Where we’re at: I’m recapping my summer of 2018, which included this trip to Florida in July. In other news: after the first week sold out so quickly, we opened up a second set of dates for my Wander Women Red Sea Retreat.
Forget Vegas, Austin and Nashville. When it was time for my girl Ashlee’s big bachelorette splash, we knew our beach loving girl deserved nothing but a send off from singlehood in the Southernmost place in the USA — Key West!
I’d long been eager to visit the Florida Keys, and Ashlee’s bachelorette gave me the excuse to finally make a big trip there happen. Now, if some of my loyal Wanderland readers are thinking, “wait, didn’t this chick already have a badass bachelorette in another Sunshine State hotspot, The Wizarding World of Harry Potter in Universal Orlando?”
Well yes in fact she did!
But tell me, why should there be just one opportunity to celebrate the wonderful women in your life… and take a tropical Florida vacation?
Especially to a destination as unique and colorful as this? (Plus, our Orlando bachelorette was more of a #BasicallyBaackes private party. This one was the traditional, big group bachelorette.)
After a mimosa-filled private transfer from Miami all the way down to Key West, we arrived at the gorgeous rental house Ashlee had found for us, right on Southern Duval Street.
Olivia and I excel in gift bag creation, and this was the perfect opportunity to really splash out. (See what I did there?) I put together an ocean-pun filled color printed itinerary for the weekend, while Olivia ordered a set of laser-cut mermaid name tags for all the ladies in attendance. Add a few mermaid shellebration decorations, and we were ready to party with the porpoises!
After settling in and enjoying a splash in our small backyard pool, we were off for a low key first night at Latitudes, one of Key West’s most lauded restaurants. Get this: you have to take a boat to get there! From the restaurant’s perch on Sunset Key, it’s a mere eight minute ferry ride across the Gulf of Mexico from the famous Mallory Square.
We requested an outdoor table to take advantage of the sunset views, and boy did that giant orb in the sky ever deliver. It was the perfect first night: the food was delicious, it was great to sit down and get to know some of the girls for the first time, and it was a lovely way to ease into a big weekend after everyone had traveled far and wide.
At a place as lovely as Latitudes, almost everyone is celebrating something. But they still lavished our bachelorette with attention, bringing our sparkly girl some sparkling desserts! It was the perfect welcome to Key West.
Back at the house, the ever-thoughtful Ashlee wasn’t going to let the weekend slip by without acknowledging another big celebration in the group: Olivia’s birthday! And right on theme, too. We slapped on some face masks and fell asleep watching the mermaid classic, Splash.
The next morning, it was time to get nauti! We chartered The High Tide vessel for a mimosa-fueled morning sail around Key West, and to the delight of our crew, arrived in full mermaid regalia.
It’s kind of a misconception that Key West itself is a great snorkeling destination — the best snorkel-able reefs in the Keys are actually in the Upper Keys, and Key West itself is surrounded mostly with sea grass. But we were just happy to be out on the water, celebrating our girl, saying hi to lobsters, and singing the soundtrack of The Little Mermaid at the top of our lungs.
While we had a blast, I do have some hesitations over whether or not to recommend this particular charter to other Key West bachelorette parties. The upside? The owner was very friendly and willing to squeeze us in to a packed schedule when we booked last-minute.
However, we were disappointed that the promised floating “lily pads” that he promised for sunbathing weren’t onboard, and while the crew was lovely, we found the spots they brought us to a bit odd — we kept pushing to head to waters not completely covered in seaweed — we kept emerging looking like creatures from the blue lagoon! We eventually got to spots we had fun splashing around in, but we were definitely scratching our head at their initial choices.
Later that night, after some much needed naps and lounging around our Mermaid HQ, it was time to party our tails off again!
Going out in Key West is a blast because you don’t really need a plan — everything is quite centrally located on Duval Street, and very few places charge a cover, so you can pretty much hop around and see what looks and sounds good for the night.
I also loved that it was a very “come as you are” situation — we splashed out and got all dressed up because that’s what we love to do, but there were just as many people rocking the dance floor in sneakers, shorts and t-shirts. In Key West, everyone is welcome.
The next morning, against all odds, bridesmaid Kelly and I made it out the door for Yoga on The Beach. It was a gentle class, perfect for our delicate conditions the morning after a big night out. At $18 it wasn’t necessarily cheap, but it was in line with what I’d expect to pay at a drop-in yoga class on vacation.
