Florida Keys: The Ultimate Road Trip Guide

This is probably going to be the longest post I’m ever going to write. It is really long. Should I separate into several different posts by location? Perhaps. Could it be a book? Probably. But the Florida Keys are beyond special to me so I wanted this guide to be perfect. I didn’t want to leave anything out and I really put my heart into it. I hope you love it as much as I loved making it!

Something that is actually really exciting to me is that I’m starting to lose track of how many times I’ve been to the Florida Keys. One visit blurs with the next and it’s just one cumulative experience at this point. I first fell in love with the Florida Keys at the age of 18. After my freshman year of college, I did an internship in Key West and haven’t stopped thinking about it since. Living on a 4×2 mile island, it doesn’t take long to become an expert. Later, my husband and I explored the upper to mid Keys and while I didn’t expect to like anywhere as much as Key West, I was wrong. I love every inch of the Florida Keys.

Table of Contents

No matter what you’re looking for, the Florida Keys have something for you

Before we dive in, let’s start with the basics. The Florida Keys are divided between the Upper, Mid, and Lower Keys, with some placing Key West in its own category. Upper Keys include the Key Largo area; mid Keys are Islamorada/Marathon area (sometimes people separate these into two categories as well); and the lower Keys start around the 7-mile bridge.

There is one road in and one road out of the Keys, the Overseas Highway, which is a destination in and of itself. Mile markers will tell you how far you are from Key West. For example, Key West is at mile marker 0, so if you are at mile marker 50, then you’re 50 miles away. I encourage you not to view the road as something that gets you from point A to point B, even though the locals will hate me for giving such advice. Instead, take your time and pull over where you feel called. Don’t worry too much about checking things off your to-do list, just live in the moment, soak it all in. That’s what the laid-back lifestyle of the Florida Keys is all about. I talked more about how we did that here.

Ultimate guide to the florida keys road trip

Key Largo

Key Largo marks the entrance to the Keys. Right away, you’ll see the Key Largo Visitor’s Center. If you have something specific in mind for your trip, the Visitor’s Center employees are knowledgeable and will help you out. They will say, “here in the Keys, we only care about two things – getting on the water or getting in the water.” Sounds good to me!

Key Largo and Northern Keys Activities and Things To Do

Explore John Pennekamp Coral Reef State Park

This park was initially built to preserve Key Largo’s coral reef and was the first undersea park in the US. It offers beaches, trails, and camping; camping reservations can be made here. A small entrance fee is required to enter the park. There is a lot to do in the park including some of the best snorkeling and diving in the world. Additional activities include glass-bottom boat tours, powerboat rentals, kayaking, paddleboarding, fishing, and an aquarium at the Visitor’s Center. With the exception of the aquarium, these activities will be an extra fee (fees vary).

Go snorkeling or scuba diving

The reefs here are breathtaking. Key Largo is also home to the famous Christ of the Abyss statue (also known as Christ of the Deep) which is about 25 underwater. The top of the statue can be seen by snorkeling if you aren’t scuba certified as the top of the statue is closer to 10 feet deep. A boat is needed to get to this location. Spiegel Grove is another popular dive site, where a retired Navy ship was sunk to create an artificial reef.

Harry Harris Park

This is a beautiful area with picnic tables, boat launches, playground, baseball fields, and a beach. The park is dog friendly and has been undergoing repairs since Hurricane Irma but is still open in most areas.

Florida Keys Wild Bird Center

The Florida Keys Wild Bird Center is a bird sanctuary for birds that cannot be released, meaning they are too injured to be released to their habitat. Admission is free, but a $10 per person donation is recommended.

Where to Eat in Key Largo

Most of the time, my husband and I stay in Miami the night before a trip to the Keys so that we can be well-rested to enjoy the road trip. Therefore, we’re not usually ready to stop for food by the time we get to Key Largo. This is unfortunate because I have many places on my list to try. While I don’t have personal experience at any of these places, these are all places recommended to me either by locals or a trusted traveler who has eaten there

Mrs. Mac’s – mom ‘n pop type restaurant with classic Keys decor great for any meal

The Pilot House – a fun restaurant on the marina.

The Fish House – nautical restaurant with fresh seafood.

Sharkey’s is a popular hangout in the diving community located along the canal near Key Largo Harbor.

