Quick 5 Days Road Trip Itinerary from the Keys to Miami

Barnacle Barneys

South Florida is a slice of paradise on Earth! To me, South Florida is as close to the island life that you can get without having to fly to some far away and remote place! From the laid-back tranquility that you can find in the Keys, to the unique landscapes of the Everglades and the bustling city life in Miami – this road trip has something for everyone! This quick 5 days road trip itinerary from the Keys to Miami combines the best of all worlds and provides you with a diverse itinerary that makes everyone in the family happy!

Best time to visit

South Florida has a mild to hot climate all year round! The summer months (June-August) tend to be very humid, and summer storms are quite common. This is also prime hurricane season (especially mid-August to mid-October), which is something to keep in mind. Therefore, the best time to visit Florida would be late fall to early summer! The good news is that for the places mentioned in this itinerary, swimming is possible year-round! 🙂

How to get there

If you’re coming from far away, the easiest and probably cheapest way to reach South Florida is to fly into Miami through the Miami International Airport (MIA). Alternatively, you can also check whether there are some decent connections that will take you directly to Key West, since there is also a smaller airport directly in the city (EYW).

Personally, I like to use Google Flights to check for the best connections.

How to get around

By Car

Since this is a road trip itinerary, renting a car is kind of a prerequisite! However, as you will see, we have tried to keep the number of days where you really need a car to a minimum. In other words, the days at the beginning and end of your road trip are in walkable or uber-able cities, where you don’t need a car.

By Uber

As mentioned in the section above, in Key West or Miami you really don’t need a car since Ubers are readily available. Especially in Miami, I would even highly encourage you to use Uber instead of battling Miami traffic and worrying about parking


By Greyhound

Instead of driving down to Key West ourselves, we decided to take the early morning Greyhound bus from Miami Airport to Key West. This allowed us to “save” two days of rental car costs, since we didn’t need the car in Key West anyway
 We had an amazing experience with Greyhound. The check in was very smooth, the drive was pleasant and we even arrived ahead of time. You can check out the ticket prices on their website.

How much time do you need in Florida?

Quite honestly, you could probably stay there forever! Florida has so much to offer, and there are of course a lot more places worth visiting besides South Florida! However, for South Florida, I would say 1 week is the absolute minimum, especially if you’re flying in from far away. 1 week will give you enough time to see the main sights at all stops, and to get a first taste of the laid-back lifestyle. However, you could easily spend an extra week exploring more of the area. At the end of the itinerary, I have added some suggestions for possible trip extensions 🙂

Quick 5 days Road Trip Itinerary from the Keys to Miami

Day 0 – Welcome to Florida!

If you’re flight gets in late in the afternoon (like ours), I will count this as day 0. You are technically already in Florida, but the action won’t start until tomorrow.

If you’re flying into Miami, you can directly get a rental car and start your drive down to Key West.

Or, you can check in to an airport hotel like us and get your rental car or Greyhound bus early on the next morning (this is what we did!). We liked this option because it allowed us to rest early on our first night, and waking up early is easy anyway because of jetlag 🙂

Where to stay

For simplicity reasons, we decided to stay close to the Greyhound bus station upon arrival at the Sheraton Miami Airport Hotel and Executive Meeting Center. It’s quite a basic hotel but will get the job done for one night. The price for one night was 150 CHF.

Days 1 & 2 – Key West

Welcome to Key West! Whatever transport option you decide on, make sure you are in Key West early in the morning, so that you basically have 2 full days in Key West!

Key West is such a fun and laid back town. In no particular order, here are some suggestions on what to see and do during your 2 days in Key West:

  • Key West Historic Sea Port
  • Southernmost Point of Continental USA (warning: there might be a line in front of the sign for taking pictures haha!)
  • Walk along Duval Street
  • Harry S. Truman Little White House
  • Drinks at Sunset Pier and/or Mallory Square
  • Try a key lime pie
  • The Hemingway Home And Museum
  • Dry Tortugas National Park And Fort Jefferson
  • Audubon House and Tropical Gardens
  • Fort Zachary Taylor Historic State Park & Beach
Duval Street in Key West
Duval Street
Sunset Pier off Mallory Square
Sunset Pier

At the end of your second day (around 5 pm), it’s time to head to the airport and pick up your rental car. We booked our car with Alamo and had a good experience.

