The Ultimate Florida Keys Guide: Planning The Best Road Trip

A Florida Keys road trip is one of those iconic U.S. travel experiences that everyone should do in their lifetime.  The Overseas Highway spans 113 miles over the ocean, with more than forty bridges crossing dozens of tiny keys (islands).

The Miami to Key West drive along Route 1 isn’t difficult, and isn’t even that far—technically you can do it in about 3.5 hours.  But you’d be missing the point.

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The point IS the journey.  In the Keys you’re on island time, no longer driven by the hustle and urban polish of Miami, but rather meandering your way along a narrow highway lined with kitschy diners, slightly careworn marinas, amazing wildlife, bobbing boats, delicious food, and—above all—the sparkling turquoise waters the Keys are famous for.

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I finally planned my own visit in March 2022, and spent six full days meandering up and down the Keys, soaking up the vibes, marveling at the beautiful water, looking for hidden gems, and trying every key lime pie I could get my hands on.

And now I want to bring you a CRRRAAAAAZZZYYY detailed guide to planning your own amazing Florida Keys roadtrip itinerary.

How this Florida Keys travel guide post is structured:

• What to pack
• Where to stay in the Keys (in and out of Key West)
• General Florida Keys itinerary tips
• How to get to the Keys, & how to get around them
• How to structure your Keys roadtrip itinerary
• What to do in the Upper Keys, Middle Keys, & Key West
• Where to eat and drink in the Florida Keys

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What to pack

• Sunscreen!  The sun in the Florida Keys is NO JOKE—any and every time of year.  Here are my favorite sunscreens for a beach trip, and a few additional face sunscreens I love.
• I packed a lot of sundresses, but it was so windy when I visited (the weather was really weird) that I wished I’d brought more super lightweight pants and tops, like my fave Athleta pants.  In general I wished I’d brought a few warmer options for nighttime/early morning (a sweatshirt, thicker cardigan).
• And that same crazy wind (which can be pretty common in the Keys) meant that a sun hat wasn’t super helpful, unless you have one that ties on tightly (like this one).  I’m more of a headband person than a hat one, so used these ones to try and control my hair in the wind.
• But just because it’s windy, doesn’t mean it’s not brutally hot during the day (even in the winter).  I wished I’d brought extra bras, because I kept sweating through mine and it was really gross.
• You’ll want super comfy shoes for walking around Key West, to not get blisters in the heat.  My absolute fave sandals for this are these Rockport ones, which balance comfort/cushioning and cuteness (party in the front, biz in the back).  For extra cute but still comfy (like walking to dinner), brands like Aerosoles and Naturalizers are great.
• Ideally, keep any sand separate from your regular walking-around shoes to avoid blisters; so if you’re walking on the beach, use simpler and easy to clean flip flops (Havaianas are my fave).
• Obviously swimming suits are important, and you will probably want at least two.  If you plan on going snorkeling, I recommend a more sturdy type like a one-piece or tankini vs. a flimsy bikini.
• A good beach tote can help you organize and keep track of your belongings as you move around (some people might prefer a backpack, but I don’t).  I love this one.
• Plastic straws are banned in the Keys (though I found many places to offer some kind of alternative), so I brought my metal straws with me
• Two items I found invaluable in helping prevent heat rash and general discomfort were thigh glide and hydrocortisone cream.
• If you’re planning to snorkel and have terrible eyes like me (I wear glasses when needed), a prescription snorkeling mask is a gamechanger!
• I recommend throwing in a small, lightweight microfiber towel for drying off after impromptu beach stops, or even if you want to sit on the ground to picnic.
• Good sunglasses to protect your eyes.  Polarized ones are key (mine are prescription, but these are good regular options).
• An external battery charger comes in handy to keep your phone from dying (taking pics all day and running GPS can drain your battery)

Other Florida Keys adventures to plan your trip!

The Best Key Lime Pie In The Florida Keys: A Definitive Ranking

Exploring Bahia Honda State Park: A Must On Any Florida Keys Roadtrip

Sunset In Key West: The Two Best Spots That AREN’T Mallory Square

Where To Stay In The Keys: Review Of Grassy Flats Resort (Marathon)

Where To Stay In Key West: Review Of H2O Suites

Florida Keys Brewing Company: A Must-Stop On A Keys Road Trip

Exploring Historic Fort Jefferson In Dry Tortugas National Park

Idyllic, Remote Loggerhead Key: Exploring Lesser-Known Dry Tortugas

What It Was Like Multi-Day Open-Water Sailing: Key West To Dry Tortugas

Where to stay in the Florida Keys

When I was planning my week-long Keys roadtrip itinerary, I knew I wanted to spend a couple nights in Key West, but then base myself somewhere more central for the remainder.

After LOTS of searching and reading reviews (and at the exact time I was visiting, hotels were for some inexplicable reason STUPID expensive), here’s where I stayed, and a few other options that were high on the list.

Where to stay outside of Key West

With the sparkling ocean and pools only a few steps away from each other, beautiful spacious rooms, a creative tiki bar, swaying palm trees, and a super central Marathon location, Grassy Flats Resort was the perfect choice.  It was only a few months old at the time and they were still building out parts of the resort.

