A Trip to Key West for a Birthday Surprise

When our friend Brad asked Sean and myself if we’d like to join in on a surprise birthday party in Key West, Florida for his wife (and my fellow crazy cat lady bff) Emily – we both blurted out, “YES!” Mind you, this was in January for a July birthday and I’m not great at keeping secrets, especially when the birthday gal is your neighbor. Key West is hands down one of my most favorite Florida vacation spots so it was going to be a long six months of waiting

.Tampa to Key West

Day 1

When the day FINALLY came to hit the road, five couples randomly showed up at different locations and on different days to surprise Emily – it was hysterical to watch her reaction. Sean and I surprised her at Alabama Jack’s in Key Largo. When we all arrived in Key West, we checked into the Key West Bed and Breakfast. This was Sean and my first time staying at a bed and breakfast and while we were a bit skeptical of the idea, we LOVED the KWBB. How adorable is this house? We HIGHLY recommend staying there!


One thing to be said about Key West if you’ve never been, anything and everything goes. Once we were all checked-in and settled, we headed to dinner, but not before being detoured by a hostage crime scene situation on Duval Street. There were police, yellow tape, chickens, and drag queens running everywhere. Hours later, we learned it was all a hoax but it was wildly insane to witness all the activity!

Key West Hostage Situation

We finally made it to dinner at Santiago’s Bodega to enjoy delicious tapas, sangria, and birthday Prosecco before heading to our favorite, Fat Tuesdays! In true birthday style, everyone made sure the birthday gal had a GREAT time on Duval Street.

Fat Tuesdays Key West Florida on Duval Street

Bright and early the next morning, our group rented bicycles from our bed and breakfast (which is a great way to get around KW!) and visited the touristy spots for photos, starting with the Southernmost Point and Mile 0. (It’s funny to see the difference multiple cameras can truly make when their photos are grouped together! This trip I had five cameras with me made up of two cell phones (iPhone/Galaxy), a point-and-shoot, a SLR, and a GoPro so don’t mind the differences in quality!)


Day 2

Southernmost Point and Mile 0 in Key West Florida Southern Glam Meagan Phillips

Southernmost Point in Key West Florida

And then…. my most favorite place EVER, the Ernest Hemingway House. Emily and I are both crazy cat ladies so we felt right at home there with all the cats. It was mid morning (and HOT!) so all the fluffies were taking a snooze but didn’t mind insistent pets from us!

Ernest Hemingway House in Key West Florida

Lunch followed at Sloppy Joes where another couple surprised Emily. It was SO incredibly hot that a dip in the Dante’s pool was definitely in order!


That night a few of us had planned to go on a sunset cruise charted by Fury where one of the couples in our group became engaged!

Sunset Cruise


Day 3

The next day, half our group went deep sea fishing (not me!) and the other half went back on a Fury catamaran for an all day excursion to snorkel, parasail (not me!), jet ski, and play water sports. I’m not one to be dropped in the middle of the ocean but I braved it and last about ten minutes! I learned it’s hard to be glamorous and take photos with 1-2 foot waves are tossing you around while wearing highly fashionable snorkel gear! Sean, however, was in his element and loved it!

Dinner that night was at Nine One Five which the birthday gal didn’t like … go ahead and skip that restaurant!


But, the dessert afterwards was amazing – we stopped for chocolate dipped key lime pie on a stick – did you get all that delicious-ness? The key lime pie is divine (duh!) but dip it in chocolate and it’s heavenly. I might have brought back a piece, or five back home! The best place to find this treat is Kermit’s Key West Key Lime Shoppe. I tend to go on a shopping spree with a cooler in hand when stopping by!

Kermit's Key West Key Lime Shoppe in Key West Florida


Day 4

Fast forward to the next day which was July 4th – we set sail yet again on a Fury catamaran for another snorkeling excursion and booze cruising afterwards.

We ended the day back where our shenanigans began – on Duval Street to celebrate the fourth and to cheers a successful birthday weekend for Emily!



Travel Tips

While this wasn’t our first trip to Key West, I did want to pass on a few tips for those planning a visit for the first time.

  • Driving – As it was stated in the Netflix series, Bloodline, plan extra time to drive through the Keys. It always takes more time than you think. It’s mainly a two lane road through the Keys, however, it’s a gorgeous ride! (I recommend watching Bloodline – it’ll make you beg to be in the Keys!)
  • Places to Stay – Sean and I rented a house with a group the first visit to KW and then stayed in a bed and breakfast this time. There are hotels on island but the B&B was perfect and I highly recommend this option. Key West Bed & Breakfast was truly amazing! We stayed in the “Yellow” room where we had our own bathroom and balcony. The breakfast each morning was delicious! Just look at this spread of freshly squeezed orange juice, warm freshly baked pastries, coffee/tea, bagels, and fresh fruit. You’re greated like family from the moment you arrive and treated as such your entire stay.

Key West Bed & Breakfast in Key West Florida

  • Bicycles – You won’t want to drive around once you’re in Key West. Park the car and rent a bicycle, or scooter, to get around town. Sean and I walked everywhere on our first trip to Key West and were grateful our B&B had bicycles we could rent daily.
  • Cats and chickens – They are everywhere and I LOVED it! Anything goes in Key West!
  • Sunscreen – The sun is crazy hot so bring sunscreen and aloe. Lots of it!
  • Duval Street – This is where you’ll want to be if you’re not on a boat. Shopping, dining, bars, and people watching are right here. Most B&Bs are within walking distance of Duval but double check when visiting that you’re staying nearby.
  • Cooler – bring a small cooler or lunchbox with you to take home key lime pie. (I’m totally not kidding!)

What an amazingly fun time we all had celebrating with Emily! Happiest of birthdays, crazy lady!


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