Any vacation is a leap of faith, if you think about it. So when your research is exhausted and you finally decide on where to go, what transportation to book, and what accommodations to secure, then all that is left to do is to sit back and hope it all works out for the best. Well in our case, for this little “kids are still home from college” trip to Key West, it most certainly did. And there were many little surprises and lessons along the way.
We normally like AirBnB, which by definition is a gamble, since it involves staying in someone else’s home, which can be riddled with potential pitfalls. But this time we took it one step further and booked an AirBnB sailboat. So not only did we decide to stay in someone else’s home, but we chose to stay in it out at sea, in someone else’s lifestyle.
My college-senior daughter and I stayed on this sailboat moored out near Fleming Key off of Key West, Florida to kick off 2020. We made the decision to do this unique experience while we were driving through a snow squall near Stratton Vermont in mid-December. We were pretty darn cold at the time and dealing with so much snow and ice. A sailboat in warm sunny Key West sounded ideal and the 88 positive reviews of Captain Danny on AirBnB had us sold! So we pushed the button while deep into our snowy drive.
The night before our departure I had butterflies in my stomach and a bad dream built off my nerves and the fear of perils that could befall us with our choice of an AirBnB out at sea. Doubt had crept into my subconscious and was taking over.
But we landed in Key West airport with only carry-on luggage, at noon on a gorgeous hot sunny day in early January.
We were up for an adventure and we were thrilled to be greeted with such sun and heat and palm trees. We bought groceries, flip-flops and suntan lotion before heading to the Thai Island marina. There, we met Captain Danny, who would be our host for our 4-day stay on his 45’ Gulfstar sailboat.
Although a Dallas native, Captain Danny is clearly comfortable at sea, and his laidback charm instantly put us at ease. He whisked us by 16-foot center console out to the sailboat, moored by Fleming Key. We boarded this beauty, with original wood throughout and plenty of charm. We settled in quickly, stashing groceries and luggage and getting the lay of the land from Captain Dan, while keeping our “thinking-camp” caps firmly on our heads.
The trip began with a calming and spectacular sunset cruise with Captain Danny at the helm and we as his guests.
But he allowed Emily to sail the boat quite often! We had some real peace and tranquility.
And then we BBQ’ed skewers of shrimp for dinner in the stern of the boat before settling in for some Marvelous Mrs. Maiseltime.
As there are flat screen TV’s all over Capt. Dan’s boat—then sleep. This was no ordinary sleep—it was a deeper than deep kind, because we were gently rocked like babies while the boat slurped and sloshed against the sea under a sky full of stars. We were really sowing our adventurous oats!
Then we woke the next day for coffee and to enjoy the cotton hammock in the bow. We then set sail for a snorkeling and fishing excursion beside what remains of Hemingway’s stilt house, perched far out at sea over a shallow reef.
It was a sensational day filled with nurse shark sightings while snorkeling, plenty of fish caught, and a very fun rope swing made from the boat’s boom. It was truly a world class outing. We even whipped up our own ceviche for lunch with our just-caught fish and ate it on the boat!
But as we finished lunch, we noticed a line of dark clouds that threatened the sky. And suddenly the day took a hard left and we found ourselves trying to outrace this completely unexpected late afternoon storm.
The wind picked up so much that we had to make a call to book a slip in the marina instead of staying overnight at the less protected mooring again. Captain Danny pulled the boat into the slip at Conch Harbor just in the nick of time. The wind kicked up to 30 knots and the rain began just as the sun set. The relief and gratitude we felt for this safe haven was immense.
We were so crazed with relief at being safe on land that Emily and I went out to celebrate at Schooner Wharf for a beer and to watch the football. We found fellow water adventurers to bond with and swap storm stories with. Emily and I were on land, but felt that woozy, still-on-the-boat feeling of swaying back and forth that happens after being on the water. It made us even hungrier and so we ate dinner at the Waterfront Brewery and slept like babies again on the boat. We felt so safe and protected in our new temporary home, sandwiched between million dollar yachts, safe from the wind and the storm.
Then we woke the next day, our second full day in Key West, to enjoy the island on foot.
We explored and experienced the full New Orleans-party feel of Duval Street, with all the bars and that relaxed open container drinking policy it felt like one giant open bar on a college campus. There is a darty on Duval Street every day.
But Emily and I were more interested in exercising and exploring. And we got 9 miles of walking in as we explored Key West from its historic seaport harbor walk and the main drags of Whitehead, Duval and Simonton. We especially loved visiting Hemingway’s house and his writing studio, the southernmost point, the shipwreck museum and the aquarium.
And we most definitely had our fill of key lime and conch–from limeades to keylime pie on a stick to conch fritters with key lime sauce!
We then went on over to check out Mallory Square for sunset and especially enjoyed the unicycle-riding street performer.
We had heard that The DirtBags band at Dirty Harry’s was exceptional but chose to return to our boat instead. There, we had our own BBQ in the marina slip and chilled out with the big flat screen in the master bedroom and went to bed early.
On our third day, we moved from the wonderful marina, back to our mooring out at sea and had yet another amazing sunset cruise with Emily at the helm. Then we hit Bagatelle for dinner, which is an awesome restaurant on Duval street in a home built in 1884. We ate unbelievable fried artichokes on the upper balcony and did some people watching. The Hogs Breath Saloon entertained us with live music from across the street, and that gave our dinner experience even more atmosphere.
Then we wandered down Duval to find some out of this world nitrogen ice cream (dairy free coconut!) for dessert. Captain Dan picked us up at Simonton Beach on his 16’ center console and took us back to the sailboat so that we could sleep like babies aboard what now felt like a true home away from home.
The next day, our 4th, was also our last and we got to begin it with a spectacular view of the sunrise
and then to relax with coffee and fruit in the bow’s hammock. Then Captain Dan arrived and took us out on the sailboat. We saw dolphin leaping alongside our boat and it was so very cool and beautiful! Then we took Capt. Dan’s paddleboard and hugged the mangrove shoreline and saw a giant orange Iguana in the tree, lots of baby sharks, sting rays and even a crocodile!
Being on the paddleboard allowed us to travel in about a foot of water so it was extremely clear and shallow and extraordinarily cool to be inside the mangroves.
Then Captain Dan took us in a small motorboat and we were lucky enough to see a manatee surface right beside us! It was a breathtaking reminder of the ocean’s majesty. Dan is a real marine life Dr. Doolittle! Having his open-hearted kindness and salt life expertise to navigate these Key West waters was alone worth every penny that we paid AirBnB for this ultimate lifestyle-borrow.
The takeaway is that life on a boat is pretty grand and we most definitely will do it again!
Thank you Captain Dan!!! We will be back!