Planning the Ultimate Vacation to the Florida Keys

Your Ultimate Guide to a Florida Keys Vacation

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Though I’ve been traveling to Florida annually since birth, it wasn’t until my 30s that I actually made it to the Florida Keys. And what fun SVV and I had! We flew into Miami the day after Thanksgiving, drove to Key Largo to start our week-long road trip through the Keys, ended in Key West and flew home from there.

Planning a Trip to the Florida Keys

This time around, we did things in reverse. We hopped a flight to Key West from Nashville that connected in Charlotte, landed a few hours later, then hit the ground running. Either way you want to do it totally works. Here’s how we laid out our trip.

Planning a Trip to the Florida Keys

Day 1

Upon touching down at Key West airport, it’s just a 10-minute drive to the heart of town. In fact, one of Key West’s biggest selling points is that it’s compact and very walkable. You can easily stay downtown without needing your own car.

Planning a Trip to the Florida Keys

We hailed a cab and headed straight for Marquesa Hotel, the most charming inn in Key West and conveniently located just a block off of Duval Street.

Planning a Trip to the Florida Keys

This historic home was built in 1884 and lands itself on every “best of” hotels list around. And with good reason: The rooms are stunning in their sophistication and the service top-notch. For those on the hunt for a bed and breakfast type of stay in Key West, look no further than Marquesa Hotel. Several locals we met throughout our stay also named the Marquesa restaurant as one of the best in town; I regret that we didn’t have time to try it, but as I always say—next trip!

Planning a Trip to the Florida Keys

After getting our bearings, we set out on foot in search of food; we were famished after a half-day of flying and wanted lunch as quickly as we could get it into our stomachs. Thanks to using the Yelp app, we found Frita’s Cuban Burgers, which is a legit hole-in-the-wall Cuban joint just a few blocks from our hotel that serves phenomenal street food (and plenty of that Key West beer!).

Planning a Trip to the Florida Keys

On our last visit, we’d done several of the big Key West attractions like the Butterfly and Nature Conservatory, the Maritime Museum and Tucker’s Provisions, so we explored the area with our cameras before returning to the hotel for a bit of much-needed pool time.

Planning a Trip to the Florida Keys

That night after cleaning up, we headed out on a boat for Wind & Wine Sunset Sail with Danger Charters. This isn’t your average booze cruise; it’s run by a handful of men who could easily double as stand-up comics. They make sure your glass is never empty and that there’s never a moment devoid of jokes.

Planning a Trip to the Florida Keys

And for those of you who are wine-adverse, there’s free-flowing craft beer. Hands down, this was my favorite sunset cruise to date in all of my travels. Oh, and the views aren’t bad either!

A Sunset Booze Cruise with Danger Charters | Planning a Trip to the Florida Keys

Our sailing adventure departed from Mallory Square, and once we were back, it was just five minutes by foot to our destination for the evening: Bagatelle.

Planning a Trip to the Florida Keys
Planning a Trip to the Florida Keys

It was a humid night, but we opted for an upstairs patio spot so we could do a little people-watching over Duval Street as we ordered a starter of lamb lollipops to share. I also tried my first ever hogfish, the specialty dish of the Keys, and now I can never go back. That might be my new favorite fish, period (sorry, walu!).

Where to Dine in Key West | Planning the Ultimate Vacation to the Florida Keys

We each sipped a couple of Manhattans as we gulped down dinner at this must-eat spot in Key West. And what else to end the day but a slice of key lime pie, my first of seven for the trip and arguably the best key lime pie in the Keys?

Where to Dine in Key West | Planning the Ultimate Vacation to the Florida Keys

Day 2

The next morning, we were up and at ’em early. Now, I’m not normally one to rise with the sun while on vacation, but we had a special reason to get out of bed: We were going diving!

Where to Go on a Keys Road Trip

We were booked for a two-tank excursion with Dive Key West, the first (and largest) full-service dive facility in the Keys. Bob and Cece, the owners, got us all decked out in our rental equipment, then drove us to the marina where Victoria, our dive master, and Jesus, the boat captain, took us to the outer reef for a morning of fun.

