How to Spend A Long Weekend in the Florida Keys

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Whether you’re taking a quick trip down from Miami, flying in for a short getaway, or visiting with plans to make your way through the rest of the Keys; Key West is the perfect launching point for a road trip through the Florida Keys.

Personally, I played out scenario 3, with a twist.

I flew into Key West, spent a couple of nights in town, drove up the rest of the Keys, and then flew back out from Miami, over the course of five days. I found this to be the perfect blend of city, nature, and scenic driving, without having to back-pedal and see everything twice. And I mean–c’mon–who wouldn’t want to road trip across the Florida Keys?

So, when Enterprise Rent-A-Car asked me to participate in the #EnterpriseEverywhere campaign, I decided to condense my trip into a four-day-long-weekend-itinerary that’s easy for pretty much anyone to follow.


The campaign is about summer travel, focusing on local destinations and the passions that fuels summer travel. The Keys are an absolutely beautiful summery location, and you probably wouldn’t be able to explore them properly without having a car to get around, so I thought it would be the perfect destination for this campaign.

With more than 5,500 offices located within 15 miles of 90 percent of the U.S. population, Enterprise Rent-A-Car offers a wide variety of car leasing, vanpooling, car sharing and hourly rental programs – and local car rental customers are picked up at no extra cost. They call it “The Enterprise Way,” and it has been the foundation for the company’s growth and success for more than five decades.

Here’s how to do Key West & the Florida Keys right:


Day 1: Key West / Big Pine Key

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Afternoon: Upon arrival in Key West, pick up your car at the airport and head for lunch at Hog Fish Bar & Grill. This will be the perfect introduction into the Florida Keys culinary scene, including the freshest of the fresh caught Hog Fish, along with a medley of other seafood items and massive sandwiches. Start off on the right foot, with your very first slice of Key Lime pie (the second best in the Keys, in my opinion). For energy, of course.

Spend your first day wandering around Key West by foot. Explore the small cobbled streets, peer into the picketed yards housing numerous chickens, and shop among the colourful street stalls. If you’re looking to cover a bit more ground and see some more of the local attractions, like the southernmost point in the continental US, hop on the Conch Train for an informative hop-on-hop-off style tour.

Evening Option 1: Grab an early dinner at El Meson de Pepe (I recommend the Picadillo Habanero) and quickly run outside for the sunset celebration at Mallory Square. This quirky show was one of my favourite parts of Key West.

Evening Option 2: Take a drive through Key Deer country (adorable miniature deer) and hit the waters between Big Pine Key and No Name Key with Big Pine Kayak Adventures, for an incredible display by Mother Nature as the sun sets over the trees, to the sound of trickling water and calling birds. Skip over to No Name Pub for a casual dinner & a drink.


Day 2: Marathon / Pigeon Key

The end of Seven Mile Bridge.

Morning: Before hitting the road, grab a hot drink and a bite at the relaxing Blue Heaven outdoor patio. Do yourself a favour and order a slice of home-made banana bread with your meal, or indulge in banana pancakes. Or both.

Start driving east and enjoy your first taste of what is arguably one of the best scenic drives in all of North America. Seriously though–it doesn’t get much better than a bridged road way over turquoise blue waters for miles on end. Roll the windows down, breathe the salty air and take photo after photos of the sea and sky, right from the seat of your car.

Sign yourself up for a bike ride over the old Seven Mile Bridge with Overseas Outfitters, for a glimpse of picturesque Pigeon Key and all kinds of Keys wildlife. I spotted a large eagle on the railing, and even a shark in the water below.

Afternoon: After you’ve worked up an appetite, stop in for a famous Lobster Reuben at Keys Fisheries Restaurant, and fuel up for the rest of the day. Any of the fish dishes here are delish (and cause accidental rhyming, apparently), and can be enjoyed at a picnic table among the hustle and bustle of the working harbour in true Keys style.

Evening: Whether you’re staying as a guest, or not, I highly recommend a stop at Kona Kai Resort. You could check out the swinging hammocks and seaside lounging, but the real draw is the surprisingly fascinating botanic garden tour. Wander the grounds with passionate ethnobotanist Rick as he shows you more plants and fruits than you ever knew existed and sample them right on the spot. Chow down on star fruit, passion fruit and the incredibly mixed miracle fruit and key lime. This tour is well worth a stop.