Hobo’s Cafe – large portions, good food, and patio seating.

My favorite thing about the Keys (not just Key Largo) is that there is no shortage of waterfront restaurants. Being waterfront as much as possible is important to us on vacation. As you drive through the Keys, you’ll see billboard after billboard advertising waterfront restaurants. We usually drive until we see a billboard that speaks to us and go there.

Where to Stay in Key Largo

There are many great places to stay in Key Largo, no matter what you’re looking for. For the cheapest lodging, you can go camping at John Pennekamp State Park, as noted above. This will run you around $43, which is pricey for camping, but definitely cheap lodging for the keys. Plus, the camping sites have good amenities for showers and restrooms.

If you’d rather sleep in the water, you can do that, too. No, that was not a typo. Jules’ Undersea Lodge provides you accommodations underwater with the fish. You don’t have to be a diver to stay here (you can enter by using hooka lines) and it is safe as the facility is monitored 24/7. The rooms are even equipped with Wi-Fi. You can book on their website.

Key Largo also has an all-inclusive resort! My husband and I prefer to wander to new restaurants and bars, so this isn’t the best fit for us. But given that it is rare to find all-inclusive resorts in the US, it is absolutely worth a mention. This resort is called Bungalows Key Largo and it is adults-only.

For more standard hotel reservations, the following are excellent options:

Baker’s Cay Resort

Play Largo Resort and Spa

Key Largo Bay Marriott Beach Resort

Seafarer Resort and Beach

There are many places to stay in Key Largo, and this is by no means a comprehensive list. If you know you want something very specific, you may want to do additional research on what the best hotel/resort will be for you. I did not check each of these accommodations, but most accommodations in the Keys include the use of things like kayaks, stand up paddle boards, etc., with your stay. Individual vacation rentals and Airbnb options are also available, but my husband and I prefer hotels/resorts, so that is primarily what you’ll find throughout this post.

Cuban Coffee

There will be many opportunities for Cuban coffee as you make your way down the Keys. Our favorite is a small, family-owned place in Tavernier (just south of Key Largo) called the Sunrise Café. This is a must-stop for us every time we are in the Keys and I am obsessed with their café con leche. We order from the to-go window outside and sip the coffee while we enjoy the drive.

Mid Florida Keys

This is my favorite stretch of the Florida Keys. It is quiet and laid back here and your activities would be typical of any island vacation. Islamorada and Marathon are the two largest destinations in the mid-keys.


Where to Eat in Islamorada

Lazy Days – Oceanfront dining, tiki bar, and a dock. Also features live music and a fish market. After dinner (or before) you can grab a drink and sip it on the beach.

Morada Bay Cafe – Bayside dining with a great view of the sunset if you eat there for dinner.

Robbie’s/Hungry Tarpon – This doubles as both a restaurant and an attraction and a must-do on almost every Florida Keys guide. Robbie’s has a dock where you can feed the tarpon and you do not have to eat there to do this. You will pay around $2 to get access to the dock and then you can buy buckets of fish if you want to feed the tarpon, or you can just watch everyone else doing it. When you’re done, grab a delicious meal at Hungry Tarpon located right on the water. 

Islamorada Fish Company – Located inside Bass Pro Shops, my husband especially likes this location and I love the menu.

Where to Stay in Islamorada

My husband and I have only stayed at Pelican Cove Resort while visiting Islamorada. We had such a good experience that it’s where we choose to return every time we’re in the area. The Postcard Inn, their sister resort, is right next door and access to the amenities of The Postcard Inn is included with your stay. While the Postcard Inn is larger and has more amenities, we prefer Pelican Cove because it’s quieter and still has all of the amenities we enjoy. All rooms at Pelican Cove are guaranteed to have a water view and we have always loved our views. However, “water view” does not necessarily mean a full, perfect view of the water and some of the views can be more obstructed.

We see billboards all over in Islamorada and Marathon advertising resorts that all look incredibly gorgeous and inviting, so if Pelican Cove doesn’t sound like a good fit for you, you’re likely to find accommodations that fit your needs. Another resort that many have recommended is the Amara Cay Resort.

florida keys roadtrip islamorada

What to do in Islamorada

Want to get on the water? You have a lot of options. From fishing trips to jet ski rentals, you will be covered with plenty of companies waiting to get you on the water. My husband and I have rented any boats or gone on any tours in Islamorada, but a large list of available companies can be found at this website.