Diving Key West | Planning a Trip to the Florida Keys

After we got back, it was well past lunchtime so we went into town and had our second day of Cuban fare at El Siboney, a local institution, then took a little photo walk as we meandered back to our hotel. The houses in Key West are so dreamy that I might just have to dedicate a future post all to them!

A Walking Tour of Key West

That evening, we ventured east once more to Ibis Bay Resort for dinner at the Stoned Crab, where I ordered … hogfish. Again. This time, it came encrusted with pistachios and macadamia nuts. Yum! The restaurant also makes some pretty delicious drinks, served up in tiki-style barware.

Planning a Trip to the Florida Keys | Where to Eat in Key West

We didn’t have to wander far for our nighttime activity as we booked to go night paddleboarding with Ibis Bay Paddle Sports, but in the end decided on kayaks instead. What an interesting spin on traditional kayaking and one of the coolest experiences of my time in the Keys (stay tuned for the next post where I’ll go more in depth on each of our water sports).

Planning a Trip to the Florida Keys | Night Kayaking in Key West

When we got back to the Marquesa that night, the hotel was also lit up and I contemplated diving right in for a second time that day. But alas, time for a little shut eye before a busy day to follow.

Planning a Trip to the Florida Keys | Where to Stay in Key West

Day 3

In the morning, we picked up our rental car and drove out to Smathers Beach for some photos in the early morning light. Key West isn’t super beachy—the sand is actually imported from the Bahamas—but there are a few stretches of coastline you can hit up if you need your fix.

Planning a Trip to the Florida Keys | What to Do in Key West

Fun fact: Did you know the Keys are made of limestone and not volcanic, hence why they aren’t actually islands?

We had to be at Stock Island at 10am for a SUP Yoga class with Lazy Dog Adventures, and I’d been looking forward to this all week long. I own a paddleboard and frequently play around with yoga poses on it at home in Tennessee, but my 90-minute class with Kyla was next-level awesome. A bonus that the water was perfectly placid.

Planning a Trip to the Florida Keys | What to Do in Key West

After paddleboarding, Kyla pointed us toward Salute! on the Beach for lunch, which was exactly what we wanted after expending so much energy out on the water. Healthy salads with a view of the ocean to boot.

Planning a Trip to the Florida Keys | Where to Eat in Key West

On our way out of town en route to the Middle Keys, we hit up the Hemingway Home for another visit. We took a more extensive tour of the house on our last trip to Key West, but the home is just so lovely I couldn’t help but swing on through again. And it happened to be ol’ Ernest’s birthday, too!

Planning a Trip to the Florida Keys | Where to Go in Key West

Plus, you really can’t leave Key West without a visit with the famed six-toed cats. That’s just crazy talk.

Planning a Trip to the Florida Keys | Where to Go in Key West
Planning a Trip to the Florida Keys | Where to Go in Key West

Next, it was on to Islamorada—with a few stops en route. Adventurous Kate also happened to be traveling the Keys the same week, so we met halfway in Big Pine Key and had a pint (for me) and an iced tea (for her) at the iconic No Name Pub, which we figured is wallpapered with more than $20,000 in one-dollar bills.

No Name Pub in the Florida Keys | Where to Go on a Keys Road Trip

Henry Flagler took a great interest in the Keys and during the heyday of the railroad, the Overseas Railroad extended all the way to Key West. It was destroyed more than 80 years ago by a hurricane, but you can still see remnants at Bahia Honda State Park, which doubles as a refreshing swimming hole and snorkeling spot.

Where to Go on a Keys Road Trip

We only stopped on Bahia Honda Key briefly before continuing to Islamorada, arriving while still light. We got situated at our hotel, Amara Cay Resort, before heading out again.

Planning a Road Trip Through the Florida Keys

As opposed to our city stay in Key West, our Islamorada hotel was right on the ocean and has an on-site water sports outfitter. I still can’t get over how glassy the water is here!

