule. Slow down, keep checking the water beside the highway, and arrive in Key West feeling like the road there actually mattered.