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Solo Trip to Key West, FL

2.5 years ago, I was at a point in life where I was trying to grow and heal from a major heartbreak. So, I decided I needed to plan a last minute solo trip to get out and begin to learn to be fully independent. This was my first ever solo trip, so I was scared, but I am so thankful for this relaxing weekend in Key West.


How did I plan this trip? Through travel blogs. This is a major reason why I launched my blog and why I have a passion of helping others plan their vacations!

Where to Stay:


To feel more comfortable on my first solo travel, I decided to stay in a hotel rather than an AirBnB. Key West is pretty pricey, so I stayed a little further from the heart of town at Margaritaville Beach House, which is previously called Barbary Beach Resort. Thankfully, they offered free shuttles to and from downtown, so it made it very easy to get around. There is also a beach right across the road, which was another selling point for me.

The beach across the street: Smathers Beach

Where to Eat:


Conch Shack - I LOVE lobster rolls, but I am used to Maine lobster rolls. So, once I saw Key West had them all over, I had to try them. When I went, this place was cash only, so keep that in mind.

DJ's Clam Shack - another yummy lobster roll place!

Blue Heaven - a GREAT breakfast spot! They don't take reservations and there was a line down the street before they opened. HIGHLY recommend their lobster eggs Benedict and key lime pie!


Thirsty Mermaid - definitely a more fancy restaurant, but the oysters were some of the best I've had. Reservations are highly recommended, but I was able to get a spot at the bar.


Sunset Pier - one of the best spots to watch the sunset! It gets very busy, so head here early or grab a drink at the bar and find a spot in the open seating area. They have live music too!


Things to Do:

  1. Watch the sunset at Mallory Square - I came here every night to watch the sunset and it was truly one of the best I've ever seen. People actually clap as the sun went down - this was such a wholesome moment!

  2. Eat allllllll the key lime pie

  3. Relax on the beach - there are not many around Key West, so that is one the main reasons I stayed at the hotel I picked

  4. Go to the Southernmost Point of the United States

  5. Visit the Hemingway home and museum

  6. Visit the Dry Tortugas National Park

Things to Know Before Going:

  1. Chickens and roosters roam all over town (and yes, they will try to steal your food!)

  2. Be mindful of the time of year you are trying to go - AKA don't go during hurricane season. I went at the end of March and it was already in the 80s.

  3. There is an airport in Key West, but if you are trying to be on a budget, I would look into flying into Miami and renting a car to drive down. I've also heard the drive has beautiful scenery.

  4. Stays are pretty pricey in Key West, so budget appropriately.

  5. This is a popular spring break area, so if you're looking for a quiet and relaxing time, then don't go during spring break.

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