Looking for a guide to the perfect Key West Girls Weekend Getaway? Sometimes it’s just nice to get away with all your gal pals, right? Key West is the perfect spot for a tropical getaway within the US. I flew all the way from California to meet up with my Childfree Girlfriends from all over the world. A small group of us were able to get together and plan this trip and I wanted to share some of the highlights and recommendations for a great girls trip to Key West!
The historical city of Key West is located in the state of Florida. It is an island city that is part of the Florida Keys archipelago. It’s also the country’s southernmost point, lying roughly 90 miles north of Cuba in the Gulf of Mexico. The weather remains tropical all year round. It features a variety of attractions and activities for all travel enthusiasts that enjoy a tropical vacation. Our trip was the first weekend of May and it was quite humid.
Due to the 2020 Covid-19 restrictions, some locations’ status may vary. Closures and hours of operation may be different from their regular schedule. Please check websites for any of the listed locations for the most up-to-date information. Stay safe, healthy and Happy Travels!
Key West Most Popular Attractions
Tour the Ernest Hemingway Home & Museum
One of the most popular museums to visit on the island of Key West is the Ernest Hemingway Home & Museum. The famous author resided on the island for many years. The property houses many historical keepsakes that tells the exciting life of Ernest Hemingway. And if you’re a cat lover, then you will know all about the many poly-dactyl cat descendants that live on the property. All related to the original cat named Snow White that belonged to Hemingway.
Admission for the Hemingway House:
Adult $16.00 | Child $6.00 (6-12 yrs) | Under 5 FREE
Visit the Key West Butterfly Conservatory
This cute little spot is popular with children and families so I wouldn’t recommend it for a Girl’s Trip. But just in case you were interested, it’s a very small conservatory that houses a variety of native and non-native species of butterflies, moths and other insects. Plus an assortment of birds, including two resident flamingos. You can walk through the entire facility in under a half-hour but if you take your time, you can possibly spend about an hour here. My all-time favorite Butterfly Pavilion is located in Denver Colorado.
Admission for the Butterfly Conservatory:
Adult $15.00 | Child $11.00 (4-12 yrs) | Under 3 FREE
Enjoy the Key West Sunset Celebration at Mallory Square
There is a common iconic phrase in Key West that is often used by the locals. “See you at Sunset!” has become part of the local history, culture and spirit of Key West. Dating back to the 1960s, Mallory Square has been home to a celebratory event held every evening, beginning 2-hours before Sunset. Everyone is invited to the free public celebration to watch the glowing sun set from pink to red and slowly sink below the horizon of the Gulf of Mexico.
Entertainment, dancing, artists, food and drinks are all abundant during the festivities. It is an incredible cultural experience for all involved. If you’re visiting Key West while on vacation or for a girls weekend getaway, you would not want to miss this nightly ritual.
Take your Photo at the Southernmost Point Monument
No trip to Key West will skip a photo op at this super touristy spot. It’s the most Southernmost Point of the United States! I get it, it’s cheesy and gimmicky but honestly, it’s a cute mini monument that won’t take more than 10-minutes. Depending on the tourist season and how busy it is, there is usually a line that forms for people to wait their turn for a photograph. We went early in the morning at about 8am and there was a short line. But it moved fast and we were able to take a quick photo within 10-minutes.
On a clear day, you can almost see all the way to Cuba, which is only 90 miles away!
Awesome Key West Outdoor Activities
Sail Away on a Sunset Champagne Cruise
My favorite tour activity during our Key West girls trip was the Sunset Champagne Cruise. It was so relaxing and amazing. We even witnessed a couple get engaged!
I was afraid that I would get seasick from the boat ride on the catamaran but I had no worries. I took a Bonine pill and kept my eye on the horizon, it was beautiful anyway, and I didn’t get sick at all. Our tour was super pleasant. There was music, champagne and light appetizers for all the guests. I believe our catamaran was able to fit about 40 guests. We had a 360-degree view of the amazing ocean and the incredible cotton candy sunset that changed from pinks and purples to oranges and reds. We even saw dolphins swimming alongside us. My girlfriends and I had a great time. I highly recommend booking this particular tour with SEBAGO at Tripadvisor.
Fly above the Ocean Para-Sailing
I never thought I would ever try Parasailing but my girlfriends talked me into it. Seriously, I am a big wimp when it comes to this kind of stuff. But I was determined to conquer a bucket-list item on this trip.
Besides, this particular excursion did double seating for the parasailing so I got to try it with my friend right next to me. And she’s done it before so it made me feel better. That’s what a Key West girlfriend getaway is all about!
We booked our parasailing tour with Fury Water Adventures and they were extremely safe, knowledgeable and friendly. There was no problems with the “take-off” or “landing” which I was the most anxious about. I highly recommend them.
Explore the Coral Reefs Snorkeling
Key West is famous for their coral reefs and snorkeling is a popular activity. It’s a super fun adventure activity to enjoy with your girls on a trip to Key West. There are so many tours and excursions that take you out to the best snorkeling spots around the island. I’m not a strong swimmer so unfortunately I didn’t get a chance to snorkel on the island during this particular trip. However, Fury Water Adventures has a great tour for snorkeling that I highly recommend.
Below are some other great Key West Snorkeling excursions!
