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After a whirlwind summer of traveling, I decided top it all off with- you guessed it: more travel! Jackie and I spent 5 of our final days of summer soaking up in the sun in The Florida Keys. It being her first time and my second, I knew there was plenty of ground to cover - especially with barely a week to make our way from the Upper Keys to Key West and then back again to Miami to fly out. 

On the motoring front, we enlisted the help of Madza's new CX-5 Signature to get us where we were going in style. I personally loved how spacious it was. Plenty of storage for our suitcases and accessories like it was nothing. And of course it didn't hurt that the bright red exterior made sure we stood out wherever we were...
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 Day 1: 
Our adventure began! We landed in Miami at 10am on Sunday, picked up our ride and embarked on the road to our first stop, Key Largo. About an hour south of Miami International, Key Largo is the beginning of the upper keys. You arrive to find the first of many Key Lime Pie shops, iconic destinations like the African Queen and incredible natural beauty like John Pennekamp Coral Reef State Park. 

One of my personal Key Largo favorites is a little slice of heaven nestled in a botanical garden off of Overseas Highway. Driving by, you can miss it easy. But if you catch it just in time you're in for a real treat: the gorgeous Kona Kai. We stayed here last year on our first Florida Keys trip and of course I instantly fell in love with the waterfront 13-villa resort. I *had* to go back. It's one of those spots where you could spend your whole vacation, soaking up the sun doing absolutely nothing. It's quiet, has water activities if you want to get your heart racing and a plenty of spots to rest your eyes under the shade of a palm tree. 
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After working up an appetite unpacking, we decided Sunday Brunch would be best spent at Marker88 with a Bloody Mary to get things started on the right foot. I opted for Cracked Conch and a blackened Mahi Sandwich. Hit. The. Spot. Jackie went full brunch with Lobster Benedict.
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Next, we made our way over to the Florida Keys Brewing Company for a tour and to try 19 of the beers they had on tap. The husband and wife duo make an excellent team, he being behind the scenes brewing the delicious recipes and she, creating the gorgeous artwork and inspiring aesthetic. The bright rainbow exterior and interior is clearly after my own heart. Each little nook and cranny is designed to a T. If you love beer and color, pop in for a pint or few. I personally love the Mango-Jalapeno.
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Finally to wind down our first day we dined beachside and watched the sun go down at the Tides Beachside Bar. (Order the conch fritters and key lime pie.)
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Day 2:
After waking up in paradise, we moseyed over to the Key Largo Conch House for an early lunch. Don't let the tiny interior fool you, this local spot is a treasure and if you don't order the Mahi Tacos you're sorely missing out. 
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Next! An adventure at John Pennekamp Coral Reef Park. With the initial intention of snorkeling, we had to cancel because of the sea conditions - but don't let that stop you from heading over - there's plenty to do and see wandering through the park. You might spot some sea life from your dry spot on land. 
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After spending some time sightseeing at the park, we departed and stopped by a tiny little fruit stand off Overseas Highway for some fresh fruit & plantain chips before heading back to Kona Kai to sit poolside until dinner. We popped open a bottle of Risata Wines Pink Moscato and tapped into our own personal self-care routine. Let's be honest for a moment, it's a real feat getting a few quiet moments to ourselves with a couple of glasses of wine on the beach. Smooth, sweet and just right for our tropical destination. Calgon, er, Risata, take me awayyy... 
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A full day spent relaxed pool and beachside, we headed to dinner. 

The Hungry Tarpon was easily my favorite meal in the Upper Keys. Per ordering each one of our waiter's recommendations, our meal was incredible. The Thai Fish Fingers were probably my favorite of the bunch but don't stop your ordering there. You have to get the Hogfish Sandwich, Peel and Eat Shrimp, and Ahi Tuna Tacos. Do yourself a favor and start off with a  Blueberry Mojito or Pina Colada to set the mood, then finish with Mango Key Lime Pie. That is a MEAL. 
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Day 3:
We said goodbye to our friends at Kona Kai and made our way down to the lower keys.

The Upper Keys: Where To Stay, What To Do and Eat:

Key Largo

Best Time To Stay: Year-round. But I loved August and September stays here. 

Must Order: Mahi Tacos

Best Time: Mornings 

Tavernier

Must Order: Lobster Roll

Islamorada

Must Order: Cracked Conch and Mahi Sandwich

Must Order: Jala-Mango 

Must Order: Conch Fritters and Key Lime Pie

Must Order: Thai Fish Fingers, Peel and Eat Shrimp,  Hogfish Sandwich and Mango Key Lime Pie

