A few years ago we committed to it for Peggy’s 50^th birthday, a full-on bucket list style sister trip.  And it finally happened. In 2019, my big sister turned 50 and we were Key West bound.

Planning our pilgrimage

Only it couldn’t be a simple trip. Oh, hell no!  Have you met my sister?  First she had to take on a list 50 things to do before 50.  And then she had to “see Dolly Parton in Concert”, which just had to happen at the Grand Ole Opry, on the way to Key West.  So there we were, splurging on a 36 hour trip to Nashville before continuing on to Florida.

Because, why should this be ordinary…or cheap. Luckily, my niece lives in Florida. So, if we just fly into Tampa we can borrow her car, thus saving the rental fees.  And it only tacked on 8 hours to our trip.  BUT, it also meant the amazing SISTER ROADTRIP experience. And we were sold!!!

Hitting the road!

And then there is me, so cute, so innocent, not even thinking about my sister’s favorite pastime:  making me cross really high bridges.

Which it turns out you find, not only just outside of Tampa, but also the entire way out to Key West. Bridges everywhere! I mean do we even need to pause to discuss the possibility of a giant prehistoric genetically altered shark jumping out of the water to eat the bridge and everyone on it, no, I didn’t think we did.

And then there is me, so cute, so innocent, not even thinking about my sister’s favorite pastime:  making me cross really high bridges.

Road Trip highlights and hazards

A few hours into our trip, we knew we were stopping at Sanibel Island, the seashell capital of the world! It was a little detour, but worth it. The towns were adorable, the bay was gorge and we had a wonderful brunch at the Sunset Grill where our lovely server directed us to drive to Captiva, the end of the road. It was soooo pretty but alas, no parking to be found anywhere. We took it as a sign to get back on the road. The Everglades, more bridges and the Keys await.

Now, sistertrip through Florida does sound amazing, and it was, all giggles and carpool karaoke, right up until, oh about mile 54, a mere 5 hours into our trip, when we hit State Route 41 aaaannddd:

WHAT IS THAT???? Oh, come on, I mean, I am already risking life and limb with all those gators. . . which it turns out are not the huge problem I thought they were going to be.  They were NOT just sitting in roadways waiting to devour my extremities.  But did you know about THIS?  I didn’t!  Panthers!  IN FLORIDA!  Peace out, not this girl. 

And this was the time this girl said NOPE to the Everglades!  Not happening….not while I’m sober. But we did pass a whole bunch of those road side tourist attractions offering air boat rides through the glades, come see our gators, come lose a hand, a foot, a nose, whatever, you don’t know, just give us your money and we will see what you come back missing.

Arriving in the Keys

Fast forward through many Kenny Chesney songs and staring cautiously out the window waiting for prey to fall out of the trees (yes, panthers take their prey into the trees!), and we get to the Florida Keys just in time for sunset AND that means dinner!

We wisely decide we should stop, eat, and see the amazing sunset by the time we get to Islamorada. I am not only trying to save drivers the distraction of us on the road during an amazing display of nature, but it is my sister’s birthday trip and she should be able to relax and enjoy the view too. Damn, I am thoughtful. We google sunset dinners and decide on Marker 88 in Islamorada, FL. It was phenomenal.

A beautiful sunset cocktail, amazing appetizers of lobster mango guacamole, blackened tuna sashimi, chips with basalmic and blue cheese. And a brilliant view of the sunset. It was amazing. Oudoor seating, acoustic band playing the perfect blend of folk songs, easy listening, and island style music.

Drinking a ‘Keys Sunset’, watching a Keys Sunset

Needless to say, the drive from this point on was very unmemorable. In fact, I don’t remember it. 8 hours of driving, laughing, food, and sunsets, and we were actually just glad to get to our AirBnB on Duvall street. Big shout out to Tom for giving up his parking space, and for having an amazing one bedroom apartment available right across the street from the drag show.

Keep reading here…Day 2

After an amazing Florida Keys and Dry Tortugas Adventure, we were up and out by 4:45 am with some super-secret stalking to do before leaving for the Everglades National Park. As we learned from the tasting room host at Pilar’s Distillery, sometimes Kenny Chesney sneaks into the Jimmy Buffet recording studio in Key West in the wee early hours of the morning to record on his off-tour time. He gets there early to get in and out without being seen. . . but we were there to foil that plan!

