My Key West Itinerary – Romantic Birthday Getaway

Key West was the BEST destination I could ever dream of for my 25th birthday! It has everything your heart could desire and then some! The Keys left my boyfriend and I feeling so refreshed and relaxed, we started looking up real estate…seriously!


Our Stay


Caribbean House

I would highly recommend staying here for several reasons, but the most important aspect for us, budget-friendly travelers: cost! Caribbean House was one of the cheapest hotels we could find which is crucial because Key West is EXPENSIVE! Expect to spend roughly $200 per night at any hotel in Key West. We booked our hotel during the slow season, so we were able to score a room for less. We also loved this hotel because of the convenient bicycle rentals at the front office. Bicycles are the only way we got around town. We would not have made it if we had to walk everywhere. Oh yeah! – breakfast is included!

Things to Do/Places to See

Oh gosh, where to even begin! There are so many things to do in Key West, and for 4 days, I think we did a good amount!

  • Southern Most Point: We tried going once before, but there was a long line and we didn’t want to wait just for one photo. On our last day, we woke up around 7:30 am and headed for the Southern Most Point one more time and I’m so glad we did. Going in the morning, there was only one group taking a photo. A local who took our photo told us that by 9 am, this place will be packed! Beat the long line go in the morning!


  • Mallory Square: This is a must do if you’re traveling to Key West. Every evening around sunset there is a Sunset Ceremony. Although it was unbelievably cloudy during our trip, there was still a huge celebration at the square every evening. Mallory Square is a lively party that is a must see!


  • Shopping!: I was pleasantly surprised when we were walking down the street and found a couple outlet stores! I love outlet malls because I always want to buy multiple items at once. The two stores I noticed, and personally love, were Banana Republic and GAP.
  • Canoeing in the Mangroves: Unfortunately, we couldn’t take any photos while canoeing. We had to leave all our personal items on shore. We went through FURY Marriott Beachside Key West Rentals. We loved this experience; however, be prepared for a looong bike ride there! I’m sure you can find other canoeing experiences closer to your hotel with a little research.
  • Dry Tortugas: This is our honorable mention. When I planned out my trip to Key West, Dry Tortugas was always a part of the plan. Unfortunately, we were looking at $185 per person and just couldn’t save up enough money to go. We plan on returning with the sole purpose of visiting the historic landmark. I would describe this as a true once in a lifetime place to visit.

Places to Eat

So many good food places! There were some places Alec wanted to visit again and some places we found just by walking around!

  • Sloppy Joes: Sloppy Joe’s must be on everyone’s list! Grab a few drinks and enjoy the environment that is Sloppy Joe’s! This was the one bar we went to more than any other. Hemingway was a regular patron of Sloppy Joe’s and if you go during July you will witness the Sloppy Joe’s Hemingway Look-a-Like Contest.


  • Better than Sex: This was the one place I really wanted to try. How can you go wrong with chocolate covered wine glasses and dessert? The atmosphere of this place is darkly sensual. The inside is dark and intimate, and you will always be seated next to each other rather than across.


  • Latitudes: This restaurant is something special and was our one splurge meal. Alec made this reservation for my birthday and kept it a secret until our dinner reservation and I was totally shocked! You first have to take a short 8-minute boat ride to a nearby island. Once you get off you step foot onto the cutest island that we did not want to leave. The food, service and atmosphere was perfect. Alec wanted so badly to have our reservation for sunset but couldn’t. If you can plan ahead make a reservation around sunset!




  • Caroline’s Café: We ate here for dinner. We were seated outside next to multi-colored Christmas lights and 100% humidity. I ordered the peel-and-eat shrimp, and my boyfriend ordered a shrimp po boy. We both really enjoyed our meal.
  • Blue Macaw Island Eats & Bar: This restaurant was a short 2-minute walk from our hotel. We ate outside for lunch under a bush (which gave us some well needed shade). This is a very chill, relaxed area to grab a quick bite. The only thing that I wish I didn’t get was the alcoholic drink. It was a frozen margarita that basically tasted like water.
  • Charlie Mac’s: We stumbled upon this place on our first day without even trying. We were so hungry that we walked into the first place we saw, and we got so lucky on this gamble! Try the Spicy Pork Mac n Cheese Balls (6ea) these were AMAZING!!! Loved this freaking appetizer so much and wish I had some right in front of me right now! I like spicy foods but don’t like too spicy and I thought these were perfect. I know Alec’s mother hates spicy anything and I know she wouldn’t like these for that reason.


  • Honorable mention: Vicky Bakery. This is an honorable mention because this was our first stop on our road trip. This is a Cuban café that is all over South Florida that we are obsessed with! Our friends from Miami showed us this spot and we have been obsessed ever since. We will always get the Cubano (which I call little coffee) and a few Croquettes (we usually go with ham croquettes)


(Latitudes is on this small island, it’s like a small town! It even has a fire-station)


(This island was so rich in color! I’m OBSESSED with these flowers!)


That is our whole trip to Key West! This was, hands down the best way to celebrate my 25th birthday! And you can make Key West whatever you want. If you want it to be adventurous with a lot of outdoor activities, you can do it! If you want to have a relaxing vacation, then this place is perfect as well! All I know is you won’t want to leave and then proceed to look up real estate like us, then reluctantly head home.

With Love,

A Simple Wildflower

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