A Girls Getaway in the Florida Keys
If you’re planning a girls getaway, the Florida Keys should be at the top of your list. The Florida Keys have the ultimate mix of sun, sand, sailing, snorkeling and seafood – everything you need for a perfect girls getaway!
Note: My trip to the Florida Keys was in partnership with the The Florida Keys Tourism Council but, of course, all opinions are my own.
The Florida Keys are a great choice for your girls getaway, if you’re looking for a luxurious beach escape without the hassle of a long haul flight. And the best part? If you’re based in the USA, you can get those tropical vibes going without having to bring your passport! Keep reading for an in-depth guide to a girls getaway in the Florida Keys.
Where are the Florida Keys?
The Florida Keys are a chain of islands in the southernmost part of Florida. If you head to Key West during your girls getaway in the Florida Keys, you can actually stand at the southernmost tip of the continental USA. Pretty cool, right?
When to Visit – Girls Getaway in the Florida Keys
Peak season in the Florida Keys starts in December and runs through May. A visit between March and May is likely to have the best weather.
We visited the Florida Keys for six days in late January and found our first couple of days to be chilly. Luckily it got increasingly warmer each day, and was positively balmy before we flew back to NYC.
Hurricane season in the Florida Keys is from June until the end of November.
Getting There – Girls Getaway in the Florida Keys
Although you can fly right into Key West, we chose to fly to Miami from NYC and drive to the Florida Keys.
The drive from Miami to Key West on the Overseas Highway (U.S. Route 1) includes the Seven Mile Bridge and is arguably THE most iconic American road trip. The views of the water, from pretty much every direction, are stunning.
We chose to drive straight from Miami to Key West on the first day, stopping only for lunch. We then made our way through the Florida Keys back to Miami at a leisurely pace during our 6 day trip, enjoying everything that the Florida Keys have to offer along the way.
There are shuttle services between both Fort Lauderdale and Miami International Airports and Key West. However, that leaves you pretty limited options if you want to explore anything outside of Key West.
Getting Around – Girls Getaway in the Florida Keys
Public transportation seemed fairly limited in the Florida Keys. If you plan to explore anything outside of Key West, you’ll need a car.
The good news is that many hotels have free shuttle services for their guests. So, if you want to dine nearby, have a couple of drinks, and get back safely you hotel should have you covered. We also found it easy and affordable to use Uber on nights that we didn’t want to drive or wait for a hotel shuttle.
Destinations – Girls Getaway in the Florida Keys
Although the Florida Keys are full of little islands and towns, we mostly spent our time at Key Largo, Islamorada, Key West and Stock Island.
Key Largo
Key Largo is most people’s entryway into the Florida Keys. We actually visited Key Largo toward the end of our trip, since we drove straight to Key West on our first day. It’s the the self-proclaimed “Dive Capital of the World” and has plenty of water sports, diving opportunities and fishing.
Islamorada
Islamorada is situated halfway between Miami and Key West along the Overseas Highway. It’s known as an ultra relaxed and luxurious destination for people seeking a low key vacation in the Florida Keys.
Key West
Key West is where the culture is at in the Florida Keys. Though many people think of Key West as a party destination, it is so much more. But yes, you can still find some lively bars if you’re looking for a fun night out.
Stock Island
Stock Island is a chilled out area near Key West. We spent a few nights on Stock Island at Ocean’s Edge Resort and Marina. I loved having a quiet place to stay at night, after spending action packed days exploring Key West.
The manmade beach at Playa Largo Resort & Spa 
Hammocks line the beach at Amara Cay Resort
Where to Stay – Girls Getaway in the Florida Keys
More and more luxury hotels are opening in the Florida Keys. These are the ones we were able to check out during our trip.
Key West / Stock Island
Ocean’s Edge Resort and Marina (5950 Peninsular Ave, Key West, FL) is an easy drive into Key West but a luxurious escape from its hustle and bustle. Ocean’s Edge Resort and Marina has six – YES SIX! – heated pools. And every single guest room has an ocean view with a balcony and coastal chic decor. We stayed here for the first three nights of our trip and loved waking up to watch sunrise from our balcony and the marina. And then getting our caffeine fix from the onsite Starbucks! The resort also offers a shuttle service into Key West every hour, which is ideal if you want to experience the Key West nightlife.
The Perry Hotel Key West (7001 Shrimp Rd, Key West, FL) is a fairly new addition to the Key West hotel scene. We didn’t have a chance to stay here, although we had dinner at Matt’s Stock Kitchen on the property. The hotel is super stylish with a minimalist aesthetic – this is definitely not your grandma’s Florida Keys!
Poolside at Ocean’s Edge Resort & Marina 
Sunrise at Ocean’s Edge Resort and Marina
Islamorada
The Amara Cay Resort (80001 Overseas Hwy, Islamorada, FL) is all about easy, tropical elegance. We stayed here for the second half of our trip and loved relaxing in the hammocks scattered throughout the property. The resort has a private man-made beach, a beautiful swimming pool, and an incredibly stylish lobby. It has 110 rooms, but still maintains the intimacy and friendliness of a small hotel (which I love). The level of hospital and service we received here was unmatched. The Amara Cay Resort also runs a free shuttle for its guests within a 4-mile radius, so that you can easily explore the area, even after a couple of drinks.
