I probably wouldn’t have taken this trip if Beast Pacing didn’t send out a call asking for pacers for the Islamorada Half-Marathon. First of all, I didn’t know about it. I’ve really only heard of Islamorada (which I found out is not pronounced eee-lamorada with a Spanish “I” but is pronounced with the long “I”) from seeing it advertised in post-holiday season winter get-away commercials and from the Netflix show Bloodline. Second, I’ve almost gotten to the point where I don’t know how to plan a vacation that doesn’t have a race in there somewhere, including a vacation to just get away. Sometimes you need a reason to get the things done.
Mostly, I felt guilty about taking another trip, even if it was just for a weekend. I’ve taken a lot of trips this year: Disney World, New York City, Roanoke, Omaha, Oregon, Ohio, New York City again, soon Omaha again, and lots of day trips to the beach or the mountains in between. Islamorada sounded expensive, considering it was close to Christmas and my budget was sapped from traveling. But it’s also been a year of many downs and I needed something to prove I was not defeated. The Florida Keys has been on my bucket list for a long time, and when life continues to be a drag, checking something off your bucket list is a great way to feel like you’re somehow still in the game. To make it happen, I knew that I probably wouldn’t be able to stay at the nicest place on the island. I would likely not get to do half the things I wanted to do there. I realized I would either have to plan things to the teeth or just let the weekend evolve on its own and save some stuff for later. But perfect can’t be enemy of the good, and sometimes a fix of emerald palms framing white sand beaches and aqua water is all you need.
This weekend was my first time visiting the Florida Keys, so I had no idea what to expect. I spent days drooling over beach resorts, daydreaming about swimming with dolphins and manatees, trying to comprehend the beauty of crystal aqua water, giggling over funky tiki bar names and Googling “conch fritter,” listening to My Happy Place playlist on repeat. Already deciding I will be back for this race next year, and making sure to put a Santa hat, my waterproof iPhone case, and “No Shoes Nation” t-shirt on my packing list. Obviously. By Friday afternoon, I was literally bouncing in my chair at my desk wondering what I would be doing 24 hours from now.
I know this is a recap of the race, but it was also a weekend get-away for me. So, for those of you reading this and considering whether to run it in the future and looking for tips, I’ll try to categorize the aspects of the race that I want to write about from what I did while on my mini-vacation. But I hope you’ll read both parts, because I feel like this race better for building around a vacation and not just popping in for the weekend, unless you happen to live close enough to make it happen.
And, since I ran as a pacer with my entry compensated, just like I wrote in my recap of the Rehoboth Beach Half-Marathon, this post represents my own personal views and not those of Beast Pacing or the Islamorada Half-Marathon.
Getting to Islamorada
I took the first flight out of DCA at 6:10AM, nonstop to Fort Lauderdale, arriving at 8:39AM. I don’t know Florida that well, so someone recommended flying there instead of Miami. Even though I brought a carry-on, Jet Blue made me check it because they thought it would be too big for the overhead bins (it wasn’t– plenty of other people had roll-on suitcases, so I lost about half an hour waiting for them to deliver it… jerks). Renting a Hyundai Sonata, I drove from Fort Lauderdale on Florida 821 to Homestead and connected at Florida City to US Highway 1, which is the only road through the Keys. There are tolls on several roads, even if you take the route I took back to Fort Lauderdale through Miami, so I added about $10 a day through the car rental agency to pay for a Sun Pass. Rental car, all costs included, was around $100 for 2 days. Not bad.
The entire trip to Islamorada was about an hour and a half from Fort Lauderdale, even in the craziest rain I’ve probably ever driven through and not counting the stops I made at Publix for water and Florida oranges or Starbucks for coffee. Next time, I’ll take the scenic drive down the infamous A1A and hope for better weather.
Experiencing the Florida Keys
Once I linked up to US-1, it really started to hit me what I was doing: I was crossing something off of my bucket list. I realized how long I had been wanting to explore the Florida Keys, and here I was, making it happen. Driving the two-lane highway over Cross Key past Blackwater Sound and over Lake Surprise and Jewfish Creek, getting closer to Key Largo and seeing a part of the country I’d never seen before. Best feeling ever.