Day 3 (continued):
The nearly two-hour trek to Key West included a few stops along the way. We popped into the incredibly gorgeous Islabella Resort in Marathon for coffee and took a few snaps of the gorgeous grounds. It's officially on my must-stay places in The Florida Keys.
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Before reaching our destination, we stopped off for lunch at Mangrove Mama's on Summerland Key. I inhaled the Black and Blue Mahi Wrap (it was insanely good) before getting back on the road to our destination: The Perry Hotel on Stock Island.
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A quick hop, skip and a jump later, we arrived at The Perry Hotel to check in. The 100-room boutique hotel packs a stylish and festive punch nestled on a marina in the middle of Stock Island. I loved everything from the decor to perfectly placed waterfront room. The unique spot right off the beaten path to Key West, is about 20 minutes from door to the heart of Key West, which isn't too shabby. (NOTE: Parking is $4 an hour in Key West and an UBER from the hotel to Key West is about $17 each way)
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After getting unpacked and settled, we hopped back into the car and headed to Key West for Fury's Commotion on The Ocean Live Music Sunset Cruise. The two-hour music-filled boat ride around the island is the perfect way to watch the sun go down: while nibbling on conch fritters and sipping on margaritas. Don't forget your camera because you're not going to want to miss a single moment from boarding to docking, and everything in between. We got lucky and spotted dolphins feeding, which of course, made my night...
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After the cruise we wandered over to Azur Restaurant for Steamed Mussels, Pulpo, Clams and Chorizo and a Goat Cheese Salad before heading back to our hotel and calling it a night. 
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Day 4: 
Up and at em! We kicked off our full day in Key West with parasailing with Fury Watersports at 9am. Flying high in the sky we spotted a school of what seemed like giant jellyfish from the sky. Who really knows how big they were. I'll just say I'm grateful we didn't land on top of them... 
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After drying off we grabbed some coffee and hopped aboard The Conch Train Tour for a peek inside of Key West's unique history and historic landmarks. (note: you get a complimentary admission to the Hemingway Rum Company Papa's Pilar Distillery with your ticket, which also includes a tasting of the infamous Key West rum. Mmm...)
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After the tour ended we hopped right onto the Old Town Trolley Tours. Sure it's the same company but it's a little longer and each tour guide has something unique to offer during each tour. A good tour guide can make or break your experience! 
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We departed for Bahama Village to have lunch at The Blue Macaw. A couple of rum runners and a blackened fish sandwich later, we wandered over to Hemingway's Home for a tour. How fitting.
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We wandered the grounds, pet the cats and took a few (hundred) snaps before the 90 degree weather got the best of us and we decided it was time for a dip in the pool at The Perry Hotel before dinner at Matt's Stock Island- which was probably the most convenient dinner location of our trip being that it was located in our hotel. Aside from being conveniently located, it was absolutely delightful.
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From the Commodore Tower for Two including lobster tails, ceviche, oysters, shrimp and ahi tartare to the Jalapeño Pineapple Mojito, we also savored each bite of the Crispy Pink Shrimp, Black Grouper with cornbread gnudi and crawfish thyme butter- as well as the Baked Yukon Potato with their take on cheese wiz, chives and bacon onion jam! 
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After dinner, we hustled back down to Front Street in Key West for The Ghosts and Gravestones Tour. If you're into ghost tales and haunts, this is the trip for you. Along the spooky tour we set our sights on all the haunted homes of Key West and some of their most bone-chilling stories, before coming face to face to Robert The Doll. You better believe I double checked over my shoulder for each shadow I came in contact with after... CREEPED. OUT.
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*One of the haunted sites from the tour in daylight*.

Day 5:
The final day of our trip was bittersweet. We had half a day to kill before heading to Miami to fly back to New York. So you better believe we covered the most ground before heading out.
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After packing and checking out, we headed back down to the heart of Key West for breakfast at Fisherman's Cafe. And holy moly it did not disappoint. I'm acutally mad at myself for not knowing it was there when we were staying nearby at The Marker Hotel last year because we could have eaten here every.single.day. But, I know now and it will always be a stop worth taking. It would be crime to walk past without ordering the El Cubano breakfast sandwich, yuca fries, plantains and iced cafe con leche. 
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The Lower Keys: Where To Stay, What To Do and Eat: 

Marathon


Summerland Key

Must Order: Black and Blue Mahi Wrap

Stock Island 

Best Time To Stay: Year Around

Must Order: Pineapple Jalapeño Mojito, The Commodore Platter for Two, Yukon Baked Potato, and Black Grouper
Must Order: All Things Hogfish

Key West 

Best Time: Morning

Best Time: 9pm

Best Time: Weekday Sunset

Best Time: Morning

Best Time: Morning
Best Time: Late Morning, Early Afternoon

Must Order: Cuban sandwich. Home of the original cuban sandwich and said to be the best in the Florida Keys.

Must Order: the Steamed Mussels, Pulpo, Clams and Chorizo.

Must Order: the Rum Runner or treat yourself to the build your own Bloody Mary bar!
Must Order: The El Cubano Breakfast Sandwich, Yuca Fries and Plantains.

So, are you ready to book your Florida Keys trip yet?

This post is sponsored by the Florida Keys. All opinions are my own. 

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