There are two breweries in this area, Islamorada Beer Company and Florida Keys Brewing Company. They’re both incredible and every trip to the Florida Keys warrants a stop at both!

florida keys roadtrip florida keys brewing companyflorida keys roadtrip islamorada brewing company

Anne Beach

A great beach for dogs and kids as it has shallow water. Anne’s Beach also has a boardwalk and picnic tables. No fishing is allowed here.

Theater of the Sea 

This is a marine mammal park that features dolphins, sea lions, sting rays, alligators, and nurse sharks. It is a good family activity with several exhibits and shows.

Dolphin Research Center 

A non-profit marine mammal education and research facility. It also serves as a sanctuary for dolphins that cannot be released.


Where to Eat in Marathon

Island Fish Co

A fun, on-the-water restaurant serving classics and local dishes. The last time we ate here, we actually saw a tiny shark!

Florida Keys Marathon Florida Restaurant

Castaway Waterfront Restaurant and Sushi Bar 

After you take a photo with the boat out front, enjoy a delicious restaurant serving both classics and sushi. Decorated old school Florida with beer tap handles throughout the restaurant. Even better? The service is as good as the food!

Florida Keys Marathon Florida Restaurant

Burdine’s Waterfront 

Located on the water (more of a canal view) with friendly hosts. I tend to be a bit biased towards the restaurant when the server greets you with “water view, right?” They give you koozies to use with your beer so that it doesn’t get cold and whatever you do, do not skip their hushpuppies. I am not even a huge hushpuppy fan, but these are the best. 

Florida Keys Roadtrip Restaurant

Sunset Grille and Raw Bar

Features the most beautiful views of the bridge and a swimming pool!  We actually haven’t eaten here yet, but it’s on our list for next time.

Where to Stay in Marathon

Isla Bella Beach Resort and Spa 

Tranquility Bay Beach House Resort

What to do in Marathon

Sombrero Beach

A great beach option with picnic tables, playgrounds, and volleyball courts. The water is beautiful here. Nice beaches can be difficult to find in the Florida Keys, so it can get crowded but there is ample parking.

Coco Plum Beach

This is the other beach in Marathon and many don’t like it as much as Sombrero. However, that comes with a tradeoff as it’s significantly less crowded here. The beach is more narrow and as with many waterfront places in the Florida Keys, there is often seaweed. A small parking lot and restroom facility is available.

Curry Hammock State Park

Curry Hammock State Park offers great kayaking or paddle boarding through the mangroves to really feel like you’re in the Florida Keys. Kite boarders love it here and are fun to watch if you’re not a kite boarder yourself. This state park also has a 1.5 nature trail and you can camp here as well. Reservations are required and can fill up very quickly, so book early. There is also an entry fee given that it is a state park.

Turtle Hospital

The Turtle Hospital is a rescue and rehabilitation center for turtles that opens to the public. They do so much for turtles in the Keys and the admission to the hospital helps support them. After Irma, they were out rescuing injured turtles before the power came back on. I love them and I love their mission; they are a place I feel great about supporting.

Crane Point Museum and Nature Center

63 acres of hardwood hammock, which is a closed canopy forest filled with tropical greens. It’s a nonprofit that features a museum of natural history and nature trails.

National Key Deer Refuge

A refuge for white-tailed deer with a walking path and nice visitor’s center. This is located just south of Marathon in Big Pine Key.

Seven mile bridge

Once you leave Marathon, you’ll notice quite a long bridge. And long it is! 6.79 miles, to be exact, and called the 7 Mile Bridge. It’s a fun experience and absolutely beautiful.

Florida Keys Aquarium Encounters

An aquarium to enjoy tropical fish, sharks, and rays.

Bahia Honda State Park

This is located on Bahia Honda Key and you’ll find it shortly after crossing the 7 Mile Bridge. It is right on the water with a few different beach areas. The Bahia Honda Rail Bridge, a Florida Keys icon, is located within this park. Since this is a state park, you will have an entrance fee. Bahia Honda State Park deserves its own post because there are a lot of details. And you’re in luck because we recently visited, so I have that for you right here!

bahia honda state park bridge overseas highway florida keys

As you start getting closer to Key West, you’ll start seeing signs to watch out for Key Deer on the road, so keep an eye out for them. Unlike the midwest, where deer are a nuisance on the road, the Key Deer are well-respected because they are endangered. They live primarily in Big Pine Key and there are less than 1,000 of them.