Go for a casual dinner at the Fish House, where the atmosphere is family friendly and laidback. I urge you to try the Hog Fish Matecumbe (my favourite dish of the trip) and the coconut ice cream. I still dream about these flavours.


Day 3: Islamorada / Key Largo

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Morning: Make it an early morning and head out to the open waters for a little deep sea fishing adventure. Follow the close instruction of the Team Warrior Sport fishing crew and you’ll be reeling them in, in no time. Even if you don’t want to fish, let the rest of your group cast away as you relax on deck or in the cabin.

Afternoon: Part of the fishing trip includes taking your catch home, and luckily, the local restaurants have a BYOF (bring your own fish) policy in which you bring in your mornings catch and they fry them right up for you at a table with a view. The kitchen at Lazy Days Restaurant does an amazing coconut battered fish plate.

Spend some time in the afternoon visiting the Rain Barrel Artisan’s Village. It’s easy to lose track of time wandering around this series of shops and sculptures. There is just so much to look at this it’s almost overwhelming, but you will certainly be able to find something to buy here to take as a souvenir gift or to remember your trip. You can also meet the world’s largest lobster sculpture here.

Evening: Head to Sundowners Restaurant for what promises to be your best overall meal experience in the Florida Keys. The entire menu is great, but do yourself a favour and order what I personally deem to be the absolute best Key Lime pie in existence. End the night with a watermelon mojito and fiery sunset show on the waterside patio deck.


Day 4: Key Largo / Miami

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Morning: Make your last breakfast count at Mrs. Mac’s Kitchen. Pile up on greasy morning food to last the day, and why not go for one last breakfast pie?

Don’t forget about the sustainable side of travel and learn what you can do to give back during your travels. Head on over to the Coral Restoration Foundation to see how local corals are being farmed and protected, and take that info home to share with others.

Afternoon: Climb aboard the infamous “African Queen” (yes, from the movie), and chug down the scenic waterways of Key Largo to the clinks, clangs and steam screams of this charming little boat. Enjoy a history of the boat from the captain and get a different view of Key Largo.

Say your goodbyes and catch your last glimpses of the sparkling blue water as you leave the Keys behind and drive inland to Miami.


And there you have it, the perfect itinerary for a long weekend in the Florida Keys.

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I could probably come up with a dozen different Florida Keys itineraries based on varying styles of travellers, but I think this one hits all angles.

Feel free to follow along on my Tumblr blog, Instagram and Twitter during the month of August for a few more suggestions of cool activities in the different Keys (ex. a trip to Dry Tortugas National Park) and more info about the #EnterpriseEverywhere campaign.

Check out a Key West alternative day trip I made on Tumblr, here.


Twitter Chat

Additionally, come check out the upcoming Twitter chat that highlights the many passions of travel, on Wednesday August 20th at 7:00 pm EST. You can follow along with the hash tag below, or join us on Twitter to let us know why you travel.


Travel Giveaway



I haven’t forgotten about you lovely readers ;]

You’ll have a chance to win an awesome set of prizes from Enterprise, including the following items:

  • $75 AMEX Gift Card: Use this on your upcoming weekend away with Enterprise.
  • Sharper Image Telescoping Selfie Arm: Take awesome selfie photos or video on your upcoming weekend away with Enterprise, and share them on social media tagging @Enterprise and #EnterpriseEverywhere.
  • $50 Snapfish Gift Certificate: Turn the photos you take into souvenirs.
  • Enterprise Carry-Me Everywhere Duffle: Use on your upcoming weekend away with Enterprise.

To enter, simply follow @Enterprise on Twitter. Then comment on this blog post and share where you would go on a weekend away and what car type or class you would rent from Enterprise for the weekend. You can check out which classes are available on Enterprise’s website.

a Rafflecopter giveaway


Got that?

Follow Enterprise on Twitter & comment below. Win. Simple.

If I were planning a new weekend adventure, I think I’d go for a black Lincoln MKX, for some rugged trails up and down the Oregon coast.

Enterprise is committed to doing things the right way: taking care of its customers, employees and the communities it serves.