Planning a Road Trip Through the Florida Keys

Where to Stay in the Florida Keys
Where to Stay in the Florida Keys

If you’re thinking right about now that it seems odd we’ve been in the Keys for three whole days and not found a brewery, I feel ya. Luckily, we changed that in Islamorada.

Where to Go on a Keys Road Trip

Florida Keys Brewing Co. had come highly recommended to us by several fellow beer lovers, so this was a priority on Islamorada. The brewery is just two years old and run by a husband-wife team, Craig and Cheryl. He tends to the brewing while she spearheads the marketing artwork—taps and beer cans included—and boy is it fun and colorful! Straight-up mermaid vibes going on at Florida Keys Brewing.

Where to Go on a Keys Road Trip

Planning a Trip to the Florida Keys | Where to Go in Key West
Planning a Trip to the Florida Keys | Where to Go in Key West

But aesthetic aside, the beer was damn good, too. I love how Craig weaves in so many local flavors, including—you guessed it—key lime. SVV’s favorite brew was the Iguana Bait, a honey hibiscus kolsch, while I gravitated toward the Smuggler’s Moon, an oatmeal stout.

Where to Go on a Keys Road Trip

Dinner that night was at Marker 88, a 50-year-old seafood establishment where we were slated to dine alfresco but a looming storm changed that plan.

Instead, we nabbed a table inside and indulged gluttonously before rolling ourselves back to the resort for the night.
Marker 88: Where to Eat in the Florida Keys

Day 4

We started our fourth day by backtracking a bit to Marathon to do the cutest activity in all of the Keys: visit the Turtle Hospital!

Visiting the Turtle Hospital in the Florida Keys

This amazing facility rescues and rehabs turtles, many of them having suffered human-inflicted injuries from boats, fishing hooks and pollution, while others having been victims of shark bites.

Visiting the Turtle Hospital in the Florida Keys

Planning a Trip to the Florida Keys
Planning a Trip to the Florida Keys

You can’t just show up and visit the premises without a guided tour—and tours usually sell out, too—so be sure and call in advance to secure your spot. It’s an hour and $22 well spent to get to see these peaceful creatures—with names such as Bonnie, Clyde, Spartacus and Donatello—up close and personal.

Visiting the Turtle Hospital in the Florida Keys

Fun fact: Any idea how they ship turtles who can’t return to the ocean to their aquarium or zoo forever homes? Fed-Ex! I’m not even kidding you.

The renowned Robbie’s and its on-site restaurant, the Hungry Tarpon, are on the way back to Islamorada, and we couldn’t resist a lunch of coconut shrimp fish tacos by the pier while we watched the other tourists feed the fish.

Feeding the Tarpon at Robbie's in Islamorada

Planning a Trip to the Florida Keys
Planning a Trip to the Florida Keys

That evening, we headed over to the Postcard Inn for cocktails at the Tiki Bar, which created the original rumrunner back in 1972. There were key lime mojitos and coladas on the menu, so I had one of each while SVV tested the rumrunner (neither of us regret our decision).

Where to Drink in Islamorada: The Ultimate Keys Road Trip
Where to Drink in Islamorada: The Ultimate Keys Road Trip

Then, we went to the Third Thursday art walk, which overtakes the “downtown” one night a month, before settling in for a meal at Chef Michael’s, the cherry on top of an already excellent vacation. More tuna, more hogfish and, yes, more key lime pie. Chef Michael’s was the best meal we had during our entire five days in the Keys.

Where to Eat in Islamorada: The Ultimate Keys Road Trip
Where to Eat in Islamorada: The Ultimate Keys Road Trip

As we left the restaurant, we ran into a local and asked her where the best sunset in Islamorada is. She first told us we were standing in front of the house on Bloodlines—seriously, I must watch that show already! the filming locations are all over the Keys—and then followed it up by pointing across the street to Pierre’s at Morada Bay.

