Florida Keys Trip for 50th Bday (Days 1-3)

I had been planning for a couple years for a grand Paris and Amsterdam extravaganza for my Fabulous 50^th birthday but thanks to COVID, I decided to play it safe and stay stateside. This led me to recently checking off an item on my travel bucket list - The Florida Keys.

The travel party of Divas included the usual suspects: my daughter (26), my best friend (age not disclosed, but she is OLDER than me, shhhh) and myself. The BFF was flying down from Jersey direct into Key West a day after we got there, and el kiddo and I originally planned to take the Key West Express Ferry out of Ft Myers. The drive from our house to Key West is just over 7 hours. The drive to the ferry is 2.5 hours and the ferry ride is about 3.5 hours. The ferry boarding starts at 7am, and with a 2.5-hour drive from our home to the ferry, we were going to stay over the night before. The return ferry did not leave Key West until 6pm so we would not get back to our home until after midnight. But then I dug deeper and priced it out. The price for this was over $400 not to include the $105 for parking! No thanks. 

Note: price included 2 carry-ons per person (a suitcase was $30 extra).  

We decided to drive and just split the trip up since we were not in a hurry. That led to us driving to Key Largo, staying a night then on to Key West for 6 nights and on the way back staying a night in Naples before arriving home. I shall now give a breakout of the trip with some of the truly wild and silly things that happened along with a few mini reviews of places and links to bigger reviews of some of the hotels. Buckle up and let's head to the Florida Keys!

Day 1 – “Let’s Get it Started” -- travel day/Key Largo/Marina del Mar Resort: 

El kiddo (you will see I call her a myriad of things from el kiddo to Miss Thang to crotch fruit and lots in between - all with infinite love) and I planned to hit the road at 10am so that we could start the 5-hour drive and get to our hotel in Key Largo around check-in time. Of course, we did not get ourselves together and out the house until a little after noon. Whatever, it was vacay!  Then we hit traffic backed up caused by an accident just as we got out of Miami and hit Rt 1, which is the start of the roughly 165 miles between Miami and Key West with most of it being one lane each way. That held us up for about 45 minutes but if we knew then what we know now, we would have kept driving and just skipped Key Largo. The Divas arrived at Marina del Mar Resort and Marina around 6pm. Let me just say, they have some awesome photo filters at work for them as it did NOT live up to the pictures online. Not that we were expecting a 5-star stay but for the $242 charge, we wanted something decent for 1 night without paying over $400 for the Marriott. We should have paid the money. We were so traumatized by our stay that I wrote a separate review Marina Del Mar Resort Review . 

Day 2 –“Let’s Talk About Sex”--Key West/Ocean Key Resort/Better Than Sex:

We usually lounge until checkout time and just barely beat the hotel staff locking us out of our room and giving us the boot but not this time. We were up and out before 9am. Would have been earlier but since we had to park next door and heard screaming in the night, needed to make sure folks were up and about to act as witnesses, just in case anything went down when we made a run for it. The hotel serves a continental breakfast, but we just rode through Starbucks and started our true adventure. I must say the ride from Key Largo to Key West is just gorgeous and even though it was an overcast day, it was still breathtaking at many points. The ride ended up taking about 2.5 hours (113 miles) over the 42 bridges connecting the various keys on the Overseas Highway. A couple of interesting tidbits because yes, I am a bit of a trivia nerd - 

 

            1) large parts of the Overseas Highway were built on the former Overseas Railroad which was an extension of the Florida East Coast Railway. Mind you, it took 7 years and $50 million to build the railway causing the death of 700 people. The route was heavily damaged and partially destroyed by the 1935 Labor Day hurricane. The railway was financially unable to rebuild so sold the whole lot to the state for $640k.

 

            2) Seven Mile Bridge was one of the longest bridges in existence when it was built, but due to damage suffered in 1950 during Hurricane Donna, it was rebuilt but the new bridge is actually only 6.8 miles long (I won’t tell if you won’t, I guess size does not always matter!). The bridge carries the Florida Keys aqueduct (which supplies fresh water) and fiber optic cables to the lower Keys.

Ok, back to regularly scheduled programming. Rolling into Key West and seeing that welcome sign brought a small thrill, as that meant we were almost to our home for the next 6 days. We were too early for check in, so decided to just drive around a bit to explore Duval Street, Southern Most Point (drive by), and other sites on the island.

