5 Day Guide to the Florida Keys

5 Day Guide to 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 …

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Best Places To Stay In The Florida Keys

If there’s one thing I learned during our trip to the Keys, it’s that the place makes the experience- the right hotel and/or resort can be the difference between relaxation and stress. When we extended our trip an additional day and moved hotels for our final night, well, it just didn’t hold up compared to the first two resorts. It’s not that it was a dump or anything, it just didn’t match what was really working for us. Luckily for you, regardless of your reason for visiting, the Florida Keys has plenty of options to match your experience with your expectations along the entire stretch of 42 bridges. For our part, we got a little of everything with each stop and I highly recommend you plan your trip around these sweet spots in The Florida Keys. To simplify things, I think it makes it easier if you break up your stay into the Upper Keys and Key West. In the upper keys, you have a chance relax and spread out in a secluded bungalow you can find in Key Largo and Islamorada. Whereas Key West is dense and happening; and because of the history can be culturally enriching and educational. There’s really a lot going on! The Upper Keys: Kona Kai Resort & Botanical Gardens Whether you’re in need of a couple’s retreat or just some peace and quiet, this is the place for you. Truth: I see myself going back to Kona Kai (at the very least) annually for some good old fashioned R&R. Tucked away in a lush botanical garden the beautifully manicured property caters to an adults only crowd (16yrs+). The only ambient noise you’ll be hearing in this little slice of heaven is the birds, if that. Which up until now, I didn’t realize I desperately needed. Don’t get me wrong, I love my brood of boys. But a few days of peace and quiet, while they vacationed with their grandparents, was exactly what the doctor ordered after a long summer of constant entertaining. The staff is incredibly accommodating and even has a resident mascot (cutest pup ever), Mr. Cinnamon. The beach-inspired decorated rooms are huge, clean and welcoming; each named after a tropical fruit. Our room, Breadfruit, came with a giant walk-in closet, full kitchen, dining table and couch. I didn’t love having to pack everything back up on our last day because, let’s be honest, a city girl could get used to all this space. Wake up in the coziest of beds to palm trees & bright blue skies and twinkling green waters peaking in from the blinds. Sip your coffee and work up an appetite for the complimentary breakfast in the main area. Enjoy fresh fruit *cut right from the resort’s own trees (!), yogurt, pastries and oatmeal while you plan out your day. Kona Kai is one of those places you don’t have to leave during your stay if you don’t want to. It has a lot to offer. The waterfront, temperature controlled pool comes equipped with a poolside cooler with fresh cut fruit and chilled bottle water, stocked throughout the day. Take a dip and soak up the sun before trying your hand at Paddleboarding straight from the private little beach. They also have kayaks and a paddleboat available from sunrise to about sunset. It’s all first-come first-serve, but there was always something available when the mood struck. Catch the most breathtaking instagram-ready sunsets straight from the dock; swing in the hammocks and lounge chairs while you make friends with one of the large iguanas roaming the property. Noteworthy On-Site Amenities include: Paddleboarding, Paddleboating, & Kayaking. Botanical Garden, Art Gallery, Pool & Jacuzzi. Free Wifi. On-site grilling (the grills were SPOTLESS, btw- incredible!). Key West: The Marker Resort Located smack dab in the middle of the Historic Seaport of Key West, The Marker offers more than just gorgeous views and the convenience of being in the middle of it all. The luxurious family-friendly waterfront resort has three pools, a pool-side restaurant and bar, state of the art fitness center and concierge to help plan your adventure in Historic Key West. The rooms were large and bright. Ours came with a phenomenal view of the seaport from our porch. The bathroom came with a separate shower and jacuzzi tub (with bath bombs for optimal relaxation at the end of the day). The staff was incredibly friendly and accommodating to families. Our valet, Ivan, was incredible and took care of everything, from bringing us our car, to luggage and little things here and there. He even let the kids bend his ear with their constant talking. While I noticed that the first two pools located to near the Bar and Restaurant was semi-opened to the public, everyone was extremely considerate to those around them. There is an additional adults-only pool on the other side of the resort that I highly recommend if you’re looking for a moment of seclusion. Furthermore, all of our water excursions, including sunset cruises, parasailing and so much more, were just steps away. If you’re looking for a spot in Key West that offers luxury and convenience in the heart of it all, I highly recommend The Marker Resort. I loved every second of our stay; you won’t be disappointed. I was a guest of The Florida Keys Tourism Board. All opinions are my own.

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Key West Itinerary – wherever.someday

This Key West Itinerary will ensure you get the most out of your long weekend in Key West. These are all the details for an unforgettable trip to Key West!

Beachfront Florida Keys Resort | Tranquility Bay Beachfront Resort

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!HOW TO GET THERE?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.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)-451-3722This 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 102601 Overseas Highway Key Largo, FL 33037 305-451-6300Next 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. 
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DCIM105GOPROG0416132.JPGSadly, 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 Resort97802 Overseas Highway Key Largo, FL 33037 (305)-852-7200You 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 Inn84001 Overseas Hwy Islamorada, FL 33036 (305)-664-5300We 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
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 House100211 Overseas Highway Key Largo, FL 33037 (305)-453-4844Key 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)-664-8070Robbie’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 Café81600 Overseas Highway Islamorada, FL 33037 (305)-664-3225We 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 West7001 Shrimp Road Drive Key West, FL 33040 (305)-296-1717A 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)-296-2088The 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 Museum907 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)-296-7701Me 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!Ultimate Adventure with Fury Water Adventures631 Greene St. Key West FL 33040Fury 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.
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C:DCIM105GOPROGOPR6206.GPRSunset Celebration at Mallory SquareSunset 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 305-922-2616Head 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 nightlifeThe night is young! Make the most of your time and enjoy the fun Key West night atmosphere.Breakfast at Bistro 245245 Front St. Key West, FL 33040 (305)-294-4000Enjoy 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 Train303 Front St, Key West, FL 33040 (305) 294-5161I 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 Tours231 Margaret St, Key West, FL 33040 (305)-294-7245This 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 205 Elizabeth St. Key West, FL 33040 (800)-507-9955This 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 & BreweryEnjoy 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.Breakfast at Matt’s Stock Island KitchenPerfect 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 hotelDepart the Florida KeysAnd 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.Florida Keys, Florida, USALike this:Like Loading…