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  • Writer's pictureErin Schoen Marsh

Girls’ Weekend Trip to Key West, Florida

Updated: Feb 22

Four women sit on the front of a boat on the ocean.

For my sister-in-law’s 40th birthday, she decided she wanted to spend her January birthday basking in the sun. Her best friend organized all the details: a girls’ trip to one of her own favorite locations – Key West, Florida.

If you are a Key West newbie like I was, there are many islands in the Keys, but the most popular island is the southernmost (the one closest to Cuba). This means that if you wish to fly to Miami and drive to Key West, you need to drive approximately three additional hours. Because of this, we opted to fly directly to Key West, which meant a layover in Atlanta.   

An orange sun sets on the horizon of the ocean with boats sailing along

Staying in Key West

Hotels and AirBnbs are ridiculously overpriced in Key West, so the seven of us stayed on a yacht, which averaged to about $850/person for three nights. The yacht was top of the line when it was built in the 1980s, but it had seen better days. That being said, we each had our own bed, a view of the ocean from the top deck, and we were a 20 minute golf cart ride from Old Town. There was ample seating for everyone, four full bathrooms and a kitchen, which allowed us to cook breakfast and dinner one day, saving us some money. For the size of our group and what we were doing, it was perfect. 

A large 1980s yacht is docked with the sun shining behind it.

Downtown Key West 

The main drag in Key West is Duval Street, located in the western part of the island. If you are staying within walking distance of Duval, then the beach and everything you need is at your fingertips. If not, I’d recommend renting a golf cart as we did. Most of the streets in Old Town are 20MPH and golf carts can travel on roads 35MPH and under. 

A two-story white house with porches on both stories that looks like it belongs in Savannah, Georgia has a sign in front of it that reads "Key West" with wings.

Old Town has a beautiful architectural blend and wonderful vibe. The houses are a mix of the old South (Savannah in particular), the Caribbean and Florida, and there is a strong Cuban influence everywhere. Then there’s the weather, which couldn’t have been more perfect – 70s and sunny/partly sunny every day in late January. 

I had heard that Key West was “super gay,” and while I certainly saw plenty of rainbows, I felt the straight-to-gay ratio was about the same as it is in most other places. I suspect that at one point Key West was LGBTQ+ heavy, but as Key West became more trendy and touristy (and expensive), the gays moved. So if you are looking for a fun gay night out, Key West is no longer the “it” place in my opinion (but I could have missed all the cool places…I am old now!). 

A delicious piece of cheesecake with chocolate stuck in it. "Happy birthday" is written in chocolate on the plate.

Favorite Restaurants: 

Off the beaten path from the main drag of Duval Street, Kaya Island, an unassuming outdoor restaurant, was our group favorite. All seven of us were happy with what we ordered from the Caribbean-inspired menu, and I had some of the best fish tacos I have ever eaten. While there was a lot of seafood on the menu, we had one who dislikes anything from the sea, and she was happy with Jamaican Jerk chicken wings and sliders. The cocktails were delicious as well. 

We had dessert at Better Than Sex to celebrate my sister-in-law’s birthday in style, and wow. Just wow. Let’s just say the name suits the venue. My mouth is watering just thinking about those desserts: double stuffed Oreo bread pudding, dark chocolate and brie grilled cheese, cheesecake with a sugar cookie dough crust…need I continue?  

Overall Review

For a girls’ weekend, Key West was tops. The weather was perfect, it felt safe and it was small enough to get around easily. It’s also as close as you can get to the Caribbean without having to bust out your passport or the big bucks. My favorite thing we did was rent a boat for the afternoon and watch the sunset on the ocean. It was perfection.


One 50-year-old woman in a bathing suit, sunglasses and coverup captains a boat while two women in their 40s sit in the sun.

My only complaint is the tourists. Despite it being January, one of the slowest months for tourism, Old Town was packed with out-of-towners. It was impossible to get a feel for the true Key West with so many visitors. For this reason, I don’t feel the need to return, although I’ve heard other islands in the Keys aren’t nearly as touristy. My first time visiting Miami, however, I only went to South Beach, and while I loved it, I didn’t think I needed to return. Then I had to return to Miami multiple times for work, visiting different parts of the city each time, and now Miami is one of my favorite cities. So I think Key West deserves another chance…perhaps just another island next time. 

Rapid Review: 

  1. Weather: 70s and sunny in January

  2. VRBO: Docked yacht with access to the club amenities

  3. Rooms: 4 rooms, 8 beds, 4 bathrooms, kitchen, living room, two decks with seating

  4. Activity: Rented a boat for an afternoon + sunset on the ocean

  5. Must do: Peruse Duval Street 

  6. Favorite restaurant: Kaya Island Eats

  7. Favorite place for dessert: Better Than Sex 

  8. Best time to go: Winter (avoid hurricane season, which is formally June 1-Nov. 30


Deaf/hard of hearing

Key West is loud and not Deaf-friendly. As a hard of hearing person traveling with hearing folks, that part of the trip was exhausting for me. It meant more lipreading, guessing and missing out, but I still had a great time overall.  

Blind/low vision

Old Town is very walkable, so if you are staying near Duval, you could walk everywhere. They do not have accessible pedestrian signals (APS) – the chirping noises when the crosswalk changes. The roads are 20-40 MPH, which is great for low vision if you are driving, but they are not well-lit at night outside of Duval Street. However, the plentiful sunshine is great for optic nerve atrophy. 


I had hip surgery a few weeks prior to this trip, and Old Town is tough to navigate with mobility issues or if you are a wheelie, I’d imagine. We rented a golf cart, but you still had to park the golf cart – and parking was limited – and walk to your destination. The sidewalks are uneven and busy with tourists, so challenging to navigate.


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