How to Have an Epic Miami to Key West Road Trip: 5 Day Itinerary
March 16, 2022
The Florida Keys are a fun and exciting destination known for coral reefs, aquatic activities, key lime pie and more. The Keys actually encompass 800 islands, but only about 30 are inhabited.
The biggest of the islands are connected to land with the Florida Keys Highway, an engineering feat consisting of 42 bridges on US Route 1. The longest and most famous bridge is the Seven Mile Bridge, which connects Marathon and Big Pine Key.
Key West is the most famous of the Keys and marks the southernmost area of the United States. Key West is a great island to enjoy fun night life, epic sunsets, historic sights and more. However, the Florida Keys have more to offer beyond Key West, and I recommend taking the time to explore the other Keys as well.
Keep reading for all of the details on a 5 day Florida Keys road trip, as well as tips for visiting.
Full disclaimer – I received complimentary tours and activities during this trip to the Florida Keys. As always, my opinions are unbiased and my own. I want to thank all participating partners and the Florida Keys tourism board for their generosity.
You have the choice of flying (or taking a ferry) directly to Key West or driving there from mainland Florida. For this itinerary, I recommend flying into Miami or Fort Lauderdale and renting a car for the drive down into the keys, so that you can explore the Upper Keys in addition to Key West.
The most popular time of year to visit Key West is in the winter months from November to March. The weather is nice but you’ll likely experience big crowds.
During the summer months and into fall, the weather will be hot and humid. This is also hurricane season, with September and October being the most likely time for storms. Because of the unfavorable temperatures, these months are your best chance to get a good deal on lodging and experiences.
If you’re aiming for that sweet spot between ‘not too crowded’ and ‘not too hot,’ November or May is the best time to visit the Florida Keys.
Hotels in the Florida Keys tend to be expensive. If you are trying to visit the Florida Keys on a budget, I recommend choosing an Airbnb in a central location to spend your week. I stayed in an Airbnb on Cudjoe Key and was really impressed with the amenities. The downside is that the Florida Keys are so spread out, so you’ll be doing a ton of driving.
If you want to save on driving times and stay at different places throughout the week, I will recommend a couple of different hotels for each day of the trip!
- Download the Gypsy Guides app for an audio tour while you’re road tripping down the Keys. The app will suggest places to go and teach you about the history and geology of the islands.
- Don't expect beaches to be the main focus in the Florida Keys. There are certainly a few nice beaches, but if beaches are your priority, I suggest going to a different part of Florida.
- Be sure to obey the speed limits when driving on the Florida Overseas Highway. There are several empty police vehicles on the side of the road to trick people, but also a lot of real ones who will enforce the speed. You should pay extra attention to the speed limit on Big Pine Key to protect the key deer on the island.
- High winds are a common occurrence in the Keys. Be prepared for some water activities to be canceled due to wind and be flexible with your plans if possible.
- Be sure to bring bug spray, especially if you will be kayaking during your trip. I recommend Ranger Ready repellents because it doesn’t use DEET and smells much better than traditional bug spray. Use code LOSTWITHLYDIA10 for 10% off.
- Sunscreen is a must on a Keys road trip! I like Neutrogena Ultra Sheer Dry-Touch sunscreen or Super Goop Unseen sunscreen.
- A hat and sunglasses will be just as important as sunscreen to stay protected from the sun.
- Be sure to bring a bathing suit, towel and swimming supplies for all of the water activities. A quick dri towel is a plus.
- If you have one, it will be nice to bring your own snorkeling mask to use in place of rental equipment.
- This is a great trip to have an underwater camera! I have the GoPro Hero 10 and it takes great photos.
- Bring a dry bag to keep your things safe during water adventures.
- It is 140 miles from mainland Florida to Key West.
- Driving straight through without traffic, it would take 3.5 to 5 hours to reach Key West. However, I recommend taking your time and spending multiple days to experience the Upper Keys as well as Key West.
- This itinerary is for a 5 day action-packed trip. If you are able to get tickets to Dry Tortugas National Park, I recommend adding on another day to go there as well!
Start your road trip on the first and largest of the keys, Key Largo. Key Largo is 30 miles long and used to be full of key lime plantations. (Growing key limes in the keys is no longer profitable and today, the limes are mostly imported from Mexico).
