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The Ultimate Guide To A 5 Day Florida Keys Road Trip

The Florida Keys is one of the most underrated destinations in the United States, if not the world. My family visited the Keys on vacation and road tripped the 160 miles from Miami to Key West throughout a 5 day trip. I could not recommend a visit to the Keys more and am so excited to share the details of my Florida Keys road trip with you all today!

Disclaimer: This blog post is sponsored by Jungle Culture. Jungle Culture gifted me some of their customized, eco-friendly Jungle Straws, along with bamboo coconut bowls and utensils. I’ll be discussing Jungle Culture more toward the end of this post. All opinions here are my own!

This post contains affiliate links. If you click and book through any of these links, I will earn a small commission at no additional cost to you. Thank you so much for reading and supporting my little corner of the internet!

About The Florida Keys

For those of you who’ve never heard of the Florida Keys, they’re a string of tropical islands located 120 miles off the coast of southern Florida. The islands separate the Atlantic Ocean from the Gulf of Mexico, giving them a Caribbean-US vibe. The Florida Keys are probably most well-known for diving, fishing, and snorkeling. There are countless islands, or keys, in this region, but the most popular are Key Largo and Key West. Key Largo has some of the best diving in the world and Key West is famous for its nightlife on Duval Street, sunsets, Ernest Hemingway’s home, and of course, key lime pie.

Getting To The Florida Keys

Getting to the Florida Keys isn’t the easiest or cheapest feat, but it’s worth it. You have two options. You can either fly into south Florida — I recommend Miami, or you can fly directly into Key West. Flights into Key West aren’t always direct and if they are, they’re probably super pricey. Like $800 roundtrip Boston to Key West on JetBlue pricey. If you’re staying in Key Largo, Islamorada, Marathon, or any of the “Upper Keys”, flying into Miami is a no brainer. If you’re visiting any of the “Lower Keys” aka Key West, the drive will be a little long but I think it’s worth it!

To be exact, the drive from Miami to Key West is about 3 hours long. I do think it’s worth it, however, because it’s a great opportunity to explore the Florida Keys!

My family and I rented a car right at the Miami airport and drove to and from Key West. We spent one full day road tripping down and then did the drive straight back on our last day. We stayed in Key West for the entire duration of our trip, which is something I recommend doing since it has the most to do. Let’s get into the itinerary for a Florida Keys road trip!

Where To Stay In Key West

Budget: South Winds Motel

This Old Town Key West motel offers two outdoor pools, high-speed WiFi, and a microwave / fridge in every room. Extras include daily continental breakfast, bike and scooter rentals, beach access, and a concierge desk. There are also two outdoor pools located here and Duval Street is just a 2 minute walk away!

Mid-range: Winslow’s Bungalows — Key West Historic Inns

Located in Key West, just an 8 minute drive from Smathers Beach and a 8 minute walk from the Ernest Hemingway Home, Winslow’s Bungalows features 3 swimming pools, hammocks, free WiFi, and a complimentary continental breakfast. All rooms feature a small refrigerator, private bathroom with free toiletries, and on-site parking.

The Southernmost Point is just 0.6 mu away and Duval Street is just 2,460 feet from the inn.

Luxury: Santa Maria Suites Resort

This Key West resort is located just one block from the Atlantic Ocean and Duval Street, and just a mile from both the Ernest Hemingway House and Fort Zachery Taylor Historic State Park. Each suite is equipped with a full kitchen, free WiFi, washers and dryers, and includes nightly turndown service. 

Two outdoor heated pools are surrounded by gardens at the Santa Maria Suites. On-site dining is available at Ambrosia, which serves Japanese cuisine. Additionally, smoothies and fresh fruit are served pool side. Guests can also enjoy a complimentary daily happy hour featuring wine and hummus. 

Florida Keys Road Trip Itinerary

Florida Keys Road Trip Day 1

Day one consisted of my family and I flying from Boston to Miami, renting a car, and driving to Key West. After leaving the greater Miami area, vacation began!

Morada Bay

Our first stop was to Morada Bay for lunch! If you’ve never heard of this place… maybe you’ll recognize it from a photo?

