Florida Keys Road Trip: 20+ Iconic Stops (and a Few You Can Skip)
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This Florida Keys road trip actually happened on a total whim. We were in Miami, saw we had a few extra days, and decided to just keep driving south. Of course, that’s when a cold front rolled through, so we didn’t get to hit every stop or spend nearly as much time on the water as we wanted. Even still, this trip completely sold us on how fun and easy a Florida Keys road trip really is, and it’s one we already know we’ll be repeating again and again!
The Florida Keys are made up of over 1,700 islands and keys, with approximately 800 being named islands, connected by 42 bridges! The iconic Overseas Highway stretches about 113 miles from Key Largo all the way down to Key West.
This guide breaks down the most iconic stops from our Florida Keys road trip, plus a few that are easy to skip!
How Many Days Do You Need for a Florida Keys Road Trip?
One of the first questions people ask when planning a Florida Keys road trip is: “How much time do I actually need?”
From my experience, it really depends on what you want to do. We spent 3 days and 3 nights exploring the Keys, staying in Key Largo, Long Key, and Key West, which gave us a good taste of each area. We have also done Key West a few times before so we were able to linger more in the other areas.
Because of the cold front and our short timeframe, we didn’t get to do as many water-based activities as we would have liked, but we still managed to fit in a lot of stops, meals, and fun moments.
If you have the flexibility, 5–7 days is the sweet spot for a more relaxed trip. This gives you time to:
- Explore each key without feeling rushed
- Get out on the water (boating, snorkeling, or kayaking)
- Enjoy local dining, hidden spots, and iconic attractions
- Take in sunsets, beaches, and those quiet little Keys moments
Even with a shorter trip like ours, it’s totally possible to hit some of the most iconic stops in the Florida Keys and still have a memorable experience!
How to Start Your Florida Keys Road Trip
The classic Florida Keys road trip starts in Miami and follows the Overseas Highway all the way down to Key West. The full drive usually takes about 3.5 to 4 hours without stops, but this is one of those routes where the stops are the whole point. After leaving Miami, we started our stops in Key Largo, the first and longest key, and slowly worked our way south, pulling over whenever something caught our attention.
What we loved most about this road trip is how flexible it is. You can do the full drive from Miami like we did, or fly straight into Key West, rent a car (we used Discover Cars to find a really good deal!), and explore The Keys as you make your way back up.
No matter which direction you go, every stretch of the drive feels a little different. One minute you’re crossing long bridges with open water on both sides, and the next you’re stopping for key lime pie, waterfront lunches, or a quick caffeine fix.
Florida Keys Road Trip Stops in Key Largo
1. Alabama Jack’s
Alabama Jack’s has been a Key Largo staple since 1953, and it’s easy to see why! It’s one of those classic dockside spots that feels like a true part of the Keys’ history. While it’s known for its massive conch fritters (which I didn’t try personally), they definitely looked tempting and are a signature dish that locals rave about. We went with their mahi tacos instead, and they were huge and delicious, the perfect fuel for kicking off our road trip.
Getting here requires taking a slightly longer route off the main Overseas Highway, but it’s worth it. The drive itself is scenic and picturesque, offering a glimpse of the old Florida Keys roads before everything connects back to the main highway. Alabama Jack’s is a great spot to pause, enjoy some fresh seafood, and feel like you’re stepping into a little slice of Key Largo history.
2. John Pennekamp Coral Reef State Park
John Pennekamp Coral Reef State Park is one of the crown jewels of Key Largo and a must-stop for anyone who loves the water (or even just wants to soak in the Keys’ natural beauty). It’s famous for being the first underwater park in the US, protecting a vibrant coral reef teeming with marine life.
We were so bummed that it was super windy the day we were in this area, which meant we couldn’t go on any of the tours—the main way to experience the park’s underwater wonders.
Normally, visitors can choose from snorkeling, glass-bottom boat tours, scuba diving, or kayaking, each offering a totally different perspective on the coral reefs and colorful fish. Even without a tour, the park itself is worth stopping at: there are walking trails, picnic areas, and plenty of spots to just enjoy the scenery and feel like you’re deep in the Keys. Entrance is $8 per vehicle.
