Epic Miami to Key West Road Trip Guide

44 min

Taking a road trip through the Florida Keys is one of the best adventures you can have in the USA. The 110 mile stretch from Miami to Key West traverses the appropriately named Overseas Highway, crossing 42 bridges while taking you on a wild ride through one of the most picturesque, quirky and fun places in the USA.

While the drive to the Southernmost city in the United States only takes 4 hours to complete, you’d be at a total loss to miss the many stops along the way. Each island offers something different and sets the tone for your arrival into the fabled Key West, 90 miles north of Cuba.

For anyone who fears that the effects of Hurricane Irma has ruined the Florida Keys, think again. Recovery efforts have been dramatic and you’ll struggle to imagine that the area was even hit in September 2017. Hold on to your hat, the Florida Keys is open for business and an epic road trip awaits you.

Miami to Key West Road Trip Facts

Distance from Miami to Key West – the total distance from the Miami International Airport to Key West is 110 miles. The entire stretch of road is paved highway.

Miami to Key West drive time – if you were to drive straight through, the drive would take you on average of 4 hours. Something to note is that the Overseas Highway is a slower moving 4 lane highway, 2 northbound lanes and 2 southbound lanes, with an average speed limit of 40MPH.

Best time to visit the Florida Keys – the best season in between March and May as the weather is stable and the large crowds from the winter season have began to disappear. You’ll also enjoy more reasonable prices. July is the hottest month averaging 86°F (30°C) and January is the coldest month averaging 70°F (21°C). The most rain falls in September.

Recommended number of days – our road trip lasted 6 days and we structured it with 2 nights in Key Largo while heading southbound, 2 nights in Key West and 1 night in Marathon while heading northbound. This said, I would highly recommend that you extend your trip to a full 7-8 days giving you an extra 1-2 nights in Key West.

Miami to Key West Road Trip - Lina Stock

Rent a Car in Miami

Unless you’ve decided to drive from your hometown, you’ll be flying into the Miami International airport and be in need of a vehicle to start your Florida Keys road trip. Be sure to make a rental car reservation before flying to Miami as all classes of rentals are in high demand and the chances of there being an affordable option available on arrival are slim.

The roads from Miami to Key West are paved and easily traveled, so it really comes down to preference for the type of vehicle you choose to rent. We went with a mid-sized car for comfort and fuel economy but that’s not to say it wouldn’t be fun to rent a jeep or convertible for the drive.

Secure your car rental through Priceline

Car Insurance – rental cars come with the minimum levels of liability insurance required by the state that is provided by the rental company. While it meets the requirements, it is not enough coverage to have peace of mind or cover you in the case of a serious accident.

You have the option of purchasing an extended policy when you pick up your rental but also remember that a good travel insurance plan will also provide you great car rental insurance.

Florida Keys Map

Miami to Key West Road Trip

Can’t Miss Stops from Miami to Key West

Skip ahead to:

Key Largo | Islamorada | Marathon | Big Pine | Key West

Miami to Key West Road Trip - Lina Stock

Key Largo

The closest Key to mainland Florida, Key Largo is an absolute gem with some amazing natural landscape to enjoy making it a fantastic first stop when heading form Miami to Key West on a road trip.

While it’s no Key West, this island is an absolute paradise bursting with local character and relaxing Caribbean vibes. Not to mention, Key Largo is an icon having debuted in literature written by Ernest Hemmingway and a famous song by the Beach Boys.

Traveling 68 miles from Miami it takes around 1 ½ hours to reach Key Largo, which is the perfect amount of driving for the first day. This gives you time to arrive, find your hotel and get settled before heading off to dinner for a spectacular sunset on one of the islands many piers.

Miami to Key West Road Trip - Lina Stock

Our stops in Key Largo

John Pennekamp State Park – the majority of our time on Key Largo was spent exploring this stunning natural area. We started our day with a boat trip out to the only living coral reef in the United States, where we spent 2 hours snorkeling in the waves.

Despite us having the privilege to snorkel and dive on some of the best reefs in the world, we found the reef here healthy and beautiful. What stood out the most were the large populations of colorful fish, so it’s definitely worth the effort.

Back on land we spent a couple hours walking the trails in the park. The trails are well groomed and easy to follow offering fantastic views of the ocean and thriving mangrove forests along the shore.