The colorful outdoor cafe at Morada Bay in the Florida Keys

Morada Bay was used for filming Netflix’s Bloodlines! There’s no hotel here, but you can dine on the beach and take in the waterfront views. I recommend trying the fish tacos!

Robbie’s Marina

From here, we drove another 10-15 minutes west through Islamorada towards Key West to Robbie’s! Robbie’s Marina of Islamorada has been voted the #1 tourist attraction in the Keys. It’s home to the world-famous tarpon feeding, a must when visiting the Florida Keys.

A tarpon is a GIANT Atlantic fish found in the Keys, and you can feed them at several locations throughout. I recommend doing it at Robbie’s so you can also experience the pelicans and manatees! My mom was lying down on the deck to feed the fish when a giant manatee came out of nowhere and swam under us! It was super cool to see one in the wild. Robbie’s also has an outdoor bar, restaurant, and shops.

Feeding the tarpons, pelicans, and manatees at Robbie's!

After Robbie’s we drove the remaining 1.5 hours through the Florida Keys to Key West, catching the sunset as we drove over the 7 mile bridge. We ate dinner nearby after checking in.

Sunset over the famous seven mile bridge in Key West

Florida Keys Road Trip Day 2

Hemingway Home

This morning we had a tour booked of the Hemingway Home! Ernest Hemingway is a well-known, 20th century, American novelist who’s most famous for his adventurist lifestyle and award-winning literature. Hemingway traveled a lot for his time, writing in Europe during WW2, traversing the continent of Africa, living in Cuba, etc. His main residence for a decade was in historic Key West, and you can tour his home today. His house is beautiful and filled with history (and cats), so I definitely recommend doing this.

Ernest Hemingway house in Key West, Florida
Ernest Hemingway house in Key West, Florida

Pro-tip: The 30 minute guided tour was $16 a person and is the best way to learn about Hemingway and the history of his home. You can book it here.

Did you know? The Hemingway home is filled with 40+ 6-toed cats who all came from one cat that was used to catch mice on the property during Hemingway’s time.

Across the street from the Hemingway home is the Lighthouse & Keeper’s Quarters. This lighthouse is super unique because it’s located right downtown, away from the coast. This was done on purpose to prevent damage from hurricanes. It was built in 1848 and was occupied by a keeper until 1969. Today, visitors can walk up the 88 steps to the top of the lighthouse, as well as explore belongings and photographs from the Keepers in the museum.

Nearby is the mile marker 0, which marks the end of route 1 in the USA.

Florida Keys road trip

Golf Cart Rental & Southernmost Point

We spent the rest of the afternoon walking down Duval Street and shopping in the historic district. For lunch, we ate at the rooftop of Schooner’s Wharf Bar right in the historic seaport. After lunch we did something that you HAVE to do if you visit — we rented a golf cart!

If you’ve ever been to Key West, you know that driving around in a golf cart is one of the best ways to explore the island. We rented one for 5 hours and did just this! They cost about $100, but was a super efficient way to bang out a bulk of our sightseeing, so I think it was worth it. There’s a golf cart rental shop located on most streets in Key West.

Our first stop in the golf cart was the Southernmost Point of Continental USA! This is one of Key West’s most popular tourist attractions, so there was a long line of people here waiting to get photos. Definitely check it out though! We browsed Duval Street a bit more before driving to the Edward B. Knight Pier near Higgs Beach. This pier is HUGE!

The southernmost point in Continental USA

Our last stop before returning the cart was to Kermit’s Key Lime Pie shop for a famous slice of key lime pie! We enjoyed these as we drove down Fleming and Southard Streets, admiring the unique architecture.

If you’re looking for more must-try food spots in Key West, check out this post!

Kermit's award-winning key lime pie in Key West, Florida
Exploring Key West on a Florida Keys road trip

Mallory Square

After we returned the cart, we walked to Mallory Square to catch one of Key West’s iconic sunsets. It’s one of the best, so don’t miss it. We ate dinner at A&B Lobster House right in the historic seaport afterwards.