Grassy Flats has regular rooms, 1-bedroom suites, as well as 2-, 3-, and 4-bedroom suites as well.  I was the first person to stay in the brand new Galleon Suite, and thought it was gorgeous.  I loved the view from my balcony, appreciated having a couch to sit on, and would stay here again in a heartbeat.

You can check out my super deep review of Grassy Flats, and look them up on Booking.com and TripAdvisor (or, if you’re looking for the more specialty suite options, their website).

The rest of the resort is equally beautiful, with excellent landscaping, very clean, and designed well.  The beach (on the Atlantic side) is actually pretty decent as Florida Keys beaches go (Keys beaches aren’t great), and there are two different pools to choose from.

The service was great, tiki bar is lovely, and the only real downside is that food options are a bit further away (5-10 minute drive).  I highly recommend Grassy Flats if you’re looking for a great central Florida Keys hotel option!

The other non-Key West accommodation options I strongly considered were Bungalows Key Largo (all-inclusive, my friends rave about), Bakers Cay Resort (gorgeous!), Cheeca Lodge & Spa in Islamorada, and Hawks Key in Marathon.

Check out my detailed review of Grassy Flats if you want to learn more!

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Where to stay in Key West

Shew, Key West can be expensive.  You can go a couple different directions with accommodation, including Airbnbs.  For a short stay and if you’re willing to pay a bit more, my recommendation is to stay somewhere central, where you can park your car.  Then you can walk, bike, or Uber wherever you need to go.

The other option is to stay a bit further out and get more bang for your buck, and either get in early and find decent (still expensive) parking, or use the free Key West shuttle (a great option!).

I stayed in two different places, and if you’re looking for a splurge then I highly recommend H2O Suites!  You can look at both Booking and TripAdvisor reviews as well, but as you can see in the pics below, it’s beautiful and peaceful, and you get your own little private pool!

I booked the Premier Luxury Suite with Private Pool, and the room was large with a separate seating area.  The staff was very welcoming and the shared hotel areas were gorgeous as well.  I was only there for one night so didn’t really get to take advantage of everything offered at the hotel, but I’d definitely return!

Check out my deeper review of H2O Suites!

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I also spent a night at the Kimpton Ella’s Cottages (here are TripAdvisor reviews too).  It was really cute, with strong Key West bungalow aesthetic vibes.  I’d actually wanted to stay at Kimpton’s Winslow’s Bungalows instead but they were full on my dates.

The service was super friendly and the property is beautiful.  There’s a small pool area and patio as well, and a continental breakfast.  While the room was simple and pretty, it’s quite small and the walls were pretty thin.  I did love the little porch I had, perfect for sitting with a cocktail in the heat of the afternoon, with the fan blowing on you.

As I mentioned above, hotels were super booked up and insanely expensive for the dates I was there, which affected my choices.  If you’re looking for a real splurge, check out Sunset Key Cottages (amazing!).  The other places I’d looked at staying were the Gardens Hotel, La Te Da(adults only), Marquesa Hotel, and Ocean’s Edge Resort & Marina (further away, but looks great).

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General Florida Keys itinerary tips

Let’s start with some general thoughts on what matters and what to expect when planning your Keys roadtrip.

While you CAN go from end-to-end in the Keys in a few hours, the traffic can be bad and you won’t actually be able to *do* anything.  So it’s good to think about the Keys as Upper, Middle, and Key West, and arrange your itinerary accordingly.

As you think about where to stay, if a water view or access is important to you, you’ll really need to think about whether your hotel is Atlantic or Gulf side.  Certainly this matters for sunrise or sunset views, but even the beaches themselves will look a bit different.  Also as a note, I thought that the water in the Islamorada area is maybe the prettiest in the whole Keys.

In particular, weekends can be nuts for crowds and traffic, and so it can be helpful to limit how much you’re driving up and down the Overseas Highway on weekends to avoid getting stuck in traffic jams.

I definitely preferred early mornings and early in the day, both in Key West and just the Keys in general…it has a very chill vibe, less traffic, and is not as hot.  Sunrise crew FTW!

There is a ban on plastic straws in Key West (and I think a lot of the Keys).  I recommend bringing a couple of your own metal straws for easy sippin’.

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When is the best time to visit the Florida Keys?

Any time of year can be great, though July through October tend to be not only the hottest and most humid, but peak hurricane season (September is also muggiest and wettest).  December through February are the busiest in terms of tourism, with the most ideal weather but also most expensive and crowded.

For my money, find the sweet spots of early March (before spring break) and late April through May.  You can also get lucky in November with amazing weather but fewer crowds (pre-Thanksgiving).

Do Florida Keys have beaches?

If you’re looking for an amazing beach vacay with sugary sand beaches, a Florida Keys roadtrip may not be quite what you’re looking for.  While Florida is known for its beautiful white sand beaches (on the Gulf side), you’ll quickly notice that beaches in the Keys don’t live up to that.

The Keys were formed atop coral reefs and are protected by those reefs, meaning the islands don’t have sandy beaches.  They’re usually rough and covered with pulverized coral.