Miami to Key West Road Trip - Lina Stock

Entrance into the John Pennekamp State Park costs $8USD per vehicle (2-8 persons) and the park hours are 8am until sunset.

Snorkeling tours cost $29.95 for a 2.5 hour trip and run at fixed times 9am, 10:30am, 12pm, 1:30pm, 3pm and 4:30pm daily.

Getting Here: the State Park entrance is located at Mile Marker 102.5

Miami to Key West road Trip - Sundowners - Lina Stock

Places to eat in Key Largo

Sundowners – this is the place to be for sunset as they have a prime location on the water. Not to mention the flowing plates of seafood and tropical cocktails on offer. Even if you just come for drinks and appetizers, we enjoyed live music and a truly spectacular sunset.

Hot tip: Be sure to make a reservation if you want to dine during sunrise.

The Fish House – just as the name suggests, this is the place to go if you like fresh fish. The perfect place to grab lunch, this restaurant specializes in fresh local seafood including snapper, mahi mahi, grouper, Florida lobster and stone crab.

Mrs. Mac’s Kitchen – fun and quirky, this is the place to meet locals while enjoying the perfect mesh of southern fare and island seafood. If the food isn’t enough to attract a visit, maybe the hundreds of licenses plates that decorate the interior of this eatery will draw you in for a look.

Places to stay in Key Largo - Kona Kai Resort - Lina Stock

Places to stay in Key Largo

Kona Kai Resort – two words for this charming boutique property, simply paradise. Tucked away off the busy highway, this resort is an oasis of smartly decorated rooms, white sand, swaying palms and salty ocean breeze.

Each room features a small apartment complete with a bedroom, sitting area and kitchen. They offered continental breakfast and a variety of complimentary non-motorized water activities from their private dock. We found the Kona Kai extremely comfortable and would recommend any length of stay while in Key Largo.

Miami to Key West Road Trip - Islamorada - Lina Stock


What we loved about Islamorada was the complete change in vibe from Key Largo. They are so close together, yet offer such a different experience and feel. Islamorada has a less commercial feel to it and was a place we felt that we could connect with the local people of the Florida Keys.

Not to mention that the road leading both onto and off of the island offers a spectacular display of bright turquoise water and accessible from small pull offs where white sand rolls gently into the water.

We used Key Largo as a base for exploring Islamorada, as the islands are very close together. This is a great option if you have a limited amount of time but still want to experience both islands. It’s also nice to check into a place for 2 nights instead of 1, so we would recommend this approach.

Miami to Key West Road Trip - History of Diving Museum - Lina Stock

Our stops in Islamorada

History of Diving Museum – featuring one of the world’s largest collections of international diving helmets and artifacts, this museum is a must stop for anyone who scuba dives, is fascinated with history or dreams of underwater exploration.

We were absolutely enamored by the layout of this museum, taking us through the entire evolution of diving from open bottom helmets to today’s popular SCUBA and everything in between.

I especially loved the display featuring the history of underwater photography and the chance to see the evolution of cameras, hard to believe how far we’ve come from Ikelite housings the size of briefcases to a GoPro.

Entrance into the History of Diving Museum costs $12USD for adult, $6USD for children 6-11 and free for children under 5. The museum hours are 10am to 5pm every day of the week.

Miami to Key West Road Trip - Florida Keys Brewing - Lina Stock

Florida Keys Brewing Company – located in the heart of the Morada Way’s Arts and Cultural District we enjoyed an afternoon in the tasting room of this locally owned brewery.

Owner Craig McBay, with his wife Cheryl, opened the doors to the Florida Keys Brewing Company in March 2015 as the first brewery to take up residence in the Florida Keys. We loved the sense of island life that they bring to their brews, featuring Key limes, citrus, hibiscus and honey.

The Tasting house is open everyday of the week from Noon to 10pm.

Miami to Key West Road Trip - Robbie's - Lina Stock

Robbie’s – this place is an institution and no road trip from Miami to Key West would be complete without a stop to feed the Tarpon from Robbie’s pier. Even if you can’t bring yourself to dangle your arm over the dock edge for the thrill of an up to 100 pound monster fish jumping up to retrieve the fish in your fingers, it is worth paying the $2.00 admission to watch the spectacle in person.

When you’ve had enough of the thrill, you’ll find that Robbie’s also offers a full market of locally made crafts to shop and quirky food stands to check out. With public restrooms available, this is a great place to pull over and stretch your legs on your drive from Miami to Key West.