The best thing to do in Key Largo is to visit John Pennekamp Coral Reef State Park. This was the first undersea park in the United States and protects some impressively beautiful coral formations.
To experience the reefs, you can take a snorkeling tour, a scuba diving tour or a glass bottom boat tour. Unfortunately, it was too windy on the day I visited to snorkel or visit the reef area.
Luckily, the park also has a couple miles of mangrove tunnels that you can explore by kayak or paddle board. I opted to kayak and most of the area was well shielded from the wind. Kayaking through the mangrove tunnels was beautiful and a lot of fun. I did not see much wildlife but enjoyed admiring the trees.
At the launch point, you will be provided a map to bring along your trip and I recommend keeping a close eye on it. I paddled through Turtlegrass Creek and Sandy Creek, but originally missed the turn into Sandy Creek and went too far.
After getting back on track, Sandy Creek was easily the best part of the trip. This is where you will navigate your way through a beautiful and narrow mangrove tunnel. I might have just been lucky, but I didn’t see another soul while on Sandy Creek, even though there were many people out paddling.
In addition to the paddling and coral reef, John Pennekamp also has a coral reef exhibit, complete with fish tanks, inside of the visitor center. They also have a beach area where you can lay out, swim and relax. The park is the perfect way to begin your Florida Keys road trip.
If you have enough time, consider stopping at the Laura Quinn Wild Bird Sanctuary on your way south. The sanctuary rescues and rehabilitates wild birds, and when you visit you will get to see all kinds of beautiful birds. The sanctuary is free but asks for a donation.
As you continue south, stop at Rain Barrel Village for souvenirs, a coffee or just to explore. As soon as you arrive, you’ll notice Betsey the Lobster, a giant sculpture that makes a popular photo destination in the Florida Keys. As you enter the village, you’ll find all sorts of locally made gifts.
Beyond the first shop, there is a village of art galleries, boutiques and a coffee stand that serves cuban coffee, cuban sandwiches and more. This is a great place to support local artists and you may even see a cat while exploring.
If you are interested in geology, it’s worth a quick stop at the Windley Key Fossil Reef Geological State Park. This park is the location of a former quarry that was used to produce decorative stone until the 1960s. You will be able to see fossil reefs, former quarry equipment and enjoy a peaceful escape from the crowds of the Keys.
If you are traveling with kids, Robbie’s is a fun restaurant where you can feed tarpons from the dock. While feeding the fish, be sure to watch out for pelicans and do not feed or touch any manatees (there was a manatee and nurse sharks in addition to the tarpons when I visited). I found the crowds to be a bit overwhelming during my visit, so try to visit during off hours or skip this spot if you want to avoid the crowds.
Robbie’s has a large food menu and you can also rent a boat or buy souvenirs here.
The Islamorada Brewery and Distillery is a colorful brewery with all kinds of beers and cocktail options. Start by ordering a flight to try a variety of what they have to offer. You can even add their house made cocktails to the flight!
I highly recommend the frozen key lime pie cocktails, where they add pie crumbles on the rim. It tastes like you’re drinking a delicious key lime pie and I even got their frozen to-go version to bring home.
The brewery has ample indoor and outdoor seating and there are yard games and a food truck in the back. There is also a distillery portion of the establishment, where you can do tastings of their rums, gins and vodkas. This is a wonderful place to visit if you enjoy drinking local drinks in a fun atmosphere.
For a more budget friendly option, the Rock Reef Resort is a great place to stay for families. The hotel is located a minute from the beach and is very close to John Pennekamp State Park. They have a pool, kayaks to borrow and other amenities.
For a higher end stay, the Amara Cay Resort has nice restaurants, a private beach and beautiful rooms. It is located on the southern end of Islamorada, making it a great place to begin your road trip south the next day.
Marathon Key is a 10-mile island that marks the center of the Florida Keys. 13 islands make up Marathon and some are known for white sandy beaches and for being nesting areas for sea turtles.
The Turtle Hospital is a must visit on Marathon Key. The hospital facility has the mission to rescue, rehabilitate and release sea turtles back into the wild. To go inside, they offer guided tours several times throughout the day. On the tour, you will learn about the common injuries the turtle face, the different types of sea turtles and so much more. You will also get to see several of their patients and residents and feed some of them at the end.