Shrimpboat Sound Studio

Cuban coffee in hand (fabulous, amazing Cuban coffee, BTW from Lil’ Lepowski Café, from the kind of place where the locals are picking up their coffees from on their way to work), we were off for some serious sister-level stalking. This is where I would like to insert our amazing story about meeting Kenny and being invited to hang out on his boat, day drinking with him and his crew. I would really like to.

However, by 6 am we came to the realization that we should probably just hit the road, leaving Kenny to wallow in disappointment when he learned via our new blog that we had been waiting for him.

It may sound completely crazy, but we had decided to spend our final night in the Keys milking out every last drop of the sun-soaked goodness. Which meant driving the entire way back up to Tampa for our flight home the next day before 4 pm, no biggie.

Sister side note (ssn) – we had one more mandatory stop before we left, the Southernmost Point marker. It had been too crowded during the day so we made time to snap a few pics on our way out of town.

Leaving Key West for the Everglades

ssn – after heading back across 7-mile bridge (I think Patti was finally getting used to it!), we started looking for places to watch the sunrise. It was not disappointing!

We grabbed some breakfast in Key Largo, our last meal before leaving our beloved Florida Keys behind. It was still early on a weekday, and we had a long drive ahead of us. So we took a pass on the all you can drink mimosa place and landed at a little place in Islamorada called Keys Bite. I had the best chilaquiles, which are my breakfast weakness, add on the steak which was sheer breakfast perfection. We really stumbled on an amazing find with this little family owned joint! Couldn’t have been happier for our last meal on this adventure.

And then we were off, leaving the Keys in the rearview mirror.

Everglades National Park

But first…after our fabulous drive through the Everglades National Park on our way south, we knew we could not possibly pass up the chance to take an airboat tour to see some gators. I mean, come on, what do you do after a seaplane except an airboat, are you on our train of thought yet? We had settled on Coopertown, because it was essentially the last one we had passed on the way down, and the first one we hit on the way back. Plus, the sign said it was the Original, you can’t argue with that, they are the original!

But First…Wildlife

A bonus at Coopertown was the Wildlife Show before the boat ride. Now, I’m not saying I was a little freaked out, but chances are I was a lot freaked out being out in the open all exposed and ready to be gator bait. Peggy was taking it like the champ that she is. Oh, look caged up croc, oh look bigger caged up crock. . .oh look, SNAKE CAGE? WHAT? SNAKE CAGE??? And this is where the “noping” begins. They brought around a cute little baby gator for us to touch while they held it all snug as a bug. But then they thought they should tell us all about the snakes of the ‘glades. Dear Lord Almighty, Peggy is taking me to be eaten by a gator. And if that doesn’t work some anaconda is going to snatch me out of that boat…I mean, I’m not J-Lo by any stretch of the imagination, but I know what snakes can do in a swamp, I saw that movie!

ssn – I touched the snake! I realize that sounds dirty but I did and it was a huge deal! The gator was cute, but I am terrified of snakes!

Everglades Airboat Ride

Then it’s time to board the boat. We were put in the back. This is a bummer, but definitely safer during an attack. Luckily they sat some 8 year old looking boy upfront. I’m pretty sure they were planning on him being the bait. If you’ve ever raised an 8 year old boy, you know he had it coming. So I was getting all safe and secure that I might survive this adventure.

The girl in front of us finally asks what we all really want to know. Has a gator ever actually jumped into a boat? The river assures us that he doesn’t think so, but it’s his first day, so he doesn’t actually know for sure. I am comforted by his humor, and by the fact someone else was on my side of preparing for death. And we depart. And it’s loud. It is also incredibly beautiful. We saw some gators, and they looked fairly harmless and uninterested in us. The airboat is pretty stinking cool gliding along the water. I ended up loving this brush with death. Then we got to switch places so I could sit on the outside of the boat, and the good happy feeling melted into a mini panic attack. Yet I still survived to tell the tale.

Back to Tampa

Side note, for those that are National Park amateurs, I had found out in the Dry Tortugas (thanks to my older and wiser sister), that there is such a thing as a National Park Passport. That’s right, you buy a passport book, and then you can collect stamps at each national park you visit. Who am I to pass up that challenge, and how cool of a thing is this to do with your family? This meant we definitely had to stop at the Everglades for my second stamp in my new book.

