Planning a Trip to the Florida Keys

A Road Trip Through the Florida Keys

[shareaholic app=”share_buttons” id=”20872686″]

I was so stinking excited to check one Florida destination off my list. I’ve probably been to the Sunshine State 50 times in my 30 years, no exaggeration, but I’d never made it so far south as the multicolored waters of the Florida Keys.

Sunset in the Florida Keys

After the months of no sleep and thinking and talking about nothing but KEEN round the clock, SVV and I had long-planned a post-conference vacation where we could do a little diving, lounge in the sun and take care of our rapidly growing reading lists (yes, we’re dorks). The Keys seemed like just the place. But first things first: How do you start in planning such a trip to a place comprising 800 islands?

I knew I wanted to start from the top and drive the full length of the 113 miles that spans the Keys. After all, it’s not a vacation if it doesn’t involve a road trip! So we booked our flights from Nashville to Miami, just a quick two-hour trip if we were to fly direct (we took the cheaper option and stopped over in Atlanta). I was shocked to learn that Miami is only an hour by car from the beginning of the Upper Keys. News to me. And it gave us a chance to grab some much-anticipated Latino food in Miami at food truck-turned-brick and mortar restaurant Latin House Burger & Taco Bar en route (delicious!).

But back to our actual vacation. We started in Key Largo, which has the third largest coral barrier reef system in the world, to get our fins wet. We were in luck in that the current and swells subsided just in time for our dives; two days before, there had been no boats going out. (More underwater coverage in the weeks to come.)

But after two nights in the Upper Keys, I was ready to arrive in the more idyllic isles of Big Pine and the Lower Keys. What no one tells you about Key Largo is that it’s full of a whole lot of strip malls and commercial establishments (don’t listen to the Beach Boys…lies, all lies). It was far from the sleeping fishing villages we had envisioned prior to losing our Keys virginity—which was fine; we were just there to dive after all. But if you’re not a diver or a snorkeler or are not traveling with kids, I would likely recommend skipping a stay in the Upper Keys and heading straight to the Middle Keys instead.

Next, we spent a night in Marathon, primarily to visit the Turtle Hospital, which was both a heartwarming and heartbreaking experience to see the pain humans can inflict upon such majestic creatures—but also to see what scientists are doing to save and rehab them. I wish we’d had time to visit Islamorada, simply because it sounds dreamy and pictures of Anne’s Beach (Mile Marker 73.5) make it appear as if it lives up to its name. But there’s never time to do everything, especially not in a week.

Snorkeling in the Florida Keys

Then it was off to Bahia Honda and on further to Big Pine Key, both places that elicited a sigh of relief: This is the Keys experience we were hoping for. We spent some time in the state park’s narrow patch of white sand then hopped in a two-seater for a paddle through the mangroves with Big Pine Kayak Adventures, which was one of my favorite parts of the entire vacation.

Kayaking in the Florida Keys

Finally, we arrived in Key West for the last four nights of our trip, and the true relaxation began. I always pictured in my head that Key West would be this major party destination, and while it’s true it has some awesome restaurants and some great bars (dive, gay, clothing-optional, you name it), I absolutely loved this island the most and would plan a trip back without hesitation.

Our days that followed on Key West included some diving, a lot of eating and even more drinking. We saw the mark Hemingway left behind (six-toed cats and all). We lounged 100 feet below the ocean’s surface with Lost Reef Adventures on the biggest wreck in the world that recreational divers can visit. And did I mention we ate a whole lot of food (key lime pie included)? That seemed to be the bulk of our time in Key West.

Diving in the Florida Keys

And then we flew home via Atlanta once more, arriving in Nashville to 29 degree—rare for this time of year; it was 65 when we left a week earlier—a third of the temperature from the 92 it had been that morning in Key West. And reality set in: Winter’s here, and I want to be back in Florida to wait out the cold months.

Key Deer in the Florida Keys

Have you been to the Keys before? I have a lot of tips and stories and photos to come—from the best key lime pie to the coolest shipwrecks—but let me know in the comments below if there’s something you’d specifically like to know that might help in planning your own trip there.

  • December 2, 2013

    Sounds like a great trip. Time to make my way to the US. Haven’t been there for more than 7 years. With all the stamps I have in my passport I’m not sure they will let me in though 🙂

    • December 4, 2013

      Seven years! Say it ain’t so.