I almost stayed in Key Largo, and I’m really glad that I didn’t. Though I don’t see any reason why you can’t if you decided to run this race. I passed the hotel I had booked and, it looked nice, but it’s almost right there as you cross into Key Largo and I was really going for that “world away” feeling. I was actually surprised at how commercial Key Largo is. And I could barely see the water because it was blocked by trees and buildings. I caught glimpses of it through gaps here and there, but otherwise I sort of felt like I was driving down the middle of a highway in Nebraska. Except that there were so many palm trees, some of them with bright chartreuse coconuts. I’d never seen that before. I also noticed a bike path alongside the 2-lane Overseas Highway with a lot of cyclists on them. I wondered if perhaps it was time to consider running the Keys end-to-end…
Before coming on this trip, I read up as much as I could about things to see or do while I was there. Since I had limited time and was on a budget, I knew I had to make some things a must-see but I also had to be okay with leaving some stuff for my next trip (I am so not done with the Florida Keys). I found this guide from The Matador Network useful in helping me prioritize my agenda (locals have the best vacation to-do lists) as well as The Florida Rambler’s “Road Trip: Florida Keys Mile-Marker Guide.” I discovered quickly that almost everything there is referenced with a mile marker and not always a whole mile marker, but that also means it comes upon you fast when you’re driving. If you want to check everything off on this list, it looks almost better to bike it.
There is no shortage of things to do, see, or eat in the Florida Keys, but for my first trip, I decided that I really wanted to just experience it and let things sort of happen on their own by stumbling on them. I had a food and drink bucket list, and my first stop on it was at Mile Marker 100.5: Key Largo Chocolates. It was hard to resist the bright pink and green decor and I was so distracted by all the truffles and the free samples of Key lime white chocolate and fudge that I forgot to ask for their famous frozen Key lime pie on a stick. I picked up some Key lime fudge and some jellybeans for my co-workers.
After that first stop, seeing that it was already almost 1PM, I decided I was ready to get my packet and then find a beach or a tiki bar for lunch. I drove straight through to Islamorada, windows down and music up of course, to the expo location at the Guy Harvey Islander Resort. I arrived at the resort just as the Beer and Beach Mile was ending and just as the rain was about to begin. It was a windy day and overcast, unlike the sun in Key Largo. Florida weather is incredibly fickle when it comes to rain. I decided to wade into the water for a little bit before getting my packet. Seeing the white sand beach and wading into crystal blue water topped my weekend list of musts and, with the rain clouds looming above and a breeze whipping through, I wasn’t sure if I would get another chance.
The expo was definitely the coolest one I’ve ever been to: it’s literally on the beach, just feet away from the ocean, in the sand, and situated in between palm trees. There were a few merchants selling some athletic wear and getting my bib and T-shirt was fast and easy. The shirt is already one of the ones I will definitely not be cutting up to put on a race quilt. They run small, so make sure to size up. Also, there was a T-shirt company on site to personalize your race shirt for $10. If you’re the kind of person who likes to pick up race swag, there wasn’t anything to offer here. Maybe in future years, they’ll offer something beach-themed as an extra but I felt like this was one of those races that the shirt, medal, and experience was enough for me. I was just glad to be there at all.
Following the expo, with it being about 1:30, I decided to go check out the Florida Keys Brewing Company. This is where the expo is held the day before and the after-party following the race on Sunday. The brewery was lively when I walked in and, I wasn’t sure how long I would stay, but I decided to just hang out for about 45 minutes on “island time.” I’m not typically the kind of person who can sit at a bar and just hang out on my own. I don’t mind doing things on my own, but I prefer the company of others at least when I am at a bar. I decided to just go with it and hang out, and I actually really kind of enjoyed just sitting there watching the bartenders serve other patrons and doing some people-watching. I tried 5 beers, all of them I recommend: Great Pumpkin Demise, the “Cold” Front (my favorite), Beach Bum brown ale, Iguana bait kolsch, and the Smugglers Moon. I also sampled Flakeys, which is beer with, as Kenny Chesney puts it, “a hiiiint of lime.” My hotel was about half a mile down the road, so I considered stumbling back there later that night after dinner. I really loved that little bar for the short time I was there!
