5 Days in the Florida Keys

Interested in a tropical vacay, but don’t feel like traveling outside the continental United States? Well then, the Florida Keys have got you covered! The Keys are comprised of a stunning chain of tropical islands or “Keys” that stretch for about 120 miles off the southern tip of the state of Florida. They are best known for their amazing snorkeling and scuba diving, having the world’s 3rd largest coral reef, as well as pretty much everything else that being on the water entails. Making it the perfect holiday destination for beach lovers.

Here is my 5 day guide to the Florida Keys to help you maximize your time there, and see all the best things the Florida Keys have to offer!


First things first, if you are not located in Southern Florida you are most likely want to fly there. There are 3 different airport options to fly into: 

  • Option A: Fort Lauderdale – 1.5 hours from Key Largo
  • Option B: Miami – 1 hour from Key Largo
  • Option C: Florida Keys/Marathon – 1 hour to Key Largo

We chose Option A, mainly because it offered the cheapest flights. This option also allows you to start at the top of the Keys and work your way down to the southernmost island, Key West. Option B also allows you do this and is 30 minuets closer, and might be the better way to go if you find a good deal.

Day 1- Key Largo

I was meeting my friend Janna from “Janna on a Jaunt” (check her out here) and decided the best way to go was to take a red eye flight to get there first thing in the morning. We both landed in Fort Lauderdale at about 6 a.m. and picked up our rental at the airport. We went with Budget Car Rental and paid $250 for our whole 5 day stay. We only has to fill it up once, for about $28.  First stop of the trip was in Key Largo for breakfast at a cute little local diner.

Breakfast: Mrs. Mac’s Kitchen

99336 Overseas Highway Key Largo, FL 33037 (305)-451-3722

This Key Largo eatery is a local’s favorite. Decorated with license plates donated by guests from all over and featuring dishes ranging from biscuits and gravy to fresh fish straight off the dock. There are two different locations, but be sure to check out the original location I linked above.

Snorkel Excursion at John Pennekamp Coral Reef State Park

John Pennekamp Snorkeling


102601 Overseas Highway Key Largo, FL 33037 305-451-6300

Next up: snorkeling at John Pennekamp. Known as the first undersea park in the United States. It encompasses approximately 70 nautical square miles. The mangrove swamps, coral reefs, and wildlife offers a very unique experience unlike any other state park! Activities include snorkeling, scuba, glass bottom boat tours, boat rentals and kayak rentals. The park also provides access to the famous “Christ of the Deep” statue. 

Sadly, there was low visibility at the location I was most excited to see  the underwater statue. However, our guide brought use to alternative location that was just as spectacular! Once they said there was low visibility I got pretty discouraged that we weren’t going to get to see much, but I couldn’t have been more wrong! The guides at John Pennekamp are all super knowledgeable and will accommodate each tour depending on the weather. They ended up bringing us to this spot that was the clearest and most dense coral reef I’ve ever seen! The water was crystal clear and we saw all types of different sea life. From barracudas to jellyfish to numerous exotic fish! 

Check in to Kona Kai Resort

Kona Kai Resort

97802 Overseas Highway Key Largo, FL 33037 (305)-852-7200

You are probably exhausted at this point. I know we were! Check into the beautiful Kona Kai Resort to freshen up & relax. Relaxation comes easy at this gorgeous, low-key Resort. Not only a beautiful inn but also one of the most sophisticated art galleries in South Florida, featuring world-renowned artists.

The property is darling and has a homey, beach cottage vibe. Because it is considered a boutique hotel, it only has 14 suites, so it never gets overly crowded. The suites include a kitchen, in case you would rather not eat out every meal. The beds were also a huge highlight for me, super comfy and fluffy  we had the best night sleep (partially from the exhaustion, haha). However, in my opinion, the resort’s best feature were the kayaks and SUP’s you can take out whenever you’d like! 

Dinner at Ciao Hound at Postcard Inn

The Perry Hotel Image # (1)

84001 Overseas Hwy Islamorada, FL 33036 (305)-664-5300

We got here just in time to watch the sunset on the marina and snap a few pics. There’s something so relaxing about boats floating on the water in the evening, don’t you think? This is an adorable spot to grab a bite and a night cap. 

 I would have never paired Florida Keys and great Italian, but Ciao Hound was outstanding! Known for their Tuscan flavors with fresh Keys-sourced ingredients. Ciao Hound is open for dinner daily.