Sorry to my international friends, but prizes can only be shipped to US addresses. Contest will run until August 22nd, 2014.

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Don’t forget to follow along the upcoming Twitter chat for #EnterpriseEverywhere.
Wednesday August 20 @ 7pm EST.

This post is part of a branded campaign with Enterprise Rent-A-Car.
As always, all thoughts & opinions are my own.

Where you would go on a weekend away
and what kind of car would you rent?


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97 Responses to “How to Spend A Long Weekend in the Florida Keys”

  1. Mary Happymommy
    August 5, 2014 at 8:07 am #

    I plan to travel to Wilmington, NC on my next weekend trip and I would rent the intermediate SUV.

    • Seattle Dredge
      August 5, 2014 at 11:25 am #

      Ooh, I just Googled Wilmington, NC and it looks beautiful. That sounds like an awesome trip :]

      • Jess
        August 6, 2014 at 2:14 pm #

        Yes, you should visit Wilmington and Wrightsville Beach! Take a Ghost Tour, watch the surfers on the beach. If you’re lucky you could end up an Extra on a TV show or a movie location shoot.

  2. Theresa
    August 5, 2014 at 2:29 pm #

    I’d love to explore Texas! It would be cool to see Austin, Marfa, and the little towns in between. And since I’d be in Texas, I suppose I’d have to drive a pickup truck to get the full effect. 🙂
    Theresa recently posted..Why I’m Returning to Burning Man

    • Seattle Dredge
      August 5, 2014 at 5:54 pm #

      Haha, yeah a pick-up truck for sure! I’d love to see Texas too, I’ve never been there myself :]

  3. Samantha
    August 5, 2014 at 9:38 pm #

    I’d love to take a drive down to The Keys with my husband, we are only about 8 hours drive to the Keys, in Tampa so it would be a great long weekend drive. We stopped on a cruise there for a few hours and loved it but I would really love to take the drive down and stay a little longer, it really was a beautiful place, loved the houses around there, they had so much character and lots of stories. I’d love to get an SUV to stretch out and have a comfy ride.

    • Seattle Dredge
      August 6, 2014 at 7:50 am #

      Yes, you HAVE to go back for some more exploring! Especially since you live so close. It’d definitely be nice to stretch out in an SUV on that amazing highway :]

  4. Natalie
    August 6, 2014 at 7:20 am #

    I would love to travel to Colorado using an enterprise convertible! I cannot wait to go!

    • Seattle Dredge
      August 6, 2014 at 7:46 am #

      Oooh, I hadn’t even considered a convertible. Nice choice!

  5. Kelly D
    August 6, 2014 at 10:15 am #

    I would go to Portland Maine and I would like a standard SUV

    • Seattle Dredge
      August 6, 2014 at 11:25 am #

      Sounds nice, I’ve only driven through Maine quickly once, but would love to go back for more exploring :]

  6. Brian Kautz
    August 6, 2014 at 10:43 am #

    I’d make a run to Cali to visit friends in a convertable

  7. wmjindsm
    August 6, 2014 at 11:01 am #

    I would love to drive down to the Keys from Miami again.

  8. Ryan
    August 6, 2014 at 11:46 am #

    I need to get down to Florida ASAP! And that photo through the fence is awesomesauce!
    Ryan recently posted..My VIP tour of the Roman Colosseum and Hypogeum

  9. Ryan
    August 6, 2014 at 12:08 pm #

    Ph, whoopsies, forgot this part! I would love to take a road trip to Alaska at some point, but that would take longer than a weekend. Hm. I’d say a road trip to Boston, always wanted to visit that city, teeming with history and of course my Irish pride is pulling me too =P And I’d say a convertible for the summer would be awesome!
    Ryan recently posted..Peering through the secret keyhole of the Knights of Malta

    • Seattle Dredge
      August 6, 2014 at 12:44 pm #

      But you could fly to Alaska and then road trip around all weekend (invite me and I’ll keep on moose-watch for you!). Also, I say keep the convertible and exercise ze manliness in the Arctic airs ;]

  10. Cindy
    August 6, 2014 at 12:26 pm #

    I would love to travel to San Diego to see my son. Driving across the country would be a great way to see so many sites along the way. I would say an SUV would be most comfortable!!

