The Best Travel Itinerary in Florida Keys – How to Discover Paradise in 5 Days #SeizetheKeys

By Kach Umandap February 19th, 2016 Posted in Travel Blog, Travel Guides 19 Comments

The Florida Keys – I had heard the name floating around in conversations, in movies and in references to where people like ‘to summer’, but I had never heard much about it in any kind of detail. To be perfectly honest it was a place I knew very little about and hadn’t thought of all that much. I went with no pre-conceptions or expectations, as much of a blank slate as I could manage, yet for some reason my brain conjured up pictures of little chunks of the South Florida stereotype strewn across a tiny series of islands; villas, resort hotels, snowbirds on beach chairs sipping cocktails with miniature umbrellas in them, and golf courses everywhere. That image could not have been more wrong!

(For the record we recently learned that there’s also a lot more to mainland Florida than those things, but that’s a whole other bunch of stories!)

I’m actually very glad the image in my head of the Florida Keys was so ridiculously far off, as it made what we did find there all the more amazing.

This realisation dawned on me as I stepped off the tiny propeller plane from Fort Lauderdale and onto the tarmac at Key West International Airport. One small building stood at the edge of the runway, a sign over the doorway which read, ‘Welcome to the Conch Republic.’ In 1982, Key West mayor Dennis Wardlow declared independence from the USA in protest of roadblocks and random searches of vehicles returning to the mainland – just one of many wonderful eccentricities of the Florida Keys!

Here is how we spent 5 days discovering the Florida Keys:

Day 1 – Arriving in the Florida Keys – Key West

Kach had been delayed by the winter snow storm in Philadelphia and New York, so I arrived in Key West alone at around 8 o’clock at night. I collected my bag from the tiny luggage belt in the single room arrivals hall and headed to our home for the next three nights, Ibis Bay Resort, a collection of coral stone beachside bungalows on the shores of a serene bay, lined with mangroves.

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We had our first taste of the Florida Keys that night, with a seafood dinner in The Stoned Crab.

Day 2 – Blue Heaven – The Hemingway Home – Jet Skiing – Stoned Crab Seafood Dinner

Waking up as the sun rose, I walked outside from the beachside bungalow to the beach, to see where I had arrived in daylight for the first time. The beach cottage was only meters from the water’s edge, in a tranquil, reflective bay surrounded by mangroves and circled menacingly overhead by watchful ospreys taking advantage of the still waters for their morning hunt.

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Breakfast at Blue Heaven

First call of the day was breakfast at a Key West historic icon, Blue Heaven. This century-old timber building has played host to cock fights, gambling and most famously, boxing matches refereed by the local legend himself, Ernest Hemmingway. The Blue Heaven garden restaurant is where I felt the first hints of the Caribbean nature of Key West, with its natural warmth, laid back vibes and weathered personality. The breakfast menu takes classic morning food from around the world and combines it with the island’s staples of fresh seafood and key limes to create unique island style dishes, including Shrimp and Grits, Blue Heaven Benedicts – a special version of the classic eggs benedict, topped with Key Lime Hollandaise and a choice of lobster or Key West Shrimp.

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This meal also marked the beginning of our quest for the best Key Lime Pie in the Florida Keys!

The Key Lime Pie is a dessert pie which originates somewhere in the Florida Keys, the exact location of which is still disputed between Key West and the Upper Keys. The Key Lime Pie comes in two forms, a simple, creamy, tart type and a more flamboyant peaked meringue topping.  The Blue Heaven Key Lime Pie was one of the latter and was going to be hard to beat!

Ernest Hemmingway Home

Key West is well-known, past and present, for being home to all manner of free-living, free-thinking, free-spirited and gloriously eccentric characters, the most famous of which is probably literary legend Ernest Hemingway, who lived in Key West for more than 10 years in his home on Whitehead Street, which he shared with his second wife, Pauline. The beautifully restored and preserved timber home is now maintained as a museum, where local guides recount colourful stories of Hemingway, his lives and his many wives, both on and off the island, including the hilarious tale of the swimming pool and the penny cemented into the patio floor. All of the guides were true Hemingway fans and each had their own styles and special insights into the life of the man which made their guided tours unique and interesting. One of the most interesting parts of the tour was peering through the wrought iron gate into Ernest Hemingway’s writing room, where he crafted his most successful works.

