Key Largo Houseboating

All Aboard Key Largo: A Girlfriends’ Getaway on Houseboat

By Kate Hartshorne

The Tobbiedee, a great home for a girlfriend's getaway in Key Largo, FL. photos by Kate Hartshorne.
The Tobbiedee, a great home for a girlfriend’s getaway in Key Largo, FL. photos by Kate Hartshorne.

We’ve done condos. We’ve done hotels. We’ve been camping. Trailer parks depress me. We all know how to go to Florida and stay in the well-advertised properties constantly popping up on the web.

For this quick winter jaunt with my three girlfriends, I wanted something different that didn’t break the bank. In my search for the optimal scenario, I stumbled upon the idea of a houseboat.

Houseboats are abundant in the Florida Keys and offer an affordable alternative to the basic condo with the sense of adventure that comes from being surrounded by water.

I found our houseboat, the Tobbie Dee, by chance when calling someone else about another (already rented) property. I got Bill, one of the owners, on the phone and made a spur of the moment decision that turned out to be a good one.

Docked at the very entrance to the Keys, the Tobbie Dee was a snap to get to after we arrived in Fort Lauderdale. Our hostess Laura was friendly and laid back, and made sure that our boat was stocked with everything we needed, including her own personal blender for mixed drinks.

Laura and Bill have a fleet of four houseboats docked together in the same marina, we chose the largest of the four for our week aboard.

Shabby Chic Houseboat

The boat was shabby in the perfect sort of way. Permanently docked in the somewhat rundown but also distinctly charming Gilbert’s Resort, our houseboat was roomy enough to fit four women comfortably (with beds for six) and allowed us to sip coffee while watching pelicans swooping down to catch their morning fish.

The comfy and cozy interior of the Tobbiedee houseboat.
The comfy and cozy interior of the Tobbiedee houseboat.constant view of the water.

The best part is that it was dirt cheap at under $200 per night, and had a We found boats as cheap as $80 per night in parts of the Keys, but given that we were splitting the bill four ways the Tobbie Dee was certainly worth every penny.

Gilbert’s offers moderately priced food and cocktails right in the sand, so for our first night after traveling it was a pleasure to have dinner at the ready on arrival. We were settled into our boat and on the beach in time to watch the sunset over the bay with a drink in hand. The food was decent and the pina coladas tasty, a great way to ease into vacation mode.

The pretty and deserted beach at Bahiahonda, Florida.
The pretty and deserted beach at Bahiahonda, Florida.

Fresh Squeezed Heaven
Our daily escapades began each day with a trip to the Casa De Los Jugos, a local Key Largo haven for coffee and juice lovers alike.

I easily consumed my body weight in freshly squeezed passion fruit juice, which (when combined with enough rum) could very well create world peace, and Cuban coffee in small thimbles, strong enough to wake any narcoleptic.

Casa De Los Jugos also made daily delicacies such as Cuban sandwiches, breakfast, and rice and bean dishes, all of which were quick and delicious. We stopped there every morning of our trip and by the end, we felt like regulars, with the jolly Cuban women behind the counter making our coffee before we had time to order.

Scouting the Best Spots

Each day we filled our thermoses with fruity cocktails and headed to a different beach, the most stunning of which was the renowned Bahia Honda State Park, located about 1 ½ hour south of Key Largo in Big Pine Key.

The Keys aren’t known for sandy beaches, it’s mostly rocky shoreline and coral reefs, so Bahia Honda is a lovely surprise for the long stretch of sand and turquoise water. We wasted no time in getting ourselves good and sunburned at Bahia Honda, an easy mistake to make in the strong Florida sun.

There were many options in the Keys for snorkeling, boating, and fishing, with charter boats leaving from every corner offering rides out to the reefs, sunset sails, and deep sea charters. We declined these options this time around, opting instead for nature walks through John Pennekamp Coral Reef State Park in Key Largo and long afternoons soaking up the warm Florida sunshine.

The snorkeling tours from Pennekamp State Park or Bahia Honda cost about $30 per person for a 2-hour tour and seem to be the only way to get a good view of the reef. I will be sure and climb aboard next time I visit the Keys, it leaves me a great reason to have to go back again soon.

Many mothers know the feeling of freedom that comes from passing the torch of responsibility for a few glorious hours, or in my case, days. I hadn’t been on a beach without my kids since they were born, and the release of not being responsible for anyone else was tremendous.

No constant scanning of the water to prevent drownings, or being dragged over the sand to build the requisite castle. I love these moments with my children, but this vacation was the polar opposite. Girl talk, from the most intimate details to the superficial, had us laughing the entire time. My anxiety over leaving my family for a few days on my own quickly subsided as my sense of self returned in full force.

Nose piercing in Key Largo: Not for the faint of heart.
Nose piercing in Key Largo: Not for the faint of heart.
Why we go on vacation.
Why we go on vacation.

The Southernmost Point

The Keys are connected by one long road, US 1, surrounded on either side by crystal blue water. It was easy for us to keep heading south after our day at Bahia Honda and spend the evening in Key West.

After catching an overcast sunset in the famed Mallory Square, the southernmost point in the United States, teeming with strange performance acts and coconut vendors, we headed to dinner at a tiny open-air Cuban restaurant, Juan Loves Lucy.

A strange combination of brilliant ambiance and terrible food, we were somewhat mixed in our take on this restaurant, but the enthusiasm of our waitress made for an entertaining experience.

After dinner, my friend Liz announced that she had always wanted a nose ring. We immediately decided that she should not spend one more day without one, and Key West was just the place to get the job done spur of the moment.

Tattoo parlors and piercing shops are abundant in this eclectic town, and it took no time to find a shop ready to pierce at 9 pm.

I have never seen something so simultaneously painful and hilarious in my life, or maybe I am just a really sadistic friend, but I had a hard time not shaking from laughter as my poor friend had a hole shot through her face.

She was quite pleased with the results and after it was done we ambled back down the long road to our houseboat in the dark, full and content from three long days of girl time.

Great for Any Budget

Drinks at Gilbert’s Tiki, where you can rent houseboats.

The wonderful thing about a girlfriends’ getaway to the Keys was that it was entirely possible to make happen even on our limited budgets. Our houseboat had a full kitchen, allowing us to have our breakfasts of fresh mangoes and avocados on board, pack our lunches, and save our pennies for a simple and delicious dinner out.

Full of fun and easy to get to made this houseboat vacation a winner for any gals looking to escape for a quick retreat.

Gilberts Resort Key Largo
Hotels in Key West

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