    • Seattle Dredge
      August 6, 2014 at 12:39 pm #

      Agreed, travelling overland is always the better way to do it, and I’d love to visit San Diego too. Good choice!

  11. allison
    August 6, 2014 at 3:04 pm #

    I would spend weekend in yosemnite

  12. Linda H.
    August 6, 2014 at 3:09 pm #

    Driving down the Florida Keys in a convertible sounds like my idea of fun!

  13. Jenn
    August 6, 2014 at 3:45 pm #

    I would get a convertible for myself and rent a truck for the band.. We would load it with all the gear and play some classic rock all the way down the Florida Keyes!

    • Seattle Dredge
      August 6, 2014 at 4:04 pm #

      Oooh, that actually sounds pretty awesome. I’m in! What are ya playing? Haha

      • Jenn
        August 6, 2014 at 4:09 pm #

        We live in Minnesota and play all over- I lived in Key West for 13 years before coming “home” and know MANY fun bars on the way from Key Largo to Key West- If I win I will pick you up and you can hang with the girls in the convertible! 😉

        • Seattle Dredge
          August 6, 2014 at 11:16 pm #

          Yeah, swing by Toronto on your way down! Haha, a classic rock, fun bar road trip sounds just about perfect 😀

  14. Donna W.
    August 6, 2014 at 4:31 pm #

    I would get a convertible and drive from Key Largo to Key West and spend more time in the ocean. My boyfriend and I are both month old cancer survivors and I am still in the process of reconstruction and he is recovering from a lobectomy. Love it there!

    • Seattle Dredge
      August 6, 2014 at 11:20 pm #

      Florida/convertible is turning out to be a popular option! But, wow–it sounds like you guys really deserve a fun road trip right about now! Congrats on one month and I really hope you win this draw 😀

  15. Mary Beth Elderton
    August 6, 2014 at 6:45 pm #

    A trip to the Florida Keys would be a dream! I
    d chose a smallish car–it’s just Hubz and me, and we like to travel light.

  16. Rachel Ferrucci
    August 6, 2014 at 9:34 pm #

    Heading down there for a Keys road trip too so will be checking some of the places out! Looks like you had a blast!

  17. Rachel Ferrucci
    August 6, 2014 at 9:36 pm #

    Heading down there for a Keys road trip too so will be checking some of the places out! Looks like you had a blast! I would need to have a convertible

    • Seattle Dredge
      August 6, 2014 at 11:27 pm #

      Awesome–you’ll love it, it’s such an amazing drive. I’m starting to regret the fact that I didn’t do this trip in a convertible myself.. everyone is choosing this, haha.

  18. Jeanette Ammann
    August 6, 2014 at 9:54 pm #

    A drive up the Atlantic Coast in a luxury SUV would make for a nice trip for me and my Husband! We’d cruise through Melbourne, stop in Cocoa Beach…drive on up to Daytona then thru Ormond Beach on up to St. Augustine.

    • Seattle Dredge
      August 6, 2014 at 11:28 pm #

      Sounds like a good trip. I’ve never been to any of these places, so I may need to do a roadtrip there myself!

  19. Luna S
    August 6, 2014 at 10:29 pm #

    California! and a SUV so we were all comfortable.

  20. Marilyn Blau
    August 6, 2014 at 10:44 pm #

    A weekend in Maine sounds great folliage time.

    • Seattle Dredge
      August 6, 2014 at 11:29 pm #

      Ah, definitely. I looove fall road trips. What would you drive?

  21. Stacie
    August 7, 2014 at 8:51 am #

    I’ve been meaning to check out the Florida Keys. Judging by your pic of Key West it looks like my kind of place. I’d rent an intermediate SUV probably.

    • Seattle Dredge
      August 7, 2014 at 9:59 am #

      I think Key West can be anyone’s kind of place! It’s definitely mine too :]

  22. iamalighthouse
    August 8, 2014 at 7:19 pm #

    I’d hop up to Minneapolis to visit in the summer! I’d rent a convertible for sure. 🙂

  23. Danielle
    August 9, 2014 at 1:45 pm #

    I’d go to Yosemite, since it’s so close yet I haven’t been there! Maybe go camping and hiking. I think i’d go for a dodge charger or challenger. One with heated seats though!
    Danielle recently posted..Fishing on the Pier in Ocean Beach

    • Seattle Dredge
      August 10, 2014 at 5:59 pm #

      Ooh, a good one. I’d definitely love to camp there!