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Wandering the Streets of Key West

Key West is one of those towns where you don’t need to be doing anything in particular, it’s possible to simply enjoy being there. The characterful, weathered timber buildings, interspersed with old art deco theatres and cinemas, the palm-lined streets and the people in them.

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I spent an hour or so just walking up and down the streets, weaving my way gradually towards the Key West Historic Sea Port, where small sail boats and private yachts are moored amongst giant wooden tall ships and classic schooners. Walking back down the pier, I spotted a dark shadow in the water, and as I kneeled down to try to see what it was, it started rising toward the surface, until finally a small, round, brown nose and two tiny eyes poked out of the water. The lone manatee took a small but noisy breath of air before sinking back down to the bottom the sea floor again.

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Jet Skiing around Key West Island

Jet skiing was something I had done several times in the past and was dying to try again was jet skiing. With our VIP pass from Key West Attractions, we could take a two-hour wave runner tour with Barefoot Billy’s water sports. This tour was amazing and was nothing like the go-slow and follow the leader tours I’ve tried in the past. The two guides allowed everyone in the group to go as fast or slow as they were comfortable with, so anyone with a heavy throttle could let loose and enjoy! We stopped at a few places around the island for some facts and history about the island, in between racing at high speed across the waves, sometimes flying the air on the wake of passing boats. About half way through the trip we stopped for some ‘free-play time’, which basically involved riding as fast as we wanted within one big area to get the need for speed out of our systems. Definitely the best way to get a wider perspective of the island whilst getting a big adrenaline at the same time!

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Night Kayak Tour

Something I think we were all looking forward to was the Night Kayaking Tour with Ibis Paddle Sports. Their clear bottomed kayaks and SUP boards are all equipped with underwater LED lights to get a unique look at life in the shallow waters in the darkness of night. Unfortunately, the strong winds and cold air from the snowstorm in the north of the US meant this wasn’t really going to happen, but it’s something we’ll definitely try next time. As we would discover over the course of the week, the Florida Keys give you plenty of alternative options when the weather doesn’t go your way!

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Dinner at The Stoned Crab

The Stoned Crab is part of Ibis Bay Resort, their signature seafood restaurant, which doesn’t just serve up fresh Key West seafood, they catch it daily in their own two fishing boats, so it’s literally the freshest on the island! As well as lobster, shrimps, crab, a range of locally caught fish and other shellfish, they specialise in the seasonal Florida delicacy – Stone Crab claws. Stone Crab is a local catch famous for its massive, succulent, meaty claws, but it’s also one of the most sustainable seafood available, as it’s actually a renewable resource! Stone Crabs don’t just reproduce, they regenerate, so when they are caught, a single claw is removed, then the whole living crab is thrown back in with one claw intact to feed, fight and whatever else it needs it for. It then has an entire year to grow a new one! This is really not that traumatic to the crab, as fish and shellfish do not have the same kind of nervous system we have, so they don’t feel pain. In fact the Stone Crab is designed this way as its claws are easily detachable as a means of escape from tight spaces and underwater crab battles.

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Our dinner in the Stoned Crab started with a speciality of theirs, the three tiered hot seafood tower – two trays filled with a selection of almost every type of seafood on the menu! It’s a great way to eat when you’re with a group of people. We ended the meal with another Key Lime Pie, this time the humble tart version rather than the extravagant meringue we’d had earlier. Without the meringue topping, the lime favour has more chance to stand out, but so far I hadn’t been able to pick a favourite.