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How to get to the Florida Keys

You’ll probably either fly or drive, depending on where you live.  If you’re flying, you can either fly into Miami or Ft. Lauderdale airports and get your rental car and drive, or fly directly into Key West (and get a rental car too, if you’re exploring the full Keys).  Any of those are good options, so just choose the best flight/airport for you.

Do I need a car in the Florida Keys?

It depends.  If you’re only going to Key West and spending a few days exploring Key West, maybe doing a couple day trips with tours (boat trip, food tour, etc.), then you can get away with not having a car.  Similarly, if you’re going to a resort and literally just staying there the whole time (with maybe a day trip tour or two), then same.

BUT if you’re looking to actually explore the Florida Keys, then yes, you definitely need a car.  There’s no good public transportation, and tons of little spots to stop off at, beautiful views, interesting eateries, cool state parks, and more—without a car, you won’t really experience the Florida Keys.

Just like with hotels, for some reason rental cars were crazy expensive for the dates I was there (also not helped by overall rental car company supply chain issues).  I ended up using Sixt (this is a 15% off link), who I’ve had great experiences with (mostly) internationally, but ended up not being as ideal for this trip.

For some dumb reason, they were charging me a $45 add-on fee for any toll roads I went on, and there are a lot of them headed from Miami airport down to the Keys.  They also charged me more than $10 a gallon for gas when I wasn’t able to re-fill my car (long story, I really tried but the gas tank cover was jammed).  So you could also check out someone like Hertz or Enterprise.

One note, the rental car place is SO far away in the Miami airport, so just be prepared for that (we were delayed & got in around 11:30pm, and the rental car desk closed at midnight so I was hauling ass to get there in time)…it’s long walks on moving sidewalks and then the train.

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Driving in the Keys

Speaking of gas, it’s definitely more affordable before you hit the Keys, so always better to fill up on the mainland if you can.  Make sure you leave tons of time to get back to the airport from the Keys, as traffic gets really bad along the Overseas Highway and also people are really slow.  I ended up accidentally cutting it WAY too close and was panicked.

Be extremely careful about speeding!!!  (Yes, three exclamation points.)  Cops are everywhere looking to stop people, and the speed limit changes constantly.  Sometimes the cops just park an empty car somewhere so it looks like a cop is monitoring you, but I wouldn’t take the chance.

Driving in the Keys is also one of those trips where the journey is just as important as the destination.  Driving along the Overseas Highway is an amazing experience!  It will take as long as it’s going to take…if you’re stuck behind someone slow, you might get lucky with a passing area, but don’t do anything stupid and just be patient.  You’re on island time.

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How to plan your Florida Keys roadtrip itinerary

One of the important things to keep in mind when planning your Keys roadtrip is that you’ll need to be flexible due to weather uncertainty.  If you’re planning any kind of outdoor activity, particularly if it’s on the water, that’s going to impact your itinerary.

One thing you’ll notice as you go through this post is that I didn’t manage to do any snorkeling boat trips.  I was SO BUMMED but the weather when I was there in mid-March ended up being kind of weird, there was a big front of rain, crazy wind, and cooler temps that rolled through just as I arrived.  But you definitely need to consider boat trips and snorkeling!

As I talk about what to do in the Florida Keys much deeper below, I’m going to go geographically from north to south (so Key West is at the end).  But I ended up structuring my itinerary a little differently.  This was entirely due to hotel availability and costs in Key West.

I drove down to Key West for my first two nights, hitting some of the Upper Keys spots as I went.  Then I based myself smack-dab in the middle in Marathon and used that as a base to explore the Middle and Lower Keys a bit more conveniently.

Here was how my actual itinerary worked out:

• Arrived Miami very late at night, got rental car, stayed close to the airport
• Headed down the Overseas Highway first thing in the morning, ended up in Key West that afternoon
• Spent two nights and one full day in Key West
• Drove up to Marathon to base myself the rest of the trip
• Spent one day more in the Marathon/Islamorada area
• Spent time down in Bahia Honda and lower Middle Keys

As I made my way up and down the Keys, from Key Largo to Key West and back, I sampled as many key lime pies as I could get my hands on.  Some I devoured in the restaurant, but more often than not I got them “to go” and enjoyed with a gorgeous Keys view, in my car, or in my jammies in bed.  I’ll speak to some of these in the post below, but you can read my deep-dive post on the best key lime pies in the Keys here!

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Upper Keys:  Key Largo & Islamorada

As I mentioned above, one of my biggest “things to do” in the Florida Keys was to try as many different key lime pies as possible, and the first spot I hit driving south was the original Mrs. Mac’s Kitchen.  It’s got a cute, kitschy diner-like vibe, and if I’d had time I definitely would have stopped for breakfast.

Instead I grabbed a piece of key lime pie to go (at 9:30 in the morning)…you can see where it ranked on my best key lime pie in the Keys deep-dive post, but the short answer is “eh”.  Wasn’t bad, but definitely not top of the list.

As you continue on your way, one cool spot to keep an eye out for if you’re a classic movies fan is the Caribbean Club, where the famous black-and-white film Key Largo (starring Humphrey Bogart and Lauren Bacall) was filmed.  You can read more about it here!

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Just down the highway you’ll see Harriette’s, who are known not for their key lime pie, but for their famous key lime muffins.

