Exploring The Florida Keys: Key Largo to Key West

Florida Keys Getaway Itinerary

Key Largo - Gateway to the Keys ( Day 1-3 )

The drive from Miami to Key Largo is a short 60 miles, transporting you from the bustling city to a lush tropical paradise. Key Largo marks the starting point of 120 miles of island paradise and is known as the gateway to the Keys and also the diving capital of the world!

Check-in for a Stay at Bakers Cay:

When arriving at the Bakers Cay Resort, one thing that becomes immediately obvious is that you have officially arrived in paradise. The resort’s contemporary island styled architecture glitters against the backdrop of turquoise waters and lush greenery – a guaranteed great first impression for any guest arriving past the gates for the first time. Staff greeted us with cold beverages and warm *You’ve arrived to your vacation! Get excited!* energy before we even made our way inside the lobby to check in.

Quick side note, I don’t know what they are pumping through the air in the lobby, but it smells so insanely good that you can’t help but to instantly become happier the second you walk inside. If anyone from Bakers Cay is reading this and can somehow bottle this scent into a candle for me, please let a girl know! 

bakers cay resort
bakers cay resort coconut beach

Bakers Cay features 200 guest rooms on property with many different variations from size, to views and location on property so there is quite a bit of range to choose from. Our room during our stay was a king waterfront room in the Coconut Wing. We were blown away by just about everything this space had to offer from its luxurious nature inspired design and furnishings to the spectacular views and balcony terrace. 

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bakers cay resort

The resort property covers over 13 lush waterfront acres and once you settle in here you will be unlikely to ever want to leave. Here’s a quick guide to everything you have access to here at Bakers Cay:

  • Hilton owned Curio Collection property (points friendly!) 
  • Dog friendly ( they even have dog cabanas on the beach, which is maybe the cutest amenity I have ever heard of )
  • Two beautiful white sand beaches to enjoy! Coconut Beach, where you will find no shortage of loungers, a tiki bar and wide range of watersports and activities available for guests to choose from. Then there’s Hammock Beach, an adults only shoreline offering a more private and tranquil spot to unwind shaded by lush greenery. 
  • Two swimming pools with beautiful waterfalls – one is family friendly and the other adults only ( this is a BIG one for me and in my experience can make or break a travel experience if traveling without children so brownie points for the adults only pool!) 
  • Fantastic onsite dining with two main restaurants to choose from – Calusa and Dry Rocks, in addition to the bars and in-room dining options.
  • Daily activities and happenings each day including bar trivia, paint and sip classes, outdoor movies, and so much more!
  • Click here for a video feature of our stay at Bakers Cay
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bakers cay resort
bakers cay resort pool

Travel from Key Largo to Key West -( Day 4 )

The drive from Key West from Key Largo is around 2 hours in length, but I would recommend planning a few stops along the way because there is truly SO much to see and do! Here are a few activities and sights to see that I recommend considering: 

  • Jet ski tour with Spray Watersports on Islamorada Island: This was one of my favorite activities during the trip and can’t recommend it enough – it is an absolute must! The 1.5 hour tour takes you through lush mangroves, to a few stunning sandbars where you’re able to swim and to the iconic Alligator Lighthouse – don’t worry, no actual alligators here! 
  • Explore the new Old Seven Mile Bridge: The once retired old seven mile bridge recently reopened but this time as a recreation bridge open for cycling, walking, running and rollerblading (and I hear it’s also an excellent place to catch a sunset)! 
  • Clear kayak tour with Get Up and Go Florida Keys on Sugarloaf Key: There really are no words that can describe how magical this tour was – whether you typically enjoy kayaking or not, this is a MUST DO experience.
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florida keys roadtrip
Florida keys kayak tour

Key West Island ( Day 5-7 )

Home to the southernmost point in the United States, Key West is a vibrant and energetic island community packed with adventure and culture. Packed with unique attractions, history, water sports, shopping and nightlife, this small but energized island is sure to keep you busy during your stay and almost certainly planning your return before you’ve even left!

Check-in for a Stay at Alexander's Guesthouse

Check in for a stay at Alexander’s Guest House: Situated in the heart of Old Key West, you’ll find a three story conch-style home hidden away on a shady palm lined street. Alexander’s is an adults only LGBTQ+ guesthouse – while you don’t have to be queer to stay here you do have to consider yourself an ally as this stay truly serves as a sanctuary for LGBTQ+ people to feel safe and free to be themselves!

As a full time traveler & also a lesbian, I can tell you that it’s extremely rare to find places you feel 100% safe in. Being able to go on vacation and show PDA without having to be constantly cautious of your surroundings is a privilege that we are usually not afforded- so places

like Alexander’s are so incredibly special and highly recommend the experience especially to my fellow queer travelers!

alexanders guest house

Other things I loved about staying at Alexander’s Guesthouse: 

  • A simply amazing experience with incredible attention to detail from arrival to departure with some of the kindest and warmest staff you could ever wish to meet
  • Beautiful swimming pool + hot tub & even a daily poolside happy hour
  • Delicious continental breakfast complimentary for guests every morning
  • AMAZING location for everything you could want to see and do in Key West ( I had a rental car and didn’t move it once during my stay, almost everything is walkable )
  • Staying here was simply so good for my soul and I felt so at home

Exploring Key West:

There are an endless amount of ways to spend your days exploring the colorful and historic Island of Key West both on and off land. Here are a few of my favorite things I did during my visit:

  • Dolphin watch and snorkeling tour with Honest Eco Tours – This tour lasts about 4 hours and is an amazing way to get out on the water and see some incredible wildlife up close in an eco friendly / conscious way! 
  • Explore Key West aboard the iconic Conch Train Tour – Fun open air sight seeing train that takes passengers around the island with a live tour guide narration and even a few spots where you can hop off and check out the local attractions! This is definitely worth doing and is a great way to get your bearings around Key West!
  • Dine at Half Shell Raw Bar– There are plenty of amazing restaurants in Key West to choose from but for the best fresh seafood make sure you dine at Half Shell Bar located right on the water at this historic seaport!
key west island
  • See a drag show at Aqua Nightclub – located on Key West’s iconic Duval Street, Aqua puts on an incredible nightly drag show in its cabaret styled performance space and it is a MUST when visiting Key West.
  • Take a sunset cruise with Sebago Watersports: Key West is known for its spectacular sunsets so booking a sunset sail is a non-negotiable when visiting! Sebago offers 2 hour sunset sails complete with live music on board, an open bar and a few delicious hors d’oeuvres!
key west sunset sail

This blog post was part of a hosted visit and paid partnership with The Florida Keys. All recommendations and reviews remain genuine, these opinions are my own. 

Check out Stays and Getaways on Instagram for extra photos and video features on our getaway in the Florida Keys & follow for more getaway inspiration

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