A Travellerspoint blog

Grassy Key - To Do Something Right, You Need to Do it Twice

“Whatever happened to Vicki_H?”

“I heard she went off the grid and is living in a yurt in Montana with 27 rescue dogs.”

“No, no, no….she’s down in St. John running a bar called the Blue Bucket.”

“Not St. John, it was the Bahamas, and it’s not a bar, she’s running a shelter for stray peacocks.”

“I heard she died from mixing Pop Rocks and Mountain Dew.”


Life happened to Vicki H, folks. So. Much. Life.

I was on a TV show. We had a hurricane. We lost a boat. We lost a house. I cut my hair off. I grew it back. We had a pandemic. I stopped highlighting my hair. I turned 50. I celebrated my 20th anniversary. My Dad broke his hip. We recovered from a hurricane. My Dad got better. I turned 51. We bought another house in Abaco. My dog got paralyzed. My dog recovered. My mother-in-law passed away. My mom celebrated her 5 year cancer-free anniversary. We bought a boat. I turned 52.

And now I’m turning 53.

Good gravy. Where did the time go?

Despite my absentee status, I am alive and well. Better than I deserve to be. I have not lost my love for travel, but just failed to write about it for a while. I have finally realized there is no way I can go back and catch up 4 years of trips. (and there were some really good ones, y’all!). But maybe I can just start today and go forward. If I get the time to do some looksbacks, I’ll do my best!

But today, in honor of the big 5-3 coming up, let’s talk about my birthday last year.


The Keys to a Happy Birthday

Two fifty-somethings in the middle cays.

I only had 3 days. So it had to be quick and easy. But good.

Like a microwave cake.

My microwave cake was a cheap flight down to FLL and a rental convertible driving through the Middle Keys.

Not quite a bakery cake, but definitely better than a Moon Pie.

FLL to Grassy Key

I used miles for free flights on Allegiant to Fort Lauderdale, which seemed like a great idea until we actually made the drive from the airport to Key Largo, seeing nothing more exciting that a ton of hot traffic. Strike one.

I also made the less than stellar decision to rent a convertible. Again, my vision and reality did not quite line up. They Keys really require a tall vehicle. We saw lots of guard rails that I am sure had beautiful water views on the other side. Strike two.

I also decided to use the Turo app for the first time. While Turo and the vehicle were absolutely fantastic, we were totally unprepared for the extra steps that one does not encounter when renting a car from a car rental agency at the airport. Like the owner forgetting to send us information to get to the car and waiting outside in the heat until she saw our frantic messages. And having to send her a photo of Matt holding his driver’s license with the car in the background…and waiting for her to approve it…then waiting for the code to get into the car. But wait! There’s more! And then having to photograph every single inch of the car and send her the photos to document the car’s condition prior to starting the engine.

Strike three.


By this time, we’d been in the hot parking garage at the FLL airport for over an hour sitting beside a car we couldn’t get into and sweating buckets. We were ready to get this show on the road!


Fast forward 2 long, boring, hot hours later (in addition to being too low to see anything, a convertible is a very HOT option when sitting in south FL traffic….), when we stopped at Gilbert’s Resort and Tiki Bar before crossing over to Key Largo to enjoy some boobies.

Not that kind of boobies.

THIS kind of boobies.


Frozen boobies were definitely in order to get the birthday weekend started.


Our next stop was Marker 88 in Islamorada for lunch with a view.


We continued on, making a final stop at Robbie’s of Islamorada, where I had heard I could find an epic bloody Mary. It was indeed epic!

Yes, yes...I know Robbie's also has some big fish you can feed, but who cares about big fish when there are bloody Marys with BACON to be consumed?


I also found a painting I couldn’t resist. Is it just me, or does that parrot look like it knows something?


We made the rest of the drive, stopping a few times so we could see more than the concrete barriers and guard rails.


We finally arrived at Grassy Key and checked into Grassy Flats Resort.

I had a heck of a time trying to decide where to stay and had narrowed it down to several places, ultimately choosing Grassy Flats because it had an “adults only” building and pool (don’t judge) and because it appeared small and laid back, both qualities that appeal to my hotel-despising nature.

The Wreckers House at Grassy Flats was absolute perfection. Our room was beautiful with an outstanding view. The resort itself was low key and had a relaxed, bohemian vibe that we really loved. The grounds were absolutely lovely.