The Postcard Inn (84001 Overseas Hwy, Islamorada, FL) is a sister property to the Amara Cay Resort. We spent an afternoon here enjoying its beach and tiki bar. Guests of the Amara Cay Resort and the Postcard Inn can take a free shuttle between the properties and enjoy the amenities at both hotels.
Poolside with the girls at Amara Cay Resort 
The beach at the Postcard Inn
Key Largo
Playa Largo Resort (97450 Overseas Hwy, Key Largo, FL) is a luxury hotel in Key Largo. We spent a very relaxing afternoon here enjoying its massive central pool, private man-made beach and full-service spa.
Where to Eat + Drink – Girls Getaway in the Florida Keys
What can I say? The seafood is fresh and plentiful and the drinks are always flowing in the Florida Keys. Here’s a comprehensive list of everywhere we ate during our trip.
Key Largo
If you like seafood and kitchy decor, check out The Fish House (102401 Overseas Hwy, Key Largo, FL). This is an experience not to be missed in Key Largo, although you may spend more time looking at the decor than chatting with your dinner companions!
Sundowners (103900 Overseas Hwy, Key Largo, FL) is a casual waterfront restaurant that has something on the menu for everyone. We stopped by for a seafood and salad lunch on our way to Key West, but we were told this is an epic spot for a sunset dinner.
Key Largo Conch House (100211 Overseas Hwy, Key Largo, FL) is a family-owned and operated restaurant set in a very charming pink house. It’s a great choice for breakfast and has awesome fresh squeezed orange juice.
Islamorada
Marker 88 (88000 Overseas Hwy, Islamorada, FL) is located on one of the few natural beaches in the Florida Keys. We had a phenomenal seafood dinner there. Order the Key Lime Seafood entree if you can! It’s also the perfect spot to watch the sunset in Islamorada with a cocktail in hand.
The rum runner cocktail was invented at the Holiday Isle Tiki Bar, located at the Postcard Inn (84001 Overseas Hwy, Islamorada, FL). Stop by to try the famous cocktail at its birthplace.
I’m not usually a beer drinker, but I loved stopping by the Florida Keys Brewing Co. (81611 Old Hwy, Islamorada, FL). We took a tour of the brewery and then enjoyed a beer flight in their backyard. The rainbow decor was so bright and cheerful, there was live music, and so many cute dogs sitting with their owners! How could I note be charmed? I love their “Iguana Bait” hibiscus beer. Don’t forget to say hi to Purr Monster, the brewery’s resident cat.
The Hungry Tarpon at Robbie’s Marina (77522 Overseas Hwy, Islamorada, FL) is a waterfront restaurant that’s famous for its tarpon feeding. Yes, you can pay $2.25 a person to hand feed giant fish. If you aren’t too scared to do it! I chickened out and chose to sip my cocktail at the restaurant and be a spectator from afar instead.
Key West
If you’re visiting Key West, you need to have breakfast or lunch at Blue Heaven (729 Thomas St, Key West, FL). Period. This outdoor restaurant has an undeniably unique and free-spirited atmosphere, with people of all ages coming in for a hearty breakfast. Blue Heaven also had live music when we visited.
Kermit’s Kitchen Cafe (200 Elizabeth St, Key West, FL) is a great spot for a quick breakfast or lunch. You’ll get to soak in that Key West charm with its koi point and key lime printed table tops on the patio.
Turtle Kraals (231 Margaret St, Key West, FL) is a lively restaurant and bar in Key West that has twice-weekly turtle races. By race, I mean the turtles walk very slowly along a small raised track. This is a chance for the turtles to get a little bit of exercise and see their adoring fans. We asked, and it sounds like the turtles are treated extremely well and aren’t brought out to “race” each other if the weather is too warm.
Stock Island
Matt’s Stock Island Kitchen + Bar (7001 Shrimp Rd Suite 200, Key West, FL) is a trendy restaurant in the Perry Hotel. Leave the fancy clothes behind though, this is the Florida Keys after all and everything is pretty laid back and casual. We had dinner here, and the seafood tower was especially memorable!
If you’re staying at Ocean’s Edge Resort & Marina, don’t miss out on having dinner at Yellowfin Bar and Grill (5950 Peninsular Ave, Key West, FL). Especially if you’ve had a long day enjoying the resort’s six swimming pools! Ask for a table outside with a view of the marina and take a seat by one of the fire pits.
What to Do – Girls Getaway in the Florida Keys
Key Largo
John Pennekamp Coral Reef State Park (102601 Overseas Hwy, Key Largo, FL) is a popular spot for diving, snorkeling, glass bottom boat rides and other water sports. We ran out of time during our trip, so weren’t able to go. But I have it bookmarked for next time!