The tours cost $30/per adult and your money is going to a good cause. I highly recommend making a reservation to visit this special place during your Florida Keys trip.
If you have kids, Florida Keys Aquarium Encounters is an interesting place to learn about several different types of animals. Outside, you will find turtles, tarpons, stingrays, sharks, lobsters and more. Many of the animals you can touch or feed. The most fascinating animal was a gigantic alligator snapping turtle.
There are also two giant attached tanks, one with coral reef fish and another with predator fish. You can actually snorkel inside the tanks to feed the fish, a stingray, and a shark through a hole in the glass. It’s a unique experience if you’re interested in animal encounters and great for families.
Key Fisheries is a restaurant on Marathon known for seafood served “fresh off the boat.” One of their most popular dishes is the grouper reuben, but they also serve lobster, crab and several other seafood varieties. You stand in line at a window to order and then can enjoy waterfront views.
I am a vegetarian so I didn’t try the seafood - but they serve the best key lime pie in the Florida Keys (in my opinion, at least!). The pie had a wonderful tartness to it and a perfect crust. If you are just interested in a drink and pie, you can skip the food line and go to the bar to order.
Sombrero Beach is a beautiful and peaceful beach on the Atlantic Ocean. The park is free to visit and includes picnic areas, volleyball courts and restrooms with showers. It is also a turtle nesting beach, meaning that Loggerhead Turtles commonly lay eggs here from April to October. This beach is one of the nicest beaches in the Keys and a beautiful place to hang out, swim or watch the sunset.
If you have time, another great stop on Marathon Key is Porky’s Bayside for fried key lime pie!
When you hear about the Seven Mile Bridge, you may not realize there are actually two bridges right next to each other - the new one and the old one. The original seven mile bridge was built in the early 1900s for the Florida East Coast Railway. In the late 1970’s, a new bridge was built for vehicular traffic.
In the years following the construction of the new bridge, the old bridge was no longer used for cars, but was a popular place for pedestrians and cyclists. After years of hurricane damage and general decay, a new renovation project has taken place over the past few years to make a portion of the bridge safe for use by cyclists and pedestrians.
The bridge reopened after renovations in early 2022 and I visited in March 2022. The bridge is wide and extends two miles. Visitors can walk the entire two miles to Pigeon Key, an island that was used as a work-camp for the workers who built the original bridge. Pigeon Key is also on the National Register of Historic Places. If you don’t go all the way to Pigeon Key, you can still enjoy the views of the surrounding water and the vehicle bridge. It’s a beautiful place to watch the sunset.
Note that parking is limited and there are only about 35 spots. If you don’t get a spot, you can go across the street and park on the street in front of the Sunset Grill. There is a walkway underneath the bridge, so you won’t have to cross the Overseas Highway.
While driving the Seven Mile Bridge, look for a tree growing out of the area where pedestrians can’t go. It’s name is Fred the Tree and it has thrived without soil and in harsh sun and winds. Your Gypsy Guide app will point it out!
Bahia Honda State Park is a gorgeous place to swim, watch the sunset or get out onto the water. If you are short on time, it’s still worth going to walk around the beaches and the bridge and admire the views. To enter the park, it costs $8 per vehicle.
The park is made up of beaches, a former train bridge, campsites and more. There is a very short portion of the bridge that you can walk up on and get a bit of an aerial view of your surroundings. If you walk on the bridge, you’ll be walking on what used to be the main road for both vehicles and trains to travel down the Keys.
When I visited, there was a warning for dangerous marine life in the water and we saw many jellyfish washed up onto the beach. Check conditions before you go, but if the water is safe, it’s a great place to bring your snorkeling gear.
There are beaches on either side of the bridge. Loggerhead Beach is on the western edge of the island and faces the Atlantic. The beach is pretty rocky and the water is shallow. There weren’t many people on this side when I visited.
Calusa Beach is on the side of the bridge that faces the Overseas Highway. This beach has less rocks and seagrass, so it’s popular for swimming and relaxing on the sand. It’s a great place to watch the sunset with the backdrop of the old Bahia Honda bridge.
Overall, Bahia Honda is one of the best beaches to visit on a Florida Keys road trip.