  24. Carly D.
    August 9, 2014 at 6:52 pm #

    I would go somewhere in VT to enjoy the quiet and scenery…in a compact with my husband!

    • Seattle Dredge
      August 10, 2014 at 6:00 pm #

      I’ve driven through Vermont and loved it, that would be a nice weekend trip :]

  25. Nicole Dz
    August 10, 2014 at 2:18 am #

    I would go to the downtown Detroit area with a few friends to explore the sites in a chevy spark.

    • Seattle Dredge
      August 10, 2014 at 6:01 pm #

      Nice, I’d actually like to do that myself, as Detroit is just a drive away from where I live :]

  26. livivua
    August 10, 2014 at 1:02 pm #

    i would go to florida and maybe rent a truck

  27. Brandon Sousa
    August 11, 2014 at 9:25 am #

    It may sound a little ridiculous, but I would rent a Cargo Van, put a single mattress in the back with a cooler and my gear, and trek out to Nebraska National Forest for some amazing hiking! It may take a little longer than a weekend to do it… but it would be one heck of a road trip and adventure!

    • Seattle Dredge
      August 12, 2014 at 9:58 am #

      Um, that may actually be my favourite one yet. Why didn’t I think of that? Haha. I’d love to do a cross country road trip like that.. sounds perfect.

  28. Elle
    August 11, 2014 at 1:18 pm #

    I would go for a weekend getaway to The Berkshires and I’d rent a Pathfinder.

  29. Karin Erica
    August 12, 2014 at 6:08 am #

    Road trip in an SUV to Yosemite in California, road trip through the National park, see some cool wildlife, like snakes and scorpions, and hike up a few ridges to take in the view of what is supposedly the most ‘American’ (think Rockies with massive trees) out there. A few American eagles circling overhead wouldn’t go amiss.

    • Seattle Dredge
      August 12, 2014 at 10:02 am #

      Haha, I’m picturing you and Kieran all dressed up in like American flag attire, searching for eagles. Can I come? I promise I won’t fall asleep :p

  30. Kelsey
    August 13, 2014 at 3:12 pm #

    I live in South FL so I am actually planning to head down to the Keys soon! My best friend who is born and raised in Key West (weird right?) just got engaged and I’m dying to check out the goods. I’m thinking I would rent a standard car, because I’m a simple gal, but do they have convertibles? 😉

    • Seattle Dredge
      August 22, 2014 at 11:24 am #

      Haha, not weird! I’d totally stay if I were born there. I hope you make it down soon, that’s certainly a good excuse for a road trip if I ever heard one. And yeah, they have convertibles! ;]

  31. Leidy
    August 14, 2014 at 6:25 pm #

    I would rent a full size car and go to Austin for the weekend. Can’t miss the Longhorns first game of the season \m/

  32. HS
    August 14, 2014 at 11:59 pm #

    Our next get away destination is Long Island, I’ll rent a standard SUV for the whole family.

    • Seattle Dredge
      August 22, 2014 at 11:31 am #

      Nice, it’ll definitely be good to have the extra space for the fam!

  33. GB
    August 15, 2014 at 10:10 am #

    I’d rent a luxury sedan and go on a weekend trip to Atlantic City!

  34. Debbie B
    August 16, 2014 at 11:18 pm #

    we’re planning a road trip from San Diego to San Francisco – I think we will probably rent an intermediate SUV

    • Seattle Dredge
      August 22, 2014 at 12:04 pm #

      That’ll be a nice drive. SUV, windows down, music up.. sounds good to me

  35. MarilynBlau
    August 18, 2014 at 12:47 am #

    fly to SAn Fran and drive down thhe coast

  36. Linda
    August 18, 2014 at 11:54 am #

    I’d go to Boston for an amazing weekend and I would rent a mid sized sedan.