Our favorite part, no surprise here, was the resort bar, Barrel and Bale. It was breezy and very boho chic, with soft chill music playing whenever we went it. They also made incredibly good craft cocktails.


We grabbed a couple of drinks and headed straight for the pool. The “adults only” pool….that is…


After some down time, we got cleaned up and headed out for “birthday night.”


We had booked a sunset boat trip out of Marathon. We weren’t really expecting much, but it turned out to be very pretty.


Next, it was on to FL Keys Steak & Lobster. It had stellar reviews, but when we pulled up, it reminded me of the old school seafood restaurants we used to go to in 1977 when my parents would take us to Gulf Shores.

“Don’t judge a book by its cover,” was spot on. The food was fantastic and we ate so much, I didn’t have room for birthday cake!


Grassy Key & Marathon


The next morning we enjoyed a beautiful sunrise.

Looking for something “different,” I had booked a jet ski cruise. We headed back to Marathon.


It was not a smooth day.

Anyone who has been on a jet ski in the ocean when it was not a smooth day knows exactly what I mean by that.

For the next 45 minutes, I alternated between desperately hanging onto Matt while my butt flew up off the seat every 10 seconds and worrying about being suddenly launched out to sea and eaten by a shark or getting a salt water enema. By the time we reached our destination, my tailbone voted for being eaten by a shark.

While it was a truly beautiful spot, I was mostly just happy to get off the stupid ocean bronco for a while. We explored for a while and, when I felt my butt could take it, we hopped back on for the return trip.


Now I remember why I stopped riding these things when I was 25.

When the jet ski ride was over, or as I like to call it, “Bullriding 101,” we headed to Castaway for lunch. I only hoped they had soft seats.


On pretty much every FL Keys “Can’t Miss It” list, Castaway was the perfect kind of eclectic, divey, locals place with incredibly fresh seafood, unique dishes, and great water views.

But if I'm completely honest, they had me at "padded chairs."


Known for their sushi, of course we had to try it. Amazing!

We also sampled the “tunachos” and the spicy tuna dog, a charred hot dog topped with spicy tuna, avocado, panko, green onions, masago, spicy mayo, and eel sauce. So yummy that I momentarily forgot about my sore tush.


On the way back to Grassy Key, we saw some more lovely water views (aka, guard rails and concrete barriers).


We had tropical cocktails on our mind, so we stopped at a cute tiki bar. When we walked into Sunset Grille, there were at least 12,897 people in there and at least ¾ of them were running, screaming children (don’t judge), so we made a u-turn and headed back to the car.

A little farther down the road, we came to Island Fish Company, another cute tiki bar that was crowd free and didn’t have a plethora of small screaming persons running about.

We sat at the breezy bar facing the water and had a couple of drinks before heading back to Grassy Flats.


I already told you that the bar at Grassy Flats had already won us over, so we headed down before dinner to have a drink and fell in love with their Mai Tai.


Then we made the .4 mile drive to Hideaway Café.

I will admit that I struggled with my decision to make a reservation at Hideaway Café. It’s no secret that I like to pour over the interwebs before I make decisions about where to go when I travel. By the time I actually go, it’s like I have already been there.

Hideaway Café has almost no online presence. While it was very highly recommended, information was limited. Add to that the fact that I actually had to call and speak to an actual person to make a reservation, and I nearly lost it.

Seriously, I'll struggle for 45 minutes with an online reservation system before I'll call an actual person and spend 30 seconds making a reservation. I'd sooner send a messenger pigeon with my request tied to its leg than speak to someone on the phone.

But something in my gut said to give it a try.

When we pulled into the Rainbow Bend Resort, my apprehension doubled.


It was pink, old school, and we were greeted with a giant sign straight out of 1957. What we didn’t realize yet was that this quaint resort was a hidden gem with lovely rooms, a stunning beachfront view, and an absolutely top notch dining experience.

We headed up the stairs to the Hideaway Café. When we walked inside, we were greeted by the glow of candlelight, white tablecloths, and roses on every table. Not to mention a view of the ocean from every seat.

With upscale French cuisine, fresh seafood, and a lovely wine list, I can’t recommend this restaurant enough. We ate so much….I still didn’t have room for cake.


Grassy Key to Key Largo


Grassy Key is known for kiteboarding…something Matt has always wanted to try, so we grabbed some bagels and he hit the beach for a kiteboarding lesson, while I hung out at the beach.