Admission to the Tarpon dock at Robbie’s cost $2.00 per person. Buckets of fish can be purchased for $3.00 each. Hours for visiting are 7am to 8pm.

Places to eat in Islamorada - Marker 88 - Lina Stock

Places to eat in Islamorada

Marker 88 – sticking to the theme of a classic Florida Keys sunset, the Marker 88 is located on a pier facing the Gulf, complete with a white sand beach, music and Caribbean vibe, it is THE place to watch the sunset in Islamorada.

Featuring Keys inspired flavors infused into freshly caught seafood, it’s a delectable place to sip on a Hemmingway and watch the sun disappear on the horizon.

Miami to Key West Road Trip - Lina Stock

Places to stay in Islamorada

Cheeca Lodge – featuring 214 spacious rooms on 27 acres of lush garden, all lined with turquoise water and towering palms, this lodge is an oasis in paradise. The property also features a 525 foot pier, touting it as the longest in the Keys, which is the perfect place to enjoy the sunset or cast a reel. This Islamorada luxury resort offers snorkeling, sea kayaking, bicycling, scuba diving and 3 first class restaurants.

Casa Morada – this privately owned hotel offers 16 upscale suites giving an atmosphere that is private, peaceful and serene.  The highlight of the resort is Casa Morada’s spectacular private island which is accessed by a dramatic footbridge and features a fresh water pool, secluded cabana and the Sunset Gazebo bar with stunning views of the Gulf of Mexico.

Miami to Key West Road Trip - Lina Stock


Our stop in Marathon was a short one, as we used the island for a transit stop to break up the trip back to Miami from Key West. We ended up leaving Key West in the early afternoon, around 2pm and began driving north.

We stopped at the Bahia Honda State Park and then cruised into Marathon by 5pm. This gave us enough time to settle into our room and head down to the water for one of the best sunsets we had during our road trip.

Miami to Key West road Trip - Bahia Honda State Park - Lina Stock

Our stops in Marathon

Bahia Honda State Park – located before you arrive to Marathon when heading northbound on the Overseas Highway, this park is stunning and to think we almost drove right by without stopping makes us cringe.

What the park lacks in green vegetation it makes up for in endless expanses of white sand beaches. It also gives you access to hike up on to one of the original bridges that was constructed from Miami to Key West.

Bahia Honda State Park did experience some damage when Hurricane Irma came through at the end of 2017 but rehabilitation efforts are in place and most of the park is still accessible. Definitely make some time to pull into this state park, bring some drinks, snacks and plan some time just relaxing.

Entrance into the park is $8USD per vehicle (2-8 persons) and the hours are 8am to sunset every day of the year.

Places to eat in Marathon Florida Keys - Lina Stock

Places to eat in Marthon

Butterfly Café – located inside the Tranquility Bay Resort, this café offers an intimate and cozy setting with a wide array of food options. Meshing together Italian fare with fresh seafood, it’s a great place to sit outside and enjoy the ocean air among tiki torches. Check out the menu here.

Places to stay in Marathon Florida Keys - Tranquility Bay Resort - Lina Stock

Places to stay in Marathon

Tranquility Bay Resort – this property is the kind of place you can check into for a week long vacation and never leave from. It’s huge, offering all the amenities you could imagine, multiple pools, a private white sand beach, towering palm trees, golf course and more.

The accommodation features spacious town house style rooms laid out as 2 level apartments with a living area, full kitchen, upper and lower decks, multiple bedrooms and en-suite laundry. It’s a true home away from home.

Miami to Key West Road Trip - Big Pine Key - Lina Stock

Big Pine Key

This part of the Florida Keys holds the essence of the island chain, an opportunity to step away from the commercialism and explore the wild side of Florida. With most of the land being a protected preserve, it’s the perfect place to head into the uninhabited backcountry with a kayak and get up close with the nature that makes Florida such an American icon.

Of all the islands on our trip, Big Pine Key was the only one that showed any lasting damage from Hurricane Irma. Unfortunately, this was the hardest hit area and the storm pulled up a huge amount of mature mangrove forest in it’s path changing the face of the island.

Despite this, it is still gorgeous and totally worth a stop for  a kayaking adventure, at the bare minimum.