Where to Watch the Sunset in the Florida Keys

She wasn’t wrong. And it took all of five minutes for us to see why Islamorada is said to have the best sunsets in all of the Florida Keys.

Where to Watch the Sunset in the Florida Keys

Day 5

On our final morning in the Florida Keys, we kicked it at the pool at Amara Cay until checkout time. The South was under a pretty stifling heat wave, and it was hard to motivate ourselves to do anything besides being fully submerged in water.

Art and Murals in the Florida Keys

Then, begrudgingly, we packed our things in our rental car and tried to prolong our trip with a second visit to Morada Bay. This time, we had lunch at the Beach Cafe—and one last key lime pie—to hold us over until we got to Miami for our flight.

Where to Eat in the Florida Keys

For divers and water sports enthusiasts, this trip didn’t include time in Key Largo and at John Pennekamp Coral Reef State Park, known for its snorkeling, fishing and diving. If that interests you, I’d suggest swapping out the time in Islamorada and focusing on Key Largo instead. Or better yet? Stay a full week, then you can allot a couple days to each!

Where to Go on a Keys Road Trip

For those of you looking for more information on planning a trip to the Upper and Middle Keys, here are past posts I’ve written, jam-packed with travel tips:


 

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Planning the Ultimate Vacation to the Florida Keys
Planning the Ultimate Vacation to the Florida Keys
Planning the Ultimate Vacation to the Florida Keys
COMMENTS
  • July 26, 2017

    Haven’t been to the Keys in years…but that turtle hospital…I need to go there!

    • August 2, 2017

      Add it to your 18-month road trip! =)

  • July 26, 2017
    Jim

    I love lamb and I love the Keys! We’re planning on going down this winter. Your pictures are inspiring us to see a little more than we planned on.

    • August 2, 2017

      That’s so awesome, Jim! Let me know if you need any additional tips =)

  • July 26, 2017

    hola.. this place is awesome.. great post. good luck

  • July 26, 2017

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  • July 27, 2017

    Looks like a great summer trip!
    And those are HUGE turtles! I hate that they’re there injured though 🙁

    • August 2, 2017

      I know! But so many of them are rehabbed and released in the ocean OR get to spend their days in leisure at the Turtle Hospital, far from the prying eyes (and mouths) of predators =)

  • July 29, 2017

    Really very amazing and eye-catching photographs, I love this place, Florida. These photos made my mind to think of a trip to Florida so that I can also enjoy its various charm.

  • July 29, 2017

    This post comes “just in time”! A friend and I are planning to visit Florida for the first time in March next year, so we are exploring our options. The Keys are certainly one of them!

    • August 2, 2017

      Yay! Good time to go. It won’t be nearly as hot then. And you can swing by Nashville on your way 😉

  • July 30, 2017

    Wow what an awesome place, love the sunset pictures. So much key lime pie, I’d love to visit one day!

    • August 2, 2017

      You can never have too much key lime pie!

  • August 2, 2017

    Ahh, great memories from when I lived in Florida. Somehow, I have yet to make it to Key West but I truly enjoyed a day in Key Largo. I was surprised by an ex and it was the very first place I went snorkeling. The food was amazing and I’d love to try out the booze cruise you mentioned.

    • August 5, 2017

      It is funny to think how close the Keys are to the mainland and yet so many people don’t go because it feels so far away! I didn’t know until a few years ago that it was just an hour from Miami to Key Largo by car.

  • August 2, 2017

    After reading your blogpost I feel like I desperately need to go to Marquese Hotel – it looks really stunning!

    • August 5, 2017

      You really do, Whitney! It’s worth the trip alone =)

  • August 2, 2017

    As soon as I saw the title of this post, I was thinking about how while I’ve taken trips to Florida for vacations and to visit family since I was a kid, I have yet to visit the Keys. So had a little laugh when reading your first line. This seems like such an amazing trip; would love the opportunity to snorkel or dive in the keys. Will definitely have to add a trip to the Turtle Hospital onto the itinerary too.