Sorry to say, the rest of the trip was pretty uneventful. A fabulous meal at Datz in St. Pete with my most favoritest niece on the planet. I had their Barry C’s Stuffed Meatloaf, which was incredible – yeah and by stuffed they mean bacon-jalapeno mac and cheese INSIDE, ketchup glaze, side of mashed potatoes and peas.

ssn – the most favoritest niece is my gorgeous daughter, Sydni. Thank you for letting us use your car!!

That got me to my coast to coast flight. Leaving my sister behind in Denver, continuing home via Spokane.

It was an amazing journey, and one of our bestest vacations ever. A Happy 50th Birthday to the best sister on the planet. Let’s do that again real soon!!!

Sister side note (ssn) – I had a momentary panic that she hadn’t come back the night before and I failed to notice. Big sister badge has been taken away.

Big Plans Today

If you missed yesterday, find it here Florida Keys – Day 2. This was our Dry Tortugas (it means turtle, I learned that at the Turtle Rescue Hospital) National Park excurion. This was high on Peggy’s gotta see, gotta do list. It is in the top 5 of the least visited National Parks in the country. It is an island 67 miles off Key West.

This was an early morning start for a vacation, but with big, big plans, we gotsta get on it. And where is my charger, anyway? We had to be at the airport by 7:30 am, and I’d pretend that is early, but we are 6 am’ers most days anyway. This was just a little slow go from the mango vodka over-indulgences the night before. But…this is where the epicness kicks in!

Sea Plane Adventure

Dry Tortugas National Park is only accessible by either a ferry, chartered boat or a seaplane. And ferries are for peasants, clearly. Actually, the deal was that the ferry is a 2-hour boat ride, you are there for 4 hours, then 2 hours back. That’s 8 hours out of our already too-short vacation and that didn’t seem like a good use of our time! The seaplane was spendy AF, but 45 min down there, 2 hours on the island and 45 min back is vacation time value! And my big sister is all about time management over funds management. She kicked in for her own birthday present and funded the flight. This turned out to be one of the bestest decisions ever.

We flew out at 8 am from Key West Seaplane Adventures with pilot John. There were only 10 people on the plane, and a copilot seat was available. “Does anyone want to sit up here?” John asked so innocently. And little did he or I know how fast Peggy could move in that little plane.

ssn – to be fair, nobody jumped on that offer AND it was my birthday so who am I to let it pass by! Co-piloting (not sure John (or the FAA) would consider me that, haha) was seriously the best thing I’ve ever done!

An amazing plane ride over the ocean, fabulous running commentary from our pilot, slight views of oceanic creatures.

ssn – we flew over shipwrecks, saw the Marquesas (reference Southern Cross, one of our top 5 songs EVER) and saw a hammerhead shark!

Dry Tortugas National Park

And in 45 short minutes, we land on the ocean and glide into The Dry Tortugas, which houses Fort Jefferson.

Fort Jefferson

This old army fort was fascinating as we got to stroll through the grounds, with only the ten of us from the seaplane. It was an amazing experience and I loved it way more than I thought I would when I was informed we were going to see an old army fort.

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Snorkeling at Dry Tortugas

We followed this up with snorkeling with the gear provided by the seaplane company. Now, your girl is a little terrified of open water, and being eaten by sharks, and I firmly believe that very soon we are going to see a horror movie of a small national park terrorized by a genetically enhanced shark (or sharktapus – yes, that’s a thing); but there I was, nonetheless, snorkeling for only the second time in my life. It was pretty fabulous, not another soul in sight (in Bali, our snorkeling consisted of being surrounded by 100
other tourists)

ssn – I think we have firmly established the shark-phobia by this point. LOL.

The Sea Plane to Dry Tortugas NP was the Best Decision Ever!

Just before 11 am we go change into dry clothes and are headed to the seaplane for our return flight, and then we see it: The Ferry. Packed to the gills with people looking like that large tourist man with the ice cream from Lilo and Stitch (Google it). And the island is descended upon by no less than 200 people. And this is why I can not recommend the seaplane option enough: we had 2 hours on this island with only the 10 of us and a handful of campers. With a grateful heart, we boarded the plane and hopped on back to Key West.