Where To Stay
In deciding where to stay, I actually went back and forth a lot. My very first choice was in Key Largo, about 16 miles up the road. I found it on Hotels.com, which is usually who I book my lodging through, and it was about $100 cheaper than where I ended up staying. I ended up at La Siesta Resort and Marina in Islamorada, spending roughly $189 for the night, which included the discount and resort fee. I decided to book there because it was one of the partner hotels for the race, so I got a 15% discount. Additionally, due to my pacing responsibilities, I couldn’t leave until the 3:00 pacer crossed the finish line, which meant I had a short window of time to get back to my hotel to shower and check out, so proximity took priority and the Postcard Inn and Pelican Cove (the host of the race and its next door neighbor) were sold out by the time I booked. Book early if you want to stay at the hotel where the race starts.
Also, I knew without having done any research on the Florida Keys that there were at least two things I wanted to do: lay out on the beach and go paddle-boarding. Going with a cheaper hotel option meant I would likely have to drive around to find a public beach, and I only found two nearby: Anne’s Beach and Harry Harris Park. Most resorts, at least the partner hotels, have private beaches with chairs. Also, La Siesta had paddle-board and kayak rentals for no extra charge (it should be included in the resort fee that is typical for resorts in this area). Seeing that most independent places charged between $25 and $50 an hour, or that a half-day was more comparable, I sort of built in that cost.
In the end, I absolutely loved La Siesta. It was quiet, beautiful, clean, and it had a luxurious feel without being over-the-top. It had that charming Florida beach cottage vibe. My room had 2 queen beds, a small kitchen, full bath, and a couch area with a dining room table, so it was big enough for a family. After coming and going for the rest of the evening, I really felt like I was coming home. So, I highly recommend it. The only reason I would not stay there again is because it is far from the race start and finish, which doesn’t work when you have to check out that same morning. So, if you only go for the weekend like I did, stay as close to the start line as you can so you can easily get back to your room before check-out and still enjoy the after-party. Or just go without a shower, but good luck explaining that to your seat mates.
That Clear Water Though…
For basically my whole life, I have adored crystal blue ocean water. There’s just something about it: I can’t look away. Add palm trees and white sand, and it’s almost too much for me to grasp. It looks like heaven on earth. My resort was totally gorgeous– a nice little beach area with yellow sun chairs and a marina. Bright pastel-colored cottages with tiki-funk names, hammocks strung between palm trees swaying in the breeze, a huge thatched roof hut covering a picnic table, boat slips and docks that were perfect for sitting with your legs dangling. So cute, it almost felt wrong not to be there longer.
I could hardly sit still just watching the clouds roll on the horizon and the sun illuminating the shallow ocean water. I had to get in it somehow, but there wasn’t a typical beach area to go wading in at La Siesta. I wandered over to the corner of the property where the boat rentals were located, looking to see if perhaps a quick SUP could happen. I wasn’t expecting much: it was “supposed” to rain for hours already, and the wind was pretty strong. The hotel staff wouldn’t rent paddle-boards for winds over 10 nauts, but I was able to grab a kayak, which isn’t my first choice for paddle sports, but at least it got me on the water.
Once out on the water, I was glad that paddle-boarding was off the table: the wind picked up pretty good in the latter half of my session. It was also my first time paddling in ocean currents, even if there are no big waves in the Florida Keys, so I had to focus. My kayak was a little narrow for my taste and I definitely almost capsized a time or ten. But looking down over the side into the water, the water was so clear I could see almost everything on the sea floor. I drifted around for about an hour, doing more drifting than kayaking. Hopefully next year, I will have my own SUP board and I’ll be able to take it out for longer and on a nicer day, but I was just grateful to have gotten some time on the water at all.