Some menu highlights:

  • Sweet Pan-Seared Florida Shrimp with Creamy Polenta
  • Grilled Mahi-Mahi Puttanesca 
  • Garlic-Rosemary Basted Tuscan Sirloin Steak

Day 2- Depart for Key West

Breakfast- Kona Kai 

The resort does offer complimentary breakfast, however if you are all about trying all the best food, here is a suggestion:

Key Largo Conch House

100211 Overseas Highway Key Largo, FL 33037 (305)-453-4844

Key Largo Conch House is a family owned and operated restaurant. It features a menu ranging from fresh local seafood to delicious desserts. The restaurant is famous for its Key lime pie and conch fritters, so be sure to check those out!

Tarpon Feeding at Robbie’s The Hungry Tarpon

77522 Overseas Highway Islamorada, FL 33036 (305)-664-8070

Robbie’s Marina is a must stop on your drive down. Robbie’s offers a mix of outdoor shops, food vendors, and the best part: tarpon feeding! Grab a bucket of fish to feed the tarpons or enjoy watching everyone else getting up close and personal with the huge fish. Definitely a one of a kind experience in the Keys! Robbie’s is also home to The Hungry Tarpon Restaurant and Bar and offers a large menu, with a variety of options for the entire family, including fresh local seafood. The restaurant will also cook anglers’ catch.

Lunch at Morada Bay Beach Café

Morada Bay Cafe

81600 Overseas Highway Islamorada, FL 33037 (305)-664-3225

We actually didn’t eat here, but it was a must for us being fans of the Netflix show Bloodline. If you’ve seen the show you’ll recognize the Rayburn Inn and other filming locations at the cafe itself!

The Morada Bay Beach Café & Bar is an outdoor Mediterranean bistro café, set in the sand. The Café’s menu is a blend of Caribbean and American cuisines showcasing fresh local seafood and produce.

Continue to Key West and check in to The Perry Hotel Key West

The Perry1-3

7001 Shrimp Road Drive Key West, FL 33040 (305)-296-1717

A completely different feel from the previous hotel, but incredible in its own way! Inspired by the industrial nature from which Stock Island has developed, The Perry Hotel Key West at Stock Island Marina blends smooth wood finishes with rustic metal details that reflect the area’s iconic maritime heritage. It’s located beside a  marina — the largest deep-water marina in the Florida Keys — which, the hotel overlooks. 

Amenities included:

  • Scheduled shuttle service to Old Town
  • Welcome glass of champagne at check-in
  • High-speed Wi-Fi
  • Concierge service
  • Onsite parking
  • Fitness center

The Key West Butterfly & Nature Conservatory

1316 Duval St. Key West, FL 33040 (305)-296-2088

The Conservatory was such a surreal experience! Filled with hundreds of butterflies and exotic birds that just flutter right by you! The conservatory is also home to an impressive collection of flowering plants, cascading waterfalls, and trees! Attractions also include a learning center where you can explore butterfly anatomy, physiology, the life-cycle, feeding and migratory world of the monarch.

Ernest Hemingway Home and Museum

Ernest Hemingway1-3

907 Whitehead St. Key West, FL 33040 (305)-294-

Visit the Ernest Hemingway House and step back in time. It was amazing exploring the rooms and gardens where the Nobel Prize winner spent the most prolific period of his writing career during the 1930’s! Fun fact: Hemingway was obsessed with cats and even had a cat cemetery in his garden! There are still plenty of cute felines roaming his property that you can say hi to when you visit.

Dinner at Hot Tin Roof at Sunset Pier

Ocean Key Resort & Spa Key West, FL 33040 (305)-296-7701

Me and Janna definitely felt like we were on a romantic date at this upscale bistro! It really is the perfect spot to enjoy a gorgeous evening with your significant other. You can either sit in the romantic banquette in the dining room or al fresco on the veranda. You can’t go wrong either way with it’s stunning ocean views! This spot offered the most delicious seafood I’ve had in quite awhile! Everything was so fresh.

Some menu highlights:

  • Oysters on the Half Shell
  • Spicy Tuna Tacos
  • Seafood Paella
  • Butter Poached Florida Lobster

After dinner head down to Sunset Pier, grab a drink, and enjoy the live music!