Back to Key West

Back and famished, we head back to our little AirBnB and default to Google for recommendations. With my desire to eat shrimp until I was sick of looking at it (spoiler alert: it didn’t happen), we ended up at DJ’s Clam Shack. Right on Duval street, it definitely fits the category of a “shack”. Mind blowingly good seafood. I ordered the fried shrimp and chips, Peggy got the clam strips, plus we had to split the lobster roll, because duh, lobster roll. It was all fresh, well cooked, and crazy good.

Hemingway’s House

It was hard to believe we started this day hungover. We cruised by Hemingway’s house, and the lighthouse, did a little strolling around the Duval Street area touristy parts, bought the kids some souvenirs, and hit up the local shops.

Mallory Square

By early evening, we hit up Mallory Square in preparation for sunset. We got there about an hour early so secure a good seat and just chilled at the water as local buskers and street artists kept us entertained. And then the show started. Oh my, now I get it, now I completely get the hype of Mallory Square. It was gorgeous, an incredible display of Mother Nature just showing off. I think my favorite part was that as the last inkling of the sun lowered over the horizon, people started cheering; and my heart grew
three sizes that day.

ssn – Mallory Square is everything quintessentially Key West. This cannot be said enough…People, island music, incredible sunsets and just plain palpable happiness.

Dinner in Key West

Even though we were heading for dinner, we stopped at this cute couple’s stand for fresh guacamole, made to order right there. DELICIOUS. We settled on sushi for dinner, and ended up at the sushi bar at MisoHappy. With a name like that, how do you not go there? I was so happy! The sushi chef and his crew did an amazing job; the entire staff so kind, and attentive. On our next trip, I am down for that Lobster Pad Thai, but on this meal we stuck with just the sushi rolls.

We headed back to our “home” to prepare for an early morning start the next day (with a purpose I will discuss in the Day 4 post). Sad that it was our last night in Key West but we crashed pretty hard, and happy.

An after dark arrival at our ultimate Florida Keys objective (see Day 1), and a quick pop-in to the 801 Bourbon Bar (and drag show), did not deter us from an early start for first full day in Key West. There was just about the cutest coffee bar on the street right behind us, The Moondog Café.

They hooked us up with some fabulous coffee for our journey back across 7 mile bridge. Yeah, who’s stupid idea was a 7 mile bridge? Why didn’t they just call it Feast For Sharks Freeway? It was this girl who insisted on seeing the Turtle Hospital in Marathon, and Peggy was kind enough to oblige, although it meant an hour back toward the mainland. But, come on, turtles! It had to happen.

The Turtle Hospital

The Turtle Hospital is a rescue, rehabilitate, and release center. We learned so much, and while they don’t let you actually touch or hold the turtles (they encourage you to not have your fingers snapped off, silly volunteers), it was informative and an incredible experience. They taught us about bubble butts, and environmental impacts on turtles, it was very moving.

We also learned that if they rescue a turtle that you find and report, you get to name the turtle. And suddenly our trip had a brand new mission! Find and rescue the future Miss Lola McFlippyfin!

Marathon Key

While that was super fun and all, it got hot, and we got hungry. Thankfully, there was Burdine’s on Marathon, just a wee bit away. You have to drive back into the boat docks and marinas to get to this place. But you are going to have to just go, and take a wrong turn or two, and circle back around to find this amazing place! They are upstairs from the boat launch, and the cases of the Catch of the Day.

Up on this outdoor patio of fabulous freshness; slight breeze blowing, amazing view, cold drinks, and wide array of local choices of food. It was every thing we ever wanted in a sister trip by the water.

Exploring Key West

I could have spent all day right there. But someone had to drive the bridge of death back to Key West, and seeing as the birthday girl drove the entire day before, that left your girl here as the designated. Once the car was safely parked for the day, the island hot spot walking tour began. And I mean this in the “we have no idea where we are going, but that way looks fun, Oooh, is that a bar?” kind of way.