For a fun dinner spot not too far from Bahia Honda (a 20 minute drive), visit the eclectic No Name Pub on Big Pine Key. This restaurant is known for having walls covered in dollar bills, great food and a down to earth yet lively atmosphere. The menu includes pizza, burgers, fish sandwiches and more.
As a vegetarian, I really enjoyed the black bean burger but was eyeing the pizza for next time. If you’re a beer drinker, be sure to try the refreshing No Name Amber. At some point in your meal, borrow a marker and staple gun and leave your dollar bill among the 1000’s around the restaurant. Try to make it hard to reach if you don’t want it to be covered up quickly!
On your way to No Name Pub, you have a great opportunity to see key deer! Be sure to drive slowly and keep an eye out for them.
For an affordable stay with a great view of the Seven Mile Bridge, check out the condo Captain Pip’s at Knight’s Key Inn. There is a pool, free bicycles to borrow and you’ll be in close proximity to the Sunset Grill.
If you enjoy Marriott stays, the Courtyard by Marriott Marathon Florida Keys is a centrally located hotel on Marathon with clean rooms and the amenities you would expect from a nice hotel.
The Lower Keys are made up of Cudjoe Key, Sugarloaf Key, the Big Torch and Little Torch Keys and a few others. It’s a great area to snorkel, kayak and escape the crowds.
As you make your way to the Lower Keys, stop at Baby’s Coffee for delicious coffee and snacks. They are the southernmost coffee roaster in the United States and have been roasting coffee for over 20 years. Baby’s has an extensive coffee menu and even has smoothies. I enjoyed a frozen latte, it was the perfect pick me up on a hot day!
In addition to coffee, Baby’s has a variety of snacks, beer and wine for sale. They also have some outdoor seating where you may see a friendly chicken walk by.
After you’re caffeinated, enjoy a kayaking adventure in the Lower Keys with Get Up and Go. Their kayaks are clear so you can enjoy the sea life and plant life underneath you without getting wet.
The adventure leaves from Sugarloaf Key and you’ll get to see the mangrove trees that line the shoreline. Along the way, you may see manatees, pelicans, nurse sharks, sea turtles and all sorts of other marine life creatures. Unfortunately my tour was canceled due to high winds, but it looks like a fantastic way to explore this area.
Get Up and Go was the first clear kayaking company in the US and now does clear kayaking tours all over Florida!
South of the Seven is a wonderful local spot to enjoy a nice dinner. Chef Paul Kapsalis draws on his Mediterranean roots to create dishes using the freshest ingredients from both land and sea. The restaurant has a perfect balance of feeling high end but still laid back. As a vegetarian, there weren’t any entrees available but I enjoyed the beneli (a flat bread with cheese, onions and mushrooms) and the feta and tomato spread. I also sipped on a delicious chocolate espresso martini.
There aren’t as many accommodation options in the Lower Keys, but there are still some good options! For a budget resort on the water, Parmer’s Resort on Little Torch Key has a pool, games like cornhole and water views.
Also check Airbnb for options in the Venture Out Resort on Cudjoe Key. There are several home options here and the community has tennis, a nice pool and pet friendly options. I stayed in this cute home and had a good experience.
Spend day four and five of your trip exploring Key West! You will likely find Key West to be much more crowded and lively than the other keys.
Start your morning with an adrenaline rush on a jet ski tour around Key West. Barefoot Billy’s offers tours from 3 locations around the island. If you’re driving into Key West from the upper keys, take the tour from Marriott Beachside and enjoy free parking.
The tour begins with a nice amount of free time to get used to the jet ski and practice in a wide open area. This was a really fun way to go as fast as you wanted. From there, you travel in a single file line with several stops along the way. At the stops, the guide talked about different areas of Key West, including Sunset Key and the military bases nearby.
While the water was choppy at times, it was a really fun adventure to explore the water on a jet ski!
Cuban Coffee Queen is a wonderful spot to grab breakfast or lunch in between activities. Not only do they have a variety of coffee options, but they also serve breakfast sandwiches, cuban sandwiches and other items. I really enjoyed an egg and cheese sandwich from their original location near the waterfront on Margaret Street. This location also has a beautiful ‘Greetings from Key West’ mural on the side, making it perfect for a photo op.