Pro-tip: Key West is only 4 miles long and about 2 miles wide, so it’s very walkable! Grab dinner off Duval Street each night, and explore the area on foot!

Florida Keys Road Trip Day 3

Smathers Beach

Today was a beach day! The Keys aren’t known for their beaches. In fact, the real charm lies beneath the surface… aka the reefs. But, I was so pleasantly surprised by Smathers Beach! Definitely set aside some time to hang out at this beach during your stay in the Keys.

Pro-tip: You can rent lounge chairs and an umbrella for $30 at the beach.

My favorite thing about Smathers was all of the palm trees! There are so many here, scattered throughout the sand. The walkways leading up to the beach are lined with them too.

Smathers Beach is a hidden gem in the Florida Keys
Smathers Beach is a hidden gem in the Florida Keys

After the beach we went to Grain & Berry Cafe for some açaí bowls and spent the rest of the day lounging by the pool. 

Florida Keys Road Trip Day 4

Today was my family’s last full day in paradise. We spent the morning biking along the beaches before heading out to Fort Zachary Taylor State Park.

Charming Key West bikes

Pro-tip: We spent 5 days total in the Keys, and had 3 full days. The perfect amount of time for this trip. If you live more locally, you could definitely see the highlights in just one weekend. the Florida Keys are one of the best girls weekend getaways in the US southeast!

Fort Zachary Taylor State Park

We were supposed to do a snorkel trip this afternoon to the reefs, but canceled due to rough seas. This was a bummer since the best coral reefs are located about 7 miles off the coast of Key West, but we tried to make the most of our time by doing some off-shore snorkeling in the state park. While I do recommend a boat tour to the world’s 3rd largest coral reef, Fort Zachary Taylor is a great option for off-shore snorkeling.

Snorkeling in Key West, Florida

Aside from the fort, there’s a beach cafe here and a nice beach with chair/umbrella rentals. We ate lunch first and then explored the fort. This area has a civil-war era fort overlooking the Gulf of Mexico and Atlantic Ocean. It was recently excavated and now houses the largest cache of Civil War armament in the world.

Fort Zachary Taylor in Key West
Fort Zachary Taylor in Key West

After exploring the fort (and the moat!), we spent the afternoon on the beach. We were able to see some fish and a sea slug while snorkeling off the beach!

Snorkeling at Fort Zachary Taylor in Key West

For dinner tonight, we ate at Bistro 245 on the water. It was so good and I definitely recommend trying it!

Florida Keys Road Trip Day 5

Today was mostly a travel day as we had a three hour drive back through the Keys to Miami. Again, I do recommend flying into Miami for your first visit so you can explore the Keys in their entirety, but if you’re a regular, definitely just fly into Key West.

Jungle Culture

As I mentioned earlier, this blog post is sponsored by Jungle Culture. I was fortunate to be gifted several of their products, including their eco-friendly coconut bowls from Vietnam, customized reusable straws, and bamboo utensils. I packed all of these items with me on this trip in an effort to be more sustainable!

Jungle Culture is an eco brand that works with organic farms and crafts workshops in Vietnam to produce a range of eco-friendly and natural products that are ethically sourced. They offer a wide range of environmentally friendly products on their website, which you can check out here.

I’m excited to announce that I’ll also be running a giveaway with Jungle Culture over on Instagram tomorrow, January 6, to offer YOU a chance to win some of their amazing products for yourself! Be sure to tune in!

Jungle Culture's coconut bowls and wooden utensils

Jungle Culture's coconut bowls and wooden utensils

Jungle Culture's coconut bowls and wooden utensils

That’s all for my Florida Keys road trip post! Let me know if you decide to follow a similar itinerary on your next trip, and definitely reach out if you have any questions! Lastly, be sure to head to my Instagram tomorrow to enter the giveaway with Jungle Culture. Thanks again Jungle Culture for sponsoring this post!

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Florida Keys road trip



  1. J.G.
    November 6, 2023 / 8:00 PM

    Where did you leave your car while on Key West?

  2. March 10, 2024 / 7:12 PM

    Hi there! We drove our car through the downtown and also found parking garages while exploring the area. It’s walkable, but was nice to have our car!

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