A First-Timer’s Guide to Key West

Sharing my tips to make the most out of your first time in the great island of Key West!

As I’m sure y’all know (you couldn’t miss it on Instagram!) I spent the past weekend with two of my best girlfriends from high school in Key West! Although we are all Florida girls, this was our first time in the Keys- and boy was there a lot to learn! We packed a lot into our three days, so I thought it would be helpful to share our tips, favorite activities, and places with y’all too!


I was so happy that I stuck to my guide to packing in a carry on because I needed it! The Key West airport is tiny so the only planes that land there are “puddle jumpers” and we had to gate check our bags to get on the 20 seater plane. Packing in a carry-on ensured that my bags arrived safely on the other side and I didn’t have to wait for them to come off the conveyor belt- I could get straight to the fun!

Since my friend Jen drove down and met us, we had her car for the weekend (although truthfully we didn’t use it once after we got to the hotel!) We stayed close to Duval Street (where all the action is) so we walked everywhere! Unless you plan on doing a lot on the “other” side of the island, you don’t need a rental car and can taxi to and from the airport. There are also pedi-cabs available to take you home if you have too much “fun” 😉 And you can rent golf carts and mopeds if you’re looking for a zippier way to get around.


The most popular option on the island for a romantic weekend is one of the plethora of Bed & Breakfast’s, but obviously that’s not what we were there for! Since we wanted to keep our $$ for activities and nightlife, we opted for the budget-friendly option of the Best Western Hibiscus. We really didn’t expect much (since it was such a great deal) but we were all pleasantly surprised! The location was awesome, only two blocks off Duval St, and the room was huge with two vanities and sink areas, two queen beds, and a sitting area. The pool area was gorgeous and modern too! While not a luxe hotel, it was perfect for what we were looking for in a girl’s weekend!



We started off our weekend here with a yummy late lunch and it was the perfect kick-off! Pictured below are my delicious shrimp empanadas (drooling over here thinking about them!) Since it was right on Duval St it was perfect for people watching and enjoying the gorgeous weather. I also recommend the Key Lime Mojito- the right way to toast to a great weekend 🙂

Better Than Sex

I don’t think you can visit Key West without visiting this restaurant! They only serve desserts and y’all they have perfected the art of baking!! Pictured below is our selections… Moscato Wine with Carmel “Rim Job”, Chocolate Chip Cookie Cake, Homeade Doughnuts with Melted Cheesecake for dipping, and Popcorn Cheesecake- SO GOOD! Warning: the theme of the restaurant is pretty sexy, so don’t plan on bringing your kiddos!

Blue Heaven

We heard from just about everyone that this was a fan favorite spot to eat so we made sure to make reservations so we didn’t miss out! Tucked away in almost a “secret garden” atmosphere, the chickens on the island roam free around you as you eat! They are known for their homemade breads, so made sure to order a main dish so you can try their cornbread! Their menu is based off of local harvests and catches, so it changes constantly, but I had the jerk chicken and it was a winner! We also enjoyed their key lime pie- topped with about a foot of merengue! Yum! The atmosphere alone is more than worth the trip here, so the great food is a wonderful bonus 🙂

Banana Cafe

We wanted a hearty brunch the day we left and stumbled upon this restaurant on Duval and once again were so impressed! I had a ham and cheese crepe (amazing!) but they have an extensive brunch menu and more hearty lunch if that’s your thing. I would best describe the fare as a French and Cuban restaurant having a baby- a unique, but yummy, juxtaposition! (No pictures because I was too hungry to pause and take one!)

Key Lime Pie (on a stick!)

Another one of those “only in the keys” dishes, we couldn’t leave without trying some chocolate covered key lime pie on a stick! Yes, it’s just as heavenly as it sounds 🙂 you can get these all over town, but make sure they are made by the Key Lime Shoppe- the originals! The tart pie covered in sweet chocolate is a huge winner!


Floridays Boat, Sunset Cruise

Probably our favorite activity from the entire weekend was our sunset boat cruise- y’all it was STUNNING! There are tons of boat excursion options, but the sunset cruise fit all of our needs/wants. We wanted to see the island, relax, sip champs, and do something safe for baby (Jen is pregnant!!) so this hit on it all. We cruised with Floridays which we loved, as it was a private yatch and there were only about 20 of us on board which made it much more relaxing. It was also an all-female crew which was fun and girl powered 🙂 The crew was so social and personable and worked hard to make us feel comfortable and welcome. On top of it all, the sunset was spectacular and the perfect way to enjoy our night on the island!