Florida Keys Kayaking - Big Pine Key - Lina Stock

Our Stops in Big Pine Key

Big Pine Kayak – Bill Keogh has lived in the lower keys for two decades, meaning he knows the area better than anyone could imagine. His daily kayaking eco-tours offer the opportunity to explore dense mangrove forests, learn about the balance of the local eco-system, see wildlife and all around enjoy a special day on the water.

If you have more time to spend and want to really get into the heart of the backcountry, Big Pine Kayak offers multi-day paddling trips that combine time on the water with camping.

Kayaking day trips on Big Pine Key cost $50USD and operate seven days per week. Bookings are essential to ensure availability, so be sure to plan ahead if you’d like to go on a kayak adventures during your Florida Keys road trip.

Places to eat in Big Pine Key Florida Keys - No Name Pub - Lina Stock

Places to eat in Big Pine Key

No Name Pub – the first time we read their slogan ‘a nice place, if you can find it’ we knew we had to visit. Lucky for us, this little dive pub is located just down the road from Big Pine Kayak and about as local as you can get.

The high of your visit will be walking through the doors to discover the walls coated in hanging currency from around the world. Not one square inch of space has been left uncovered. You’ll find typical pub food, generous portions and friendly locals. Our recommendation? Try the Fish Dip.

 Miami to Key West Road Trip - Lina Stock

Key West

Glorious, iconic and legendary, this island at the end of the road lives up to its reputation. For as long as I can remember I’ve dreamed about a road trip from Miami to Key West, to not only visit the amazing islands along the route but to arrive in Key West and partake in all the adventure there is on offer.

The dream finally came true this year and Key West didn’t hesitate to meet and exceed my expectations. From the history to the exciting adventure on offer and everything in between, Key West is a place that every traveler should visit at least once in their lives.

Miami to Key West Road Trip - Helicopter Tour - Lina Stock

Our adventures in Key West

Backcountry Helicopter Tour – hands down the most spectacular way to experience Key West is from above. The standard flight takes you over and around the entire island before landing you back at the airport.

However, we would highly recommend a splurge on the Ultimate Experience tour that includes the standard and eco backcountry tours in an amazing 30 minute flight.

Flying away from Key West, over the massive reef that surrounds the island and out over a vast expanse of uninhabited islands was the highlight of our trip. Not only is it absolutely gorgeous but the amount of marine life you can see from the air will have you second guessing a swim later. The day of our flight we saw several sharks including a massive Bull Shark that was easily 12 feet in length.

Helicopter tours with Air Adventures, the only helicopter tour operator on the island, leave from the Key West International Airport.

Key West Parasailing - Divergent Travelers

Parasailing – for as long as I can remember I’ve wanted to take a road trip from Miami to Key West and go parasailing. Call me crazy, but it was a fulfilling moment to be tethered from the back of a speed boat soaring 300 feet up in the air over the bright blue waters off the most southern tip of the USA.

We sailed high above the water with Fury Adventures and loved the fun staff and top notch equipment. Parasailing trips last 1 hour and depart on the hour from 9am to 6pm daily.

Things to do in Key West - Reed Snorkeling - Lina Stock

Reef Snorkeling trip – one of this things that makes Key West appealing is the close access to the only living coral reef in the United States and there is no shortage of available boat tours that will take you there. We booked a morning snorkel trip with Sebago Watersports and lucked out with perfect weather, meaning we were able to travel out to one of the most beautiful sections of the reef.

Not to mention, since Key West is a notorious party destination, the morning snorkel departure was only half full. This made for an amazing, uncrowded snorkeling trip. Our hot tip, skip the drinks the night before and book a morning tour to really have an intimate experience with the Florida Keys reef.

Miami to Key West - Shipwreck Museum - Lina Stock

Shipwreck Museum – not only is Key West a fantastic place to soak up the tropics but it is also an island that is rich in history. During the times of pirates and colonization many ships ran aground on the massive reefs off the shores of Key West. It became known as one of the richest places to plunder and salvage amongst ship crews.

As a result, many ships rest on its shores and the museum takes you through the history of the many shipwrecks fabled pasts. If you like pirate lore or are at all fascinated by the colonial days, this museum is worth a visit.

Miami to Key West Road Trip - Smathers Beach - Lina Stock

Smathers Beach – the best beach in Key West is an obligatory visit. As you can imagine, it features stunning stretches of white sand that ease gently into warm Caribbean waters. Beach chair and umbrella rentals are available on site, as well as free parking access in a lot across the road from the beach entrance.

