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Home » Trip Reports » Trip Report: Explora Journeys Cruise – Key West
Explora JourneysFamily TravelTrip Reports

Trip Report: Explora Journeys Cruise – Key West

Kyle Stewart Posted onDecember 24, 2023December 24, 2023 5 Comments
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As part of our trip throughout the Caribbean, we spent ten days onboard Explora Journeys and it was an all-inclusive five-star resort at sea. The first port of call was Key West, Florida. 


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My travel agency earned a complimentary cruise with Explora Journeys but we have also purchased several more tickets because we love the product. This trip report traces that journey taken in late November 2023.

Kimpton Key West explora journeys

Trip Report Table Of Contents

  1. Overview
  2. Miami: Kimpton Epic
  3. Explora Journeys
  4. Key West, Florida
  5. Sea Days
  6. Spanish Town, British Virgin Islands (Virgin Gorda)
  7. St. John’s, Antigua and Barbuda
  8. Deshaies, Guadeloupe
  9. Gustavia, St Barth’s
  10. Basseterre, St. Kitt’s and Nevis
  11. Castries, St. Lucia
  12. Bridgetown, Barbados

A Familiar Stop

We try to winter in Florida when the fates align and as such we have made our way to Key West on a handful of occasions. We love the time capsule charm of the spot. I am particularly captivated by Hemingway’s time on the island after he returned from Europe and before his time in Cuba where both his writing and his personal life were in decline.

Key West captures the island vibe of the Caribbean with an old-world Floridian charm that isn’t replicated anywhere else. It feels like the opposite of Art Deco Miami Beach or modern Miami today. We love it there and while I wouldn’t usually cheer a stop so close to our Miami departure point, any time I can get to Key West without a 4-5 hour drive from Southwest Florida, I welcome it.

Kimpton Key West old key west

A New Discovery

We were traveling with my sister-in-law, her mother, and her daughter as well as my family of four and some friends. My sister-in-law wanted to take our daughters to the Hemingway House and while I love it there, I have been many times before. With Frankie too small to understand or appreciate it, my wife and I opted to take our son across the street to a Kimpton I have never seen before.

Hemingway cat Key West
A famed six-toed Hemingway cat

Kimpton Key West Lighthouse

A series of one and two-story cottages, the Kimpton Key West Lighthouse Hotel was exactly what I’d expect from the brand. It was small, local, boutique, and every bit the Key West experience.

Kimpton Key West cottages

Meandering through the tree-lined pathway, we arrived at a central pool and the hotel’s bar and restaurant, Isabel’s. We asked if we could sit awhile and enjoy the weather ordering a couple of Coca-Colas, the first order of the day around 11 AM.

Kimpton Key West Isabels

Kimpton Key West Isabels inside

Kimpton Key West drinks

The Kimpton welcomed us to dip our toes in the water and though we were not hotel guests, they wouldn’t have batted an eye if we chose to swim. I’m not sure if it’s encouraged officially, but the staff could not have been kinder or more welcoming. Our son, Frankie, loves the water and relished the chance to soak up the sun and splash a bit.

Kimpton Key West pool

Kimpton Key West pool with frankie and carly

Kimpton Key West kyle and frankie

I’m not sure when we will be back to Key West, but there’s no question that we will absolutely stay at the Kimpton Key West Lighthouse Hotel on our next visit. To that end, after staying in a couple of Kimptons recently and using the new IHG One Rewards program, I have moved from one of its staunchest critics to mildly impressed with the program and confident about its stewardship of premium brands.

An Old Favorite

Did you even visit Key West if you didn’t have conch fritters? Probably not. I know they are mostly fried dough balls, but the dips add an element, and when in Rome, do as the Romans do. They are easy to share, reasonably priced, and satisfying. When we stop in Key West, we visit The Conch Shack on Duval. It’s in the heart of everything and close to the pier as well.

Conclusion

Our day stop in Key West saved us from driving the distance on the beautiful, but slow, oversea highway and gave us a taste of a place we have long loved. It was great to revisit old favorites and discover new ones before our next trip.

What do you think? 

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About Author

Kyle Stewart

Kyle is a freelance travel writer with contributions to Time, the Washington Post, MSNBC, Yahoo!, Reuters, Huffington Post, MapHappy, Live And Lets Fly and many other media outlets. He is also co-founder of Scottandthomas.com, a travel agency that delivers "Travel Personalized." He focuses on using miles and points to provide a premium experience for his wife and daughter. Email: sherpa@thetripsherpa.com

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5 Comments

  1. Mick Reply
    December 24, 2023 at 2:39 pm

    Well done mate. Looks like a great little stopover.

  2. JoeMart Reply
    December 24, 2023 at 3:56 pm

    I had a memorable stay at this Kimpton. Not sure how it compares to the newly remodeled Hyatt Centric. Key West is all about the fresh seafood brought daily by the fishermen. Conch is brought frozen from other countries. Try a fresh Hogfish snapper sandwich, pink shrimp,Pompano,tuna or stone crabs.

  3. Alert Reply
    December 24, 2023 at 4:04 pm

    Lovely cat .

  4. George Reply
    December 25, 2023 at 8:40 pm

    Even though you are purchasing future cruises with them (at a discount?), the fact that you are a travel agent for this cruise and received this for free, makes this review biased, and one that has a conflict of interest. It’s difficult to trust that this is an honest review

  5. Walt Reply
    December 29, 2023 at 12:06 pm

    Love visiting KW. Truman’s Little White House is a neat stop (easy walk from cruise port) and brunch at Banana Cafe is a must for us.

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