Ghost Hunt Tour of Key West

The unusually cold weather had put a stop to our night kayaking, but Key West always seems to have plenty else to keep you entertained. Our final activity on our first day in Key West was a real life ghost hunt with local David Sloan’s Key West Ghost Hunt, a 90-minute walk through the Old Town, searching for ghosts and famous local spirits who are known to haunt the island. From haunted houses, graveyards, spooky dolls, our entertaining guide kept us involved with a tools of the trade including ghost diving rods, temperature sensors and a ghost detecting dolls with creepy light up eyes. The guide’s story telling skills kept us all entertained, if not completely convinced, but even for the non-believers, the local stories of massacred tribes, piracy, murder, mystery and scandal made it worthwhile. The tour ended in a haunted art gallery and theatre, with resident ghosts making contact through the static of a wireless radio!

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Day 3 – Seaplanes and Starlight Dinner

Kach had arrived late the previous night, so we woke early to take some photos together in the hammocks and the picturesque floating platform right outside of our beach bungalow, then joined the others for a seafood breakfast next to the pool in the Stoned Crab!

From here, we jumped in a big yellow school bus to the local airport to catch our seaplane to Dry Tortugas.

Seaplane to Dry Tortugas

We were really excited about this one, our first seaplane flight! There’s something about a small propeller plane which sparks feelings of adventure, walking across the tarmac to the plane standing there, with its pontoons beneath it, waiting to be dipped in the water. We climbed into the narrow metal tube, with two rows of seats and put on the large earphones, partly to dampen the noise of the engines and to hear the pilot pointing out islands and shipwrecks along the way.

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The plane flew low to the clear, blue water, just low enough to the spot the peaks of small waves and to see the outlines of shipwrecks and sea life, like sea turtles, swimming through the water. After about an hour, we circled low over Garden Key, home to Fort Jefferson, a huge hexagonal fortress built in the 1800’s and one of the largest brick-built structures anywhere in the western world.  When we stepped off the plane directly onto the beach we started exploring the fort, which is open to roam around all the different levels, including the walkway around the top, giving amazing views across the neighbouring Bush Key, which is home to nesting and migrating birds, turtles and tropical fish. There’s some great snorkelling around the island amongst perimeter of the fort and between the rusted supports left over from the old docks. The fort is a great place for taking photos, through the ragged-edged brick windows looking out onto the blue sea outside. On our flight back to Key West, we flew over the private island where we would have dinner in just a couple of hours’ time.

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Sunset celebration in Mallory Square

On our way to a seriously special dinner, we stopped at Mallory Key for a Key West sunset tradition which has been going on informally since the mid 1960’s, then run formed as a non-profit organisation in 1984. Every day of the year, 2 hours before sunset, locals and tourists gather on the west facing pier for the best sunset view on the island, while street artists, acrobats, musicians and performers put on shows for the crowds.

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Dinner at Latitudes on Sunset Key

Probably the most exclusive restaurant in Key West, but it’s not actually on Key West! To get to Latitudes, we had to take a private launch across to Sunset Key, part of the Sunset Key Cottages resort. As the boat neared the island, we could see palm trees wrapped in bright white lights and white-clothed tables overlooking the water.

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Despite being one of the best-respected (and proportionately expensive) restaurants in the Florida Keys, the ambiance is relaxed, friendly and warm, so you can get dressed up if you like or just enjoy your meal in Florida Keys uniform – shorts and flip flops!

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We all shared a selection of starters, then and I had a main dish of tender, succulent Wagyu steak, which has raised the bar for how I look at steak forever! Kach stayed true to the Keys style and ordered a mixed seafood risotto! Desert levelled up the search for the best Key Lime Pie, with another meringue topped classic not quite as flamboyant as the first, but with the same strength of lime as the second, like a perfect middle ground between the two!

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Day 4 – Turtle Hospital and Biking the Old 7-Mile Bridge

Tour of the Turtle Hospital

It was time for a location change today, so after another Stoned Crab breakfast we hit the road north towards Marathon, a city spread across Knight’s Key, Boot Key, Key Vaca, Fat Deer Key, Long Point Key, Crawl Key and Grassy Key. Originally a motel with the largest saltwater swimming pool in the Keys, the owner’s daughter once asked him why there were no turtles in the pool. This innocent question is what prompted the change to motel to Turtle Hospital back in 1986.