From there your final stop for the day is going to be in Marathon. During your drive to Marathon, there are 2 spots I recommend for you to check out:

  • No Name Pub: The fun things about the Keys is that there are so many random, fun things to explore! The No Name Pub is a pub in the middle of nowhere. It’s become well known because its walls are plastered with dollar bills from people that pinned them there  It’s a fun pitstop to add to your road trip!
  • Barnacle Barney’s restaurant: If you can, make sure to time your drive JUST IN TIME to watch the sunset at Barnacle Barney’s restaurant! This was by far our favorite restaurant on this trip. It’s so laid back, has fantastic views and the food was also good 🙂 I highly recommend checking it out!
No Name Pub
No Name Pub
Sunset views from Barnacle Barney's
Sunset views from Barnacle Barney’s

Where to stay in Key West

Key West is not a cheap destination. If you are somewhat on a budget, you might need to opt for an accommodation that is not perfectly central. With that being said, we stayed at The Palms Hotel. It’s a super cute hotel that’s still within walking distance (20-30mins) of most things, so I would definitely recommend it! We paid 160 CHF per night.

The very cute The Palms Hotel
The very cute The Palms Hotel

Where to stay in Marathon

As Europeans, the Sea Dell Motel was our first ever real “motel” experience! As you might expect, it has all the basic facilities that you might need, a small pool and a parking right in front of your room! It’s perfectly located right on the main road, and in close vicinity to some nice restaurants and Sombrero Beach! For 130 CHF per night it’s great!

Day 3 – Marathon to the Everglades

Start your day with a visit to Sombrero Beach! We decided to get takeaway breakfast (from McDonald’s, not very creative lol) and have a breakfast picnic at the beach. It was very nice to get there so early since we had the beach practically to ourselves!!

After a relaxed morning, it’s time for some action at Robbie’s in Islamorada! Feeding the tarpons was definitely another trip highlight! It’s a really fun activity and you will definitely have some laughs – this is a must do on a Florida Keys road trip!

Tarpon feeding at Robbie's
Tarpon feeding at Robbie’s

Next up, beer tasting at the Florida Keys Brewing Company! At the Florida Keys Brewing Co you can get a beer tasting board with 5 different beers / ciders of your choice. They have a very cozy backyard where you can enjoy your taster-beers. Since this is a road trip, make sure that the designated driver is focusing on the “tasting” part and not the “drinking” part 😀

Florida Keys Brewing Company
Florida Keys Brewing Company

Finally, the John Pennekamp Coral Reef State Park. This is your last stop on the Keys! The State Park is famous for its snorkeling and diving. If you have time, make sure to get on one of their glass bottom boat tours, which allows everyone (in and out of the water) to experience the marine life! We were unfortunately too late for all the tours, since they were already booked out!

If you’re just looking for a nice beach to relax at, then maybe skip this place – there are nicer beaches out there 🙂

At the end of the day, slowly make your way towards the Shark Valley or Homestead Everglades entrance!

Where to stay near the Everglades

Depending on which entrance you want to enter from, you should either base yourself in Florida City or around Miami Doral.

Since we loooove The Cheesecake Factory, we decided to stay near the Miami Dolphin Mall in Miami Doral (Shark Valley entrance). We stayed at the Best Western Plus Miami-Doral/Dolphin Mall, which was only a 10 min drive from the next Cheesecake Factory – our dream :)))))) We paid approx. 110 CHF per night.

Day 4 – Airboat ride at the Everglades

We were so excited for this experience! An airboat tour is definitely the best way to see the Everglades. Since it does get quite hot and humid in Florida, I’d recommend to do this tour either early in the morning or in the late afternoon. Personally, we decided to do it first thing in the morning.

We booked our tour with Everglades Safari Park. The tours include an airboat ride that usually lasts about an hour. Our guide was very knowledgeable and funny, and we saw several alligators on the tour 🙂

Example of an air boat
Example of an air boat

After the boat ride, there is another short info session about alligators on land, and if you’re feeling adventurous you will even get an opportunity to hold a baby alligator and get some photos with them.

