Written By: Alex Richwagen
This is the second part of our Key West Beach Review. If you missed Part I, go ahead and click here to review and go back. Otherwise, let's get rolling.
Next I’d like to tackle where to plan ahead and stay for 3-4 days. I’ve mentioned a few places along the way, but let’s really key in to make sure the advice stays with you.
There are several options around the Key West area trying to find where to stay such as a condo, hotel, private housing, luxury, on a budget. Let me start by saying don’t discount private housing as folks could really get a steal without the disturbances of a hotel. There’s options like vrbo.com, which allows people to rent out their house at specific times of the year. You might just get lucky enough to grab a house in Key West on a deep water canal (like I did) and live among the locals. There's some great spots to play some water games with your friends, like H2ole from Cornholeonwater.net. If you had a boat, this could come in quite handy to hook it up to the inner sea wall canals.
Hilton Grand Key Largo – This is a great spot that has all the amenities like a tiki bar, great beach setup (that’s super close), and a few pools to spare. The inside is a bit outdated (and sometimes smelly) like the bathroom and shower specifically, but hey…it’s a hotel Key Largo, so no complaining. There’s a boardwalk around the area to stroll the area and catch the sunset. Speaking of which, do yourself one huge favor. When booking the hotel, be sure to ask for a higher elevated room. Why, you ask? The fantastic sunset on the Gulf side is much easier to see from the third floor and up to escape the palm trees.
Islamorada Resort (Hampton Inn & Suites) – As mentioned before, it has a great tiki bar, outback steakhouse attached and free docking for the boats (if you bring a boat). The restaurant, Outback, in Islamorada will also cook your fish – flash fried the fish, scored on each side, with sea salt, add a bit of lemon on some yellow tail snapper (at the old Hampton Inn). That’s another dinner that’s fantastic.
Remember the information above about renting a house from the locals, well check out the scene at Big Pine Key. This is the area where I got lucky as it has deep water canals, showers in the backyard, dual porches with screened in 1st/2nd floor, and is minutes from the beach.
The last and most inexpensive way to travel down to Key West is via a hostel. It’s mainly used by backpackers and travelers on a severe budget. If you have that kind of budget, this would be a great alternative place to stay. There are literally plenty around like the Seashell Hotel in Key West. They have options for private rooms, dorm room style quarters, or renting with others to keep your costs down.
I feel since the abundance of fresh food that’s in the area, we have to dedicate more time for just food in general. There’s a fantastic spot called the Marathon keys fishery that has some of the best stone crab claws I have eaten for very reasonable prices. They have a bar on stilts (2 story stilt bar), where folks can only sit on 2nd floor by walking up the stairs that overlooks the beautiful gulf. Oh yeah, they have complimentary sunset celebration shots for everyone too. Getting back to the food. Since it’s a fishery, they have a fish market to place your order that serves items like fresh fish, spiny lobster, grouper (blackened, grilled, or fried) and served with coleslaw (so good!). Oh yeah, don’t forget to grab the loaded crab dip with crackers. One last thing, they actually ask you where you are from instead of your name, and that’s what they call to call your order, which is pretty cool.
Islamorada Fish Company – This is another great spot (that has other locations) and is affiliated with Bass Pro Shop or Sportsman World. The restaurant has a huge bar on the water that is obviously great for outdoor seating. The last time I was there, I grabbed the Yellow Tail Snapper served blackened with a side of fries and coleslaw. The Snapper was nothing short of spectacular to pair with the great scenery. Before you sit down for dinner, there’s a tarpon pit (game fish/sport fish) overlooking water to check out as well just to watch for cheap entertainment.
Kelly’s Key West Caribbean Bar – It’s located on Whitehead Street and has a really great outdoor atmosphere with tables accompanied by candlelight. So yes, it’s a great date spot. They have some really great food that’s reasonably priced. One of the dishes I found really tasty and unsuspecting was the Bife Ancho. It’s a nice size Ribeye (I think around 12-16 oz) with a light dusting of chili and a generous covering of chimichurri sauce (cilantro/garlic/oil based mix). It was cooked a perfect medium rare with a loaded baked potato. Dress with a collared shirt and you’ll be fine.
Sloppy Joes – This is a great night time spot that has good music every day of the week. I haven’t eaten here except for appetizers, so I can’t speak for the dinner menu; however, the drinks are tasty, the music is good, and there’s plenty of folks dancing. The Conch Chowder was really close to the Caribbean and the Buffalo wings were pretty good, but don’t worry, stick to it as a good bar. Check out the events calendar here to see if anyone is performing you know in advance.
Hog’s Breath – Another great bar near Duval Street to go bar hopping about the area in Key West. The Mahi Mahi Key West dinner was super fresh with an islandy topping of mango, pineapple, cilantro, and jalapeno to give it some spice. That’s my only dinner recommendation as this place serves as another great spot for live music and strong drinks. It’s kinda like one of those bars you loved in New Orleans without the smell of Bourbon Street.
The Whistle Bar / Garden of Eden – These spots are literally on top of each other within the building. I loved hanging out at the Whistle Bar on the bar hopping trail for the music and cocktails. On top floor, there’s the Garden of Eden. This Duval Street’s only optional clothing bar for those nudist out there. So feel free to “Come as You Are” regardless of how much clothes you start out wearing as they take the Key West slogan to another level. Lots of fun here including Beer Pong at times (ask the bartenders).
Southern Most Hotel – Yes the actual hotel is named the Southernmost Hotel, that’s pretty cool. We stayed here once last year around Bartender’s Bash and it was such a cool place to be. They have a great happy hour (from Sun-Thurs, 4-6) with a really nice outdoor bar called the Pineapple Bar. The hotel is at the corner of Eden and Duval Street. Even if you aren’t staying, drop by for happy hour, as the staff is super friendly.
Mallory Square – Have you ever heard the phrase, “See you at Sunset”? Well, I invite you with the rest of Key West to go do just that. Mallory Square is located at the west end of Duval Street on the gulf side. Daily, they have a sunset celebration with street performers, vendors, jugglers, clowns, and even magicians. It’s a great daily experience with a picture perfect sunset every time. Just thinking about it makes me want to go back.
After so many visits, you can obviously see that Key West is one of my favorites. Key West Beach just has a great vibe, spirit, and way of life among the people and community that service it. Make sure to keep this on your to do list sometime in the next 12 months (heck 6 months since it’s always warm) and be prepared to “Come as You Are”, following the mantra. It’s an absolute fantastic spot for birthdays, bachelor parties, and getaways here and it never disappoints. Speaking of which, if you need to plan a bachelor party and need help collecting the funds, check out Grouppaybook.com. If you would like to add to the article or feel like I missed your favorite spot, please feel free to leave it in the comments section so others can see too. I’m always willing to learn a new spot or ideas when it comes to Key West.