If weather was on our side, this is the snorkel tour we would have done (and plan to do next time)!
3. Caribbean Club
The Caribbean Club is a Key Largo classic, best known as the filming location for the movie Key Largo. It’s a laid-back waterfront spot with a real dive-bar charm. Think pool table, dark cozy interior, and an outdoor area with amazing waterfront views. While we popped in, it looked like rain was rolling in so we didn’t stay long, but you can immediately feel why this place has been a staple for decades.
It’s famous for its Key Lime Pie Rum Punch, and it’s one of the best spots in Key Largo to catch the sunset. They also have live music Thursday through Sunday. It’s cash only, so plan ahead if you want to grab a drink or two.
4. Skipper’s Dockside
We stayed at the Holiday Inn Key Largo, which ended up being the perfect spot for our trip. Our bartender at Alabama Jack’s even told us afterward that it was one of the best places to stay in Key Largo, and we can definitely confirm. Being able to walk to Skipper’s Dockside from our hotel was so convenient. It’s right in the marina area, and the whole spot has that relaxed Keys energy with waterfront views and live music.
Dinner here was easily the best of our entire Florida Keys road trip! We went with the crab-crusted black grouper served with crispy potatoes, lemon butter sauce, heirloom tomatoes, and crispy onions and it was unreal!
And we couldn’t resist trying one of their bloody marys, which were perfectly balanced, featuring Tito’s vodka, San Marzano tomatoes, fresh lemon and celery juices, balsamic vinegar, horseradish, and a house-seasoned rim. Not too heavy, totally delicious.
5. Blond Giraffe Key Lime Pie Factory
Blond Giraffe Key Lime Pie Factory, is technically in Tavernier, just a short drive from Key Largo. This place is known for their chocolate-dipped key lime pies on a stick, which are frozen, so give them a little time to thaw if you want the full experience (I didn’t have the patience).
They also have plenty of key lime goodies to take home or for the road, like key lime pie cookies, meringues, pecans, dressings, and more. We ended up going here between lunch and dinner as a little early dessert, and it was the perfect stop. Definitely a can’t-miss Florida Keys road trip stop!
6. Coffee Stops in Key Largo
There are a few coffee spots around Key Largo, and we tried Coco Plum Place and Cafe Moka in Tavernier. Both were good, but honestly, my favorite coffee in the Upper Keys ended up being in Islamorada, so if you’re only planning one stop, I’d recommend waiting for that one.
Coco Plum Place is a really cute spot with some fun, unique drinks. I tried their Cocoplum Latte, which has butterfly pea powder and vanilla. It was different, but I liked it! They also have a solid menu if you’re hungry, plus juices, which makes it a nice little stop for a snack or light breakfast.
Cafe Moka is another cute coffee stop. I had a hot latte, which was good but nothing mind-blowing. I also had my eye on One Grind for their breakfast crunchwrap, but unfortunately, they were closed the morning we were leaving Key Largo. Definitely on my list for next time!
Other Tours in Key Largo
In case you end up with extra time in Key Largo (or want to swap out a stop or two), here are some popular tours you may want to check out.
- Fishing Charter – Fishing is a big part of Keys culture, and half-day charters are beginner-friendly. Most captains handle everything and tailor the trip based on conditions and what’s biting. This charter even includes lunch and snorkeling equipment!
- Half-Day Scuba Diving Trip – Key Largo is known as the dive capital of the world, making this a great place to try scuba diving. Most half-day trips visit multiple reef sites, so you can experience the underwater world without committing a full day!
- Mangroves and Manatees – Guided Kayak Eco Tour – A slower-paced way to explore the Keys while learning about the local ecosystem. You’ll paddle through mangrove tunnels and calm waters, with chances to spot manatees, birds, and other wildlife!
- Key Largo Bay Dolphin Sunset Tour – A relaxed boat tour focused on dolphin sightings that wraps up with sunset views over the bay, making it a great option for an easy, scenic evening on the water.
- Cruisin’ Tikis Sunset Cruise – A floating tiki bar experience that’s laid-back and fun, especially for sunset. They have these all over Florida, and I always find them so fun!
