About The Keys
The babes started their trip off by flying to the Miami International Airport. After we landed we picked up our rental cars and drove the hour and a half to our first stop in Duck Key. From Duck Key, we later drove another hour and a half to Key West for the second half of the trip. From there you can either drive back to Miami or fly out of the Key West airport.
The only way to get around the Florida Keys is by rental car. There was Uber/Lyft in Key West but as you’re driving down and stopping in Islamorada, there weren’t any rideshare. You could also take a bus from Miami to Key West.
Where to Stay
Hawks Cay Resort – You can find Hawks Cay in Duck Key, Florida. This resort is a AAA Four Diamond Award winner and has everything you need for a relaxing stay. The property has 250 tw0 and three-bedroom villas and 177 guest rooms. We stayed in 2 three-bedroom villas which was amazing since we each had our own room and bathroom along with a shared kitchen, living room, and back patio. Our back patio had a gorgeous view and at night was perfect for stargazing or relaxing with a glass of wine.
The resort also has six restaurants, a saltwater lagoon, an adults-only pool, and swimming with dolphins. The resort offers so many activities and is very family-oriented. It’s also perfect for couples or girl’s trips who need a little R&R and time drinking a daiquiri by the pool and reading the latest murder mystery.
Southernmost Beach Resort – When we got to Key West, we checked into the Southernmost Beach Resort. This resort is so expansive and is in the perfect spot in Key West. You’re close to the water, close to Duval Street and within walking distance of everything, there is to do in Key West. The amenities include four bars, three heated pools, two beaches, a fitness center, a spa, and an oceanfront restaurant. Don’t be afraid if you see lots of roosters walking around a crowing!
We spent some time relaxing at the Tranquility Pool and also the Pineapple Pool and Bar. Our rooms were also so spacious and amazing with two queen size beds, large bathrooms, and a patio to enjoy the sunset with your morning coffee.
Fun Things to Do in the Florida Keys
Snorkeling with Fury – You can’t go to Key West and not do some snorkeling. Guests are on a spacious catamaran and get to explore North America’s only living coral reef. The excursion is three hours long and all you need to bring is a towel, your swimsuit, food and drinks, and cash to tip the crew. A waterproof camera or go pro is also a fun thing to have on hand to capture your adventure.
Parasailing at Robbie’s of Islamorada – Initially we were going snorkeling at Robbie’s but the weather conditions weren’t great for that activity. Turns out that a windy day is perfect for parasailing! None of us had been before and were so excited about this activity. At Robbie’s parasailing starts at 9 a.m. and runs on the hour until 5 p.m. Flyers must be at least 6 years old and you’re in store for a fun adventure! Two people go up at a time and your toes don’t even touch the water if you don’t want to. Once you get to the top enjoy views as far as the eye can see and the calming quiet. It’s something everyone should do at least once.
Jet Skiing at Barefoot Billy’s – If you have a lead foot and a need for speed, go see the boys at Barefoot Billy’s in Key West. This was one of our favorite activities and at the top of our list of fun things to do in the Florida Keys! We put our hair in ponytails, strapped on our life jackets, and hit the water! There are three different jet ski tours to pick from:
- Casa Marina Island – This is a 90-minute tour that takes you around the island of Key West and you get to see the Atlantic Ocean and the Gulf of Mexico.
- Marriott Beachside – Also a 90-minute tour that takes you on a tour with a guide.
- Reach Resort Island – The third option is a 90-minute tour where you travel up to 26 miles around Key West with the Barefoot Billy’s guide.
When you arrive, get there 30 minutes early to fill out all the paperwork and take an open book test. It may give you SAT flashbacks but the multiple-choice test just helps you understand what to do on the water and what different flags and hand signals mean when you’re out. We all passed with flying colors! We left our phones at Barefoot Billy’s but our guide took some fun videos and photos of us and their total pros at angles and getting just the right shot for your Instagram. You can Venmo them a tip once the tour is over.
While there are tons of different water sports and adventures you can do in the Keys, we also love mixing in some relaxing and recharging. Here are some fun things to do in the Florida Keys that will help you chill out.
Sunset Sail on Commotion on the Ocean – When we arrived in Key West, we headed to Fury Sailing for the Commotion on the Ocean Sunset Tour. Enjoy the ocean with live music, drinks, and appetizers. Most of the time the tour starts at 6 p.m. and is two hours long. When we arrived we went straight to the top deck to have a spot for our purses and cameras. When the sun started setting we took photos of the gorgeous views and enjoyed dancing and singing along to the live music.
(Some of the babes get a little seasick so we recommend either taking some Dramamine or wearing some Relief Bands for motion sickness. Also, don’t forget to bring cash to tip the crew.)