Key West

Here’s the big one! This is going to be a larger portion than the rest of the locations due to the many activities available in Key West. While the mid to upper Florida Keys are primarily about laying back and enjoying the water, Key West is busier and definitely more of a party scene. Of course, boating, fishing, and getting on the water are equally possible here and you can still have a laid back vacation in Key West if that’s what you choose.

Just like I encourage you to enjoy the drive as you make your way down the Florida Keys, in Key West, I recommend walking around and stopping when and where it feels right. The main street is Duval which is where a lot of action will be with bars, restaurants, tours, and shops. My husband and I love to wander the streets of Key West so don’t be scared to leave Duval!

You’ll notice chickens wandering throughout Key West, the infamous Key West Gypsy Chickens! They originated from Cuba and the Caribbean Islands and were brought to Key West by island ancestors for food and cockfighting. They are not used for either anymore so they now wander the streets of Key West.

Getting Around

Key West is a 4×2 mile island so it is walkable for the most part provided you stay near Duval. There are some destinations on the island you may want to visit that will be too far to walk and for those, you have a few options. Bikes and scooters are available to rent if you want a bit of an adventure. If that doesn’t sound like something you’d be interested in, Ubers and taxis are also plentiful and affordable. My husband really wanted to rent a scooter when we were there and I reluctantly agreed. I was so nervous at first but it ended up being my favorite part of the trip.

florida keys roadtrip guide

Mallory Square

At one end of Duval is Mallory Square which is home to the nightly Sunset Celebration. This involves watching the sunset with vendors and performers (and about a million other people). During the day, cruise ships will dock at Mallory Square and many boat tours will leave from here as well (dolphin, snorkeling, etc). We make it a point to stop at Mallory Square during each trip because it’s tradition, but people tend to love it or hate it. Locals will tell you that there are better places to watch the sunset and they’re not wrong, but Mallory Square is a rite of passage in Key West.

There is a restaurant right on Mallory Square with views of the sunset called the Sunset Pier and it’s part of the Ocean Key hotel. You do not need to make reservations, just grab a seat if you’re lucky enough to find one. We somehow managed to snag one last year during the most incredible sunset we’ve seen. It was nice to not have to worry about our view being blocked while enjoying a couple of drinks. Mallory Square will be packed around sunset, but if you go during the day, you’re going to be practically alone. It’s really only packed for a couple of hours a day unless a cruise ship is unloading. If cruise ships dock there, they have to be gone before sunset so that they don’t ruin the view.

florida keys roadtrip guide

Things To Do and See

Key West Bight Marina

While you’ll want to wander Duval Street, this is another fun area to wander. It’s filled with shops and restaurants. We haven’t eaten at any of the restaurants here yet but a lot of people recommend Turtle Kraals for their happy hour appetizer specials.

Southernmost Point

You will find a line of people as long as the block to look at this and get their photo here, so I recommend going early in the morning. Please enjoy this photo of me at the Southernmost Point 13 years ago:

Key West Florida Southernmost Point

Mile 0

Located at 501 Whitehead Street, it’s the end of the road! Literally mile 0.


I did this within 3 weeks of being in Key West for my internship at the age of 19 and it was much less scary then than I think it would be now! Another intern and I used the company Skydive Key West and had a great experience. My favorite part was that we got to fly around the Keys a bit while we got high enough to jump, so the views were spectacular. Of course, I probably didn’t enjoy them as much as I normally would because of nerves. The Florida Keys are a great to skydive because of these views!

florida keys roadtrip key west florida skydiving

florida keys roadtrip key west florida skydiving

Ghost tours

Key West is full of ghost stories and even if you don’t believe in ghosts, the stories are fascinating. During the summer of my internship, a group of us went on 3 haunted tours because we found them so interesting. Back then, we met inside the La Concha and walked to the different sites. However, that was 13 years ago and now it seems that the ghost tours are conducted are via bus, I don’t see the ghost tours walking around anymore which is unfortunate. It’s possible that I just haven’t seen them, so I encourage you to do some research if this is something you’re interested in. Hearing these stories made me feel more connected to Key West and the tours are enjoyed by many.