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The centre rescues, treats, rehabilitates and releases loggerhead, green, hawksbill and Kemp’s ridley turtles. They also provide permanent residence to those turtles too badly injured to survive in the wild. One of the most endearing features of the program is that each turtle has a name written on its back, given by the person who found them, often children! The patients of the hospital are often victims of injuries by boat propellers, fishing nets and other ocean garbage, but some have been attacked by sharks, losing bite-sized chunks of shell, or even entire flippers. Other common ailments include Bubble-butt syndrome (yes it’s a real thing!), where micro air pockets form on a healing shell wound, and chronic intestinal gas, both of which stop the turtle from diving.

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Biking the Old Seven Mile Bridge

Our next activity and one I was really excited about was biking along the old seven-mile bridge, which began life as part of the overseas railway connecting the Florida Keys to the US Florida mainland. Now that the new parallel highway has replaced it, Old 7 has been closed to all traffic, save for a small 2-mile section of the original bridge, which  is maintained for bicycles, pedestrians and fishing.

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If you face away from the new bridge and put your fingers in your ears, there’s something very post-apocalyptic about standing on Old 7 – the cracked tarmac and the rusted guardrails made out of recycled railway tracks. The remaining open section of bridge is also the only last land access to Pigeon Key, where many of the workers building the old railway lived during construction. The weathered old bridge and the glimmering ocean all around make a fantastic setting for some truly unique photos too!

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Lunch at Sunset Grille & Raw Bar

After all the cycling we jumped back in the van and headed or lunch at the Sunset Grille and Raw Bar, a waterside restaurant with incredible views of the new 7-Mile Bridge. It was a laid back place a huge menu. We opted for the raw tuna salad and others bought a huge tray sushi and maki!

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When we were finished we headed for our accommodation for the next two nights, Ocean Pointe Suites, a fully furnished apartment hotel, with full kitchen, separate bedroom, two bathrooms, large open living room and a sea-view balcony. This seemed like the perfect option for larger groups or families who like to cook for themselves and have the extra independence of a full apartment.

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We were all still pretty full, but we all met up again for dinner at local restaurant, The Fish House, which is known locally for its fresh local seafood and chilled, fun atmosphere.

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Day 5 – Shark Feeding – Giant Tarpon – Local Brews – A Gastronomic Finale

Indoor diving and shark feeding experience

Our original plan had been to take a kayak tour of Indian Key, but the strange and unseasonal weather forced us to look indoors for a morning activity. Luckily there’s no shortage of stuff to do in the Keys and we switched a cold and windy kayak session for an indoor diving session with Florida Keys Aquarium Encounters. We pulled on wetsuits and climbed into the aquarium, home to over a dozen species of fish. After a short instruction course to learn how to use a breathing regulator, we submerged and started swimming around with the fish. For the first part of the encounter, we fed the fish from squeezy bottles and with fish pieces from our hands. After that we moved across to the shark feeding area, where the sharks are separated by a plexiglass wall, with small feeding slots to push fish through. The nurse sharks swim to the glass and grab the fish right out of your hands, without any risk of getting bitten! It was a pretty cool experience and can be done by anyone from kids to adults. Other attractions you can try include Stingray Encounter, Lagoon Encounter, Nurse Shark Encounter as well as some others.

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Feeding the Giant Tarpon

Our lunch stop was over on Islamorada, on Robbie’s Marina, where tarpon fish have learned to hang out round the marina to pick up fish scraps from the fishing boats coming in and out. The story goes that the fish started coming here around 18 years ago, when Robbie rescued an injured Tarpon fish with its jaw torn open, stitched it back together and rehabilitated it. Ever since then, more and more tarpon have been collecting in the area, growing to incredible sizes in the shallow, food rich waters of the marina.

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Feeding the giant tarpon at Robbies Marina is a really fun experience, dangling a whole fish into the water, until one of them jumps up out of nowhere at lightning speed and grabs the fish from your hand, or often with you hand. These fish have no teeth, so there’s no danger of being bitten or injured, but their jaws are very strong, so you can get a bit of a bruise as they clamp down on your hand! Belligerent, hungry pelicans hang out around you the whole time, trying to find a way in to your fish bucket!