I’m firmly on the record as being anti-muffin (insanely caloric and taste/enjoyment does not live up to it), but their key lime pie muffin is pretty darn good!  Super moist but not crazy sweet.  And again, a really cute diner feel so would be great for a meal.

And then we started getting to the real key lime contenders!  My next stop, Blond Giraffe Key Lime Pie Factory in Tavernier, ended being my overall #1 key lime pie in the Keys.

They have many different offerings, all the same key lime pie base but a variety of toppings (whipped cream, meringue, chocolate, frozen on a stick with chocolate, etc.).  I got the meringue even though that’s not usually my thing, but the girl at the counter said it was the traditional one.

The pie’s filling was light and creamy but delightfully tart, the crust was great, and the meringue thankfully didn’t distract from the pie itself.  Near perfection.  I ate my pie out in their peaceful Serenity Garden, which has an amazing sign basically saying that children must be seated and quiet at all times—my kind of place!

Blond Giraffe definitely deserves a short stop on your Florida Keys itinerary!

See the rest of my definitive ranking of Florida Keys key lime pie options!

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At this point, I was JONESIN’ for some real coffee.  At both Mrs. Mac’s and Hariette’s, they only had drip coffee and that’s not really my fave.

So I swung by the adorable Café Moka for an iced latte (in deference to the already blazing mid-morning heat) and some avocado toast…I mean, you gotta soak up all that sugar from the pie at some point.

They have a menu of light lunch fare, delicious-looking pastries, and great coffee, plus not only a cute indoors but nice little patio area as well.

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John Pennekamp State Park

So this one’s a biggie, and I’ll fully admit that I didn’t do it justice.  Renowned as the county’s first undersea park (established in 1963), John Pennekamp State Park encompasses 70 nautical square miles of well-reserved marine life—on Key Largo and about 3 miles into the Atlantic Ocean.  People rave about the beaches, wildlife, snorkeling, and boat tours.

When I was planning my Florida Keys roadtrip, it kept coming up as a must-visit, so it was definitely on my list, and I particularly wanted to do either the glass-bottom boat tour or a snorkeling tour.  Unfortunately when I arrived, the boat trip time I needed was already booked up, and the next one would have been too late for me to make my Key West sunset sail reservation.

I did make a quick stop by both Cannon Beach (first couple pics below), deemed one of the most chill beaches in the Keys, and the tiny Far Beach.

Read more about visiting John Pennekamp park & tips for your visit!

From the underwater coral reefs to the mangrove swamps, John Pennekamp Coral Reef State Park gives visitors a glimpse of one of the most diverse and beautiful ecosystems.  But overall I don’t think it’s is the kind of park that lends itself to a “drop by”, unless you just want to hang out at the beach for a bit or have a quiet picnic next to the water.

But it’s definitely worth a visit!  It just takes a little planning to make sure you really *see* the things you want to see, particularly the snorkeling or the glass-bottom boat (book ahead!).  And activities such as kayaking, snorkeling, fishing, or camping require time.  Make sure you plan ahead!

Two other Key Largo things to call out that I didn’t get to do…Molasses Reef is supposed to be some of the best snorkeling in the Keys, and can be a great boat trip destination.  And if it’s your kind of thing, kayaking through the mangrove tunnels is a unique thing to do in the Keys (check out Florida Bay Outfitters).

Now we’re making our way south into Islamorada, a village actually encompassing six small keys.  And Midway Café & Coffee Bar is our next stop, one of those “must stop” spots everyone touts.  I tried to visit here on my first day as I was driving south, but it was PACKED, with a line out the door (I think it was a Thursday or Friday).

I strongly recommend avoiding weekends if you can, unless you’re fully in the off-season, or go at a super off time.  So instead this was the very last spot I stopped on my way back to the Miami airport at the end of my trip.  I got an iced coffee and roast beef sandwich that was quite delicious, and their avocado toast which was mediocre.

And of course, the key lime pie.  The filling was great, one of the best, but the crust (a basic pie crust, not graham cracker) really let it down and the meringue didn’t add anything.   It made the upper tier of my list on the filling alone, but there are better options out there.

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Having already sent ourselves into a blood sugar coma, we’ll totally switch gears with our next stop, which is the popular Florida Keys Brewing Co (this is actually a slight backtrack from Midway, by like a minute).  It’s located in the Morada Way Arts and Cultural District, and their kitschy tasting room and colorful beer garden certainly reflect that.

FKBC was the Upper Keys’ first microbrewery, serving up delicious seasonal and tropical-inspired craft brews seven days.  You can take a tour of the brewery, build your own flight of beers to taste, grab a bite from the food truck outside, or play games or listen to music in the garden.

I selected my flight of beers and sipped them out in the back garden.  Out of all of them, the Honey Hibiscus Kolsch and the Hazelnut Hole Irish Red were the most surprising and delightful.

Overall FKBC has a fun vibe and is a great place to while away an hour (or three)!

Read more about visiting the Florida Keys Brewing Co here!

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This is a great stretch to just enjoy the view as well, and stop off from time to time if you see a really beautiful ocean vista.  To me, the water in the Islamorada area was maybe the prettiest…really intense aqua colors, almost opaque at times (like glacier run-off).

