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11 Tips for Your First Trip to Key West

I must be living in La-La Land because all this time I thought visiting Key West meant beautiful beaches and hot surfer guys. While the drive from Miami to Key West is beautiful and the island is a lot of fun…you might want to be a little more educated before you get down there. I sure as hell wasn’t.

Here are 11 tips for your first trip Key West…so you won’t be disappointed like I was.

The beaches kind of suck

As I said, call me crazy but I was imagining Key West to have amazing, crystal clear beaches…WRONG.

Did you know all the beaches there are man-made?

Making them at an average temperature of about 85 degrees. WTF. Maybe I have been living under a rock but I had no idea! I’m sorry, but when it’s a sweltering 100 degrees outside with 95% humidity, the last thing I wanna be doing is floating in warm bath water. The sandbar in some areas goes out for several yards, so even if it was cool, you couldn’t get more than ankle deep.



Okay, guys yes it’s South Florida, but if I knew I was gonna be paying Miami prices I would have stayed in Miami. At least their beaches are real. Not to be all cynical and shit but I guess my expectations were a lot different, so maybe that’s my fault for letting myself down.

At $10-15 a drink, it’s easy to spend $500 on food and alcohol in a couple of days. Key West is definitely a tourist destination, so I get it, but it’s suppose to be laid back, flip-flops, bathing suit’s and $5 bucket’s of Rum right??

One night we went to dinner later (around (9:30 pm) didn’t buy a bottle of champagne, instead had like two drinks each, an app and two entrees, $150! No view and no bottle. It adds up so just make sure you know that before you get stuck doin’ dishes in the back.

Funny side note: We flew out of Miami and had lunch there, the bill was $70 and we were like wow, this is cheap! Damn you SoFla!


Look, bitches, this is my opinion. I promise I’m not here to dog down Key West, I just like to be straight up about what I experience to help y’all with future traveling! I use to live off the coast of North Carolina, and I’m pretty sure I’ve had way better seafood there.

We went to a restaurant called Latitudes. You have to take a boat over to a private island, the view is just stunning. We ended up getting Tuna Tartare (my favorite!) as an app, and then I ordered the steak while my BF ordered the fish. Both meals were good, but for the price, it was more about the overall experience more than the food. ($250 for two people excluding tip)


I feel like some people go to places and hype them up. Just because it was very expensive doesn’t mean it’s always going to be good. Eat a big lunch if you are trying to be budget friendly and find a place that sounds appealing to YOU. Top 10’s aren’t the best for everyone.


See, not totally hammering Key West…the nightlife is the best part. Really reminded me of being back in North Carolina. Super laid back beach bars where you can dance in flip flops and sing Jimmy Buffet until your voice goes hoarse.

I always love towns where you can walk from bar to bar, drink in hand. We met some awesome people while throwing back Green Tea shots, the atmosphere and overall feel of Key West is like meeting up with your crazy, fun uncle you haven’t seen in years. You can do the Duval crawl like most people, we tried and made it to bar #6 before we were pretty much crawling haha. Lot’s of fun.


If you have to rent a car, rent a convertible. We flew into Miami so we could drive over the ocean highway since neither of us had ever experienced that, but we wanted to do it the right way. It might get a little hot at times, but those early morning drives to the beach or sunset cruises around the island make it all worthwhile.



We stayed at the Gates Hotel, which had really nice rooms and a cool bar area, but there was no real restaurant on site (just a food truck with again, okay food) The pool was always packed with screaming kids, and once we were finally tired of the salt water, we decided to chill by the pool, only to discover some kid had SHIT IN IT. So it was closed for the rest of the day. I saw Key West offers many hotels labeled Adults-Only, so that might have been a better option.

bedroom at the gates hotel


The Southern Most point of the US. Do you really have to take a picture for people to believe you’ve been there? Do people even care if you’ve been there? We rented a golf cart to drink up and down Duval but figured while we had it, we would go see what all the hype was about.

Pretty much a long annoying line of tourists waiting to take a picture with a block of cement. We saw it, I took a picture of how ridiculous people looked waiting, and then we left. Supposedly this was “slow season” too.tourist

We didn’t do the Hemingway House because we just didn’t care to, but we did rent jet skis (remember we are more adventure travelers) but of course, our group had slow people…so slow in fact we had to stop every couple of miles and wait on them. And for $300, we expected a lot less waiting and a lot more exploring.


We learned from our trip to Bali that vacation time is precious, especially when you only have 4 days. The Dry Tortuga National Park is about 70 miles off the coast of Key West, a 3-hour ride one way. As much as we would love to go explore, it just wasn’t worth it this time around. We are NOT fans of group tours, to begin with, and wasting 6 hours of relaxation time just didn’t sound appealing.


