Living the Dream: Do the Florida Keys Like a Pro (Photos)

Reading Time: 5 minutes

Pirates, pina coladas, salsa music, and sailing was an experience calling our name.

That’s the type of call you pick up.

Finally, I had made my way to Miami (with a girl I’d just met) and was prepared to road trip and sail the Florida Keys with someone I had yet to meet.

Somehow, it was perfect.

You would think it would be impossible to be unhappy road tripping and sailing the Florida Keys with the right people. Happy is an understatement!

Great travel companions come in all shapes and sizes. Who would you like to travel with?Click To Tweet

Need a preview?

Here’s how to do it:

1. Pick an Awesome Group of People, and Hop in a Car with Them

Have you ever spent time with someone that you felt like you can be yourself around? All of yourself?

Hopefully.

Now multiply that by a party of three, having met through social media and each knowing each other only just then.

Introducing Matthew Karsten from ExpertVagabond.com, and Lauren who came to my Napa meet up and bought a flight to join me in Miami within 24 hours of us meeting.

We hopped into a black convertible jeep on a day as hot as the city itself. Miami to Key West… let’s go!

Because we booked a jeep through Tons of Fun Tours, we were free to stop wherever we wanted, exploring the keys at the comfort of our leisure.

With the breeze blowing, the music blasting, and a stuffed shark pet between us, we made our way from Miami to Marathon, Florida.

2. Catch the Sunset in Marathon, Florida

I think mother nature is teaching us how to color.

Staying and catching the sunset at the Faro Blanco Resort and Yacht Club.

3. Eat Local Fish and Indulge in a Florida Keys Culinary Experience

Best Restaurans in Marathon, Florida:

Tarpon Creek Bar & Grill

Lighthouse Grill, Faro Blanco Resort and Yacht Club

Best Restaurant in Key West, Florida

Bagatelle, Key West

You probably caught photos of my favorite meals on Snapchat (TravelBreak) — it’s a cocktail and seafood haven.

4. Sail the Florida Keys. Be a mermaid.

Soak in the sunshine with Sunset Sail Key West.

5. Do the iconic (cliche, but worth it) tourist attractions.

Drive/ Walk the Seven Mile Bridge.

Feed the scarfish at Robbies in Islamora (it’s terrifying!!).

Catch the sunset at the Key West pier.

Sunbathe at Fort Zachary, the “best” beach in the Florida Keys.

Where to stay?

For an apartment style resort suite, consider the Marriott Key West Beach Side, who partnered with us to share the gorgeous Florida Keys. I spend a lot of time in the hotel room catching up on work (the world is my office), so staying somewhere that I really enjoy is important to me :)