After kayaking, I checked into my hotel and grabbed a shower. I was totally drenched from kayaking and sweating all day, so a hot shower felt completely refreshing. Afterwards, I realized that I had not eaten much of anything all day long, so I was definitely ready for dinner. But, since I was the “team lead” for the Beast Pacing team, I had a few things to take care of before I could eat. One of them was waiting for me in a text message: some of my team members needed me to pick up their packets for them, and it was already almost quarter to 5 when the expo shut down. I quickly drove back to the Islander Resort, about 4 miles away, and grabbed their packets just as the rain started to pour.
And pour it did. It poured for probably about 12 hours straight that evening and into the next morning. The sun was starting to set behind thick rain clouds as I headed back to my hotel, and it was so gorgeous over the water that I had to follow it and try to find a place to get a good picture of it. Luckily, Anne’s Beach (one of the nearby public beaches) was close. I quickly drove to it and was able to see the sun set, even in the pouring rain. Kite boarders were just packing up at Anne’s, and I ran into a few fishermen who just didn’t care what was going on. I had thrown on a dry shirt in my hotel room, but that was now soaked again.
Pardon a terrible pun, but the rain really didn’t put a damper on my trip. Sure, I would have preferred a clear day of sun and water with a warm, balmy sunset painting a clear sky for my time in the islands, but I learned that the rain and storms in paradise are just as beautiful. It’s hard to be upset about a little rain when you’re in one of the most beautiful places on earth.
Where To Eat
I had literally not eaten anything except Pop Tarts, coffee, Key lime chocolates, and beer all day. I had been saving my appetite for some of the Keys’ legendary cuisine, but I had somehow been so busy enjoying the environment that I had forgotten to eat it! All I knew is that I needed carbs for the race, and I wanted to try conch fritters and top it off with a slice of Key lime pie. Finding a place that sold coconuts with straws to drink from it would have been a bonus, too.
There are many iconic restaurants in Islamorada, including lots of roadside seafood shacks (the kind of thing to give you major pause in the Midwest, but totally fine here since it’s caught fresh daily), but I needed a place that would give me a bang for my buck: seafood, dinner on the water, entertainment, great meal, nice view. I drove up the road a little ways, in the pouring rain, to Lorelei’s Cabana Bar. Hardly anyone was there, which could have been because it was already dark and the rain was crazy insane. I still expected an indoor seating area, but there was none. So I took the second recommendation, Lazy Days. It was highly recommended by the hotel staff to make reservations if you plan to dine here.
I found a seat at the bar and ordered conch fritters and a rum runner. Sitting at the bar and eating dinner sort of made me feel awkward, unlike the fun I had at the brewery earlier. At that point, my inner introvert was screaming “red alert!” so I decided to order the rest of my meal (pasta rosada and Key lime pie) to go.
When I left Lazy Days, the rain had stopped and the wind was rustling the leaves of the palm trees. It was actually very serene as I stood next to my car, listening to the wind in the trees and the lively sounds of the restaurant light up the darkness in the parking lot, knowing the ocean was just to my right. I realized that I loved it here.
Back at my hotel, as the team leader, I had to put together the pace team’s race signs. I used a hot glue gun, anticipating that the wind would be insane during the race because it was already kicking up. It was pouring rain again, so I stepped outside onto my porch and stood there watching it come down in sheets from the porch above me and in the lights of the cottages in my view. I’m still convinced I have never seen that much rain in my life. While the glue on the signs dried, I grabbed my pasta and Key lime pie and sat outside listening to the rain fall and the wind rustle the palm leaves. I could have probably sat out there for hours just listening. I wished I had my ukulele with me to play Christmas songs. The view from my porch was kind of like that Corona Christmas commercial. I was in love and, for the first time in awhile, fully present in the moment. Not that it was hard to be.
