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Key West Travel Guide – Luxury Edition

May 7, 2018

Palm tree-lined streets, perfectly-manicured neighbourhoods, opulent yachts bobbing in their slips, swanky hotels… These are a few things you can expect when visiting Key West (aka Cayo Hueso).

Key West Travel Guide, Florida Keys

Once the richest city per capita in the United States, it’s now a magnet for luxury travellers. But one character sets the southern Florida gem apart from stuffy, luxe vacations spots around the globe: its decidedly independent spirit (thanks to a colourful past) makes Key West the ultimate destination for approachable luxury. With a local population that’s down-to-earth, eccentric and fun, it’s the kind of place you can let loose while still enjoying the finer things in life. Which is exactly what we did on a recent trip…

Luxury Key West Travel Guide

Helicopter Ride With Air Adventures, Luxury Key West Travel Guide

Key West Luxury Hotel: Oceans Edge Key West

As the newest and largest Key West luxury property, Oceans Edge Key West Resort Hotel & Marina is the place to stay in my opinion…

Key West Travel Guide, Oceans Edge Resort

As soon as we pulled up to the main lobby, I knew it would be a memorable and luxe stay. Everything from the design elements to the service at this resort is refined yet comfortable. Our suite was spacious (they have the largest rooms in Key West), dotted with cobalt blue accents and boasted a stunning private balcony overlooking the pools…

Key West Travel Guide, Oceans Edge Resort

But it gets better: EVERY every single room at Oceans Edge has oceanfront views! This, my friends, is a hotel that lives up to its name: you will literally wake up each morning on the ocean’s edge. And for those of you who love poolside lounging as much as I do, Oceans Edge is basically your dream resort since they have SIX pools for you to choose from. Add to this al fresco dining at Yellowfin Bar and Grill, upscale amenities (like the complimentary 1 hr rental of paddleboards, kayaks or bikes) and on-site access to fishing charters or snorkel boats and you’ll basically never want to leave the property.

Key West Travel Guide, Oceans Edge Resort

This is the perfect resort for those looking for a luxe escape away from the hustle and bustle of downtown. That’s because the property is tucked away on Stock Island (a 15 min drive) and hugged by a newly renovated marina. But you need not worry about getting around because the hotel offers a free, hourly shuttle service to and from downtown between 9 am and 9:30 pm. Or, if you’d prefer to rent a car like we did, there’s plenty of parking available onsite. The pool and ocean views, large suites and exceptional service make this property worth trekking to and from — trust me. Especially if you’re travelling with a family or large party.

Key West Travel Guide, Oceans Edge Resort

Key West Restaurants

If there’s one fine dining experience you splurge on when visiting The Florida Keys, it should be Latitudes Restaurant. Perched on Sunset Key, the beachfront restaurant is something out of a dream. Surrounded by swaying palms, we sipped cocktails and enjoyed a leisurely lunch while taking in the dreamy views. Do yourself a favour and indulge in the Key Lime Colada — it’s the best cocktail in Key West in my opinion…

Latitude's Restaurant, Luxury Key West Travel Guide

I’d love to head back to Latitudes for a sunset dinner (it’s been rated as one of the 100 most romantic restaurants in America), but since we were travelling with Little L lunch was a great option for us. TIP: Reservations are mandatory since they have a private boat that will take you to and from the restaurant. Oh, and don’t hesitate booking if you’re travelling with family. They’re very family-friendly: you can bring your strollers, they have high chairs and even offer colouring books to kids!

Latitude's Restaurant, Luxury Key West Travel Guide

Other spots for great food in Key West: Garbo’s Grill (food truck), Seven Fish, Little Pearl, Hogfish Bar & Grill, Santiago’s Bodega, Pepe’s Café and Cuban Coffee Queen.