  • December 2, 2013

    My boyfriend works in Key West for the winter months – over at Sunset Key’s restaurant, Latitudes. I went down the last time he was there, and we tried 915 – DELICIOUS. You’re right – there are so many great restaurants, but I’m not as big a fan of Key West. I found it a bit crowded and very much party central. All in all, he’s there again this winter, so another trip down will be had in February!

    • December 2, 2013

      We went to Latitudes–it was delicious! Yum. I didn’t think Key West was crowded UNLESS you went toward Mallory Square, then it was a whole different scene around the cruise port (one I didn’t like). But we stayed a little further south down Duval, where it was pretty quiet (then again, we were there just before the holidays so pre-high season) before moving to the Hyatt on the waterfront (I preferred staying away from the madness).

  • December 2, 2013

    That’s so funny, I just blogged about MY recent trip to the Florida Keys! We did a lot of the same things. I had a work conference in Key west but flew into Miami and drove down, staying in Key Largo on the way down and up on Key Biscayne on the way back. I went diving in both Key Largo and Key West (no Vandenberg for this newbie though – the divemaster said the current was so strong it would have been NO fun!). I agree with you about the strip malls and really enjoyed the beautiful secluded beaches of the middle keys. It it was quite interesting going to Garden of Eden with my coworkers and BOSS! Looks like you guys had a fantastic and well-deserved vacation!

    • December 4, 2013

      Ha! It was raining the night we went to the Garden of Eden so we didn’t get the typical experience (one dude was topless and that was about it HA).

  • December 2, 2013

    I’ve never been to the Keys but it looks pretty incredible, especially those turtles!

    • December 4, 2013

      The food in Key West is REALLY GOOD, which I know you’d appreciate =)

  • December 2, 2013

    The Keys are such a special place! We snorkeled in Key Largo and off Key West- but haven’t dived yet. Need to get certified!

    So, what was the final tally for key lime pie?? 🙂

    • December 4, 2013

      Get certified, get your advanced, and do the Vandenberg! Trust me on this one =)

  • December 2, 2013

    Ooh, so pretty! I’m going to be in Miami in February – maybe I’ll get a chance to drive down to Key West!

    • December 4, 2013

      If you’re going all the way to KW, I’d give yourself 2-3 days so it’s not rushed. It’s not a long distance but the drive can be slow due to it all being on bridges!

  • December 2, 2013

    From the turtles to the kayaking… the Keys sound like a place I’d love!

    • December 4, 2013

      Yes, perfect for the active traveler—we’re not very good at sitting still so it was a good vacation spot for us =)

  • December 2, 2013

    Haven’t been to the Keys in decades but loved the lush little islands and fun in Key West. Even snorkeled there.

    • December 4, 2013

      Snorkeling this time of year is a bit off-putting as it’s jelly season (see this Friday’s post for Scott’s sting!).

  • December 2, 2013

    Great tips here….I was crazy and drove the entire Keys in 1-day. Enough time for a wander around Key West and a few quick stops….but not nearly as much fun as your trip! Next time I go…I’ll know where to stop with more free time.

    • December 4, 2013

      Wow! And I thought we were ambitious to cover it all over a handful of days, ha =)

  • December 3, 2013

    I did the drive from West Palm to Isla Morada many, many years ago. This makes me want to take the whole route though! I’ve never been to Key West and I would love to!

    • December 4, 2013

      Oooh you stopped when the pretty parts began! In my opinion, Islamorada to Key West is the best stretch of the Keys.

  • December 4, 2013

    Take me (back) with you!

  • December 6, 2013

    I really, really, really want to visit the Keys. I’ve never been, but it’s super high on my list. I’ve heard such great things and I love six-toed cats so much that I just know I’d fall in love with the place.

  • December 7, 2013

    I went to Key West one time for 2 days, and it was way too short! I don’t know what it is about that place, but the relaxation just melts into you…it feels impossible to be stressed. Everything is at a slower pace, but not in a way that is annoying. The vibe was so welcoming, so easy, it felt like anything fancier than flip flops would be way overdressed. I could absolutely see myself living there!

  • December 7, 2013
    mamma Lori

    Kristen thanks for your post with pictures. We have reservations to tent camp in Sugarloaf Key (lower keys) soon! Any suggestions?

  • December 7, 2013

    You of all people deserved a vacation — I’m so glad you took one! I’d love to dive the Keys, so I can’t wait for that coverage!

  • December 9, 2013

    Thanks Kristin, this was helpful as I’m just starting to plan a trip there for the end of Sept. Good tips!

  • December 9, 2013

    aw! the deer!