- Jet Ski Rental – A more adventurous way to explore the water, giving you the freedom to cruise around and see the Keys from a totally different perspective.
Where to Stay in Key Largo
There are so many options for where to stay in Key Largo, and I definitely recommend spending at least a night here. You’ll want to give yourself time to explore all the stops along this stretch, and it’s nice to have a base so you can enjoy the next parts of your Florida Keys road trip without feeling rushed. Here are a few places we think work really well:
- Holiday Inn Key Largo – This was our pick, and it was perfect. Conveniently located for walking to spots like Skipper’s Dockside, Sharkey’s, and a handful of boat tours. Plus we loved their amenities! They had 2 pools, a jacuzzi, and a tiki bar which we took full advantage of.
- Sunset Cove Beach Resort – A great option if you’re traveling with kids. The resort has family-friendly amenities, a nice pool, and easy access to the water. Plus, the sunsets here are amazing.
- Bayside Villas by Islander Resort – If you’re looking for something a bit more spacious or private, these villas are right on the water and feel like a little escape. It’s a nice option for couples or small groups who want to relax after a day of exploring.
Check out all available options in Key Largo for your dates here!
Florida Keys Road Trip Stops in Islamorada
7. Betsy the Lobster & Rain Barrel Village
Betsy the Lobster is one of the most iconic roadside stops in Islamorada, and it’s hard to miss! Standing 30 feet tall and 40 feet long, Betsy is one of the most photographed landmarks in the Florida Keys, second only to the Southernmost Point Buoy in Key West. If you’re doing a Florida Keys road trip, this is one of those classic pull-over-and-take-a-photo moments.
Right behind Betsy is Rain Barrel Village, which is much more than just a quick souvenir stop. The village is set along shaded garden paths and is home to a collection of small studios and shops featuring handmade crafts, contemporary artwork, beachwear, home goods, and Florida Keys–inspired souvenirs.
It’s a really enjoyable stop to stretch your legs, explore the gardens, and get a feel for the artistic side of Islamorada.
8. Day Drippin Coffee
Day Drippin Coffee was hands down my favorite coffee stop in the Upper Keys. It’s a cute little coffee truck set outside a marina, and it’s exactly the kind of low-key, local spot that makes a Keys road trip feel special.
I ordered the fortune cookie iced latte, and it was so good! If you’re only planning one coffee stop between Key Largo and Islamorada, this is the one I’d recommend waiting for. It’s delicious, quick, and such a fun little break along the drive.
9. Islamorada Brewery & Distillery
We loved the vibe at Islamorada Brewery & Distillery, and it ended up being one of our favorite stops in Islamorada. It’s a super relaxed spot where you can sample their spirits, do a flight of their beers, or order one of their cocktails. They even have some fun mocktails, which is great because someone needs to be the DD!
I loved that I could do a flight pour of their frozen Key Lime Pie drink, which was perfect for trying something fun without committing to a full cocktail. Remi was a big fan of their No Wake Zone, a coconut key lime blonde ale that felt very on-brand for the Keys.
The outdoor area is spacious and fun, with yard games and food available, making it an easy place to hang out for a bit rather than just popping in and leaving.
10. Florida Keys Brewing Co.
Florida Keys Brewing Co. is just about five minutes down the road from Islamorada Brewery & Distillery.They have plenty of great beer options, and the vibe here is just as laid-back, with a spacious outdoor area that’s perfect for hanging out for a bit.
This is another Keys road trip stop that really highlights the art scene in Islamorada. The brewery is surrounded by galleries and boutiques filled with colorful artwork and creative details, and I loved being able to walk around and take it all in while Rem enjoyed his beer. It’s a fun mix of local culture, creativity, and classic Keys energy!
11. Midway Cafe
Midway Cafe was right before our lunch spot, but since we stayed nearby in Layton, we actually came back the next morning for breakfast. If you’re staying in Marathon or further down, I’d still say it’s worth stopping here just for dessert. Grab a slice of their key lime pie. I was not expecting it at all, but this is hands down the best key lime pie I’ve ever had!
