An Easy, Fun Florida Keys Itinerary Guide

 

Recently my best friend, Fran, and I decided we wanted to go somewhere warm and sunny for our next trip together. Here’s our easy, fun Florida Keys itinerary in case you want to copy it for your own girls’ trip!

We decided on the Keys for a few different reasons, the first being that neither of us had been in ages. Fran had gone camping with her husband a few years ago while I’d only been from training trips in college. All I remember for Islamorada were the pools, my bed, and this giant conch we all took a photo in front of. You can’t really enjoy the continental US’s most southern area when you’re worried about making it through 5 hours of practice every day!

We decided on a bit more of a girly trip instead of a totally adventurous one, so this itinerary is more of a relaxed one than anything. There are a lot of cool water sports and outdoor adventures you can get up to, and while we did one or two, we mostly just enjoy our beautiful surroundings and, of course, the food!

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Florida Keys Road Trip Tips

Yes, You Need a Car

You’ll obviously need a car as the Keys are very spread out. From Miami – Key West, it’s 3 hours, and I’m not even covering the lesser known northern Keys! I was gifted a 2019 Mitsubishi Outlander Sport for the trip, and it was a ton of fun to drive! The gas actually lasted quite a while — for all our driving we only filled up once towards the end. It’s as fancy as you’d expect a new car to be, and it felt even fancier to me because my normal car is, to put it lightly, very old. Old as in, I play music from my iPhone speakers because there’s no bluetooth audio or proper way to plug it into the speakers.

We took full advantage of the Carplay to blast Fran’s road trip playlist! If you want to listen to it yourself, here it is. Just a warning — lots of country mixed in.

You’re basically on one long highway

As you can see from any map, the Florida Keys are a super thin stretch of land from Key Largo to Key West. There’s basically one main highway that runs both ways through it, so it’s very hard to get lost! Of course, I used Google Maps for directions (or some of my friends prefer Waze). Time wise:

  • Miami – Key Largo: 1 hr
  • Key Largo – Islamorada: 1 hr
  • Islamorada – Marathon: 40 min
  • Marathon – Key West : 1 hr

What to Pack for This Itinerary

For the first time in forever, I found myself needing my swimsuits! I haven’t been swimming since my little summer trip to Jeju almost a year ago. Kind of weird when I think about the fact that I used to have the scent of chlorine embedded into my skin. 

Anyway, you’re definitely going to want a swimsuit for all the water activities! Otherwise, the Keys are very warm and humid, so think light, breathable clothes. I mostly wore dresses to keep cool! We didn’t do a lot of walking, so I think any pair of sandals will do. I would bring a pair that can get wet. I always forget my Birkenstocks rub badly when they get wet, so I had a pretty sizable blister after John Pennekamp! Here’s a quick list of the clothes I brought:

  • A few dresses
  • denim cut-offs
  • Birkenstocks
  • Nicer sandals
  • Loose shirts
  • 2 bathing suits (okay 3, but I didn’t wear the 3rd)
  • A waterproof camera or cover (well I bought this but I should have gotten one)

Our 4-Day Florida Keys Itinerary

Day 0: Land in Miami

I landed in Miami in the evening and Fran got in a few hours after me. It was easiest to stay in a hotel near the airport, and I just grabbed a small dinner at the hotel. 

If you have some time, we did check out the Wynwood Art District before we made our way south. It’s famous for all its colorful walls! The main area is Wynwood Walls, but the whole district is covered in murals, so you don’t necessarily need to wait until the Walls section is open.

Day 1: Key Largo

After getting breakfast in Miami, we made our way down to the Keys! Our first stop was John Pennekamp Coral Reef State Park for some snorkeling.

Noon: John Pennekamp Coral Reef State Park

While the tour starts at 1:30pm, they encourage you to arrive 90 minutes beforehand. You’ll have plenty of time to wait between checking in and the start of the tour, so I’d go hangout on the little beach area. 

The Snorkeling Tour

The snorkeling tour we did was about 2 hours with an hour for swimming around in a designated area. It’s about 30-40 minutes to get out to the spot by boat, so you can enjoy the ocean views! 

If you don’t have any equipment, don’t worry as they provide goggles, a snorkel, and fins, and you keep the snorkel afterwards. They also have a shop there to buy anything you may have forgotten like reef-safe sun screen, waterproof cases for your phone, towels, suits, and more. These photos are from Fran’s camera because I couldn’t get mine to work in my waterproof bag.