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Just down the highway from our beer stop is another great dining or just hanging/drinking option…Lazy Days Restaurant is a fun beachfront restaurant with (supposedly) great sea food and a very chill atmosphere.  It’s definitely worth a stop for lunch, dinner, or just to have a drink and enjoy the view.

I stopped here later in my roadtrip for an impromptu drink and snack, but it was too early for lunch at the time.  I had their key lime pie (good filling, meh crust), a mojito, and sweet potato fries…LOL late breakfast of champions!

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Fueled up on mojito, my next stop was Anne’s Beach, which was a bit of a surprise.  Located on the south end of Lower Matecumbe Key (considered Islamorada), it’s really more of a long interconnected series of tiny beaches, with a great walkway between.

It’s also dotted with pavilions, great for a family get-together or impromptu picnic with some cover from the sun.  The beaches here are a great option for kids, because the water is shallow and calm.  I wasn’t in the mood for laying on the beach (or dressed for it), so I just took a little stroll and enjoyed the view.

For time context, Anne’s Beach is about a 30-40 minute drive south from John Pennekamp State Park.

A few other Islamorada-area things to call out:  

• One thing I REALLY wanted to do was a snorkeling trip out to the lighthouse at Alligator Reef.  it’s supposed to have gorgeous waters and lots of sea life, but the weather did not cooperate with me.  Check out Wild Dolphin Tours as an option.  Though I still think I might pick Molasses Reef over it.
• Founders Park is supposed to be a beautiful beach, good for kids (but costs to enter, and I didn’t bother).
• I did make a stop at Green Turtle Inn for the key lime pie as well (it did not do well in the rankings)

Middle Keys: Marathon, Seven Mile Bridge, & Bahia Honda

I’ve already talked about the wonderful Grassy Flats Resort, but it’s right here at the top end of Marathon, and a great central option—a joy to stay at!

Then as you head down the main drag of Marathon, one of the most traditional white sand beach options is right as you’re hitting the Middle Keys…behold, Sombrero Beach!  I stopped by briefly to check it out in the mid/late afternoon and it was definitely busy and very active, but not crowded.

As Keys beaches (ha! my phone tried to autocorrect that to “please bitches”) go, it’s pretty and a great option with kids.

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And now we lunch!  A MUST VISIT in the Marathon area for either lunch or dinner is Keys Fisheries Restaurant & Marina.  This place is a total dive that is so great!  It offers a variety of seafood-based dishes, all super fresh.

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I visited first for lunch, and I had  the fish fingers and sweet potato fries, and tried the key lime pie (solid, in the top tier).  Then I came back a couple days later for dinner and got the fish tacos (a little more disappointing) and snapper Reuben.  There was quite a line at dinner, but it moved fast enough.

Seating is first-come, first-serve, and there’s a great view out over the marina.  This is a total locals place you need to try.

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And now, smack-dab in the middle of the Keys, we come to one of the things that almost EVERYONE says you need to do.  And that’s visit the Turtle Hospital!

Opened in 1986, it was the first facility of its kind in the US (maybe the world), focused on rescuing, rehabbing, and then releasing all kinds of sea turtles.  The tour takes about 90 minutes in total, visiting different areas where the turtles are recovering, and learning tons about them.  For instance, that sea turtle brains (even the giant turtles) are about the size of a thumb—they’re known for their instinct, not smarts.

You definitely should book ahead if possible, particularly during busy season.  Tickets are $30 (when this was published) and it goes to helping keep the (non-profit) center running.  And an important tip, a decent amount of the tour is outside, so wear sunscreen and bring water!

Read more about visiting the Turtle Hospital here!

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Continuing to head south, Porky’s Bayside Restaurant & Marina is a great spot for breakfast, lunch, or dinner, and even has a front seat on the water at the marina.

They have a great drinks menu (I hear the mojitos are great!), but I wasn’t quite ready to dive into cocktails right after all the beer I’d had at FKBC, so went with a refreshing strawberry mint lemonade to go with my fried fish tacos.

The other reason I had to stop by Porky’s???  They’re known for their fried key lime pie, so it was on my must-try list.  It was okay, but texturally not my fave.  One note on Porky’s, they also have live music in the evenings.

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Before we move on from Marathon, one thing I didn’t get to try out was a helicopter tour of the Keys, which is supposed to be amazing—especially at sunset!  One company I saw recommended was JD Premier Aviation Helicopter Tours, and they depart from Marathon Airport.

Otherwise, we keep heading south in the Middle Keys, and are stopping at the awesome newly re-opened walking/biking path on the Old Seven Mile Bridge.  It’s on the right if you’re driving south—I didn’t see signs or anything, just a small parking lot (35 spaces!) on the Gulf side, right before your hit the actual (new) Seven Mile Bridge.

It’s a great path with awesome views, and you have a good chance of seeing lots of wildlife.

And if you’re up to it, you can go a step further and visit isolated little Pigeon Key.  It’s only accessible by walking or bicycling the Old Seven Mile Bridge (about 2.2 miles each way) or by ferry boat.  The ferry departs from the Pigeon Key Gift Shop at 2010 Overseas Highway, mile marker 48.

