There are little known places that match up to Key West. Even if you’ve been to the Caribbean, it still doesn’t compare to the eccentric quirks this island is known for. It’s what keeps everyone coming back for more, this leisure, open attitude slightly reminiscent of New Orleans and an earlier Florida era.
History is everywhere. It’s the only beach town where Jimmy Buffett and Ernest Hemingway are naturally-related figureheads, both artists who took their obsession with the island to another level. I’d like to think they’d be friends, and perhaps were Mr. Hemingway still alive, he’d have a bar or bookstore right next to Margaritaville. This is the kind of paradox Key West is. You can have a little bit of everything here, depending on where and when you visit.
I have been coming down to Key West, Florida since I was a child. As I got older, my trips where for partying purposes and we were more half hazard with our research and venue selection. However, as I’ve grown older and travel for different reasons, like truly getting to know a city, I’ve come to be more purposeful with my itineraries. My boyfriend, a fellow travel gypsy, is always up for some deviating but by and large appreciates my pre-planning-pinning bonanza. Prior to my last visit, I researched quite a bit reading what travel writers and bloggers took their time to put together, a habit i’ve gotten into now that I write about my travels and know the work that goes into recommending a destination and capturing the experience.
Here are some thoughtfully-crafted places to visit, things to drink and eat, and even a long-time local tradition. At the end of the post, a free downloadable travel itinerary is available (complete with specific tips for each venue and a link to map each location!).
Ditch the hotel, live like a local.
This is nothing earth shattering i’m revealing, but renting a small vacation home tucked away in a residential area provides a much more authentic experience. We found the perfect option for the weekend. I was a bit obsessed with it (more specific details on venue and booking information in the downloadable). Our 1/1 was teeny, but it was exactly what we needed. Key West is not for staying in your room, but the few moments we were there felt like an episode of Blood Line (without the drama). The large house (or apartment building) had that typical Key West Old Florida look which tugs at my heart strings. I wish New Florida modeled itself more around this architecture, but I guess its rarity only adds to the charm.
There are roosters everywhere, and expect to be woken up every morning by their thoughtful crowing. It’s not annoying because you’re in paradise. I am an early riser and our room was way too small to enjoy my coffee inside (without waking up Jaime), but I actually appreciated this as it forced me to go outside. The porch had comfortable chairs and our view was the residential area right off Duval Street. I felt like I lived there every morning as I leisurely drank my coffee… AND it was the most inexpensive renting option. Seriously, I googled and called like a mad woman.
Drink where the locals do.
There is an abundance of awesome bars in Key West, but I wanted to find out where the locals went. There are two places that were my absolute favorite: The Porch (pictured below) being the first. The ambiance is everything here and its actual porch sets the tone for what this place is about. You can tell it’s a local spot as soon as you walk in. Usually the tourists are getting all sauced up, but here you can see writers with their laptops sipping craft beer and wine, respectively. It’s actually one of the few places we went to that had an extensive list of craft beers available, so the beer drinkers will love this option.
The second was Viva Saloon. This place was only just opening when we went, but the manager was so kind we ended up there 4 times during our trip (and are going back to visit for his birthday!). The way he runs this bar is exactly the way he makes all the patrons feel, like you’re close friends. If you tuned in to the last post, you can see photos of the place and the hand-crafted pina colada Paul went out of his way to make. He has a knack for specialty drinks and shots (must-order shot included in the downloadable itinerary). Ask for him if you go!
Eat fresh seafood & feel like a sailor.
I’m a sucker for themes. I’ll say it again and again, and you won’t judge me because secretly you are too. The Key West nautical vibe is everywhere, obviously, but there are certain little gems that channel this specific type of sailor vibe. DJ’s Clam Shack has a dive bar charm, except there is no grime and everything is fresh. It’s a little hidden place to enjoy great seafood and reggae music. It’s easy to miss so map it and pay attention (specific dish to order and directions in the downloadable!).
Yes, Key West has beaches.
I was really amazed at the overwhelming response of people asking me where the hell I found a beach in Key West. They exist, ladies and gentlemen! And they’re awesome. We ventured over to Smathers Beach, but I have a few other beaches locals recommended us for our next trip. While I LOVE Duval Street, taking a break from it in order to experience that crystal blue water and smooth sand beneath your feet is a little slice of heaven on its own. We packed a cooler with some snacks from the local grocery store and were off. It was a really lovely- and cost effective- way to spend our afternoon.
Experience travelers' long-time sunset tradition.
I seldom take the time to seriously soak in the sunset, despite living in Miami, Florida. However, the crowd that gathers every evening was even more of a draw than that gorgeous view of the sun melting into the water stretched before you. There was a camaraderie formed as everyone gathered arm-to-arm distance on the dock. We sipped our beers or fruity island drinks as we waited for the sunset. Boats passed by and everyone waved. The good cheer was was really infectious and we easily made friends. No one minded if we had to walk around them, there was a mutual respect among the travelers gathered on the eve this sacred tradition.