The tour itself is fun! I haven’t been snorkeling since… my island hopping in Thailand probably! The water was a little rough when we went — enough that some of the smaller kids didn’t stay in very long. But if you’re a decent enough swimmer, you’ll be fine. The coral reefs are beautiful, and I saw a stingray swimming by while Fran saw a shark. Check here to book a snorkeling tour & see their other tours

Stay: Ocean Point Suites

By the time we finished snorkeling and got back to land, it was around 4. We hung out on the beach for a little to finish drying off and then made our way over to Ocean Point Suites in Tavernier – a town about midway between Key Largo and Islamorada, though technically a part of Key Largo.

It was such a nice apartment, and I wish we’d had a bit longer to enjoy it. Besides our room and bathroom, we had a whole nice sitting area and kitchen. If you’re staying in the Keys for vacation, I’d definitely base myself here for a few days to see Key Largo, Islamorada, and Marathon. Plus they have their own little beach area, a pool, and a bar to enjoy. Check here for rates & availability 

Dinner: Sundowners

Once we cleaned up and checked in, we went to Sundowners for dinner! As its name probably suggests, it’s a restaurant on the water with gorgeous views of the sunset. Unfortunately, when we went it was cloudy and on the verge of thunder storming, so we didn’t get to see much of a golden glow. It was still nice on the water though and, of course, the food was delicious! 

When we sat down to pick out what to eat, we decided to try conch fritters as an appetizer. I got a mahi mahi dish, and Fran got a yellowtail snapper dish. My cousin told me before I left that I had to try mahi mahi, a dolphinfish found off the coast of Florida. It was pretty good! I wound up getting it another time later in Key West.

We finished off with Sundowner’s version of key lime pie. They actually have this nice meringue on top that helps balance the tartness of the pie but still keeps the whole dessert light. Super nice way to end the day, and we even had some kitty companions wander by! See their full menu here

Day 2: Islamorada – Key West

Moka Cafe

After we checked out of our suite, we decided to look for some coffee and tea before making our way over to breakfast. When I looked up local coffee shops, Moka Cafe popped up! It’s a super cute place, and we stopped by on our way back too. If you go, the parking is in the back. It’s kind of tiny on the road, so we accidentally drove by it twice.

Robbie’s Marina

Coffee in hand, we headed down to Islamorada to check our Robbie’s Marina and get breakfast Hungry Tarpon’s Restaurant. Fran remembered loving the area when she went before, and I can see why! It’s just a cool area off the highway. Besides the restaurant, there’s an open air market with little shops, a ton of water sport activities, fishing, and the Thirsty Tarpon Bar. Oh, and of course… feeding the tarpons! You can see all the different activities here.

Hungry Tarpon’s Restaurant

But first, we got breakfast! It’s served 6:30am – 11:00am, and we got ours around 10. Be prepared, friends. The portions at Hungry Tarpon’s are huge, which we should have guessed based off its name alone! I love breakfast food, and I’ve been known to polish off huge plates, and even I couldn’t finish my meal. 

I had the Hump, which is 3 eggs scrambled with bacon, ham, chorizo, and cheese with a homemade biscuit. You can see all their menu options here. When we joked with the waiter how big the portions were, he said the biscuit itself was a meal! Oh, also, we had a fun breakfast companion:

Feeding the Tarpons

Of course, we then went and fed the tarpons! Fran was much more into this than me, in case you couldn’t already tell which one of us is more outdoorsy. I wasn’t brave enough to hold mine and wait, so I threw mine into the mix. So much for my childhood dreams of winning “Survivor” haha. 

Since we weren’t parasailing because of the weather earlier, we decided to just enjoy the marina for a bit before heading down to Key West! There’s a nice beach area where we sat and hung out. And I got some shave ice which was delicious and also stained my mouth the rest of the afternoon.

Curry Hammock State Park

After we hung out for a bit, we got back on the road since we still had about 2 hours of driving left. In between Islamorada and Key West is Marathon and the Lower Keys, and we stopped off at Curry Hammock State Park to see the beach there.

It was so quiet and pretty! If you’re camping, there’s a nice site here for it. The water was like a massive reflection of the sky, and all we saw were some people fishing and a kayaking tour. If we didn’t have to check in to our accommodation around 4, I would have fished out my Kindle and stayed here for the afternoon reading. 

Curly’s Coffee

Another coffee break! Well, in my case, an iced chai latte break. This is a cute little stand in Marathon. You don’t really sit and hang out, just get your coffee and hop back on the road. 

Arriving in Key West

And we made it to Key West! We actually chose to stay at an Airbnb on Stock Island, which is about 5 miles from the downtown area. It was a sailboat in this marina and the perfect way to spend our nights after spending the days exploring. 