By all means, if you want to take a full day exploring then I say, DO IT. But if you are headed to Key West to relax and get away from the hustle and bustle I say, save it for another time. Unless of course, you have $315 per person to shell out for a seaplane ride over there instead.


Every trip I try to do something fun and exhilarating. Surprisingly I had never been parasailing, and this was the perfect opportunity to spend some quality time with my man while experiencing something new! The whole experience took maybe an hour and luckily we got put on the boat with this couple and their drunk in-laws. Parasailing itself lasted about 15 minutes, but the view of the city from the water was unbeatable.


The ride is very smooth, not what I was expecting at all! It was probably one of the highlights of our trip, and at $120 for two people, well worth the money. I recommend Fury Water Adventures because the staff was young and you can book and sign waivers online making the whole process easy without all that damn paperwork. No, I’m not making money by saying this either. You KNOW I would tell you if they sucked.


Before this trip, I saw girls at Coachella riding swans, pool parties of people swimming in donuts, and I thought, how can I stand out amongst everyone?? BEHOLD…the unicorn float! This thing was seriously the best $80 I’ve ever spent. Not only is it a 2 person float but IT’S A FUCKING UNICORN. It shit’s on any swan, flamingo, donut, piece of pizza float there is.


We packed it in our backpack and I used it a handful of times. We blew it up with the blow dryer on cool and threw it in the back of the convertible. Imagine driving around with a unicorn ass sticking up, what would you think haha?? Since the water was so warm, this was perfect to float around for hours on. Plus I was like a local celeb on the beach.

Barb and I in the car…yes we named her Barb


Didn’t mean to rain on your optimist parade about Key West. It’s a fun city to go and enjoy for the weekend. But let me tell you, as much as the beaches and tourists might suck, the views don’t. Every part of the island gives a different perspective on what island life really means. Soak up the sun, drink yourself under the table and watch the sunset in Key West, you won’t regret it.

Overall, I would rate our Key West experience a 6/10. It might not have been everything we expected it to be, but it was a nice relaxing/drunk getaway from reality. I usually plan every trip down to the minute, but since it was my BF’s birthday, he wanted to take it easy and just let things happen as they did. Hopefully y’all can learn from my trip to the Key’s and plan accordingly next time you head to the depths of South Florida.

Did I forget anything?? Have you been to the Keys? Let me know about your experience!

xo Bonvoyage Babes

  1. Maggie says:

    Key West is one of our favorite weekend getaways! We stayed at Casa Marina, which is amazing and one of the few hotels with an actual beach. And breakfast at Blue Heaven is a must, we went every morning that we were there.

  2. Joe says:

    Great and refreshing to see a blog post that tells it like it is, and calls something shit if it’s shit 🙂 A well balanced piece, and glad to hear that you did get to experience some good stuff too. But yeah, man made beaches are not cool…

  3. It’s been a few years since I’ve been to Key West but I really enjoyed it! Touristy definitely but a nice vibe. It reminded me a lot of the time I lived in the Caribbean.

  4. Kevin Wagar says:

    I’ve been meaning to head down to the keys and do some diving. Looks like my kids will be asking me for a unicorn.

  5. Brianna says:

    Yeaaah.. Key West does not look like a place for me. I like to be able to swim in the ocean and travel on a budget. The sunsets would probably be cool, but you can get those in other (cheaper) places 😛

  6. Vyjay says:

    It is good that you present Key West with all frankness. It is always wise to know the good, the bad and the ugly of a place before or after getting there. In spite of a lot of minuses, the food and the scenery are really something that will make up for the negatives.

    • Tatum Skipper says:

      I like to write about every place I’ve been with frankness just so it can help the next traveler who goes. Before I started my blog, no one really did this, and I kept going on trips with high expectations and getting let down. The scenery is amazing, the food…yeah it was okay I guess. For how expensive it was, it should have been way better in my opinion.

  7. Julie Cao says:

    Been to Key West five years ago, the scenery and the sunset is wonderful, and it is a great road trip from Miami to FL Keys. And I agree it is a super expensive place to visit and the food sucks too (the price is not on par with the quality of the food). I was home-based in Hawaii when I travel to Key West, so my first thought is it is so like Waikiki – the most expensive and touristy place in Hawaii. Interesting to see your written up and appreciate your honesty.

  8. Lindsay says:

    “nice relaxing/drunk getaway” is basically always how I’ve envisioned a Key West vacay. It’s nice to read something that doesn’t sugar coat the entire travel experience. – helps to know what to expect and what to avoid!

    Also I had to laugh when you mentioned the kid shitting in the pool. So many levels of wrong.

    • Tatum Skipper says:

      Just so you know, your comment was hiding in the spam section! 🙁 ANYWAYS, yes that is really the whole point of my blog is to not sugar coat anything! Plus, I’m just tired of reading boring posts. But yeah, TOTAL BUZZ KILL. That’s why I don’t have kids haha, those little demons.

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