I specifically wanted Rem to try one with a meringue topping since we had been talking about it, and I didn’t think we’d have time to make it to Blue Heaven. This one totally surprised me and, in my very humble opinion, was better than Blue Heaven! The meringue was so light, creamy, and just perfect. We also tried Moondog Cafe’s key lime pie and it didn’t even come close for me.
If you do come for breakfast, they have a solid menu. Rem and I ordered the same latte—his hot, mine iced—and weirdly enough, I didn’t love mine but really liked his. Hot latte is definitely the move if you need a caffeine fix.
12. Lazy Days
You better come hungry for this stop. Lazy Days was our second favorite meal of the entire trip, and honestly, it was close to being first. We shared a hogfish sandwich Lazy Days style. And let me just say, whatever you order here, be sure to get it Lazy Days style!
It’s encrusted with Japanese breadcrumbs, sautéed, and topped with tomatoes, scallions, parmesan cheese, and their homemade Key Lime butter. The combination of flavors is so good. It’s fresh, rich, and perfectly balanced.
We shared because we were trying to save room for our next stop, but in hindsight, I’d say fill up here. The food at the next stop doesn’t even come close. And on top of that, you’re treated to some of the most beautiful waterfront views while you eat, which makes the whole experience even better!
13. Robbie’s
This may just be the most iconic stop on a Florida Keys road trip. If you’ve seen photos of people holding fish while massive tarpon launch out of the water… this is that place.
At Robbie’s of Islamorada, you stop here to feed the tarpon, and it’s every bit as chaotic and fun as it looks. You pay a small fee to walk out onto the dock (even if you’re just there to watch), and if you want to feed them, you can grab a bucket of bait for $5. They warn you to keep a close eye on your bucket—and they are not exaggerating. The pelicans here are sneaky, fast, and fully committed to stealing your fish if you’re not paying attention.
There’s netting along the dock with holes where you stick your hand through to feed the tarpon, and watching them rocket up out of the water is honestly wild. This was definitely one of the most fun and memorable stops of the trip, whether you’re feeding them yourself or just watching the madness unfold.
We also grabbed a quick bite at The Hungry Tarpon, Robbie’s on-site restaurant. I thought it was just okay. We ordered the coconut shrimp based on our server’s recommendation. I’d definitely say fill up at Lazy Days, then come to Robbie’s for the experience, not the food.
14. Anne’s Beach
If you’re looking for a stop to get out, stretch your legs, and enjoy some fresh air—without eating or drinking—Anne’s Beach is such a good one. It’s a small, peaceful beach area in Islamorada with limited parking, so it never feels overwhelming, which honestly adds to the charm.
What really makes this spot special is the long wooden boardwalk that weaves through the mangroves and over the shallow water. It’s perfect for a slow stroll, taking photos, or just soaking in that quiet Keys energy. There are a few little sandy areas where you can sit by the water.
This is one of those places that’s easy to overlook, but it’s such a nice break from driving. While I don’t think you need to do both stops on this trip, there is also Long Key State Park nearby!
Where to Stay Near Islamorada
If you’re planning to spend a night or two in Islamorada, there are plenty of options, but I really loved our stay at Lime Tree Bay Resort. Unfortunately, due to the weather we weren’t able to enjoy all the amenities—but even without that, I thought the price was incredible for what you get.
The pool is gorgeous, and the resort also provides bikes and kayaks that you can take out on the water, which is such a fun way to explore the area if you have time. There’s also a restaurant next door, which we didn’t end up checking out because we drove down to Marathon for dinner—but honestly, I kind of wish we had stayed close and just eaten there.
Overall, Lime Tree Bay Resort is a solid option if you want a central spot in the Upper Keys with easy access to both Islamorada attractions and activities in the surrounding Keys.
If you don’t stay here, I recommend going a little farther and just staying in Marathon, check out options for your dates here!
Florida Keys Road Trip Stops in Marathon
15. Sombrero Beach
If you’re looking for a classic Florida Keys beach stop in Marathon, Sombrero Beach is a solid choice. It has white sand, clear water, a playground, picnic areas, and is dog-friendly (on leash), making it a great spot for families or anyone traveling with pets.