East Martello Museum

If you go on the haunted ghost tour, you will hear the story of Robert the Doll. He is kept at the East Martello Museum so during my internship, we visited for the sole purpose of seeing Robert. We loved seeing Robert, but also fell in love with the museum which is filled with art and history. It is kept in an old fort and is on the U.S. National Register of Historic Places. I took my husband here when we were in town over the 4th of July and somehow, we were the only people there. We were also there alone when we visited 13 years ago. I don’t know if this was just a two-time-fluke or not, but it was very special to have this place to ourselves. It is truly a must-visit!

florida keys roadtrip key west florida martello museum

Boat tours

Want to get on the water? Any tour you could possibly want is here – jetskiing, snorkeling, dolphin siting, parasailing – you name it. There are many companies ready to get you on the water and they are all wonderful, but my favorite is Fury. We used them multiple times and always had a great experience.

florida keys roadtrip key west florida jetski rentals

Dry Tortugas

This is one tour I haven’t done yet and is definitely on my bucket list. A ferry will take approximately 67 miles south of Key West to an island where you’ll find an old fort. The day can be spent exploring, lounging on secluded beaches, or snorkeling. Some of the other interns went and said it was one of the best things they’d ever done. This is subjective, of course, as we were only 19 and didn’t have a whole lot of experience under our belt. Regardless, I cannot wait to finally get to Dry Tortugas!

Hemingway House

As the name suggests, this is Hemingway’s old house. The house is stunning and you learn a lot about his life. Also, the cats on the property are descendants of his so they have 6 toes just like his did!

florida keys roadtrip key west hemingway house

florida keys roadtrip key west hemingway house

Shipwreck Museum

The view from the watchtower makes this museum worth it alone. Inside, you’ll learn a lot about shipwreck salvage from the Keys. Note that  if the weather isn’t absolutely perfect they will close the watchtower, so check the weather before you go.

Mel Fisher Maritime Museum

This is another museum of treasures that Mel Fisher himself found. He was a diver and American treasure hunter who found the 1622 wreck Nuestra Senora de Atocha. Diving was something Mel Fisher’s entire family participated in, and his son and daughter-in-law perished when their boat sank in 1975.


This small aquarium is located near Mallory Square and features a touch tank as well as fish, birds, sharks, and turtles.

Truman Little White House

The Harry S Truman Little White House is where Harry Truman spent his winters when he was president. It is Florida’s only presidential museum and filled with original memorabilia from that time. Other presidents who have used the house include Taft, Eisenhower, Kennedy, Carter, and Clinton. And it’s no surprise that they would love it here, the house and grounds are beautiful and warrant a visit.

Conch Tour Train

The Conch Tour Train will take you around the island of Key West to point out the highlights. This isn’t my preferred way of getting around the island as I love taking my time and walking, but this can be a good way of squeezing everything in if that’s something you’re worried about. Some other interns and I rode on the Conch Tour Train during internship because we were given a free pass, and we enjoyed it. The driver is full of knowledge and they always appear very friendly (and patient as they deal with traffic consisting of tourists on their bicycles!)

Key West Butterfly Museum

My roommates decided to visit this museum on a whim one Sunday afternoon when I was an intern. I didn’t really want to go, but reluctantly tagged along and it was incredible. I loved this museum! They had so many different butterflies and beautiful foliage throughout.

florida keys roadtrip key west florida butterfly museum


I normally don’t recommend shops, but I will make an exception for this one. A little down the road from Mile 0, located at 803 Whitehead is my favorite shop. It’s called COAST. It is the cutest store and the people who work there are lovely.

Where to Stay

You will probably want to be as close to Duval as you can. The first time my husband and I stayed in Key West, we stayed on the north side of the island and while we liked the hotel, it was a pain to be so far away. There aren’t many hotels on Duval itself with the exception of the La Concha. When I interned in Key West, people talked about this hotel a lot and it was the place to stay. Back then, they had a bar on the roof where you could grab a drink while taking in the views. Sadly, that has since closed. However, the La Concha is a part of Key West’s history which you just may hear about if you choose to partake in a ghost tour. I was really excited to stay there last July and we did have a great experience.