  • December 9, 2013

    Our family used to vacation in the Keys a lot. Mom and Dad would rent a house for a month in the summer or a week during Easter or Thanksgiving. We always stayed on Lower Matecumbe Key and snorkeled on the reef right in front of our house! We’d take the boat to Indian Key to explore artifacts or Lignumvitae Key State Park (but the horse flies were terrible and hurt!) The house we rented had a separate kids wing, and my mom made sure we had nintendo to entertain/distract us from ever being bored. There were four of us kids at the time, and different family friends would come visit/stay with us each week. It was a pretty sweet set-up! When we got a little older, we stayed closer to Key West and brought friends/significant others with us. We’d drive in to Key West some days and bar/restaurant hop. Love they Keys!

  • December 12, 2013

    The Upper Keys – from Key Largo to Islamorada – are cluttered with touristy shops and motels, and from the highway you can’t even see the water. But as you go further south into the Middle Keys , the land starts to open up, offering the startling realization that you’re actually driving from island to island. Trailing off like ellipses, the islands get smaller as you reach the Lower Keys, which is everything from Little Duck Key on. But far from petering out, the keys reach their grand finale at the end of the highway in Key West – many visitors’ favorite key of all.

  • December 16, 2013

    I’ve been fiending for some diving lately. Being landlocked is eating at my soul!

  • December 28, 2013

    Your journey is really beautiful and full of colorful waters. Thanks for sharing your journey. I have included Florida in my bucket list.

  • October 4, 2014

    That is really interesting information. We provide Best Event’s to our customers in Florida and its near places in USA.Please do visit at our website or contact us any time, we would love to help you.

  • January 21, 2015

    Thanks for the tips, Kristin! We went out with Big Pine Kayak Adventures today and it was a blast. The creek through the mangrove trees was just as beautiful as your pictures and our guide was so knowledgable about all the marine animals and wildlife. So glad to have your insider knowledge on where to go!

  • June 5, 2016

    best deal of homes selling and buying in florida

  • January 10, 2017

    Florida is an awesome destination. Author scribbled in a nice way. Worth reading.. Cheers!!

  • May 10, 2017

    nice post, thanks for the share

  • May 10, 2017

    good post, thanks for the share

  • July 4, 2017

    Hello Kristen,
    I really enjoyed reading your post. My question is whether we should be driving from Miami or doing a 1-Day tour instead.
    We’re drivers under 25 of age, meaning that car rental would be expensive, but if a trip to Key West is worth it we wouldn’t mind. Also, how many days would you recommend us to stay in KW?

    Any suggestion would be greatly appreciated. Thanks in advance.

    • July 7, 2017

      Hi Rachel! Funny you should bring this up, as I’m headed back there in two weeks myself. To get down there and back up, you’d need a solid three days (though more is obviously always better!). It’ll take you a solid half a day to reach Key West as you’ll want to stop over and see things en route and then you need two days there if you can swing it, as it’s so pretty (and very walkable!).

  • July 5, 2017

    What’s up,I log on to your blogs named “How to Plan a Killer Trip to the Florida Keys – Camels & Chocolate: Travel & Lifestyles Blog” like every week.Your story-telling style is awesome, keep up the good work! And you can look our website about free anonymous proxies.

  • December 28, 2017

    Planning a trip in March. Would love to not be on a schedule and stop and stay where ever we feel like it. My question is on hotel / motel availability. Would you recommend advanced reservations? Any hotel recommendations? Thank you in advance.

    • December 31, 2017

      Hey Marla! I actually have new Keys content from this summer you might want to check out:

      I’d highly recommend staying in the Marquesa in Key West and Cheeca Lodge in Islamorada. I’m not sure about availability because I don’t know if that’s still high season. I would imagine January-April are the busiest times there, however, I think with the hurricanes, you might be in luck on being able to maintain a flexible plan. We were there in summer, which isn’t high season, and there were plenty of hotel rooms to come by!

  • June 18, 2018
    Julio Vila

    Sorry to say hurricane Irma devasated Ann’s beach not much left of it, parking is under water unless they bring in sand and remake it wont be much of anything but a shoreline

  • September 16, 2018
    Ann Marie

    We went to Key West for four days in April 2016 and absolutely loved it. We are headed back there for our honeymoon in April 2018 and will be there for 6 days flying into Miami and driving down to our hotel halfway. Important to me was driving on the 7 mile Bridge, I grew up in Miami and loved that drive! Can’t wait

Leave a Comment