Baby gator!
Baby gator!

Lastly, at Everglades Safari Park you will also be given access and free time in the end to explore some of the walking trails in the area. If you’re lucky, you might spot some more gators along the way here on your own…

Hidden alligator
Hidden alligator


finally, and perhaps a little controversial, you might also stop for a quick snack at the restaurant. Can you guess what’s on the menu? If you guessed gators
 that’s correct!

Overall, a very fun, diverse and educational experience that I would highly recommend it!

Once you’re done at the Everglades, it’s time to head into Miami to return your rental car. I hope you are comfortable driving, since the 6 lane highways around Miami are nothing like the empty roads on the Keys!

Once in Miami and settled into your accommodation, it’s time to head to Miami Beach and explore the South Beach area!

Art Deco buildings in South Beach
Art Deco buildings in South Beach

Where to stay in Miami

I’d highly recommend to stay in the South Beach area! We got a very good last minute deal on the Ithaca South Beach hotel. We scored a studio apartment for only 90 CHF per night, a steal for this area! Even if you pay regular price, we really enjoyed this accommodation and I would definitely recommend it! The hotel is located on the street right behind Ocean drive , which is still a perfect location! We also loved that the door lock was numeric (you type in a pin to enter the room), so we could easily leave the room with nothing but our swim suits and some towels and head to the beach, without worrying about any of our belongings! Not even a key to carry around 🙂

Day 5  – Miami!

Miami is such a vibrant city and has so much to offer. Here’s just a couple of things you could do during your short time in Miami. I have to remark though, you won’t be able to do all of these things in just one day!

What to do in Miami:

  • South Beach / Ocean Drive / Art Deco tour
  • Española Way
  • Lincoln Rd Shopping
  • Wynward Walls
  • Miami Design District
  • Cape Florida Lighthouse / Key Biscayne
  • Little Havanna
  • Vizcaya Museum & Gardens
  • Frost Museum of Science
  • Institute of Contemporary Art
  • Upper Buena Vista Shopping

Personally, we checked out the Art Deco buildings on Ocean Drive, strolled a little along Lincoln Rd, then went to the Wynward Walls and then spent the evening at Española Way 🙂

Wynward Walls Graffiti Art
Wynward Walls Graffiti Art

Day 6 – Time to head home 🙁

Ideally, you’ll have a flight out of Miami. Depending on the time of day, you could spend another day exploring some of the things mentioned above in Miami or have another beach day. If you’re silly like us tough, you might also have a flight out of Tampa – yep, Tampa. This was not entirely voluntary in our case, but it turned into a nice addition to our road trip!

Since we somehow needed to get to Tampa, we ended up renting another rent a car for the day. We crossed over to the Gulf Coast on the I-75 highway. On the Gulf Coast, there are several smaller towns and stunning beaches you can stop along the way! Since we have some family connections to the area, it was super fun for us to see some of these more residential “Florida for retirees” gated communities.

We also stopped at Siesta Beach in Sarasota, rated as the 2nd best beach in the US in 2024!! I’ve been lucky enough to see some amazing beaches, from the Maldives, to Costa Rica, to Australia, Spain, Thailand, etc
 and I can truly say that Sarasota beach is definitely up there with the nicest beaches I’ve ever been to! The beach is made of silica sand, and it is truly probably the finest and whitest sand that I have ever seen and felt. We were definitely not mad that we got to experience this on our little flight-home-detour 🙂

How to extend your trip

Option 1: More time in the keys

In this itinerary you spend a total of 3 full days in the Keys. If you want to extend your time in the Keys, here are some more things you might want to add to your itinerary:

  • Bahia Honda State Park (diving?)
  • Turtle hospital
  • Kayak in mangroves
  • Swim with dolphins
  • Sunset cruise

Option 2: Check out other parts of Florida

  • North Florida: Orlando, Disneyland, NASA, 

  • More Gulf Coast: Naples, Marco Island, Clearwater Beach, 

  • Florida Panhandle: 30a Beaches & Towns (this is my next dream Florida destination!)

That’s all, with this quick 5 days Road Trip Itinerary from the Keys to Miami you’re all set for your sunshine state adventure! 🙂

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