Luxury Key West Travel Guide, Cuban Coffee Queen

Best Key Lime Pie In Key West

You really can’t visit The Florida Keys without tasting a slice or two (or ten in my case) of key lime pie. I went on a mission to find the very best and had a hard time deciding between Old Town Bakery, Kermit’s Key West, Blue Heaven and Key West Key Lime Pie Co. But the perfectly-torched meringue at Blue Heaven won my vote. This, my friends, is truly a heavenly slice:

Best Key Lime Pie In Key West, Blue Heaven

Key West Attractions

1. Helicopter Ride With Air Adventures – In my opinion, nothing will give you better appreciation of the keys than hopping in a heli ride with Air Adventures. As Key West’s only helicopter tour operator, these guys offer five unique experiences depending on your budget and desired tour length. Since we had Little L with us, we opted for the 10 minute island tour which had us soaring over historical landmarks, beaches and Mallory Square. We even spotted a few manatees from above! If you’re a nature-lover, definitely book the 20 min Eco Tour (their most popular) and get a bird’s eye view of marine life like stingrays, sea turtles and sharks.

Helicopter Ride With Air Adventures, Luxury Key West Travel Guide

2. Wind & Wine Sail With Danger Charters – If you’re travelling with the grandparents or have older kids who can babysit, this is one experience you’ll want to use their services for. Leave the littles at the hotel with loved ones and enjoy this very romantic excursion with your partner for a date night. I promise that you will never forget it. The sunsets are jaw-dropping, the wine flows endlessly (the crew is very knowledgeable about the varietals and vintages served) and the journey itself is the perfect length. Take a camera to capture the breathtaking unobstructed views…

Luxury Key West Travel Guide, Wind & Wine Sail With Danger Charters

3. Ernest Hemingway House – Built in 1851, the historic property in the heart of Old Town Key West was Hemingway’s private residence for over 10 years. It’s a must-see for all of you book and cat lovers — yes, I said cats. Descendants of Hemingway’s furry friends still roam the property. Keep your eyes peeled for the cats with extra toes! I was chatting with one when Hubster snapped this shot…

Ernest Hemingway House, Key West Travel Guide

4. Conch Tour Train – No visit to Key West is complete without a ride on the Conch Train. Looping through Old Town Key West, the 90-minute journey has been entertaining visitors since 1958 — including legends like Hemingway. The tour begins at the Front Street Depot and ends behind Mallory Square with three stops along the way (one is a 10 minute rest stop which is just enough time for a washroom break/diaper change). You also have the flexibility to disembark on the second stop (Truval Village) to do a bit of sightseeing and can hop back on a later train. TIP: Take the first tour of the day at 9 am to avoid cruise ship crowds. There were just five people on our train! And if you’re travelling with a baby, there’s room for your stroller onboard.

Luxury Key West Travel Guide, Conch Train

5. Sunset Celebration At Mallory Square – Of course you’ll want to take in the glorious sunsets with the entire family as well. For this, there’s no better place to head than Mallory Square. The sunset celebration is a Key West tradition so it draws a huge crowd of visitors and locals alike. Think: buskers, vendors selling everything from conch fritters to elaborate pineapple drinks and hundreds of people snuggled up to the shoreline watching the sun dip below the horizon. It’s a beautiful thing when so many people come together to celebrate mama nature…

Luxury Key West Travel Guide, Mallory Square Sunset Celebration

Although we filled our days in Key West with many more activities and dining experiences than listed above, this itinerary highlights the crème de la crème for those planning a luxury vacay. I hope it inspires you to visit the eclectic, charming and lavish destination. I’m counting down the days to our return…

Key West Travel Guide

Our accommodations, meals, activities and flights to The Florida Keys were complimentary as part of a press trip with Visit Florida. As always, all reviews and opinions are entirely my own. 

Luxury Key West Travel Guide

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20 Comments

  • Reply
    Julia Dent
    May 16, 2018 at 7:26 pm

    I went to Key West once and didn’t stay in the nicest place, so you’re making me want to try and go back again! That Wind and Wine excursion looks like so much fun, and I NEED that key lime pie!!

    • Reply
      Solmaz
      May 16, 2018 at 8:13 pm

      I hope you visit again — the hotel def makes a difference in the overall experience. And yes, the Wind & Wine is a MUST. So memorable.