The beach is equipped with restrooms, showers, and cleanup stations, so it’s easy to spend a few hours swimming, sunbathing, or just relaxing. Paid parking is enforced, so don’t forget to pay.
We stopped here even though the weather wasn’t ideal, just to see if it was worth adding for a future trip, and I would definitely say yes. Even on a weekday with less-than-great conditions, it was pretty busy, which is a good indicator that it’s a popular spot for a reason.
If you stayed overnight nearby, and haven’t went snorkeling yet, make time for this epic 3-hour snorkeling adventure on a pontoon at Sombrero Reef.
16. The Turtle Hospital
This is one of the most meaningful stops you can make on a Florida Keys road trip. The Turtle Hospital in Marathon is a working rehabilitation center that rescues, treats, and releases injured sea turtles, and it’s also one of the best ways to actually learn about marine life in the Keys.
Visits are done through guided tours, where you’ll hear the stories behind the turtles currently being cared for and learn about the threats they face in the wild. It’s educational and it’s a great non-food stop to break up the drive. If you’re traveling with kids or just want a deeper appreciation for the Keys beyond beaches and bars, this one is absolutely worth your time.
17. Seven Mile Bridge
Driving across the Seven Mile Bridge is one of those moments where the Florida Keys road trip really hits you. Stretching for just over seven miles between Marathon and the Lower Keys, this bridge feels endless in the best way possible, with water stretching out on both sides as far as you can see!
There are a few pull-offs nearby (before and after the bridge) where you can safely stop for photos, and it’s worth taking advantage of them if you can. Whether you’re crossing it at golden hour or under moody skies, this drive is iconic for a reason and easily one of the most memorable parts of the entire trip.
Florida Keys Road Trip Stops in Big Pine Key
18. No Name Pub
First things first: while you’re driving through Big Pine Key, keep an eye out for the adorable Key deer! We saw so many running across the streets! It’s honestly the cutest thing—but make sure you’re alert and driving slow.
No Name Pub is probably the most iconic bar on this stretch of the Keys. It has a fascinating history—it used to be a brothel—and today it’s decorated floor to ceiling with dollar bills, giving it a quirky, one-of-a-kind vibe.
We unfortunately weren’t hungry when we stopped (you’ll hear about some of the spots we went to, but that next time I’d skip, later), but don’t make the same mistake. Save your appetite for the famous pizza and fish spread—you’ll want it. While we only had room for a little bit of the fish spread, it was absolutely some of the best I’ve ever had, almost on par with what we had in Traverse City.
19. Blue Hole
Blue Hole is another nice, quick little nature stop. This is a small, freshwater pond tucked in the middle of the Keys, perfect for a quick stretch, a photo, or a moment to enjoy the outdoors.
The lookout area gives you a great view of the water and surrounding greenery, and as soon as we arrived, we immediately spotted a gator friend hanging out!
20. Baby’s Coffee
This stop is technically in Key West, but it’s not quite in town. I couldn’t resist popping in, even at 4 PM. I probably didn’t need another coffee, but I’m so glad I tried it. Baby’s Coffee’s cold brew with cold foam was hands down the best coffee we’d had on the trip up to that point. Perfect little pick-me-up before arriving in Key West! And honestly I think this coffee was the reason I was able to stay up until 11 PM haha.
Stops You Can Skip (or Decide for Yourself)
Everyone has different tastes, and honestly, some of these spots—even if someone told me I could skip them—I’d probably still go to just to see for myself! I’m not trying to deter your support for these businesses, just giving my honest take on what worked (or didn’t) for us. Most of these are in Marathon, so keep that in mind as you plan.
- Island Fish Co. – We were so pumped about this spot, but it really fell flat. We did their stuffed grouper and… honestly, it was bland (you can kind of tell from the photo). The bartenders were sweet and great, but the food just didn’t compare to other meals on our trip. We also tried their deep-fried key lime pie coated in cinnamon sugar—Rem loved it, but it wasn’t my thing.