It was now 2 days post-birthday, and I still hadn’t had a birthday cake…a first! So, I did the only thing I could. I bought myself a key lime pie and ate it for breakfast.


As I sat and watched Matt’s 4 hour introductory kiteboarding lesson, I couldn’t help but ask myself….why would one want to strap oneself to a giant kite and attempt to ride a surfboard? As expected, a first lesson is more “kite-dragging” than “boarding.” The longer I watched, the happier I was sitting on the beach with a mai tai and pie.


Then, as soon as it began, our time at Grassy Flats was over. We had booked a room in Key Largo for our final night to make the drive time to the airport shorter the following day.

We headed back up toward Key Largo, stopping at Lorelei’s for appetizers, the Postcard Inn Tiki Bar for drinks, and the Fish House for more appetizers to break up the drive.


We were feeling good, with bellies full of drunken shrimp and key lime martinis when we arrived at Azul del Mar, a small waterfront guest house in Key Largo.

Want to know how to kill a perfect day drinking buzz in 7 words or less?

“I locked the keys in the trunk.”

Our little convertible was parked in the parking lot. While Matt went into the registration office, I thought I would be helpful and get our luggage out. In the process of doing so, I put the keys inside the trunk and proceeded to close the trunk.

We searched for a trunk release inside the car for 30 minutes with no luck. There was no car manual in the glove compartment. I Googled. Nothing.


What we found was a way to get into the trunk from inside the car, we thought, so Matt set about dismantling the car piece by piece in the 97 degree heat, sweating and cursing.

I honestly didn’t think he could get any angrier at me.

That was, until I found the trunk release that I said I couldn’t find, after Matt had been sweating and cursing for 45 minutes trying to dismantle the back seat of a Fiat.

You'll be happy to know that one thing hasn't changed during my travel blog hiatus....I am still an idiot.

This is not the face of a happy man.


Being married to me is hard, people.

We were finally able to go into our suite and relax. Azul del Mar was just lovely.


When Matt had fully recovered emotionally, we cleaned up for dinner.

Before dinner, we decided to stop in at the Caribbean Club. Open since 1938, it’s the oldest bar in the upper keys. It had character, stiff drinks, live music, and a great sunset. Interestingly, it’s the only place in Key Largo where the movie, Key Largo, starring Humphrey Bogart and Lauren Bacall, was filmed. The rest took place in Hollywood.


We wrapped up our last night with big bowls of pasta at DiGiorgio’s Key Largo, because spaghetti is always a good idea.


As we made the dull 2 hour drive back to the airport the next morning, Matt and I agreed that we absolutely loved Grassy Flats and wanted to return. Matt wanted to try a proper 3-day kiteboarding lesson and I wanted to explore more of the upper keys.

Who knew we’d be back so fast!

Grassy Key 2.0: Suite Dreams Are Made of This

Matt and I returned to Grassy Flats just 7 months later.

Grassy Flats Resort was opened by retired professional kiteboarder Matt Sexton and his partners in 2019. Despite opening just before the pandemic shut everything down, Grassy Flats survived.

Thank goodness it did.

Grassy Flats is an eco-friendly watersports-oriented boutique resort reborn from three old Florida mom & pop resorts that had gone by the wayside. There are less than 40 guest rooms, keeping Grassy Flats small, personal, and nostalgic.

We were excited to return.

It was late evening when we flew into the Key West airport. There would be none of this “driving from Fort Lauderdale” nonsense this time. There would also be no shorty convertible this time.

Once inside our properly tall Jeep, we headed toward Grassy Flats.

It was late when we arrived and our key had been left for us by Poppy, so that we could let ourselves in. Although we had reserved a basic room, we had been upgraded to the beautiful Galleon Suite at the Wreckers House.


Wanting nothing more than sleep, we climbed into that big, beautiful King bed and were out!

We enjoyed a beautiful sunrise on the deck the next morning with coffee.


Today was supposed to be Day 1 of Matt’s 3-day intro to kiteboarding. We got up super early and grabbed a quick breakfast at Island Fish House.


We had booked specifically for the end of February because that’s when wind is almost guaranteed.

Unlike death and taxes, wind on Grassy Key is not certain.

The water was flat as a fritter. Wind? A mouse fart would generate more wind than we saw on Grassy Key that week.

So, with several days that were now free of kiteboarding lessons, we did the only thing we could do….see how many places we could eat and drink before it was time to go home!

We headed to lunch at Bongos at the nearby Lagoon, Grassy Flats’ sister property, a 50 acre day resort with watersports, a tropical café, and botanical garden.


