Sister Trip – Tampa to Key West – Day 1

For years we discussed Key West.  It was the Mecca.  After Running Scared (movie, Billy Crystal, Google it) in our teenage years, and Jimmy Buffett in our 20’s and beyond, we always talked about the “someday” of Key West.

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