  37. Arienne
    August 20, 2014 at 5:29 pm #

    Amazing photos as always Seattle! If I had a weekend away, I’d fly out to San Francisco and drive north up the coast to Portland. Of course the only car to do this would be a convertible with the top down but a standard SUV from Enterprise would work just as well too 🙂

    • Seattle Dredge
      August 22, 2014 at 10:55 am #

      Thanks, Arienne! Ooh, that’s a good one–I love both SF and Portland. I feel like a convertible would be good for Cali and an SUV for Oregon 😀

  38. Christina
    August 20, 2014 at 6:48 pm #

    I just booked a flight to Italy over Winter Holiday! But for a weekend, I would head up to Victoria Island in Canada to do some kayaking. I live in Seattle, so its a pretty easy weekend vacation.

    • Christina
      August 22, 2014 at 11:11 am #

      Also, I would want to rent a hybrid.

    • Seattle Dredge
      August 22, 2014 at 12:28 pm #

      Ooh, I love Italy :] But, yusss come on up to Canada!

  39. Mariska
    August 20, 2014 at 7:37 pm #

    I would go to Vancouver Island and drive a comfortable SUV and head to Tofino and Long Beach for some surfing!

    • Seattle Dredge
      August 22, 2014 at 12:34 pm #

      Love it–and you could easily carry surf boards with an SUV! Yay Canada 😀

    August 20, 2014 at 10:17 pm #

    I would rent a basic economy car and travel to Austin, TX to a football game

  41. Kassandra Sosa
    August 21, 2014 at 3:02 am #

    As a Texan, I recognize the massive size of this state filled with lots of culture and roads to drive in! I would love to specially travel East Texas through the small towns! I have seen spectacular sunsets on lakes from East Texas and it’s just something I’d really love to do! If I have to choose, I would definitely go with a Chevy Spark (:
    Kassandra Sosa recently posted..My Fourth of July (Quick post!)

    • Seattle Dredge
      August 22, 2014 at 11:14 am #

      My mom and her bf are always driving through Texas and it makes me jealous, haha. I just googled East Texas and it’s certainly more forested and green than I had imagined. Great choices!

  42. Sarah Gael
    August 21, 2014 at 6:01 am #

    I would go to the South Island of New Zealand, with friends, to explore the rest of the beautiful country I grew up in. I would have a Luxury class car, so we can cruse from place to place in comfort and style. (That wasn’t meant to sound so much like an advert!!)

    • Seattle Dredge
      August 22, 2014 at 12:40 pm #

      Hahah, do you work in advertising? :p I love it though, I would totally do that one myelf!

      • Sarah Gael
        August 22, 2014 at 6:49 pm #

        I don’t actually… There must be too many adverts around at the moment! How rude and annoying!

  43. liz l
    August 21, 2014 at 10:30 pm #

    For Disney travel, I would like a standard SUV

  44. Brooke
    August 22, 2014 at 12:47 pm #

    I’ve been to Florida several times, and we visited this place called Palm Island once and it was beautiful there!

  45. Megan
    August 22, 2014 at 12:49 pm #

    I would probably rent a compact car and take a trip to California! Sounds soooo cliche, but I think that road-tripping is the best way to explore CA.

    • Seattle Dredge
      August 22, 2014 at 6:25 pm #

      Definitely not cliché! I totally want to do the same thing :]

  46. Anna H.
    August 22, 2014 at 4:25 pm #

    I’d love to travel to California since I’m all the way in the east coast. Your Florida trip looks great too! So maybe I should consider that instead. Haha Any vacation is a good vacation! I’d love to drive a cozy small car from Enterprise with a best friend or two. Thanks for the recommendation! I’ll definitely check them out next time I travel.

    • Seattle Dredge
      August 22, 2014 at 6:29 pm #

      Yeah, living East Coast-ish myself, I’d definitely love a cross country road trip to California. Maybe you can do both!

  47. Chinello
    August 22, 2014 at 9:17 pm #

    I would get a premium elite Lincoln MKZ so we would have room for luggage, maybe even camping equipment. I want to go to the Grand Canyon with my husband, only seen it on TV. I can only imagine how beautiful it must be in person.

  48. jacop3c
    November 19, 2016 at 7:47 am #

    Awesome post!! I want to spent some time here. this is looking so beautiful. Thanks for the shearing.

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