You can plan your visit at the Pigeon Key website, and also read more tips and reviews on TripAdvisor.  I ran out of time and didn’t get to visit, but would have loved to!

The Florida Keys featured on “places I’m dying to visit in 2022” list!

And now it’s time to drive over the famous Seven Mile Bridge! This is the new version of the bridge, built in the 1980s.  And it IS actually almost 7 miles long.

The thing you always have to remember is that a Keys roadtrip is really about…a roadtrip.  It’s one of those “it’s the journey not just the destination” things.  And this stretch you’re on from Islamorada to Marathon and down toward Bahia Honda is GORGEOUS!  (I realize the pics don’t do it justice.)

In particular, the view of the old railroad bridge running parallel to the highway is super cool.

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I don’t know exactly where this is, but thought it looked really cool.  This was just a random place I pulled off the road on one of the Keys, and had to stop and take some pics!

Bahia Honda State Park

And Seven Mile Bridge will take you over to Bahia Honda Key, home to Bahia Honda State Park.  This is our last big stop before hitting Key West, and is one of my top recommendations for things to do in the Florida Keys!

Boasting iconic Keys scenery, some of the best white sand beaches in the Keys, and gorgeous turquoise and green water, it’s a pretty small park that’s easy to explore.

I was coming early/mid morning on a weekday, so got to enjoy some solitude and and crashing waves with the Cuban cortadito and empanadas I’d picked up on the drive.  Fueled up, I walked up the (short) old Bahia Honda railroad bridge…you definitely can’t beat the views!

Read more about visiting Bahia Honda (& the bridge’s history) here!

Then I went down to walk along Calusa Beach, which is small but gives you a pretty iconic view of both the old railroad bridge and the current Seven Mile Bridge.  Sunset from here would be amazing!

On the opposite side of the railroad bridge (just a 2-minute walk) is Loggerhead Beach.  To me this is the best beach at the park, and it also has a fabulous reef close to the shore, which provides a fairly unique beach snorkeling experience.  Good beach snorkeling with really interesting fish isn’t common (usually you need to take a snorkeling trip) and I’ve heard here it’s pretty great.

In my opinion, Bahia Honda gives you one of the biggest bangs for your buck—in terms of awesomeness vs. time—of almost anywhere in the Keys.

Read more about visiting Bahia Honda (& the bridge’s history) here!

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Now from Bahia Honda Key I skipped over to Big Pine Key, to visit the famous No Name Pub.  I bellied up to the bar to try their key lime pie (meh) and had a beer…yes, I know, weird combo but their drinks menu didn’t appeal.  The pub is about 10 minutes off the highway, so it’s less convenient for a quick stop.

And just a bit down the road on Summerland Key, I did stop briefly at Mangrove Mama’s as well.  I was tempted to have some food, but it was a weird time of day and I was antsy to get to my next stop, so just got some of their key lime pie to go (you can see where they landed on my ranking).

To me, both of these stops were skippable.  Don’t get me wrong, both have a fun dive-y feel (like dive bar, not like scuba dive), and if you’re looking for a cool vibe for a chill beer they’d be fine.  But I think you have better options for eating.

Spend a couple days in Key West

And FINALLY, at the very southern tip of the Keys, we come to Key West!  This little 2-mile by 4-mile island (key) boasts some fun history (you can read more about it here), and makes a great getaway—whether your interest is history, watersports, Civil War-era forts, booze-fueled nightlife, key lime pie, or snorkeling along barrier reefs and enjoying the year-round sunshine.

I stayed two nights in Key West, and tried out two different hotels (I recommend H2O Suites!!).  I made sure both provided parking, so I could avoid the traffic and expensive street parking, and just get around on foot while exploring this cool city.  Actually, it was HOT, soooo hot!  And that was in March…I can’t imagine what July is like.

One of my first orders of business was trying all the amazing coffeeshops…gimme that Cuban cortadito!  I did a lot of just wandering, soaking in the shaded greenery of the sidewalks, white Conch-style houses, and cool historic buildings.

Read my detailed guide to Key West, including some super handy tips!

Duval Street is the center of Key West’s nightlife, but also worth a stroll in the daylight.  It’s lined with tons of restaurants, bars, and shops, including all kinds of live music at night.

At night you can just walk down the street and listen for a style of music that suits you, then head inside.  You’ll also see plenty of bachelor and bachelorette parties swarming (that’s the scientific term, a “swarm of bachelorettes”…).

I was on a mission to try as many key lime pies as possible, and while my overall #1 was not in Key West, there were three Key West spots in my “cream of the crop” grouping.  I definitely recommend Pepe’s Café, Banana Café, and Kermit’s Key West Key Lime Shoppe…I preferred all of these to the impressive but somewhat-bland “Mile High Key Lime Pie” that’s famous at Blue Heaven.

I also enjoyed a brief rum tasting stop at Key West First Legal Rum Distillery.  I think they offer brief tours too, but you can just belly up to their bar and taste different rums or get a cocktail—I recommend getting their piña colada to go, it was great!  And yes, you can walk and drink in Key West…

And of course, you may decide to get in some quality beach time.  Again, the Keys aren’t known for their amazing beaches, but Key West has a few decent ones for you to try out.  The water and sun are gorgeous regardless.