We made it to the Mile Marker Zero sign, and BOOM right there was the Southernmost brewery, First Flight. The coolness oozed from this place. It is home to the Pan Am office where the very first tickets to the first Trans-Atlantic flight were sold, and is themed around old airplanes and the vibe of the 1920’s tropics. And, hot day/cold beer is one of my favorite combinations.

sister side note (ssn): First Flight is owned by Kelly McGillis!

Papa Pilar Distillery

I am ever so slightly literary idol fascinated. Our stop back had to include not just Hemmingway’s house, but also a visit to Pilar’s distillery. Best rum I have ever had! EVER! The regular and the spiced. The gift shop had awesome unique items, and the tasting room host told fabulous stories, and shared some fun facts about the island and it’s inhabitants (including one hysterical story of Hemmingway and friends drunkenly stealing the bricks for the wall around his house).

We ended up having too much fun to get back there and get some rum, but save your money, the rum is now available at Wine and More, so if you don’t get to the Keys, go get yourself this rum!

Conch Republic

And it was about this point where the horrifying true confession comes out: I had never had a conch fritter. Luckily, we found The Conch Republic Seafood Company was right down the street. The Conch Republic was right on the docks, open air as most places tend to be in Key West, amazing live music and conch fritters. It was definitely worth it for the experience of conch fritters, but nothing I need to really have again soon. I found them kind of MEH. But now, I’ve had them.

Caroline Street

Aside from my literary history love, I also have a slight obsession with locations in song lyrics. It’s true, I am known to belt out lyrics randomly, without shame, in perfect pitch. MY pitch, not societally approved pitch. So, we meandered on over to Caroline Street, just so I could have a picture taken AS the Woman Going Crazy on Caroline Street. Seriously? Yes! Google it! Do you even know Jimmy Buffett? Follow us, people, it’s a Key West Weekend, we are bathing in Parroty goodness.

Let the Birthday Celebrations Begin

We made a quick side stop for a potty break at this little hole in the wall I can’t find on a map that is Shots Only. . . where I discover Peanut Butter Jelly shots, and Peggy finds Mermaid water.

ssn: It is actually called Shots and Giggles and it was adorable!

This path led us naturally to Sloppy Joe’s, a Key West staple, that consistently makes the tourist list of places to go. It was cool, and I highly recommend a pop-in. Again, they had live acoustic music, dual bars for better service, island décor, worth the touristy stop. And that is where we met some new friends celebrating one of their birthdays, and HEY, it’s Peggy’s birthday too, FREE DRINKS!

ssn: Sloppy Joe’s has a live cam!! Check it out!

We Went Down to Captain Tony’s

After a couple more Key West inspired cocktails, we took our new friends and went down to Captain Tony’s (no, seriously, if you don’t know that reference, we can’t be friends anymore, sorry). And if this is where our story ends, and I die happy.

ssn – this is not where our story ends…

This is all I ever need, my sister, Key West, and Capt Tony’s!

– Drunk Patti

Y’all IT’S FOR REAL CAPTAIN TONY’S!!!! Bras hanging from the ceiling, dollar bills everywhere, cool-ass stools with singers names painted on them (Peggy got David Allen Coe, I got Senator Ted Kennedy. Hey wait, that means they weren’t all singers. . .hmmm.

The guitar player was taking requests (You don’t have to call me darlin, darlin), a hilarious couple telling us about the time they had sex in the Capt Tony’s bathroom like 20 years earlier. And the night gets a little fuzzier and fuzzier. We head back to the AirBnb, Peggy heads for bed, I head for the car to get my phone charger.

ssn: Wowwww…she forgot a LOT! First, we left with the purpose of going on a Walking Ghost Tour. Turns out, we were way too “tired” to focus and stealthily slipped away about 5 minutes in. Second, she made us get massages. Which I don’t remember but I know things were spinning and I didn’t want anyone touching me. Haha…

The End of a Fantastic Night

But then I apparently met more new friends who were celebrating another birthday and had the best Bahn Mi of my entire life at The Old Town Tavern & Beer Garden. Thanks AirBnb Host, Tom, for that recommendation. There are no pictures but it was phenomenal! Then I was off to bed after a crazy awesome Day 2 (and celebrating Peggy’s birthday in perfect #sisbehaving fashion.)

Continue the adventure…on to Florida Keys and Seaplane Adventure to Dry Tortugas National Park – you won’t want to miss this one!