Back at the house, the other mermaids were stirring, and it was time to let the sea set us free! We had designated this the official “mermaid’s choice” day where everyone could have some structured free time to make sure they got to live their big Key West dreams. These were the suggestions I included in our cute little welcome booklets:
• Fun in the sun! The pool is open, and beaches are abundant! Fort Zachary Taylor, Higgs Beach, or Smather’s Beach are within a twenty minute walk, but teeny South Beach is moments away.
• Retail therapy! Use your pearls to shop till you drop.
• DIY Rum tour! There are guided tours and tastings at Papa’s PilarRum Distillery every hour starting at 1PM, free tastings all day at Key West Distilling, and free mojito making classes at 4:30PM at Key West Legal Rum Distillery.
However, everyone was having such a good time we decided to stick to our pod and spend the day together, starting with some much needed substance.
Eventually, we made our way to Fort Zachary Taylor Beach. This state park is a bit tucked away, but well worth seeking out — it definitely disproved the oft-repeated rumor that there are no real beaches in Key West. This one was a beauty! You walk past a Civil War fort to reach the pebbly white beach, where there is loads of shade, a little cafe, and the clearest water we’d seen in Key West.
There is a $2.50 entrance fee for all pedestrians which is super reasonable and I think keeps it from being overrun.
On the walk back to our house, we wandered into a few cute boutiques, including Key West Pottery, who I sought out after following them on Instagram for some time. And look: it’s like they knew we were coming!
That evening, we had one more surprise for Ashlee stuffed in our shell bras! A Splish Splash Private Supper, provided by a local private chef. She was a hoot, and kept us laughing with local lore as she prepared us a beautiful multi-course meal.
I’m a big fan of doing an at-home meal for a big weekend like a bachelorette party, and think I’ll try to incorporate it into all future events of this kind — it gives you a break from the constant hustle bustle of restaurant meals, and gives you a chance to enjoy the beautiful house you’ve rented for the occasion.
And while the meal itself is often a bit pricier than your average restaurant, you can somewhat break even since you can supply your own alcohol.
We also had a really special moment where Olivia presented the book she’d had made of memories from all the special women in Ashlee’s life. We all cried as she read them aloud and showed off the fun photos and memories they came with — it was a reminder of what an incredible woman we’d all gathered to shellebrate!
And of course, we all had a big laugh when we saw Ashlee’s surprise of a custom cake earlier in the weekend came right back at her — with a different underwater-themed cake, this time in her honor. Good thing sugar makes up such a big part of the average mermaid’s diet!
Though there’d been some discussion of taking things easy before everyone traveled the next day, we simply couldn’t resist the siren song of one last night out on Duval Street! What Bourbon Street is to New Orleans, what Broadway is to Nashville, Duvall Street is to the weird and wonderful little island that is Key West. And we had a blast enjoying it.
By this point, we’d found our favorites — we were big fans of Durty Harry’s and Sloppy Joe’s, both of which had rocking dance floors and a propensity for playing Britney Spears.
The next morning, it was time to call it a wrap. We’d had plans for an official “Back to the Ocean Goodbye Brunch” at Blue Heaven, but they don’t take reservations and they were packed — so we grabbed something simple to-go elsewhere and indulged in much-needed foot massages at a tucked away reflexology place off Duval instead. Hangover, be banished!
And then it was time for some sad goodbyes — though luckily in my case not to the Keys, as I was heading right around the corner to a Key West hotel to start the scuba diving portion of my trip (stay tuned to hear all about that, of course!)
But alas, the girls were leaving. We all agreed, we’d picked the perfect spot. Compact Key West is a winner for bachelorette parties in my book — accommodation is pricey but well worth it, there’s a laid-back but bustling nightlife scene, endless entertainment, and lots of sunshine and smiles to go around.
Ah, I love bachelorette parties! From Angie’s surprise shark-themed bash in Bonaire to Ashlee’s wizarding weekend in Orlando to Kirsten’s Nash Bash in Tennessee, they’ve all gone down in the books as incredible weekends — I never take for granted the opportunity to spend special time with the women in my life. Ashlee, this one is to you, my girl!
What’s your favorite bachelorette destination?