Wandering around downtown Key West

Once we got all cleaned up, we decided to walk around downtown Key West for a bit before our dinner reservations at 8. The first stop, of course, was Books & Books because I have an independent bookstore addiction. I wound up stopping myself from buying all the books and instead got this very cute postcard set of all the world’s famous bookstores. They even give you two version of each — one for you and one to send a friend. Remind me to bring these with me when I know I’m going somewhere, and I’ll send them to one of you guys!

Anyway, after the bookstore, we wandered around the streets, and I did a little shopping because I really needed to replace my broken purse. There are a lot of cute boutique-type stores if that’s your style, plus some typical souvenir shops with fun shirts and cheesy magnets. 

Sunset at Mallory Square

And, of course, we had to see if we could see the sunset at Mallory Square. Even if it’s cloudy, they have a daily Sunset Celebration where the square is full of different live performers. You can even find a psychic or two! We skipped all those and settled ourselves by the water to enjoy the view, though I did get us these ridiculously fun drinks above. They’re kind of pricey at $10, but you do get a free refill!

Dinner at Turtle Kraals

Before the sun could fully set, we walked over from Mallory Square to Turtle Kraals. We then spent about 1 1/2 -2 hours eating! I swear we rolled out of there with food babies. The food was so good, and Will, our server, showed as all the best stuff on the menu! 

Appetizers & Drinks

He started us off with some fancy drinks — Turtle Kraals’ own key lime margarita and for me a virgin Miami vice. YUM. Fran wound up getting two of the key lime margaritas. And, don’t worry, those are paper straws. Can’t expect a restaurant with “Turtle” in to still be using plastic straws. Appetizer-wise, we got some beer-steamed shrimp. We foolishly thought 1/2 lb wouldn’t be enough, HA.

The Ceviche

As we finished our shrimp, Will brought over their Key West ceviche. I normally don’t love ceviche, so we were going to skip, but he suggested we at least try it, and he wasn’t wrong. Apparently when Curtis Stone visited for the Food Network, he cleaned up two of their ceviche flights, that’s how good they were. And, yeah, I can see why.

I think whenever I go back to Key West, I’ll take whoever I’m with to just try the whole flight so I can try all the different types! Ours was made with hogfish, avocado, sour orange, jalapeño, cherry tomato, and basil. Beware the jalapeño! I accidentally ate one and my mouth was on fire for at least five minutes. The hogfish, though, was amazing. Like, if you’ve never tried hogfish, I strongly recommend you try it ASAP. They don’t call it the filet mignon of the sea for no reason.

Entrees

Entree-wise, I got the fisherman sandwich, and Fran got the tacos, which wound up being the perfect things to eat in the midst of all our food! I think anything heavier, we would’ve burst. 

Will also rustled us up some stone crabs to try since it was the last day of the season for them. I didn’t know crabs could be so meaty! Fran and I are used to Maryland blue crabs and whatever soups had crabs in Korea, and they’re, frankly, kind of thin, wimpy things in comparison. 

Dessert

Andddd to polish off this huge meal — dessert! We obviously had to try the key lime pie, and Will brought over banana bread pudding, a brand new menu item. The pudding was good but definitely too heavy for us after all that food. The key lime pie was perfectly light and actually closer to a cheesecake.

We basically got back to our sailboat and just sat on the deck for an hour letting all that food digest! See their full menu here

Day 3: Key West

Breakfast: Fisherman’s Cafe

We started the day by heading over to Fisherman’s Cafe for breakfast! It’s a cute place by the water, and they use only the freshest local ingredients. We had some freshly-squeezed orange juice while Fran got an egg and cheese sandwich, and I got the “El Cubano” breakfast sandwich.

Key West over all is pretty relaxed, but it felt especially nice at 9:30 in the morning. Most of the visitors who go out at night were still asleep, and you just saw some locals going about their business and saying good morning to each other. Chef Rick came and chatted with us while we ate and gave us a bunch of other places to try! We only had time to go to one, but here’s his list for you guys:

  • Five Brothers
  • Alabama Jacks
  • Riviera Cafe
  • Sandy’s Cafe
  • Garbo’s Grill

He also pointed out that we were sitting and facing a little, unassuming building where Jimmy Buffett does some of his recording!

Morning: Trolley Tour

From Fisherman’s we made our way over to Mallory Square to pick up the trolley tour! It’s such a cute way to see the city since we didn’t want to keep driving around downtown. They trolley has a bunch of stops at places we wanted to see, just make sure you keep your boarding pass on you. Some of the drivers were fine with a sticker, others wanted to see the physical passes. 