Bongo’s was a tropical explosion of orchids, garden paths, and art murals next to a shallow lagoon. Breezy tables sat under umbrellas as mango mimosas and Bloody marys flowed to the music of a live band.

There were worse ways to spend the morning.


After wasting the morning at Bongo’s, we wasted the afternoon at the Grassy Flats pool with mai tais from Barrel and Bale.

There were worse ways to spend the afternoon.


We ventured to the far end of Marathon for dinner at the Isla Bella resort’s Polynesian-inspired restaurant, Mahina.

Isla Bella was a beautiful property and Mahina was visually stunning.

Tables sat scattered under the swaying palms as soft music played and the sunset glowed low in the sky.

There are worse ways to end the day.


With no lessons to get up early for, we spent a lazy morning enjoying the beach at Grassy Flats.

The water was shallow here. Wide flats of shallow water hug the ocean side of Grassy Key where the resort is located. Soft reggae played from the speakers at the poolside tiki bar. Hammocks swayed in the breeze. The resort’s kayaks, paddleboards, and Hobie Cats sat in the soft sand waiting for someone to jump on board for an adventure.

We realized this was a truly magical place.


Grassy Key doesn’t have the celebrated status of Key West or the dive-capitol fame of Key Largo. Nor does it have the gated exclusivity of some of the smaller keys. What Grassy Key has is the salty essence of true Florida and we loved it.

We enjoyed brunch at Sparky’s Landing, where the BOGO mimosas and seafood ciopinno were calling, but spent most of the day simply enjoying Grassy Flats.


Sunset called for cocktails at Barrel and Bale.


We also decided to return to Hideaway Café for another lovely dinner.


The following day was supposed to be the 3rd day of Matt’s kiteboarding lesson, with us returning to Key West in the afternoon, but with no lessons, we decided to head to Key West as soon as we checked out.

After enjoying one more lovely sunrise, that is.


What to do with a bonus day in Key West? Eat brunch at Blue Heaven, of course!


Followed by painkillers at the Rum Bar….


And margaritas at Sunset Pier……


And don’t forget oysters at Pepe’s……


There was nothing left to do but crash in our blessedly cool suite at Winslow’s Bungalows, so early that I am embarrassed to tell you what time.


Because we never really had dinner the night before, we woke up ravenous.

We grabbed breakfast at the nearby Key West Cuban Coffee. I’m glad we were hungry, because the chorizo and eggs were MASSIVE (and delicious!).


We spent the day shopping, eating, and drinking our way through Key West, because that’s our favorite thing to do!

With only 1 day, we hit all of our favorites. There were mimosas and bloody Mary’s at Hanks, tacos from Garbo’s, more rum from the Rum Bar, more oysters from Pepe’s, sunset from Mallory Square, zombies from the Tiki House, and nachos and margaritas from Amigo’s.


Stick a fork in me, because I was done! We had painted the town AND the front porch and we’d eaten anything that didn’t eat us first. I felt as fat and happy as a boardinghouse cat.

It was time to go home.

The best part? Well, we’d have to come back now, wouldn’t we? I mean, we still had those kiteboarding lessons to do…..

Posted by vicki_h 20:18 Archived in USA Tagged beach island tropical florida key_west marathon islamorada fl florida_keys key_largo middle_keys grassy_key grassy_flats

Email this entryFacebookStumbleUpon

Table of contents


So glad you're back I thought I was blocked or something! Great trip report as always!

by ryanboz7

Guys! You don't know how excited I was to receive that email notification that you're back! Made my day as I sit here bored in a cabin in Alaska recovering from stupid covid. Wonderful report as usual, and made me start dreaming more for a tropical getaway soon. The food and drink look awesome, and you both look awesomer! Thanks for restarting and catching us up. Cheers, chin-chin and salute!

by ed4000

great to see you posting again. 3 years? wow.

by bluegreg

So glad you are back!!! What adventures are you planning in the future???

by Twolittlebirds

Yay! I’m so happy you are back!

by wendygeo

So happy my favorite trip blogger is back!
I love your wonderful writing style, your love for food and your honesty on mishaps. Thank you for taking us with you on your trips again!
Happy travels Vicki!

by Sternchen_16

This really made my day to see you are back with your informative posts and great photos. All I can say is thanks so much!


This blog requires you to be a logged in member of Travellerspoint to place comments.