Morning Yoga with Salute to the Sol – Everyone can use a little ‘namaste’ on a beach trip. Salute to the Sol owner, Rebecca had us all set up when we arrived at the Truman Waterfront and we enjoyed a morning vinyasa flow session. Salute to the Sol offers customized sessions from all levels and is committed to making sure attendees get the most out of their yoga practice. You can schedule a private session or join them at The Perry Hotel & Marina Key West every Sunday for vinyasa on the event lawn.
Wander Ernest Hemingway’s Home & Museum – Ahhh Hemingway, get to know the man behind the pen at his Key West Home and Museum. You can tour the home yourself or go with a guide. We preferred wandering around ourselves and spending time in the gardens and petting the six-toed cats. This is such a beautiful property and you’ll love exploring and learning about this writing legend. The museum is open daily from 9 a.m. to 5 p.m. and only takes cash for admission.
Florida Keys – Where to Eat
Eating and drinking definitely constitute as fun things to do in the Florida Keys. Here’s our list of some of our favorite places we visited!
Angler & Ale – Our first night in the Keys was spent at one of Hawks Cay’s restaurants, Angler & Ale. It was a short walk from our villa and they also have a shuttle golf cart that can pick you up and drop you off. In late April it was a little chilly to sit outside so you can either bundle up or move inside to enjoy your meal. This restaurant overlooks the Hawks Cay Marina and is a casual restaurant with lots of seafood options. We recommend the Whole Fried Snapper, ceviche of the day, and the Tuna nachos. If you enjoy fishing you can also take advantage of Angler & Ale’s ‘Hook N Cook’ where you bring in your catch of the day and the chef there prepares it the way you like.
Robbie’s of Islamorada – We stopped at Robbie’s for breakfast before we went parasailing. The Hungry Tarpon Restaurant and Bar has a large menu for breakfast, lunch, and dinner and has a variety of options for anyone you’re traveling with. For breakfast, we had coffees, Bloody Mary’s, Mimosas, and Breakfast Sandwiches. Our favorite was the Silver King breakfast sandwich and the Cowboy Combo. When you’re done with breakfast head out back to feed the Tarpon and see some big birds with major attitude.
Islamorada Brewery & Distillery – After parasailing, we headed down the road to Islamorada Brewery & Distillery. You can’t miss this place thanks to its yellow and teal interior and exterior decor! We headed to their cool outdoor patio and did tastings of their gin, vodka, and spiced rums. We also did a flight of their beer and canned cocktails. It was a great way to taste some local brews while enjoying the gorgeous Florida weather.
Morada Bay Beach Café – If you want to feel like you’re on a glam Caribbean Island, book dinner at Morada Bay Beach Café. Morada Bay is an outdoor Mediterranean bistro in the sand with food that’s a blend of Caribbean and American cuisines. The menu really shows off the local seafood and produce! The outdoor space is very fun and colorful with the most spectacular views of the water. Bring your camera and take some time to enjoy the beautiful space for yourself.
Half Shell Raw Bar – The Florida Keys did not disappoint with all the fresh seafood! Half Shell Raw Bar was close to the Fury dock so we headed here for dinner after the Commotion on the Ocean sunset tour. You can find the Half Shell Raw Bar in the Key West Historic Seaport which is a casual restaurant that serves everything from fish and chips to their famous Half Shell conch ceviche. The staff here was exceptional and so fun and friendly. They gave the best dinner recommendations and we enjoyed all the delicious seafood. A 10 out of 10 for us!
The Docks Stock Island – The last dinner of our trip was at the new Docks Stock Island. This restaurant has only been open a few months and is already a Key West hot spot, so be sure to add it to your Florida Keys itinerary. The Docks Stock Island serves seafood but it’s sustainably sourced and the decor is upcycled island style. We enjoyed apps like Figs in a Blanket, Tuna Carpaccio Pizza, and Grilled Calamari. Then we enjoyed cheeseburgers, the Cauliflower Bake, Seafood Scampi, and more. Come here for lunch or dinner! They’re open 7 days a week from 12 p.m. to 9:30 p.m.
Hope you loved this Florida Keys girls trip! What are some other fun things to do in the Florida Keys that we should add for next time? Let us know in a comment below!
Thank you to the Florida Keys tourism board for hosting the Babes! If you’re looking for more fun things to do in the Florida Keys, check their website for more planning tips.
A huge thank you to our partners:
Aerie, Spanx, Cupshe, Peixoto, Bromelia, Tote N Carry.
Looking for more travel inspo? Find our other travel guides here.