All of the hotels that are located near (or practically on) Mallory Square look really nice though we haven’t stayed in them. When we visit Mallory Square, I’m always jealous of the resort guests enjoying the view of the sunset from their pool. This is definitely the area that I’d choose.

Some of the hotels in that area on our radar include:

The Pier House Resort and Spa
Ocean Key Resort and Spa (this one is actually top on my list, which I think comes from my internship days when I was in awe that people could stay so close to Mallory Square and have balconies! The innocence of a 19-year-old!)
Hyatt Residence Club Key West
Hyatt Centric Key West Resort and Spa
Margaritaville Key West Resort and Marina.

If you don’t feel like you want to stay close to Mallory Square, Casa Marina Key West was recommended by some of our family members who loved it.

There are many adorable inns in Key West, but I don’t have experience staying at any of them though I love to admire them from our walks. The Southernmost House Hotel is a B&B that always takes my breath away. It looks charming, but best of all the pool there looks incredible.


Cuban Coffee Queen – Everyone will tell you that you *have* to go here for coffee, so I’m including it. If we’re nearby, we will stop but this isn’t a place we tend to go out of our way for.

Coffee Plantation – this we will go out of our way for. Coffee Plantation is our favorite coffee shop. We like to stop here and then wander the side streets nearby. That’s actually how we found this coffee shop in the first place!



This is our first stop every time we are in Key West. No exceptions. It’s a rule. I fell in love with their shrimp club on my internship and talked to my husband about it for 6 years straight. He thought I was exaggerating and wasn’t expecting much, but let’s just say it isn’t just my rule that makes Fogartys has to be our first stop. He loves it just as much as me. Even if shrimp isn’t your thing, I recommend Fogarty’s anyways. They have a great menu, It’s outside, prices are good, and portions are generous. If you want a drink, this is a great place to grab a slushie. I get chocolate and it literally tastes like a frosty from Wendy’s.

florida keys roadtrip key west florida restaurants fogartys

Blue Heaven

This is on our to-visit list because everyone says it’s the best breakfast in Key West. We tend to sleep in too late to get there before the rush, but one day we will eat there!

Better Than Sex

A dessert restaurant, need I say more? You’ll want to make reservations because they fill up quickly.


This is for a special occasion or if you’re in the mood to splurge. We haven’t been there yet because our Florida Keys vacations tend to be spontaneous and low key, but I have heard amazing things. Latitudes is actually not technically on Key West, it’s on its own island that requires a ferry to get to. They will pick you up from the Margaritaville Resort on Mallory Square and it is a 7 minute boat ride. You will sit on the sand near the water to eat your meal. Reservations are required.

Overall, I recommend wandering and finding a place that looks good. We’ve tried many different restaurants and have loved them all. A few honorable mentions are Caroline’s, Two Friends Patio Restaurant, Wicked Tuna, and Hog’s Breath.

I always have to get a chocolate covered key lime pie on a stick (no particular place, they’re all perfect). Also, you’ll see a few different shops selling huge huge cookies. They’re delicious, too.


Key West is known for nightlife, and as I’ve mentioned, I recommend just wandering around and going into any place you feel is calling your name. Here are some of the highilghts:

Sloppy Joe’s

I’m only including this because it’s a “must-visit” and a Key West tradition. In complete honesty, we have tried to go here every time we are in Key West and every time we immediately walk right back out. We just don’t love it even though we want to. It seems like everyone else loves it, so I’m sure you will, too. Hemingway loved Sloppy Joe’s (it used to be in the Captain Tony’s location) and every year, they have a Hemingway lookalike contest.


Rick’s is my husband’s favorite place and I absolutely love it, too. We love getting drink buckets from here. Rick’s is technically in a complex with a few other bars, so that’s why you see Durty Harry’s in the photo below (also worth a visit)!

florida keys roadtrip key west rick's

Cowboy Bill’s

This is my favorite place. It is a country bar, as its name suggests, and the music is live. Even though it’s located right on Duval, it’s easy to pass on by as the entrance is small. If you like country music, do not miss Cowboy Bill’s!