For your afternoon water adventure, join a dolphin watch and snorkeling tour with Fury Adventures. You can also pick a tour that allows you to snorkel twice if you’d like. On my dolphin watch and snorkel adventure, we were able to see a large number of dolphins. There were groups of them jumping out of the water and swimming all around our boat.
During the snorkeling portion of our tour, we went to a reef area and saw a great number of fish and different types of coral. The best part was seeing several stingrays swim right below us. On the way back to Key West, we saw more dolphins and the boat crew provided drinks (including mimosas, beer and wine) for whoever wanted them. It was a really fun adventure and a great way to see wildlife around Key West.
Kermit’s Key West Key Lime Shoppe is the perfect place for an afternoon treat. Not only do they serve great pie on its own, but they have the unique treat of chocolate-covered key lime pie on a stick. Combinations include strawberry key lime pie covered in dark chocolate and regular key lime pie covered in white chocolate. It is absolutely delicious to enjoy the frozen treat on a hot day.
Kermit’s also has a beautiful patio area where you can enjoy your pie next to a koi pond. In addition, their gift shop has some unique Key West souvenirs, like Key West monopoly. Kermit’s a must do in Key West and one of the best places in Key West for key lime pie!
Parasailing in the water next to Key West is an amazing way to see the island from above. If you’ve never been parasailing, it’s a peaceful experience where you get to feel as if you are flying. I enjoyed parasailing with Sebago Watersports, who offers a variety of water experiences in the area.
The Waterfront Brewery is a great spot to enjoy a drink with waterfront views. The brewery is huge with two levels and even has some arcade games in the back. They also have an extensive beer and food menu. I enjoyed the passionfruit shandy, which was light and refreshing.
Hidden behind Hanks’ Bar, you’ll find an airstream serving a unique combination of hot dogs, burgers and poke bowls. Garbo’s was featured on Diners, Drive-ins and Dives and the food is full of flavor. I enjoyed the vegetarian poke bowl packed with veggies and rice, while my partner enjoyed the kogi dog. Inside of Hank’s, you’ll see a photo wall of all the dogs who have visited. There is also often live music at Hank’s and it's a fun place to hang out.
Be sure to make time to watch the sunset in Key West, they have some of the best sunsets around! A sunset celebration occurs every night in Mallory Square. At the celebration, you’ll see a variety of street performers, food vendors and many people who have come to watch the sunset over the water. Bring cash to tip the performers and enjoy magic, fire tricks and all sorts of things as you wait for the sun to go down.
If you want a seat on the wall for an unobstructed sunset view, go early to grab a spot. The celebrations tend to be crowded but a lot of fun if you enjoy a festival atmosphere.
Key West has many hotel and bed and breakfast options, but it’s hard to find much on a budget. One unique place to look at is the Mermaid & The Alligator. This B&B is for adults only and has a lounge, hot tub and gardens to enjoy. It is centrally located on the island and not far from popular attractions like the Hemingway House.
Another hotel to consider is the Key West Marriott Beachside Hotel. It is outside of the main downtown area but provides a shuttle for guests. It also has a beach and a pool, and jet ski tours leave from their beach.
For your second day in Key West, explore on land and end your trip with a sunset cruise!
Ernest Hemingway is a popular figure when it comes to the history of Key West and the Keys in general, and the Hemingway House is a must-visit in Key West! He spent a lot of time in a French Colonial style home on Key West and today visitors can take a guided or self guided tour of the home.
Perhaps the most famous aspect of the house is that a large population of polydactyl cats live on the property. According to legend, the cats descend from a cat that was given to Hemingway as a gift.
Today, there are 58 cats living on the property and about half of them are polydactyl (meaning they have extra toes on their paws). They allow new cats to be born every few years to carry on the population without allowing it to grow out of control. It’s a fascinating place to visit to learn about Hemingway history and also see the cats.
The adult admission is $17 and the house is open year round.
Right across from the Hemingway House, you can visit the Key West Lighthouse and learn some Key West history while enjoying views of the island. It’s a bit confusing to see a lighthouse that isn’t right on the water.
Originally, a different lighthouse was right on the water but it was destroyed in a hurricane in 1846. They decided to rebuild the second lighthouse further inland on a high point in Key West so that it would be better shielded from damage.