My top two picks for best beaches were Smathers Beach and the beach at Fort Zachary Taylor State Park.  Both are pretty good on the sand/laying out front, as well as for watersports or swimming.  I also visited Higgs Beach but didn’t like it as much.

Read more about the different beach options in Key West here!

Two other things that many “what to do in Key West” lists will tell you are a must…

One is visiting the buoy marker for the southernmost point in the continental United States.   Yeah, it’s kind of cheesy and touristy, and i personally wouldn’t wait in line for a pic.  I caught it on an early morning run without the crowds.  I *would*, however, skip the Mile Marker 0 photo op.

The second is exploring Fort Zachary Taylor State Park.  If you’re planning to really make the most of the experience and enjoy the beach and picnic areas, do some snorkeling, walk around the historic fort, and maybe even catch the sunset, I’d definitely recommend it.

If you’re only going to see the fort…meh??  It’s fine I guess, but there isn’t much to see, and doesn’t have great views either.  I would STRONGLY recommend taking a day trip to see Fort Jefferson at Dry Tortugas National Park instead (more on that in a minute!).

A visit to Key West—and the Keys in general—wouldn’t be complete without planning out our sunset strategy.  The famous thing is to head to Mallory Square for their nightly Sunset Celebration, but I wanted to avoid all the crowds and craziness.

One way to combine both a pretty sunset AND getting out on the water (a favorite pastime of mine, and perfect here)  is to book a sunset sailing cruise.

In my research I looked for sunset sail companies offering something chill and not crowded, and ideally on more of a traditional sailboat vs. a giant yacht or catamaran.  I went with Danger Charters “Wind & Wine” tour (see Viator reviews as well) and was really happy with the overall vibe, and the different wines we tried  Not just cheap plonk!  Sebago also gets great reviews

You can read more about my Key West sunset sail here!

On my second night in Key West, I again eschewed Mallory Square and instead grabbed an Uber over to Fort Zachary Taylor State Park (I walked back to downtown afterward).  Note, it does cost to enter the state park (I paid $4.50 as a single-occupant vehicle).

The sunset views from the park’s beach are amazing, and while there were plenty of people there, it never felt crowded at all.  This was exactly the peaceful sunset vibe I was going for.

Read more about the best Key West sunset spots here!

Take a day trip to Dry Tortugas National Park

This is an absolute must on any Florida Keys roadtrip or any Key West itinerary!  Dry Tortugas National Park is one of the most remote U.S. national parks, about 70 miles west of Key West and 150 miles south of the U.S. mainland.  The park is 100 square miles of water, with seven tiny islands in it.

One of those tiny islands houses Fort Jefferson, built in the mid-1800s to protect the U.S.’s shipping interests.  It takes up the entire island it’s on, is the largest all-masonry fort in the U.S., and is SO much cooler than Fort Zachary Taylor!

Most people who visit Dry Tortugas do it as a day trip from Key West, either by sea plane or ferry.  I’d love to try sea plane sometime!  When I visited, I actually did a 5-day private sailing charter, so got to see some other parts of the park (like stunning Loggerhead Key).

Read more about visiting Dry Tortugas & Fort Jefferson!

Where to eat & drink in the Florida Keys

We’ll chunk this off by Upper, Middle, and Key West again, for simplicity.  Starting with the Upper Keys, here are some places I tried and my thoughts.  I’ll also mention a few places I didn’t get to, in case they’re of interest.  And we’ll start with the Upper Keys—largely Key Largo and Islamorada.

• The original Mrs. Mac’s Kitchen.  It’s got a cute, kitschy diner-like vibe, and if I’d had time I definitely would have stopped for breakfast.
•  Harriette’s, who are known not for their key lime pie, but for their famous key lime muffins.
•  Blond Giraffe Key Lime Pie Factory in Tavernier, ended being my overall #1 key lime pie in the Keys.
• Café Moka – Delicious coffee, pastries, or light lunch options, with a pretty inside and cute little patio area.
• Midway Café & Coffee Bar – Super popular so can get crowded with long lines (try an off time), but really cool spot and good menu.
• Florida Keys Brewing Co – This cool microbrewery gives you the chance to try some local beers, maybe grab a taco, and enjoy a fun, quirky back patio (with live music sometimes).
• Lazy Days Restaurant – A fun beachfront restaurant with (supposedly) great seafood and a chill atmosphere.
• Bayside Gourmet – This feels like a real locals spot, I came here for some key lime pie one night it was pouring.  I didn’t get to try any of the other food but it gets good reviews.

A couple spots I wanted to try but didn’t have the chance to were Lorelei Restaurant & Cabana Bar (great waterfront spot) and Chef Michael’s.

Now we’ll talk Middle Keys, where I spent quite a bit of time.  Most of these are grouped around the larger Marathon area.