Green Parrot

Located just off of Duval, many also consider this a “must visit.” It has the reputation of being “where the locals go” but I’m not entirely sure that’s true.

Captain Tony’s

Captain Tony’s is the original home of Sloppy Joe’s and also said to be haunted by a number ghosts. First, the building used to be a morgue and a hurricane came through washing up bodies. Second, a lady came into the bar with her infant and had a mental breakdown when she found her husband drunk; she killed the baby and herself in the bathroom. Last, and most famous, was the “Lady in Blue”. Inside the bar, you will find a tree that Captain Tony’s was built around. The tree used to be used for hangings and this is where The Lady in Blue was hung after killing her husband and two sons. Finally, it is Key West tradition is to try to land a coin in the fish’s mouth on the sign out front while standing backwards.

Smokin Tuna

florida keys roadtrip key west smokin tuna

Hog’s Breath

florida keys road trip key west hogs breath

Key West Brewery

If there’s a brewery, I’m probably going to recommend it. Come here for a flight and order an appetizer or a meal if you’re hungry.

florida keys road trip key west bar brewery

801 Bourbon Bar

This is a drag queen show that I cannot recommend more as long as it isn’t too far out of your comfort zone.


Beaches in Key West aren’t particularly nice. They are beautiful, but the price of the Florida Keys having the only living coral barrier reef in the continental US is that it keeps the sand from getting to shore. This is a fancy way of saying that the beaches are rocky. I am not trying to discourage you from the beach, I just want to make sure you have realistic expectations. If you would like to explore the beach, your options are:


The biggest beach. Sometimes it smells due to the algae. Locals will tell you that it isn’t due to the algae but from cruise ships dumping human waste. I’ll let you decide which it is.


Just down the road from Smathers. It is smaller but still has amenities.

 Harvey Rest Beach Park

Smaller area with more nature/trails

South Beach

Also very small. When I interned in Key West, I always thought this was a private beach owned by the local hotel.

Fort Zachary Taylor

This is the beach most worth visiting as there is an old fort here from the civil war. As it is a state park, you do have to pay to get in.

Florida Keys Closing/FAQs

When is the best time to visit? 

The Florida Keys have beautiful weather year-round, but it will be especially hot in the summer. We live in Florida so we are used to hot weather yet found ourselves struggling with the heat when we visited in July. Key West is home to events like Fantasyfest and during those times the hotel prices will skyrocket. Many websites will tell you that there are less tourists over the summer but the truth is that the Florida Keys has consistent tourism year round. Like anywhere, prices will increase around things such as holidays and spring break. The simple answer is this: anytime you can get to the Florida Keys is the right time.

Are the Florida Keys good for kids/families?

The Florida Keys can be whatever you want them to be. If you want your vacation to be a party filled with booze, then probably not. The upper to mid Keys are more kid friendly than Key West. But there are a lot of water activities as noted throughout this article and it’s easy (and fun!) to include kids on your fishing trips, snorkeling, boat rides, etc. They’ll also enjoy the sanctuaries and parks noted throughout the article. So, it’s not a hard yes or no. It’s completely up to you and how you design your vacation. Kids can certainly have fun in the Florida Keys.

How long should I stay?

How much time do you have? OK, but seriously, do you ever hear people who love Vegas exclaim, “I love Vegas, but 3 days is enough!” Well that is not the case for the Keys. If you’re like me, even a month wouldn’t be enough time. I see a lot of guides saying things like “How to see The Keys in 7 days!” Can you? Yes. But just because you can do something, that doesn’t always mean you should. I’d rather see you get to fully experience only the upper Keys, for example, than rush your way through. With that being said, I’d recommend around 2-3 nights in each setting (upper, mid, lower) if you can.

In closing:

What I love most about Key West is that it does not matter who you are, you are welcome. This means that you can go out at night in your sweatpants or you can get all gussied up and either way, you are welcome and no one will judge you. It also means you can start drinking at 10 am or you can not drink at all and either way, you’ll have a blast.

Let me know what you’re looking forward to most about visiting the Florida Keys!

florida keys roadtrip

The Ultimate Florida Keys Roadtrip Guide


9 thoughts on “Florida Keys: The Ultimate Road Trip Guide”

Leave a Comment

Your email address will not be published. Required fields are marked *