Lunch at Robbie’s Marina

Robbies Marina on Islamorada has been voted the number 1 place in the keys that everyone should visit. It definitely has character, made up of a collection of ramshackle wooden and corrugated iron buildings, housing a restaurant, marina and a number of shops and stalls selling unique crafts and souvenirs, like picture frames made from old lobster pots.

The bar and restaurant are down by the side of the marina, so you can watch the weather and the boats coming in as you eat. They’re very well-known for putting ‘gourmet seafood in baskets’ and for having the best shrimp burrito you can find anywhere! We had the Fried Seafood Basket and the Shrimp Burrito, which both lived up to their reputation.

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Tour of the Florida Keys Brewing Co.

After a quick stop at the hotel to get changed, we headed out to visit the only Florida Keys craft brewery which actually brews its beer in the Florida Keys! Florida Keys Brewing Company, located on Islamorada is the joint project of Canadian refugee Craig and his local ‘island girl’ wife Cheryl. Together they have been brewing great beers since 2012 and are about to expand their operation to meet the huge local thirst for decent artisanal beers! Everything about the brewery shouts ‘island life’, from the brightly painted signage, to Cheryl’s paintings on the walls to hilariously brilliant business ideas and partnerships, like Yoga and beer ‘detox-retox’ days, and girl scout cookies and beer deals. The beer is amazing, but but it’s the creativity and personality of the people behind the beer that make this place special! We tried a full wheel of sample beers, everything from IPA’s and wheat beers, to chocolate or chili ales! If you’re into your beers, you need to visit this place, and if you’re not, go anyway, because this is a brewery that anyone can enjoy.

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Dinner at Marker 88

It was our final Florida Keys dinner that night, so it had to be something pretty special. We were taken to Marker 88 in Islamorada, a keys favourite which was opened by owner and chef, Bobby Stoky, back in 1967. It’s usually famous for beachside dining on one of the Florida Keys’ only completely natural beaches, but the weather had come in, so we all sat around a big round table in a private dining room.

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The story behind the restaurant comes from Bobby’s childhood days when he would go out fishing with his brother, then come to the very same place to sell their fish to the restaurant owners, eventually evolving into them deciding to prepare and sell their catch themselves! Bobby now also has four other restaurants in the Upper Keys. Before we ate each course, Bobby put on a cooking demonstration of each dish, so we could see the fresh ingredients that go into each plate. The first dish was Bobby’s homemade crab cakes, which he pan fried on a small hot plate, served alongside a walnut, strawberry and mixed leaf salad, showing just how simple good food can be in the right hands.

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Next was an encrusted yellowtail snapper, a locally caught fish, seasoned with a mix of various colours of rock salt and peppers, plus his special blackening spice mix. We ended with a mixed dessert plate, including our final Key Lime Pie, a return to the peaked meringue!

Day 6 – A Mrs. Mac’s Breakfast – the African Queen – Key Largo Chocolates

Breakfast at Mrs. Mac’s Kitchen – An Iconic roadside diner

Our final eating experience in the Florida Keys, an American diner breakfast, Keys style, which we’ve learned means taking breakfast classics from around the world and adding fresh local seafood! One of the things Mrs. Mac’s is most famous for is being decorated almost entirely with number plates, from the rustic wooden sign outside to the interior walls and even the lampshades – all made out of license plates!

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Visit the African Queen

A small boat with a big history – The African Queen was built in 1912 and has had a rich and varied life, having been used for the East Africa Railway, in the Congo to transport mercenary fights and much later starring in the movie she was re-named after. Someone found the boat in bad shape in Cairo in the 1970’s, then shipped it back to the USA, where it has been restored. She now has a nice quiet life taking curious tourists out on little pleasure rides around Key Largo!

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Visit Key Largo Chocolates

Our very last stop before driving to the airport was at Key Largo Chocolates, a small, family-owned chocolate factory specialising in handmade speciality chocolates like truffles, chocolate roses and even Frozen Key Lime Pie on a stick!

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We watched how the chocolates were made, from raw chocolate to finished, decorated product. It was amazing to see just how scientific and precise the process of making chocolate really is.