Day 4- Water Adventure in Key West

Ultimate Adventure with Fury Water Adventures

fury water adventure1-5

631 Greene St. Key West FL 33040

Fury Water Adventures really packs all the best water activities into 1 action packed day! We decided to go on Fury’s most popular excursion – Ultimate Adventure. Such an epic day where Fury takes you parasailing, jet skiing, kayaking and snorkeling! They also offer individual excursions for parasailing, sunset cruises, eco tours, jet skiing, snorkeling and other activities.

Sunset Celebration at Mallory Square

Sunset Celebration is a free nightly “street carnival” at Mallory Square, overlooking Key West Harbor. It features arts and crafts exhibitors, street performers, food carts, psychics, musicians and other entertainers. Crowds of visitors from around the world flock to the celebration each evening to observe and applaud the setting of the sun over the water. Event begins at 7 p.m. each evening.

Dinner at Lucy’s Retired Surfers Bar & Restaurant

221 Duval St. Key West, FL 33040 305-922-2616

Head down Duval Street, Key West’s most famous street and grab a bite to eat at Lucy’s Retired Surfers Bar & Restaurant. It is absolutely adorable in here! With a surfer shack decor and twinkle lights, Lucy’s offers coastal-inspired cuisine and surfer-inspired cocktails. Such an authentic and laid-back place to eat, drink and mingle. The menu features appetizers, salads, sandwiches, tacos, entrees and vibrant cocktails.

Some menu highlights:

  • Shaka Ceviche
  • Surf’s Up Wings
  • Sue’s Spicy Queso Blanco
  • Catch of the Day

Enjoy Key West nightlife

The night is young! Make the most of your time and enjoy the fun Key West night atmosphere.

Day 5- Explore more of Key West

Breakfast at Bistro 245

245 Front St. Key West, FL 33040 (305)-294-4000

Enjoy casual dining with breathtaking views of the Key West Harbor. The restaurant serves breakfast, lunch and dinner as well as Sunday brunch with complimentary champagne service. We made sure we came for Sunday brunch for a buffet style dining. Bistro 245 offers the typical yummy brunch foods such as eggs Benedict but also offers fresh seafood that I definitely took advantage of! Everything is very high quality and super tasty!

Conch Tour Train

downtown key west1

303 Front St, Key West, FL 33040 (305) 294-5161

I admit, this is probably the most touristy thing you can do but we had such a fun time riding around town and learning all about the history of Key West. Our tour guide was so knowledgeable and had lived there his whole.

Key West Eco Tours

231 Margaret St, Key West, FL 33040 (305)-294-7245

This is something we didn’t actually get the chance to do but is something I would’ve loved to have experienced! Key West Eco Tours provides personalized tours of Key West’s mangrove islands and back country. You can choose from a catamaran combo trip, kayaking and paddle-boarding tours and rentals. Such a unique way to see Key West! 

Sunset Sail with Sebago Watersports 

Key West Sunset Cruise

205 Elizabeth St. Key West, FL 33040 (800)-507-9955

This is the perfect way to end our last night in the Keys. The best way to watch the sunset in Key West is definitely from a boat. We had an amazing evening with Sebago. They offer drinks and appetizers throughout the tour with complimentary champagne, wine, chilled beers and soft drinks.

Dinner at First Flight Island Restaurant & Brewery

Enjoy one last meal at First Flight. It’s well known for being the birthplace of Pan American World Airways, since Pan-Am’s first tickets were sold out of the restaurant building in 1927. Located in the heart of downtown of Key West.

Depart the Florida Keys 

Breakfast at Matt’s Stock Island Kitchen

Perfect spot to enjoy breakfast since it is located at The Perry Hotel Key West. Matt’s serves “American coastal comfort food” with innovative twists — such as iced cold seafood presented in a fisherman’s tackle box. Matt’s even won Open Table’s 2018 Diners’ Choice Award for best ambiance! 

Check out of hotel

Depart the Florida Keys

And that’s that! I hope you enjoy your visit to the keys as much as we did! Please let me know in the comments if you do visit any of the locations mentioned or if you have a favorite spot that I left out, I’d love to hear! Thanks so much for stopping by!

Thanks to the Florida Keys for hosting us during our stay. As always, thoughts and opinions expressed here are entirely my own.

3 thoughts on “5 Days in the Florida Keys

  1. Now you make me wanna go go Florida Mariana! So sad that I love so far away! But wow! All the photos are amazing and thanks for all the details!


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