Rum & Reggae Afternoon Snorkel and Sunset – $53.70 per person
Key West Double Dip: 2-Stop Reef Snorkeling Trip – $62.30 per person
Key West 3-Hour Snorkeling Adventure – $49.40 per person
Pedal the Ocean on Hydro Bikes
For a unique outdoor water activity, I highly recommend the Hydro Bikes in Key West. It’s a great way to enjoy the ocean without getting wet while you pedal and float across the calming waves. Book a tour that takes you to a snorkeling destination, or time your tour during sunset. This particular excursion is operated by only one tour company in Key West so make sure to book it in advance.
In addition, you can book 1-2 hour tours, or take one of their excursions see Historic downtown Marinas, along with Mallory Square Sunset pier. There are also Glow Tours during the evening night trips. Enjoy day trips to Christmas Tree Island and Sunsets on the waterbikes.
BONUS: Spend a Day at Dry Tortugas National Park
The Dry Tortugas National Park are seven tiny islands about 70 miles West of Key West that you can get to by Catamaran Ferry or by Seaplane. It’s an amazing destination to spend the day and explore. The seven islands make up only 100 square miles of the National Park and is home to the 19th Century Fort named Fort Jefferson, the largest masonry structure in the western hemisphere. You can snorkel and swim during your visit in the National Park. Followed by exploring the grounds and history of the fort. You can also camp overnight on camp grounds located in the park. Note that there are no hotels or other amnetities on the island.
To reach the island by Catamaran, it will take over 2-hours in rocky waters that I have heard lots of horror sea-sickness stories about. But if you have a strong stomach, click here for tickets and pricing.
To reach the island by Seaplane, it will take less than 1-hour and even though the cost of a ticket is much higher, there is less risk of getting seasick. Click here for tickets and pricing.
Other Fun Key West Experiences
Shop & Eat on Duval Street 
Enjoy fresh coconut juice 
Try authentic key lime pie 
Free range wild Key West roosters 
Attend a drag queen show 
Encounter the infamous Key West nudist
How to Get to Key West
Getting to Key West can be easy, or it can be difficult. There are only four airlines that fly into the tiny airport on the island.
- Delta Airlines – services flight to/from Atlanta, Georgia
- American Airlines – direct flights from Miami FL, Dallas TX, Charlotte NC, and Washington, D.C.
- United Airlines – flights from Chicago IL and Newark NJ (return)
- Silver Airways / Jet Blue Airlines – only operates flights from Florida (Fort Lauderdale, Fort Myers, Tampa, and Orlando)
I would avoid Silver Airways if at all possible. We had a horrible experience flying OUT of Key West due to bad weather on the main land. Silver has the lowest seniority compared to the other 3 airlines and the flights will be pushed and delayed as much as possible in order to allow the other airlines first flight out of the island. Our flight was delayed for over 3 hours and we ended up missing our connecting flight to Fort Lauderdale. We had to end up sleeping at the airport overnight, then caught a new flight the next morning that took us backwards to New York, then finally back home to California.
I suggest the other airlines even if cost may be a bit more. If you can fly into Miami or Fort Lauderdale and then take the 3-4 hour scenic drive to and from the island, you’ll have less of a risk of flight problems. I highly recommend this. Plus, if you schedule a day for the drive, you can add additional stops along the way.
Where to Stay in Key West
Ultimate Vacay at Southernmost Beach Resort
For our particular girls trip to Key West, some of us shared a couple of rooms at the Southernmost Beach Resort. It is a beautiful resort located right along the beach with multiple suites and accommodations that span a large area of the Historic Old Town District. It is a short walk from the fun Key West shops, nightlife, and signature architecture of Duval Street. We spent hours at the resort pools, relaxed in peaceful hammocks below palm trees and drank cocktails all day long. Or maybe my friends did, and I just watched since I don’t drink much.
Stay at an AirBNB like a Key West Local
We had about 10 girls in our group girls trip to Key West, and about half of us stayed in two different AirBNB locations. We didn’t all stay in the same resort above, but we planned our activities and would meet up together no matter where we stayed. Check out these two beautiful Stays below that I highly recommend. They are in great areas that are close to everything. And can easily be shared up to 2-3 guests.
Colorful Key West Condo
Private King Room & Bath at local Bed & Breakfast
I used to visit Key West as a child, but now I need to go back as an adult! Your Airbnb looks so beautiful, and it seems like such a relaxing place. I would also love to try hydrobiking! I had never heard of that before, but it sounds like such a blast!
Key West sounds like the perfect place to vacation with a group of your besties, with lots to do. The sunset celebration sounds like a lot of fun and it’s the best time of the day! I also didn’t know that it was the southern most point of the U.S. Now I just need the Canada/US borders to open up!
Your Airbnb looks amazing! I’ve traveled to Florida a couple times but have yet to visit the Keys. It’s definitely on my list for my next trip down. Thanks for these tips!
Ah, this is the second post I’ve read about Key West this week…it is calling to me! The sunset cruise sounds magical! Dry Tortugas looks stunning too! Unfortunately, I think it might be a while before I next get to the US due to covid, but Key West is definitely on my list! Thanks for the fantastic guide!
I loved Key West! We only stayed for a night and I was there with my parents and brother – they wanted to do Hemmingway’s house but me being me I really wanted to go to the aquarium haha. It was a lot of fun wandering the streets there. My grandma and granddad used to own a condo down there for years.
We planned my friend’s bachelorette in Key West but couldn’t make it due to the storm. I can see how it could be a fun destination for a girls trip. Lovely post and beautiful pictures..
What a gorgeous place to stay, you must have had such a lovely girly holiday in Key West! Sunset champagne cruise with girls sounds like the best way to spend time! <3