  • Reply
    Christie
    May 16, 2018 at 8:36 pm

    I never really knew much about Key West, but it looks so beautiful! Definitely adding it to my US bucket list 🙂 The Wind and Wine tour sounds incredible, and the views of the sunset look so nice!

    • Reply
      Solmaz
      May 16, 2018 at 9:32 pm

      I didn’t know much about it either until our visit. There are tons of historic homes and water adventures to fill your days with.

  • Reply
    Sarah - Borders & Bucket Lists
    May 16, 2018 at 8:51 pm

    This looks so fun!! Like Julia, I also didn’t have the greatest experience in Key West, but this makes me want to try again! Especially for the best slice of key lime pie and that private boat ride to a restaurant (how cool is that?!).

    • Reply
      Solmaz
      May 16, 2018 at 9:34 pm

      Just out of curiosity, did you visit via cruise? I’m trying to figure out if the visitor experience is different in short spurts. Regardless, I do hope you re-visit! You must eat at Latitude’s if you can.

  • Reply
    Viola
    May 16, 2018 at 9:00 pm

    Omg that suite is beautiful! Looks like such a relaxing vaca! Take me there please 😛

    • Reply
      Solmaz
      May 16, 2018 at 9:35 pm

      I wish I could send you there asap. Such an interesting destination. Def different than the rest of Florida!

  • Reply
    valerie
    May 16, 2018 at 11:00 pm

    I have been so pining to see this place for years now and your post totally fueled my wanderlust to get there soon! Amazing pictures and top notch post..LOVED IT !! Key West look so so dreamy!

    Valerie

    • Reply
      Solmaz
      May 17, 2018 at 9:14 am

      I hope you get a chance to explore. Lots of little gems there.

  • Reply
    Candy
    May 17, 2018 at 12:20 am

    It’s been over 10 years since I visited Key West and I would really love to make another visit. Sadly, I never tried the Key Lime Pie when I was there! Next time I go, I’ll definitely get the KLP you recommended 🙂

    • Reply
      Solmaz
      May 17, 2018 at 9:15 am

      OMG girl — RUN. The key lime pie is worth a visit alone lol. Of course, everyone has a different fave but you must try the one at Blue Heaven.

  • Reply
    Nafisa Habib
    May 17, 2018 at 1:31 am

    Every attraction I’m loving from Key West. Heli ride with Air Adventures, WOW!! So much fun indeed…And I can only feel the taste of Key Lime Pie, heheh. Yummm

    • Reply
      Solmaz
      May 17, 2018 at 9:16 am

      Yah they offer such a great range of adventures — from land to water. The glass bottom boat that takes you out to North America’s only living coral reef is cool too.

  • Reply
    Weekend Haven
    May 17, 2018 at 10:06 pm

    Lovin’ the vibe. And a sunset cruise definitely screams luxury. Love your photos!

    • Reply
      Solmaz
      May 18, 2018 at 9:10 pm

      Thank you! Def recommend it.

  • Reply
    Michelle Stelly
    May 17, 2018 at 10:33 pm

    I want to actually go in January and that Oceans Edge looks like the perfect hotel! How beautiful. So many pools but I love that! I will have to start planning soon.

    • Reply
      Solmaz
      May 18, 2018 at 9:11 pm

      It’s honestly a fab hotel to stay at. The pools are all boutique chic. Rooms are amazing! Hope you have the best trip!!

  • Reply
    Victoria Holmes
    May 22, 2018 at 1:24 am

    This is the best place for spending your vacation. These places look gorgeous, You capture some outstanding views and your guideline makes all for best travel experience, I got married almost 1 months ago, I just excited to spend some wonderful time with my hobby in key west and I must go for Wine Sail With Danger Charters and enjoying the sunset. I think this trip makes us more closely, and taste the popular lime pie. Thanks for your wonderful article.

    • Reply
      Solmaz
      May 24, 2018 at 6:19 pm

      Hi Victoria! Hope you have the best time in Key West. Definitely don’t miss out on the sail with Danger Charters — it will be a beaut memory. Congrats on getting married!!

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