    Also, AMAZING shots!

    • August 5, 2017

      Right, Jasmine? It seems so much more far-flung, like a Caribbean trip that’s going to blow the bank. But it’s not—super easy to reach and if you fly in/out of Miami, same cost for airfare (I think flying into Key West is a bit pricier). If you’re wanting to snorkel/dive, I suggest starting in Key Largo at John Pennekamp State Park (we did this last trip) then ending with a two-tank dive at the Vandenberg, one of the biggest recreational wreck dives in the world. So cool!

  • August 2, 2017

    Wow!! Firstly, your pictures are incredible! Every location you visited looks out of this world, this post has definitely put Florida Keys on my bucket list! My boyfriend loves diving so I’ll be bookmarking Dive Key West for future reference!

    • August 5, 2017

      You definitely should! And you should request a day when they’re going out to “the Vandy” (the Vandenberg wreck). It’s TOO cool!

  • August 2, 2017

    I’ve heard so many great things about the Keys, and this showed me just how spectacular it is. The architecture is beautiful, and the sunset addict in me could just sit there for hours watching the colours change.

    • August 5, 2017

      The colors truly are magical! I hope you make it there someday, Bernadette =)

  • August 2, 2017

    The Keys look amazing! your pictures are so beautiful, Marquesa Hotel looks so lovely! it’s so cool the place where there are different types of beer and I’d love to visit the turtle hospital and offer my help 🙂 amazing article!

    • August 5, 2017

      Thanks, Kate! I hope you get to visit the turtles there someday =)

  • August 2, 2017

    I want to stay in that hotel in downtown so badly! It looks so clean and elegantly beachy. I went to the Keys 6 years ago with my then boyfriend (now husband) and we were very much on a college spring break budget! I would love to go back again with some looser purse strings and see more of the area. You’re right about the Ernest Hemingway House…a must see! I’ll never forget it.

    • August 5, 2017

      It’s the best hotel I’ve ever stayed in while traveling the Keys! Such great service and so pretty. And I agree: It’s a lot more fun to travel when you’re a bit older and have some income to spend 😉

  • August 3, 2017
    Chloe

    Your time in Florida keys looks like paradise!! I’d love to go sailing there, and scuba diving looked so much fun. Those turtles are so cute, that’s amazing they rescue them!

    • August 5, 2017

      The diving there is great! It’s probably the best diving I’ve ever found in the US.

  • August 3, 2017

    Your photos are so beautiful! I can almost taste the key lime pie. I would love to visit that turtle rescue. Such an amazing experience!

    • August 5, 2017

      Thank you, Kate! I need to write a key lime Pepsi challenge post one of these days 😉

  • August 5, 2017

    Looks drop dead dreamy! Just catapulted the Keys to the top of our wish list 🙂 What would you rate the kid-friendliness???

    • August 5, 2017

      Very kid-friendly! The best part, in my opinion, is that you can walk everywhere. We only took a Lyft a couple times and that was to get to/from the dive shop and the SUP.

  • August 5, 2017

    Beautiful place to go! Thanks for sharing this to us! Beautiful pictures 😀 I think what I will enjoy here the most is scuba diving and getting by with the turtles.

    • August 6, 2017

      You definitely would love scuba diving there!

  • August 11, 2017

    ‘Love this piece. I’ve never been to Florida, but my brother has, and he liked it very much!

    Very nice indeed!

    • August 14, 2017

      It’s got a little bit of everything: from theme parks (Orlando) to city life (Miami) to the most gorgeous water ever (the Keys)!

  • August 22, 2017

    This whole post is awesome. I personally would like to thank Kristine for the pretty pictures. I just love the keys now. We live in the NYC but never been to the keys. But guess what, Steve my husband said “let’s hit the keys” today after I passed him this link. I’m so excited. wish me luck.

  • September 15, 2017

    Florida is a number one place I want to visit as soon as I get to USA. It’s really unique place with awesome things to see and take some vacations at. Thank you for this awesome post, Kristin.

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