The trolley tour has a few different stops, but the main ones we wanted to get off at were Stop #5 and Stop #12.

Lighthouse & Museum

Once we got off at Stop #5, we went first to the Key West Lighthouse. Built in 1847 to replace one destroyed by a hurricane, it actually isn’t right on the ocean’s edge like most lighthouses I’ve seen. This was to protect it from the same fate as its predecessor. Once you get your ticket, I’d recommend going over to the old Light Keepers Quarters to see the museum and then climb up the 88 steps to get to the top for these views:

Ernest Hemingway’s House

Right across the street from the lighthouse is Earnest Hemingway’s home. You know, oddly enough, I don’t think I’ve ever read one of his books in full or even seen a movie! Just some of his short stories, and I read the book, The Paris Wife, about his first wife last year. I should probably get on that. 

Anyway, Hemingway first considered moving to Key West after hearing about it while living in Paris when his second wife wanted to move back to the States in 1928. Her uncle then brought them a carriage house in 1931, which is now known as the Hemingway home. I noted two interesting things about the house — that it was the site of the first in-ground pool in Key West, and that cats rule the roost here!

Seriously, though, enjoy all the cats. And let’s be honest, that was the main reason we made it a priority to stop here — so we could pet all of them. Some are descendants of Hemingway’s six-toed cat. See if you can find which ones by their paws!

Stop #11: The Southernmost Point

We then hopped off at Stop 11 to see the southernmost area of the continental US. This is by far the most touristy part of the whole Keys, so we didn’t linger too long. We just went to see the Southernmost House (and the Southern-Southernmost House), and went by the Southernmost Point. There was a line waiting to take a photo with the marker, so I just waited for a pause to get my shot quickly. 

From there we rode the trolley through its different stops and enjoyed the scenery from our seats. 

Danger Charters Sunset Cruise

Around 6 we headed over to Margaritaville Resort to check in for our Danger Charters sunset wind and wine cruise! It was the best way spend the evening with good food, fun company, good wine, and, of course, the sunset! We were worried in the morning as it was gray and cloudy initially, but the clouds had completely opened up by and the sunset was even better than the evening before. Book a seat on the cruise here

The food was perfect. I can’t comment on the wine since I didn’t drink any but Fran like what she tried. We actually wound up sitting in the best place for food! After they brought around the dishes twice for everyone to eat, they left the leftovers next to the door below deck. Guess who was sitting right next to that door? Heaven.

Evening: Garbo’s Grill 

Fran was still hungry after the cruise, so we walked over to Garbo’s Grill, which a lot of people recommended. It’s got a cool, backyard BBQ feel without the hipster pretentiousness I felt in another similar place I’d been to before. The food is made in this airstream, and then everyone can gather around and listen to live music. I normally hate live music unless I’m at a concert, but this guy, Rob Benton, was really good! And he sang songs people actually knew!

Day 4: Key West – Miami

Lazy morning on the boat

Since we had a later night, we decided to relax and enjoy our sailboat a bit. If you still have energy, the only other thing I had on my list that I wanted to do was to see Truman’s Little White House. Apparently while Truman was in office, he became so exhausted his doctor ordered him to go somewhere warm for vacation. He decided Key West, and since 1946 he would go there every winter.

Me standing in front of a Greetings from Key West Florida sign at Cuban Coffee Queen

Cuban Coffee Queen 

Before we hit the road, we stopped by the Cuban Coffee Queen! It has a fun Key West sign on the side, and Fran remembered her husband loving the coffee there on their trip. Get the Cuban coffee frappe! So, so good. See if you can see all the rooters running around in the parking lot too. Those guys are everywhere in Key West, and they walk around like they know they’re heavily protected!

Lunch: Moka Cafe Islamorada

On our way back, we stopped for lunch at Moka Cafe again since we weren’t super hungry. They have light dishes, so I got a sandwich and Fran got an acai bowl.

And that was it! Fran’s flight was around 4, so I dropped her off at the airport before returning my car and heading to the airport myself.

We spent our last minutes together picking at each other’s airport food court dishes — hers Chinese and mine Italian, which I think is pretty much the best image you need of our friendship haha. It was such a lovely trip and the extra dose of summer sunshine we both needed as the rainy parts of spring still lingered where we lived.

Have you been to the continental US’s most southern region? What did you fit into your Florida Keys itinerary? 

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I was a guest of the Florida Keys & Key West, and thus many of my meals and activities were covered. However, all opinions are my own.

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