• Keys Fisheries Restaurant & Marina – This place look like (and is) a total dive, and it is so great!  I loved the fish fingers and sweet potato fries, and all their seafood is really fresh.
• Porky’s Bayside Restaurant & Marina – A good option for breakfast, lunch, or dinner, with a pretty big menu and a front seat on the water at the marina.  I had fish tacos (delish!) and the drinks menu is great too.
• Sunset Grille – This was a cool spot right before Seven Mile Bridge, and would make a really great sunset option (and happy hour!).  They had delicious sounding apps, I grabbed the short rib tacos, fried Brussels sprouts chips, fried cheese curds, and a mojito after touring the Turtle Hospital.
• Morada Bay Beach Cafe – I’m sure this probably would have been a great restaurant for sunset, but was POURING when I visited for dinner.  So I didn’t really get the full experience, but found it overpriced (especially the drinks).  I got the fish & chips (red snapper), and it was pretty good though the coleslaw was terrible.
• SS Wreck – Definitely a locals place, fun to watch people interact. I got takeout because the weather was nutty and super windy, I was tired and it was the only thing super close to where I was staying.  The food was okay, nothing great.
• Curly’s Coffee – A little drive-thru or walk-up in Marathon, fairly basic (coffee wasn’t great but it was my best option). Try the Happy Keys Latte, iced…made with coconut and cinnamon.
• Marathon Bagel Co – I had an early weekend morning breakfast here and they have lots of choices.  I got the special with brisket (too crazy for me, but a fun idea), and a bagel with lox.
• No Name Pub – Famous for some reason, this dive bar was a bit out of the way, and I didn’t see anything special.  I didn’t have a meal there, so maybe the food is good?
• Mangrove Mama’s – Similarly, I made a quick stop here for key lime pie but didn’t try the food.  It’s cute but felt skippable.

A couple places I wanted to try but didn’t get to were Castaway and Marathon Grill & Alehouse, both in Marathon.

One thing to keep an eye out for is little hole-in-the-wall spots, shacks, food trucks, and the like.  I found some delicious empanadas and Cuban coffee one morning and took it over to Bahia Honda State Park for a beautiful breakfast moment.

A shout-out to El Habanero Cuban Coffee as well, a cash-only little stand I stumbled upon along the highway fairly close to my hotel in Marathon.

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And finally, all the delicious things to eat in Key West!  I had trouble finding good dinner options, because I didn’t plan ahead and make reservations, and I’m not willing to wait more than like 15 minutes for a seat.  But my breakfasts and lunches were primo.

• Banana Café – A great and extensive menu, I had a delicious veggie crepe with beets, asparagus, caramelized onions, goat cheese, and avocado, and one of my top-five key lime pies.
• Pepe’s Cafe – Similarly, the breakfast and key lime pie here was delicious (my #2 key lime pie overall!).  They’ve got a really solid-looking menu overall
• Cuban Coffee Queen – They have two different locations, serving breakfast, smoothies, sandwiches, and of course, delicious Cuban coffee.  The Margaret St. one has the iconic Key West mural.
• Keys Coffee Company – They make a frozen café con leche that is DELICIOUS!  It’s not a true slushy frozen, just bits of ice flecked throughout.  I had like four of these in two days.
• Key West Cuban Coffee – This spot had a fabulous menu but I’d already eaten way too much, so didn’t get to try the arepas or other delicious things on the menu.  I did, however, get an iced cortadito and it had WAY too much granulated sugar in it—blech.  The guava and cheese empanada was great though.
• Kermit’s Key West Key Lime Shoppe – One of the best key lime pie options in town!
• Blue Heaven – Tends to appear on every Key West list, but also tends to have a long wait.  I had a decent fresh fish meal along with a mojito and their famous “mile high meringue” key lime pie (which I wasn’t a fan of).
• Moondog Café – I devoured the Frenchman burger, truffle fries, and sweet potato fries with lime curry sauce while sipping their peach basil sangria.  Lol, so I liked it.
• Tiger Bar – I had dinner here one night and it’s definitely unique.  They have an interesting wine menu (I got the Lambrusco) and no real cocktails.  It’s a limited small plates menu, with some fascinating dishes (many of which I couldn’t eat).  I tried their tea-deviled eggs (delicious and interesting), beef tartare (good but hot, my favorite), Korean fried chicken (delicious but spicy), and lamb ribs (great flavor but fatty and hard to eat).
• Lagerheads Beach Bar & Watersports – A hidden gem right on the water, with a beach shack vibe and its own tiny beach you can sit on (note, the beach is public).
• Flamingo Crossing – Yummy ice cream!!  I tried the strawberries & cream and Cuban coffee flavors and both were great…I wish I could have tried more.  Note, it’s cash-only.

Boy, the list of places I didn’t get to try out is loooong…here’s the short list 🙂

• 5 Brothers Grocery – Supposed to have great café con leche.
• Sarabeth’s – Supposed to be delicious breakfast, and in a pretty older building.  I did have the key lime pie and was not a fan.
• First Flight Island Restaurant and Brewery – The southernmost craft brewery in the U.S., but is also located in the building where Pan American World Airways started in 1927.  Supposed to be a cool setting with good food and very good beers (and apparently, homemade sangria).
• Santiago’s Bodega – Great tapas (reservations required, even for the bar).
• Nine One Five – On lower Duval, supposed to have an imaginative menu and well-presented cocktails.

I am so glad I finally spent some time exploring as many nooks and crannies of the Keys as I could cram into one week.  Hopefully this Florida Keys roadtrip itinerary is super helpful to you for planning your own adventure!

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