How to Spend a Weekend in Key West

One of the best parts about going to school in Miami is that the beautiful Florida Keys are only a stones throw away! Before my recent trip, I’ve only ever been to the keys once in my life, which is surprising since I was born and raised in Florida (LOL). This passed summer was the first summer spent away from home since moving to Miami. And thankfully, a friend of mine was also staying in Miami for the summer so we were able to plan a fun road trip together! Here’s how to spend a fun weekend in Key West.

When to go

One thing you’ll quickly learn about the Florida Keys is that staying there isn’t cheap! It’s all about finding the best deals at the right time. Because of the yearlong warm weather and the keys’ prime location, the difference in their high and slow season prices are miniscule. To miss the crowds, plan to go between March and May, when the snow birds have all left for the summer!

Even though Paola and I went for the 4th of July weekend (rookie move), it was still so much fun–and luckily, affordable! The whole town was so lively and gave off the happiest of vibes. So, if you plan ahead and look for all the good deals, you just might be able to spend an affordable weekend in Key West.

Where to stay

One of the most unique things about Key West is the variety of stunning bed & breakfasts available to stay at! When we went, it was my first time ever staying in a B&B, and I loved it! They’re all so cute and quaint, which makes for a great place to relax after a long (touristy) day! Now obviously since we’re just college students, we didn’t have the biggest budgets to work with. So, the only way we were going to make this road trip work is if we were able to find a good deal on a place to stay.

I’ll be honest. We totally got lucky. We found the best deal on a B&B that we just couldn’t pass up. It’s all about being persistent and checking at different times/days when you’re in the planning stage of your trip. I suggest looking in advance to find the best deals or staying on one of the other less expensive keys! Marathon and Key Largo are great places to stay if you have a car, since the drive isn’t far down to Key West. Plus, it helped that we got to split the cost. So, traveling in a group to split costs is also a great idea if you’re on a budget!

Getting around

When you’re spending a weekend in Key West, you might as well take in the island lifestyle and walk it out! Fortunately, everything you’ll want to see and do in Key West is mostly within walking distance, or a quick bike ride! Yes, this means restaurants, bars, convenient stores, cute little shops & galleries, the beach, etc. Paola and I were there for two days and did not pay for any kind of transportation since there was no need for it.

Other than a nice walk or bike ride, there are also cute little mopeds for rent and a local trolley system to use!

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Here’s what to do during your weekend in Key West


  • Duvall Street for shops, galleries, and restaurants
  • Southernmost point in the U.S.
  • Southernmost Beach Café, Hotel, House, etc.
  • Mile marker 0
  • Eat at Mangia Mangia Italian restaurant
  • Mallory Square
  • + many, MANY more activities including scuba diving, fishing, boat and sunset tours, etc!
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Key West is hands down one of the most beautiful places I’ve ever been to, and would definitely go back! I highly recommend putting this location on your bucket list through college or even for a romantic getaway with your other half! What ever the occasion may be, it’ll be a trip you’ll never forget!


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