Throughout the night, even as my porch sliding door was closed, all I could hear was the wind and the rain. It wasn’t so loud that it kept me up (in fact, it was quite lovely to fall asleep to!), but I was definitely nervous for race day conditions. My alarm went off at 5AM. I stumbled around, getting dressed and packing up, trying to sip coffee from the Keurig in my room. I drove to the Postcard Inn, about 4 miles away, in the pouring rain. I was supposed to meet my team at 6AM, and I did not want to be the one who was late. When I got to the Postcard Inn, which was where the race starts and ends, I was a little bit alarmed to find no one there. Usually, when I pull up at a race site, there are already tens of people wandering around.
It was still incredibly dark outside. Not much overhead or street lighting, which between the pouring rain and the driving wind threatening to carry the race signs out of my arms, I was kind of overwhelmed. I was wearing flip flops to keep my shoes dry as long as possible and a rain poncho, but I was walking around through more puddles than I could count. Some of them were so deep I half-expected a crocodile to have already claimed it. Finally, I saw a runner in a bright yellow shirt: another pacer. Thank the Lord! I called to him and we found the start line, around the other side of the hotel, with a few more pacers underneath the start line banner. The rain had slowed down, almost suddenly, and the wind was still strong. Once we got the rest of the pacers together, I went back to my car to change into my shoes. Other runners were starting to show up, and I was feeling a little less panicked that somehow I had gotten the start line wrong.
After a quick photo of the pace group on the beach, we lined up with the runners and started. My gun time was around 42 seconds, and there were no corrals. Instead of using the three watches and pace band like I did in Rehoboth, I decided to just rely on my Garmin Fenix 3 because I saw that the timer was reliable, even if I couldn’t nail down my pace per mile until the end of the split.
The Islamorada Half-Marathon and 10K are flat, with just a slight elevation going over a bridge you will cross 4 times that links two of the islands in Islamorada. You are in the tropics, so you can absolutely bet on having a warm and muggy race, unless you book during one of Florida’s infamous polar vortex conditions of 60 degrees (ha ha). There may also be a little bit of wind. I read that the winter months in the Keys are windy, which also makes it for great kite-boarding weather. Honestly, the wind wasn’t the worst part except going over the bridge each time. The water under the bridge is so beautiful, it’s hard to complain with 30mph wind in your face.
The course itself winds down part of Overseas Highway and onto the side access road and bike path in some parts. There is a turn-around at the first 5K in the Upper Matecumbe Key, and you loop back up to the Postcard Inn for the second 5K. There is plenty of room for spectators, but there were hardly any so expect a relatively quiet course. If you are running the half-marathon, you continue on past the Postcard Inn and make a loop near the Windley Key Fossil Reef Geological State Park before turning back around and heading back to the Postcard Inn for the second loop. Because of the rain, you’ll likely run through some puddles and there is a little bit of a bottleneck in the first 10K as there are two races going on at the same time.
This year’s course may differ from courses in future years, since the race directors had to change the course due to construction. But it was a nice course just the same. It went past the tiny little shops in Islamorada, some of the beach cafes and resorts, the History of Diving Museum, the Hurricane Memorial, and the Theater of the Sea marine life attraction.
As far as aid stations, they were a little bit sporadic and very tiny. Most of them were run by local volunteers, including girls from a local dance academy. One older man was handing out water and Gatorade by joking, “Martini? Rum runner? Here’s your margarita, sir!” It made everyone around us laugh. Definitely make sure you bring a lot of fluids for this race. The humidity is very tropical, so you’ll likely need a lot more than what was offered. There was also no Gu or nutrition on course. If you plan to run this race, remember what you do to train in the peak of summer and do that for this race.
As a pacer, the mile markers were not clearly visible and were about a quarter mile off from my Garmin, so I found that to be very stressful. I didn’t see markers until Mile 7, but making the loop around in the back 5K, I saw there were mile markers that were yellow cones and some of them were turned around. That made pacing the last few miles very difficult. My timing was completely accurate, but I had to slow down to under a 12:00 pace to keep from finishing too quickly and then speed way up in the last .1 miles to keep from crossing over 2:30.
