Key West is a destination filled with contradictions. It’s where island time intersects with city convenience. A place that is ridiculously expensive but also has a laid back feel. A place with few locals but many people that visit for 6 months, for the past 20 years. It’s a place of sunshine, nice weather, and a slightly funky smell. It’s everything and more.

To be honest, Key West is one of those places we had heard of, but never dreamed of driving to mile 0 on the USA map. As we were crossing the bridge from Miami to Key Largo, we almost drove over a 4 foot iguana. We’ve nearly hit deer, bears, mountain goats and a variety of other mammals on this trip across North America, but an iguana?  That was unexpected.

Now Key West is just one of those places you have to go to understand. And save up a lot because wow it was expensive. We ate at home most days but when we splurged to eat out, a regular Mexican dinner costs $50+tip. We were slightly expecting this, being one of the top tourists destinations in the USA, but were still surprised. In the video above,  you’ll see most of these highlights, but for a quick snapshot, here were our favorites in Key West.

Restaurants – The Best of Key West

We had some great food experiences and then we had some pricey mediocre food as well.  Key West is one of those places you have to do your research. Don’t just walk into a place because it’s busy–we had a few sub-par experiences doing this. After that, we check reviews beforehand, and have experienced some of best of the best of Key West. And was it worth it!

Blue Heaven– Well worth every penny spent. The video above shares our culinary experience but long story short, our tastebuds were tantalized for sure.

De Luna’s – We went here almost everyday for two weeks. We typically make our own coffee but the T@B does not have a freezer and nothing sounds worse than hot coffee on a hot day! So we *just had to* go across the street to get the best cuban coffee in town. They literally take fresh squeeze sugar cane to add to their espresso mixed & add milk- blew our mind! And the plantains! If you’re in Stock Island, this is a place where they know you by name and a locals favorite hole in the wall. Second best cuban coffee was Cuban Coffee Queen. It had long line but conveniently located on the pier in downtown Key West.

Sarabeth’s Kitchen – Trendy brunch spot that’s worth wait…plus there are great galleries and boutiques to explore while you wait for a table

La Crêperie French Café– Delicious french cuisine!

The Stoned Crab– The name explains it- lots of stone crab and other seafood served overlooking the water.

Fresh Local Caught Seafood

There’s only one place you should buy fresh caught fish on the island and it’s Fishbusters located 10 minutes away from downtown Key West. We purchased the world famous colossal stone crab claws and we were not disappointed. While there, we ran into a local chef, who goes there for is personal fish, as well as to stock the kitchen of his high-end restaurant. The staff there was also incredibly friendly and kind. The best part is they cracked the claws for us to make the experience that much better.  Delicious!

Outdoor Sports Galore


So much off shore fishing here! A little insider tip: Valerie accidentally went fishing at Mallory Square during sunset-the most popular tourist destination in Key West. People said she would have to stop when the crowds came to watch the sunset–but a local street performer said you can keep fishing in the little boxed off section to the right of the shore. Valerie was literally able to watch the sunset among 1,000 people, with her own private, front row VIP box, while she fished. Can’t really beat that.

You can also fish while kayaking! We caught the largest fish from the kayak, but we hear the big guys come to shore regularly too.


Jessi loves to row. Anything with a paddle and the water, she’s one happy camper. Valerie, on the other hand, loves to fish so we tried them both! So glad we did because it was one of our favorite days in Key West. Jessi paddled around the mangroves while Valerie kept her pole in the water. We caught a small barracuda and grunt and also discovered the coolest Mangrove tunnels. For us, it was totally worth the $75/day price tag.  We worked with Kayak Kings on Stock Island. The manager there was a super laid back dude with little worries in life.


So many people bike around Key West that there sometimes seemed to be more bikes than cars. And the trails going to and from town were large, well maintained and were very bike friendly. And the views! All around a very bike-able city.

Paddle Boarding

Have you ever been paddle boarding? Yeah us neither. It’s one of those glamorous things that people with six packs and toned arms do. And their photos are always during the most beautiful sunsets. Geez those people always seem so…cool.

Being the cool, glamorous, and toned kids that we are (JK), we tried it and it was a ton of fun!  It’s a great way to get out on the water and explore the island.  It most definitely gets your core muscle twitching and your arms will feel like they’re about to fall off at times. And it’s really not that hard to stay up. Valerie fell twice and Jessi, being the champion that she is, simply stayed standing or kneeling the entire time. And when it got too hard or the wind was two strong, we simply sat down to paddle. Fun little exercise!


We have big dreams of sailing around the world one day, catching our own food, and living in the Caribbean. We had the opportunity to sail on an old pirate type ship and had a wonderful time. It was relaxing, gorgeous, and another new way to see the island. Sunset was the best time to go because it wasn’t too hot and the view was gorgeous. There are a lot of cruises to choose from but we’re not boozy so we went on a BYOB trip which cost about $100 less. The company we went with was called Schooner Jolly– playful crew, funny banter, was extremely knowledgeable about sailing and were passionate about the ocean.

Dream Big

With its easy island pace, great food, and fun water sports, Key West has a vibe unlike anyplace we’ve travelled so far. It is a place of dreams and sparks the imagination.

We have so many dreams in addition to sailing around the world.  We dream of traveling through Latin America, one day living in Sweden, and hiking the El Camino in Spain. We dream of one day writing a book. And everyday we dream to help LGBT individuals travel safely. And the list goes on and on and on. We call this interaction “dreaming and scheming” and we talk about dreams practically everyday. Oprah talks about when proper planning meets opportunity, you have to leap. We discussed the dream of living tiny and traveling for 100’s of hours (literally, we talk a LOT).  So when the opportunity presented itself to live tiny AND travel, it was an easy “Yes.” (Ok, not really THAT easy it was kinda terrifying but it also felt right. Combo deal type thing.)

So if you want to live the island dream for a bit, come to Key West. It’s a perfect destination to relax, explore the ocean, eat great seafood, and get a taste of the island life.

Dream big and happy travels!





  1. Great article! Brought back memories of family camping in Florida and Key West a few years back. We had a great time, loved the Key Lime Pie! Hope to return again one day soon all the way from BC Canada! 🙂

    • Valerie Reply

      Thanks Robert! And yes- key lime pie was amazing 🙂

  2. I had the biggest smile watching the video of ya’ll in the Keys! I got married in Key West, and it’s part of my mission to move down there eventually, so watching the documentary of your trip down there made me feel so much at home. And doing it the way ya’ll did – with the camper – sounds like an awesome way to visit!!

    Did you take the conch train tour while you were in key west??

    • Valerie Reply

      Aww, what a beautiful place to get married!!! We didn’t do the conch train but we ate conch! Delicious.

  3. marysue Ryan Reply

    Hi, my daughter and I will be in Key West for mere hours about 5. what would you recommend we do? I am an artist and would maybe like to see Hemmingway’s house? I just want to see some local sites and maybe have an inexpensive sandwich somewhere.

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