When visiting, you can climb the 88 stairs to the top of the lighthouse and get an incredible 360 view of the island. There is also a museum where you can learn about how the keepers of the lighthouse lived and worked. One interesting aspect they cover is the amount of women who were lighthouse keepers, which was rare at the time. Admission is $17 per adult but you can purchase a cheaper ticket if you buy online.
Moondog is a cafe and bakery right down the street from the Hemingway House and the lighthouse. They serve a variety of brunch and lunch options, from pizza to eggs benedict to omelets. They also have a great amount of vegetarian options. The restaurant has both indoor and outdoor seating and a giant, colorful mural inside. I really enjoyed the caprese croissant benedict and a mimosa.
The Butterfly House and Conservatory is a tropical greenhouse with 100’s of butterflies and colorful birds. You can walk through the space and enjoy the flowering plants, the large number of butterflies and the beautiful flamingos. Take your time and a butterfly may land on you.
Note that this spot can get very crowded and it’s very humid inside. If possible, visit on a weekday or during a less popular time to avoid the crowds. General admission is $15 per adult.
While you’re walking around Key West, be sure to stop at the US Highway One sign for mile marker 0. It is a fun quick photo op! Right next to it, also check out the impressive Kapok Tree.
The Conch Tour Train is the most popular sightseeing adventure in Key West and has been in operation since 1958. The train route takes 75 minutes and makes 4 stops around the island. You can use it as transportation and hop on/hop off, or stay on the entire route. The entire time (except for two short residential areas), the guide talks all about the history of Key West with sound effects mixed in along the way.
One thing I loved about the Conch Train was that our guide was born and raised in Key West! The train costs $35 if you pay for it online but can also be used for transportation for a whole day. You can also get a discount if you buy a two day ticket.
The Conch Train will drive right past the most famous Key West landmark: the southernmost Point Buoy. If you want to take a photo with the buoy, be prepared for a very long line.
If you have enough time, Blue Heaven is a popular restaurant with eclectic decor, outdoor seating and live music. The restaurant serves breakfast, lunch and dinner, but expect a wait because it’s very popular.
If you don’t need to eat, you can enjoy drinks and pie at their bar area across the street. Their key lime pie towers high up into the sky with marshmallow fluff and is great to enjoy for a snack or dessert.
An alternative option to dinner at Blue Heaven is the Old Town Tavern & Beer Garden. This casual space has an extensive beer menu and some great menu options for vegetarians. They also have a beautiful outdoor patio space. I enjoyed the corn and zucchini fritters and the blackened cauliflower wrap.
The Key West First Legal Rum Distillery is a fun place to visit if you enjoy rum! The distillery offers free tours and a variety of cocktail options that you can take to go or enjoy there. I had a mojito with their house coconut rum, and it was a refreshing drink to walk around with.
End your time in Key West with a sunset sail! Danger Charters offers intimate sunset sailing experiences that include a wine tasting and light bites. Their tours are smaller than other companies and take place on an actual sailboat. There are 8 different types of wine and snacks include cheese and chocolate. It was wonderful to watch the sunset in a small group with an all-female crew.
The Danger Charters Wind and Wine Sunset sails typically cost $110 per person. I highly recommend them, but there are plenty of other companies who also have sunset sails. Choose one that meets your needs and enjoy getting up close to the sunset on the water.
Watching the sunset from the water is an incredible experience in Key West and a great way to escape the crowds from watching the sunset on land.
These are a couple things that I didn’t have time for, but would love to do next time.
- Fort Zachary Taylor is a state park on the southern tip of Key West. At the park, you can explore a former military fort or relax at the beach. It’s a great place to watch the sunset without the crowds. Admission to the park is $6 per vehicle.
- The Key West Tropical Forest & Botanical Garden is a garden and forest area that encompasses 15 acres in the northern area of Key West. It’s a beautiful and peaceful place to walk around and enjoy the outdoors. Admission costs $10 per adult.
If you have another day and are able to plan ahead, add a day trip to Dry Tortugas National Park to your Florida Keys itinerary. Dry Tortugas is a remote island that is home to a former United States military fort. Today, it is home to rare birds and is an incredible escape for those looking for solitude. You can visit by ferry or seaplane but reservations fill up months in advance, so plan accordingly!
Thanks for Reading!
Let's stay in touch!
Join the Lost with Lydia email list to get monthly travel guides and tips!