I will say that driving the streets is an exercise in patience and agility as they are very compact and people have no concept of the damage a 1.5+ ton vehicle can do to your person if you pop out in front of it. You will lose that battle every time. 

Around 1pm or so we headed on over to the Ocean Key Resort and Spa (see my detailed review here - Ocean Key Resort Review). The hotel was great, in spite of a few mostly minor inconveniences. We valet parked and check-in was smooth. Thankfully our suite was ready early, so we got complimentary rum punches to take with us on our stroll to suite #217. 

 

Talk about exhausted, after an almost sleepless night, where we “slept” fully clothed, in-between the top sheet and the comforters, the non-child and I just wanted to relax a bit so we ordered the 1^st of many room service meals. We mixed up a couple drinks with our brought-from-home El Padrino mango tequila and some Sierra Mist and the party was on! 

Side note: we got the tequila a few weeks before by accident and just fell in love with it! 

The rest of the afternoon was settling in and resting as we had ressies that evening for Better Than Sex – an all-desserts restaurant. See The Divas Review for details on this experience (Better Than Sex Review).  

Day 3 – “Oh My, Sir” -- Key West/BFF Arrives/El Mason de Peppe:

One of my very favorite things to do on vacation is sit on my balcony early morning and watch the daybreak and see the world awake in peace. That is why, whenever I can, I get an Ocean Front room with a balcony. I spend hours out there. Well Key West had quite the Howdy Do for me this morning. 

Sitting out on the balcony around 6:30am listening to the morning sounds (and plenty of roosters, by God those buggers are loud!). This dude was asleep on one of the cabana beds by the pool. I ignored him and was reading a book then I heard a loud thump. Ole boy for real rolled off and fell on the floor. He laid there for a bit, perfectly still. I kinda kept an eye out and then he started kind of rolling around and wiggling, waaay too close to the pool for my liking. I was like crap; this guy is going to fall into the pool and I am the only one out here and I am going to have to hobble down and try to save him. He finally got his must-be-drunk behind up and wandered to another bed, turned around facing me and stripped off his swim trunks, showing his twig and berries, then dropped down on the bed with legs spread. I ended up calling the front desk, who were horrified and apologetic and then went back to the balcony to watch the show with security.

I will say security showed up very quickly and dude was pissed when he saw the guy. He walks over and says, “I literally get off in 3 minutes, and I have to deal with this sh*t?” I cracked up and startled him. He proceeds to try to wake drunk guy up without actually touching his sweaty, naked body – did I mention how freakin humid the Keys are? The guy finally comes around, junk swinging and seems to realize where he is and grabs a pillow off the cabana and presses it to his groin. Security says “Man, no one wants to see that, go back to your room and sleep it off. I thought we were cool. I thought we were friends.” The guy slurs out something like, “We are friends, we are more than friends. You my main man!” Security says nope – my friends don’t act like this, now go back to your room. Dude shimmies into his trunks and sort of waves in my direction and mumbles an apology. Security sincerely apologizes to me and just shakes his head. I sat out there for a bit just to see what would happen and I must report that no one came to change the sheets on the cabana bed or change out the swamp crotch pillow. I had been looking forward to grabbing a cabana one day but that killed that plan.

 

Today was the day that the BFF flew in. We headed to the airport to pick her up and let me just say, Key West airport is tiny and a mess.  Makes sense I know but we ended up going next door to park at the “bus terminal” to wait for her to get off the plane as they were delayed on the runway. She finally got off the plane then it was a zoo to get luggage. Over an hour after she landed, she finally emerged victorious, well in one piece anyways, from the airport. Because I am a smartass, I had the song Darling Nikki by Prince cued up to play as we pulled up (yep, her name is Nikki). She did not find it nearly as funny as we did but I still stand by my choice. LOVE YOU GIRL! 

 

Our hotel is right on Mallory Square so for a late lunch we cut across the square to check out El Meson de Pepe, a Cuban spot. See the review here El Meson de Pepe Review. It was an easy rest of the afternoon just hanging out. Since we could see Mallory Square from our balcony, we sat out there sipping libations from the bar that we  brought with us (I am sure bell services thinks we are lushes) to watch the Sunset Celebration. It was cool to be away from the crowds but still feel apart of the festivities. Is it overrated? Yeah probably, but we had fun anyways. 

Stay tuned for the next Installment –(Days 4 – 9)