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Final thoughts on the Florida Keys

Visiting the Florida Keys is like stepping into another world, where people from all walks of life, countries, cultures and the outer fringes of society have come together to live life the way they want to live it, with one common goal, to enjoy life, be happy and most importantly, chill! It seems that people from the Keys, or who have moved here, find that they can achieve anything they can picture, any idea that springs into their mind, and turn it into a success. It that inspires creativity, individuality, and energy, where anything can happen and probably already has!

Accommodation and Hotels in the Florida Keys

The Florida Keys has some of the most unique and relaxing luxury hotel accommodation in the world, with unbeatable beachside views and true Caribbean vibes!

Find the best luxury hotel deals in the Florida Keys on Expedia

Compare the cheapest rates for Florida Keys Hotels online, here (for FREE).

You can also read reviews from real customers here.

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Note: This trip wouldn’t have been possible without the help and support of the official tourism office of Florida Keys, who arranged the whole trip and coordinated with private companies for our sponsored hotel stays and tours. Thank you!

Thank you to everyone we met along the way who all helped to make this such a special experience. It was an incredible visit to the Florida Keys and we will never forget it!

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19 thoughts on “The Best Travel Itinerary in Florida Keys – How to Discover Paradise in 5 Days #SeizetheKeys

  1. Loved reading about my favorite home-key west. Still haven’t tried blue heaven- but will next trip. Latitudes was awesome and the ghost hunt was fun! . Enjoyed this

    1. Hi there Dorothy, we really enjoyed everything in Florida Keys! we wish to go back soon. Haha. Hope you’ll be able to stay at Blue Heaven, we really had a great time there and I’m sure you’ll have too! Happy travels 🙂

  2. Would love to do night kayak or SUP tour. Those Key West houses look really nice. I would love to live in a bright pink house. 

  3. I’ve only been to Miami in Florida, but Key West looks gorgeous. You have some beautiful photos here, but honestly, you had me at Hemingway’s house. I would go just to see that. And the manatees and turtles are an added bonus.

  4. Amazing pictures!! Good compilation of details about Florida trip. All seems worth visiting. Thanks for sharing your Experience.

  5. I loved this article! I’ve been in Key West (and in Hemingway’s house) and it’s one of my favourite places in the US. This will go on my Twitter 😉

  6. The way you have explained the Keys, it just livens the place up. It’s as if I went there myself. Great job. I am bookmarking this itinerary if I ever visit – Someday, I hope.
    The night kayak looks so amazing and the picture came out so well – Which camera did you use ? Did you add any effects/photoshop ?

  7. we’re surprised we haven’t heard more about this place!! the sights, food and activities look amazing!! we’ll need to look into it a bit more!

  8. Oh wow, what a comprehensive guide and itinerary for spending a few days in the Florida Keys! I’d love to go here one day. When I last visited Miami I was going to go down on a day trip but now I’m kind of glad I didn’t. There’s obviously so much to do that a day would probably have been pretty pointless. The night kayaking and SUPing sounds pretty awesome and it would be right up my street.. Hopefully you get to try it out on your next visit! And right now I’m craving some Key Lime Pie thanks to this post, I’m not sure I’ll find any of that in Yorkshire but a girl can dream! 😀

  9. Everyone I’ve talked to that has gone to the Keys have loved it! I haven’t made my way down there since it’s a bit of a trek (even living in Florida), but I think one of these days I’ll have to take a long weekend and make the trip!

  10. The night kayak tour looks so awesome! I live in south Florida and next time I go to the keys I’m going to do that!

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Written by Kach Umandap

Founder of Two Monkeys Travel Group. Since 2013, Kach has visited all the 7 continents (including Antarctica) and 151 countries using her Philippines Passport. In 2016, she bought a sailboat and went on sailing adventures with her two cats - Captain Ahab & Little Zissou in the Caribbean for 2 years. She now lives in Herceg Novi, Montenegro where she's enjoying her expat life and living on a gorgeous Stonehouse. She writes about her experiences traveling as a Filipina traveler with a PHL Passport. Also tips on backpacking trips, luxury hotel experiences, product reviews, sailing & adventure travel.