I actually finished in exactly 2:30. That was both awesome and terrifying. I prefer a healthy time cushion, so I was lucky to have realized in the last few minutes of the race that I might not cross the finish line without a surge. I also don’t like to surge when I pace races, because I am very aware that people around me are giving it all they’ve got and may not be able to keep up with me. I ran most of the race with someone who just had knee surgery and then met up with a runner named Morgan from Marathon, Florida who was 25 and running her first half. In the last mile, she caught up with her dad who ran with her for a little bit, coaching her. I could hear him say, “Follow the pacer; she’ll get you over the bridge.” I realized just how important and rewarding pacing can be. And I was also nervous again that I would miss 2:30 and hand someone a disappointment. I was kind of lucky with this race, and I’m learning more and more how to “run by feel.”
Rounding Out My Trip
Once I checked out of my hotel, I had about 2-3 hours to check off a few last-minute explorations before heading back to Fort Lauderdale. I decided I wanted to find a beach where I could wade into the water, especially since the sun was out now. I decided to go back to Anne’s Beach, which is known for its very shallow waters. While it was very beautiful and watching kite boarders in the distance skate across the water, there’s nowhere to sit down and relax and part of the deck connecting one end of the beach to the other through mangroves was broken. It’s definitely a better beach for launching water sports than for laying out in.
Following my stop at Anne’s Beach, I decided to head back to the Postcard Inn for some lunch on the beach before I drove back to the airport. However, on my way up, I was driving next to the most unbelieveable crystalline waters I’d ever seen. There was literally no way I wasn’t going to stop at a little area to pull off and get some pictures. It was unreal. I waded into the waters, not going far enough when I really just wanted to swim in the water. In the distance was a very small remote island. If it weren’t for the sounds of the cars on the highway behind me, I might have been convinced I had been marooned somewhere. That was probably the prettiest stretch of land I had ever seen, and stopping and wading into the water for even just a little bit was definitely the highlight of my trip.
Hands down, I recommend this race. Everything was well-organized, everyone was friendly, and it was a good course. If you run it for the views, you might only get a glimpse of the water as you run over the bridge to Upper Matecumbe Key, but you see it 4 times and it’s so gorgeous at sunrise that you’ll want to stop and stare if not dive in.
Also, there is nothing better than a race that starts and ends on the beach, has a tiki bar for its after-party location, has an after after-party location at the Florida Keys Brewing Company, and a barefoot Rastafarian DJ at the finish line. I don’t recommend running the race for time. In fact, if I pace this race next year, I’m going to jokingly cross out the time on my sign and replace it with “Island Time.” But really, it is almost too muggy to run for time, especially if you are coming from a colder part of the country. It might feel like a shock.
Since it is a little bit far from pretty much everyone and travel costs can be considerable, it’s maybe not a great race to come and run and then leave like I did. It’s perfect for incorporating into a honeymoon, extended vacation, business trip, or if you live in Florida and don’t mind the drive. The 10K makes a great family event, and the after party is fun. Grab breakfast at your hotel, then hang out by the pool all day.
Leaving the Florida Keys was hard, and there was definitely a sad feeling in my heart to leave a place where I felt a sense of belonging. I’m excited that I still have so much to explore and look forward to with the Keys, and I’m glad I only bit off a little piece for now. I can’t wait to come back next year to run the race, hopefully as a pacer again, and to hopefully continue my trip into the lower Keys. Until then, “this ain’t a good-bye, it’s a ’til I see you again.”
Below are some additional tips about making a race-cation possible with the Islamorada Half-Marathon and 10K.