Get Your Spa On
A girls getaway in the Florida Keys isn’t complete without a spa treatment or two. Or three. We visited the OceanSpa at the Playa Largo Resort (97450 Overseas Hwy, Key Largo, FL) for Key Lar-GLOW Organic Brightening Facials.
Now, I’m usually hesitant to get facials after my first (and last) time getting extractions. But my facialist at the OceanSpa was gentle on my skin, didn’t pressure me to get extractions, and my skin was positively glowing afterwards.
Islamorada
You can feed giant tarpon fish at Robbie’s Marina (77522 Overseas Hwy, Islamorada, FL) for $2.25 a person, if you dare! To be honest, this wasn’t really up my alley after Googling what tarpon look like. But the people who did it looked like they were having a blast!
Key West
No girls getaway in the Florida Keys is complete without a couple of days in Key West. Key West is both the cultural center of the Florida Keys and also a great place for a night on the town.
Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum (907 Whitehead St, Key West, FL) is a cultural experience not to be missed. You’ll have a chance to walk through Mr. Hemingway’s house, tour his gardens and see his writer’s studio.
Ernest Hemingway lived here for 10 years – you get to walk through the very rooms in which he wrote major contributions to American literature.
You can also see the famous six-toed Hemingway cats. During our visit, some of the cats were napping on Hemingway’s bed and one was sleeping in the eaves of his studio. SO cute.
General admission tickets are $14, admission for children aged 6-12 is $6 and children 5 and under are free. Tickets can be purchased at the door. There’s no need to buy them in advance.
On the terrace at Ernest Hemingway Home 
Hemingway Cats on Ernest Hemingway’s Bed 
Another sleepy Hemingway cat
Key West Lighthouse
Lighthouse buffs can tour the Key West Lighthouse (938 Whitehead St, Key West, FL ), including the old keepers quarters and walking 88 steps to the top. Admission is $12 for adults, children aged 6 and up are $5 and children 5 and under are free.
Key West Butterfly and Nature Conservatory
The Key West Butterfly and Nature Conservatory (1316 Duval St, Key West, FL) gives you the chance to walk among 50 to 60 butterfly species and over 20 exotic bird species. It’s a magical experience, but humid and hot so dress accordingly.
Southernmost Point
A giant buoy marks the southernmost part of the continental USA (Whitehead St & South Street, Key West, FL). But, if you want a photo with this famous marker, expect to wait in line!
Mallory Square Sunset Celebration
When you’re by the southernmost part of the continental USA, it’s no surprise that the sunsets are epic. Locals and tourists gather daily at Mallory Square (400 Wall St, Key West, FL) for a Sunset Celebration. Come a bit early to get a good spot for viewing the sunset over the water. Local vendors sell drinks, food and souvenirs and street performers entertain the crowds.
Fury’s Reef + Ritas Snorkeling Trip
The Florida Keys are known for their crystal clear water and coral reefs. Fury’s Reef + Ritas (the dock is behind the Margaritaville resort – 245 Front St, Key West, FL) snorkeling trip was a memorable way to experience both.
The hilarious and gregarious Fury team took us out sailing for the afternoon, taught us what we needed to know about snorkel safety and reef responsibility, and then let us loose to explore in the water. While the boat was anchored, we even saw a pod of dolphins swim by!
Once we were all safely back on the back on the boat, the margaritas started flowing (and flowing). Then, we cruised back to Key West.
Danger Charters Wind + Wine Sunset Sail
This was by far my favorite night of the trip. Danger Charters hosts a Wind + Wine Sunset Sail (the dock is behind the Margaritaville resort – 245 Front St, Key West, FL), where you are served generous helpings of appetizers, wine and beer aboard a historic sailboat. Yeah, these guys don’t scrimp on the wine, beer and eats.
The Danger Charters team couldn’t be more friendly, and we joked and laughed with them for hours.
Onboard Fury’s Reef & Ritas Day Trip 
Danger Charter’s Wind & Wine Sall
See the Colorful Buildings
Key West has incredible charming and colorful houses and buildings. Take a walk around town to see some of the beautiful restored spots.
Key West is full of charming homes 
Tropic Cinema in Key West
Bahia Honda Key
You may not know this, but the Florida Keys aren’t really known for their sandy beaches. Bahia Honda State Park (36850 Overseas Hwy, Big Pine Key, FL) is an exception to that rule. It has a long, thin, wide sand beach and the crystal clear water you can expect from the Florida Keys.
Whew, well that wraps up my ultimate guide to a girls getaway in the Florida Keys. Overall, I was impressed with our luxury accommodations, the beautiful crystal clear ocean, the fresh seafood and the incredible service we had during our trip. People are just so nice in the Florida Keys! If you’re looking for a girls getaway, the Florida Keys should definitely be a destination you consider.
xx
Vicki
Many thanks to The Florida Keys Tourism Council for sponsoring this post, and to all of the local businesses & resorts that hosted us during our fabulous girls getaway in the Florida Keys.
This looks like so much fun! I’ve been dying to visit Islamorada!