Duval Street- Shopping & Nightlife

Duval St is really the heart of the entertainment on the island- the bulk of the shops and restaurants can be found here, so when in doubt you can’t go wrong with strolling up and down the streets grabbing drinks and shopping! Like Savannah and New Orleans, you can take drinks “to go” and walk with them- there are even roadside stands to pick up a daiquiri or margarita 🙂

Come nighttime, this is also where all the bars and clubs can be found. Our favorite was Sloppy Joes which had the most fun crowd, music, dancing and drinks! But word to the wise… their signature Margaritas are STRONG! 😉 Other favorites include Hog’s Breath, Willie T’s, and Margaritaville (sometimes Jimmy himself makes an appearance… but no such luck for us!)

Songwriter’s Festival

When we booked our weekend we had no idea that it happened to coincide with Songwriter’s Festival, but it was an awesome surprise! Throughout the weekend there were almost 200 free concerts (which were awesome!) including a finale on Duval St with Jake Owen! Singing and dancing in the streets to fab country music? Sign me up!

PS- Dates for next year were just released… May 10-14, 2017!

Ernest Hemingway’s House

We couldn’t leave the islands without learning a little something 😉 We toured Ernest Hemingway’s home and it was really interesting learning more about the writer and his life in the keys! We even found one of the famous 6-toed cats! Tip: They only take cash ($13 ticket) so don’t come without it!

PS- If you’re looking for other options in Florida, Great Value Vacations has a great package for Miami!

Whew! If you’ve made it to the end of this post, yay you! I hope that you found it helpful and if you plan a trip to the Keys in the future, please feel free to reach out to me at gentry.adams@gmail.com with specific questions! And if you’ve been, did I miss anything?!


Happy Key West-ing!

Sylin in St Louis

Linking up with The Mix


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  1. May 12, 2016 / 10:59 am

    I've been to Key West twice – once as a kid and once as an adult as part of a port on our cruise!! We had the whole day and the food was amazing! My friend actually lived there for 4 years so she was able to give us so many recommendations! I think it's so smart that you guys picked a budget friendly hotel to spend on things like going out and food – which is more fun anyway!! xo, biana –BlovedBoston

  2. May 12, 2016 / 2:56 pm

    Key West is a fun place. Whenever my family goes we also go budget on hotel since you don't spend too much time there. The dessert place sounds great.

  3. Tatum
    January 14, 2019 / 10:40 am

    Better than sex is a MUST for visiting the key west! We had the homemade doughnuts too and they were so amazing. Can’t wait to visit again 🙂

    • girlmeetsbow
      January 15, 2019 / 5:09 am

      So so so good!

  4. Giulianna
    January 15, 2019 / 6:08 pm

    This trip looks amazing! Only makes me look forward to spring break more and more. Thanks for sharing your tips!

    • girlmeetsbow
      January 15, 2019 / 7:56 pm

      Yay!! I’m so glad your excited & have a great trip!!

  5. Fiona
    January 16, 2019 / 9:26 am

    This trip looks awesome!! Need to make a trip back to Florida soon and this Key West read may have convinced me to go to Key west! That key lime pie looks amazing!

  6. Andy
    January 16, 2019 / 12:17 pm

    I’ll be by the Keys for Spring Break, definitely going to stop by and try some of these ideas! Thanks!

  7. Avery
    January 16, 2019 / 7:38 pm

    Those desserts look amazing! I would love to try the “Rim Job”…it looks delicious! Thanks for sharing your experience! I am trying to plan a trip for spring break and we don’t know where to go yet but I am absolutely going to suggest the Keys

  8. Michael
    January 17, 2019 / 7:23 am

    The keys look gorgeous! I’ll have to put these tips to use on a trip of my own!

  9. Paul
    January 19, 2019 / 1:14 pm

    We docked at Key West for a day when I was on a Caribbean cruise, but I need to go back. One day was not long enough and this post just confirms that there is so much more to do and see!

  10. Allison
    January 19, 2019 / 8:50 pm

    Key West looks like so much fun! Margaritas and shopping at the same time on Duval Street sounds like the perfect combination! I would love to visit in the winter time!

  11. Shawn
    January 20, 2019 / 8:56 pm

    I hope to visit Key West one day soon. I’d love to be there right now with all the snow I’m getting. I really want to try those shrimp empanadas too; they look delicious.

  12. Jessie
    January 22, 2019 / 5:04 pm

    I went to Orlando last year. First time in Florida

  13. Sarah
    January 27, 2019 / 8:19 pm

    Traveling to somewhere new is always a challenge so these tips are great for first time travelers to Key West! To much snow here right now wish I was that first time traveler to Key West!

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