The most enjoyable aspect is the boardwalk style access points that lead you through avenues of palm trees. Many food trucks also frequent the area so you could easily spend a full day here if you had the time.

Miami to Key West Road Trip - Southernmost Point - Lina Stock

Southernmost Point – when you stand at this monument you can look out and know that you are exactly 90 miles from Cuba. You’re also at the Southernmost point in the continental United States. It’s a fantastic spot for an obligatory travel photo but keep in mind it’s probably one of the most popular things to do in Key West.

It’s best to arrive either first thing in the morning or in the evening as the lines in the middle of the day can go on for blocks. I am talking hours of wait time to have your chance at the buoy.

Mallory Square Sunset Celebration - Key West - Lina Stock

Sunset at Mallory Square – watching the sunset in Key West is an obligatory activity and you haven’t done it right until you’ve attended the sunset celebration at Mallory Square. The iconic celebration takes place daily, starting two hours before sunset.

The square fills with people and vendors selling a variety of Key West nibbles like conch fritters, fresh made guacamole and coconut drinks. Not to mention the street performers. It is the perfect way to end the day.

Miami to Key West Road Trip - Night Kayaking Key West - Lina Stock

Night Kayaking on Ibis Bay – we’ve never gone for a paddle in illuminated kayaks before, so this was something very unique for us to try in Key West. The tour departs from the pier in front of the Stoned Crab restaurant next to the Ibis Bay Resort after sunset and spends the better part of 3 hours paddling around the Ibis Bay in search of marine life.

It is an eco conscious tour and we found the guide to be both funny and informative. He pointed out a wide variety of marine life and we learned a lot about the eco-system of the waters that surround Key West.

The glass bottom kayaks with light illumination provided an interesting element and allowed us to see everything on the ocean floor as we passed by. If you’re looking for something unique and different, definitely give the night kayaking tour a try.

Places to eat in Key West - David Stock

Places to eat in Key West

The Stoned Crab – simply put, this place is amazing and our favorite place to dine in Key West. Set on the pier at the Ibis Bay Resort, The Stoned Crab allows you to enjoy the atmosphere of Key West paired with the most amazing options of seafood one could wish for.

All of their seafood is locally sourced and at the end of each meal you are presented with the cards of the fisherman that made your catch. It’s a unique aspect and an all around enjoyable experience.

Places to eat in Key West - Kermits Key Lime - Lina Stock

Kermit’s Key Lime Shoppe – while you can certainly order a sandwich here, your primary reason to visit is their famous Key Lime Pie on a stick. No visit to Key West, or the Florida Keys for that matter, would be complete without a visit to Kermit’s Key Lime Shoppe. And it doesn’t stop at the pie, you’ll also find Key Lime salsa, chutney, taffy, jelly beans, tea, olive oil and well, you get the picture.

Lucy’s Retired Surfers Bar – what we loved about this restaurant was the location, away from the bars and busy piers on Key West. From the moment we were seated, we were able to relax and enjoy the quiet ambiance around us.

It’s a refreshing place to get away from the hustle of Duval Street and they serve a delicious variety of seafood, creative burgers and tropical island cocktails. Be sure to order a Shark Attack drink.

Miami to Key West Road Trip - The Marker Hotel - Lina Stock

Places to stay in Key West

The Marker – featuring 96 guest rooms with private balconies, swimming pool, dining options and onsite valet parking, The Marker blends the traditional architecture of the island with luxury. Notably, it is the only new hotel to be built in Key West in 20 years.

We loved our spacious room and found the location to be perfect for exploring more of the island on foot. The hotel is located roughly a 10 minute walk from Duval Street and it’s easy to hop right onto the boardwalk that follows the edge of the city.

One of America’s Best Road Trips

It’s undeniable that a road trip from Miami to Key West through the Florida Keys is a classic American road trip. From the moment we arrived in Key Largo until we drove all the way down and back, we found ourselves immersed in unique American culture, stunning scenery and a place like no other in the USA.

Someone once told me, ‘you haven’t lived until you’ve road tripped through the Florida Keys’ and I have to admit, they were right.

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This post was made possible in partnership with The Florida Keys & Key West. All opinions, recommendations, insane love for the Florida Keys and personal experiences are 100% mine, as always. 


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