- Georgie’s Coffee – My small coffee here cost more than my coffee on Miami Beach with pink cold foam… and honestly, it was just okay. If you’re not craving a caffeine fix in Marathon, you can totally skip this one.
- Herbie’s Bar & Chowder House – We stopped for at least a cup of chowder while trying to save room for other meals. It was fine, but I felt like we could’ve spent our appetite elsewhere. Cute little spot though, and people rave about some of their other menu items—maybe it was just the chowder that was meh.
- Keys Fisheries – They’ve sold almost half a million lobster Reubens! I thought I was clever asking for mine on Texas toast instead of rye. It was good, but I’m not sure I totally get the hype. Still, it’s kind of an iconic stop, so maybe it’s worth seeing for yourself. Do what we did—share a sandwich so you still have room for No Name Pub. We also tried their key lime pie, and it definitely didn’t compare to Midway Cafe, so skip that.
Welcome to Key West!
At this point, you’ve officially made it to Key West! There are so many fun things to do here, and it really depends on how much time you have. Some absolute musts:
- Mile Marker 0 – The official end of the Overseas Highway and a fun little milestone if you drove all the way down from Miami. It’s a quick stop, but it really makes the road trip feel complete.
- Sunset at Mallory Square – It’s classic Key West, full of street performers and gorgeous views.
- Duval Street bar crawl – Tons of fun bars and a perfect way to get the Key West vibe.
- Southernmost Point Buoy – Go early to avoid long lines and snag that iconic photo.
- Cuban Coffee Queen – The coffee here is next level (they even use coffee ice cubes), and the Caliente Cuban mix is a seriously bomb sandwich.
If you have more time, check out my guides for unique things to do in Key West and the best things to do in Key West—there’s no shortage of adventures in this little island paradise!
Where to Stay in Key West
There are so many great places to stay in Key West, whether you want to be in the heart of the action or somewhere a little more quiet. Here are a few options we loved:
- La Concha Key West – Outdoor pool + pool bar? Yes, please! Modern, spacious rooms (and bathrooms!) make this a total win. The best part? It’s right on Duval Street, so you’re perfectly positioned for all the bars, restaurants, and nightlife.
- Douglas House – This adults-only inn is perfect for a romantic escape. Just a 5-minute stroll to the beach and 2 minutes from the Ernest Hemingway Home. Features a shared outdoor pool, free parking, and even pet-friendly vibes!
- Tranquility Guest House – This is where we stayed during our road trip. We booked last minute and it was one of the more affordable options available. The place is super cute with a great pool area (wish we could’ve used it!). It’s about a 15-minute walk to Duval Street, which was totally fine for the price—and the walk was actually really nice.
Still searching? Check out the full list of Key West accommodations for your dates here!
Florida Keys Road Trip Tips
- Don’t be scared to ask for recs – Some of our favorite stops (Skipper’s Dockside and Lazy Days) were recs from our bartender and locals hanging out at Alabama Jack’s! I mean who knows best?
- Plan your meals strategically – Some stops (like No Name Pub or Skipper’s Dockside) are worth saving room for. You don’t want to miss out because you ate too much earlier.
- Weather check – A cold front or windy day can change your plans quickly. Flexibility is key!
- Bring cash – Some spots (like the Caribbean Club) are cash-only, so it’s handy to have a little on you.
- Don’t rush – Even if you only have 3–4 days, try to slow down at each Key. It’s better to enjoy fewer stops than zip past everything.
- Gas – We only used about half a tank from Miami to Key West, so it’s easy to just refill near the airport before returning your car. No need to stress about finding gas along the way!
Are you ready for an epic Keys road trip?!
Despite the weather, we had so much fun on this Florida Keys road trip, and I know you are going to too! There are so many cool, quirky, and delicious stops to make along the way.
Whether you follow this guide exactly or use it as inspiration, I hope it helps you plan a Keys road trip that fits your pace, your taste, and your travel style—and makes you want to come back for more.
Before you go, be sure to follow me on Insta @guidedbydestiny and check out some of my other Florida blog posts:
Awesome Restaurants on the Tampa Riverwalk
How to Spend 3 Days in St. Pete, Florida