Entry Fees: $70-$90 (half-marathon), $50-$60 (1oK), $35 (Beer Mile)
Bag Check: Yes
Runner Tracking: No
Race Photography: Yes, courtesy of Race Wire
Shirt Fittings: Male and female sizes, runs small
Medals: Yes, for both 10K and half-marathon finishers
Timing: Provided by Race Wire
Where to Stay
I drove past a lot of little hotels, resorts, and marina-resorts in Islamorada, but from what I could see, there is something for everyone. Here’s what I recommend just from the time I spent there and seeing it first-hand.
Things I Wish I Had Done
1) Snorkeling. I’ve never seen coral up close, and now coral reefs are under threat more than ever. I want to see them before they get obliterated (sorry, I don’t have much faith in people about caring more for the environment).
2) Kite-surfing. Winter is a great time for sports that require wind because it’s very windy in the Keys. Definitely wishing I had gone somewhere to try it out because it looks super fun!
3) Got my shirt personalized for $10. The race offers personalization of your race shirt for $10. After I saw a lot of runners with funny sayings (my favorite being “Tiki huts and coconuts), I realized that the whole “I’ve done this before” aspect of running half-marathons takes the fun away from race experiences themselves. I definitely wish I had personalized my shirt, although I’m still undecided about what it would have said.
4) Drive to Marathon. I feel like I can’t be a marathoner and not visit Marathon, Florida. The photo-op is worth the 28 miles from Islamorada.
5) The Beach and Beer Mile. It’s right on the beach, and you get a beer every quarter mile. Considering that I went to the Florida Keys Brewing Company and got faced on a flight of brewskis, this would have been perfect!
6) Swim with a dolphin or manatee. Next time!
7) Looked up the guidelines on interstate commerce. I would have loved to bring home a bottle of local rum or a bottle of Kenny Chesney’s Blue Chair Bay Coconut Spiced Rum. That would make a killer egg nog.
8) Stayed at the after-party. Like I said, I absolutely loved my stay at La Siesta, but I had to leave the after-party without enjoying it so I could shower off before my check-out time at 11AM. Originally, that wasn’t the plan, but the race was so friggin’ muggy and gross that it would have been kind of a miserable day without a post-race shower.
9) Booked an extra day or two. This seems obvious, but there was so much going on and I was having a hard time taking it all in while trying to relax! I would consider going for 3-4 days next time, if you want to do what I did and make a quick trip of it.
Things I Wish I Had Brought
1) A dry bag for kayaking or paddle-boarding. The resort I stayed at didn’t have any to rent and I wasn’t checked into my hotel room to drop anything off in, so I just brought it all with me. I’m glad I had my waterproof iPhone case with me while kayaking, but the kayak I used was a lot smaller than the ones I’ve rented at the Key Bridge Boathouse that are large enough to store your bags without them getting terribly soaked. Some of the stuff I had with me didn’t dry off the entire time I was there.
2) A purse that wasn’t made of cloth. Trying to be minimalist, I brought a canvas purse that I used when I am at the beach because I don’t care if it gets dirty. But I do care if it gets wet and it did, and it never dried off so I had to go without. Kind of defeats vacation minimalism when you have to carry your keys, wallet, phone, sunglasses, and glasses case in one hand.
3) Extra clothes. I got caught in the rain a lot, and I sweat like a pig. Also, because it’s so humid there, nothing really dries off, including the moisture-wicking Oiselle tanks and shorts I was wearing or the race shirt that I stuffed in my wet purse.
4) Pool shoes or water socks for wading. I stopped at Anne’s Beach and Indian Key to wade into the clear blue water. The sea floor is not only gross but kind of rocky, and it killed my feet. As I write this on Monday, I swear I can still feel the crackly shells under my feet and I’m still not 100% convinced I didn’t step on something alive. I would have gone in much further if I had been wearing them, but they are practically a requirement for getting past the stuff near the shore.
5) Extra flip-flops. All the rain made the ground extra soupy and I had to trash the flip flops I brought with me because there was just too much sand and white mud caked on them.
6) Trash bags. For all the wet stuff. And to keep it from leaking onto dry clothes.
7) Someone else. I wish I had someone with me to do all the driving so I could hang out the window like a dog and taking pictures like a crazy lady!