While informative and true, we want you to know that this post was written as an entry for Celebrity Cruises Ultimate Caribbean Cruise Itinerary contest. Winners of the contest receive a cash prize, social media recognition, and a guest post on the Celebrity Cruises blog. Opinions expressed are our own and are based on our actual cruising experiences.

If you’ve followed our blog for any time at all, you know that we’re a middle-aged, married couple from rural Nebraska, smack-dab in the middle of the United States and about as far from water as you can get. So yes, we dream about cruising often, which makes us experts in imaginary cruise itineraries. With this in mind, we offer our guide to the ultimate Caribbean cruise itinerary.

At port while cruising on the Celebrity Constellation.

Let’s face it, everywhere we’ve been in the Caribbean has included a beautiful island, crystal-clear water, warm temperatures, golden sand, lush palm trees, and friendly locals. But we have to start somewhere, so Steve will start in Key West, the heart of the fabulous Florida Keys.

Key West, Florida

STEVE: Ahhh….sunny Key West. I’ve been going the Keys and Key West to visit family since I was a boy, so feel that I know it well. But that isn’t why it makes our list. I include it because it is one of the most laid-back, relaxing places I know. It’s a place where no one takes anything too seriously, and everyone, including the chickens that populate every corner, just wants to have a good time.

Our view of Key West from the Celebrity Constellation.

Key West offers something for everyone, including an actual passport from the not-so-actual Conch Republic and fresh seafood that makes even the most entrenched landlubber drool. The shopping is divine, offering everything from high-end, luxury boutique items to natural sponges collected from nearby waters.

We loved shopping for sponges in Key West.

In Key West you can be literary and tour Hemingway’s home, or historical and visit Truman’s Little White House and then learn about Flagler’s Overseas Railroad. But whatever you do, don’t be too serious — this is the town where they throw stale Cuban bread at a U.S. Navy ship once a year, after all.

The Key West Butterfly and Nature Conservatory housed 50-60 species of live butterflies.

A day spent in Key West can be action-packed with activities like parasailing, snorkeling and wave running, or laid back with a cocktail on the beach or a visit to the Butterfly Nature Center and Conservatory. By the time the sun sets on Mallory Square, visitors to Key West feel a sense of deep relaxation, the tensions of everyday life forgotten. For these reasons, I think that any traveler to the Caribbean should set their sights on Key West. 

Travel Tip: Take the Conch Train tour. It’s a great overview of the island and its history, and it’s only 90 minutes long so it won’t take up your entire day.

Basseterre, St. Kitts & Nevis

ANN: My ideal Caribbean cruise would have to include a stop in beautiful Basseterre St. Kitts and Nevis. I fell in love with this perhaps lesser known island a couple of years ago and we wrote about it HERE. As soon as I set foot in Port Zante, I was immediately attracted to the island – the iridescent waters, the lush flora, and blue skies made me feel like I’d died and gone to Instagram heaven. #nofilterneeded

Arriving at the port in Basseterre St. Kitts.

In addition, everyone there was so nice and legitimately seemed happy. And why wouldn’t they be? Kittitians share a 65-square mile island surrounded by pristine beaches, beautiful gardens, and all the mangos they can eat. Oh, and there are cute little monkeys everywhere!

That’s the Atlantic Ocean on the left and the Caribbean Sea on the right.

We would recommend a visit to Brimstone Hill Fortress National Park where you’ll learn about the island’s history and take in one of the most gorgeous views you’ve ever seen.

The incredible view from the top of Brimstone Hill in St. Kitts.

An excursion to the Caribelle Batik Factory at Romney Manor is also a must. Artists there demonstrate this unique Indonesian method of resisting dye with wax to create beautiful designs on fabrics. 

Batik fabric in St. Kitts

And don’t head back to the ship until you’ve stopped at a local eatery and tried salt fish and provisions. This dried fish dish is a local favorite and is served with salad and “provisions,” including a coconut dumpling, sweet potato, white potato, dasheen and yam.

Travel tip: Find your way to Timothy Hill Lookout for a stunning, iconic photo of St. Kitts and Nevis surrounded by both the Atlantic Ocean and the Caribbean Sea.

Phillipsburg, St. Maarten

STEVE: St. Maarten is one of those beautiful Caribbean islands whose palm trees, soft breezes, warm sand beaches, friendly inhabitants, and slow pace of life connect to your inner being in way that makes you happy to be alive. More importantly, for airplane fanatics like me, it is also home to Princess Juliana Airport and Maho Beach.

It was surreal to watch these planes land literally yard from where we standing on the beach.

Have you ever watched one of those YouTube videos where people are standing on a beach and they are so close to a huge jet landing that they look like they could almost jump up and touch it?

That’s Maho Beach.

The government in St. Maarten has actually put up warning signs telling people not to get too close to the end of the runway. And they mean it. Jet blast from arriving and departing planes is very dangerous. But if you stand off to the side of the runway, you have an amazing view of planes taking off and landing.

We had a great table at the Sunset Bar and Grill where we could enjoy a sandwich and guava berry colada while watching airplanes come in for landing.

And if you go a little further to the side you can find a nice little bar where you can relax with a cold beverage and take in this fantastic aviation experience. 

Travel Tip: Check the flight schedule for Princess Juliana Airport in St. Maarten to make sure you’re there when the BIG planes come in.

Costa Maya, Mexico

ANN: Although we haven’t been to Costa Maya … yet … It makes our ideal Caribbean cruise port list because there’s so much to see and do there. You can lounge on the beach, shop for tourist favorites like pure vanilla, serapes, and tequila, and even explore ancient Mayan ruins.

Neither one of us had ever seen one of the Seven Wonders of the World until we visited the pyramid at Chichen Itza in 2017.

Neither one of us had ever seen one of the Seven Wonders of the World until we visited the pyramid at Chichen Itza in 2017.

We also highly recommend strapping yourself up in a bright orange life jacket and jumping off a rock into a cenote.

Swimming in the crowded cenote.

Swimming in the cenote.

Steve and our daughter, Meghan, checked this off on their bucket lists a couple of years ago while in Mexico and loved the experience. (I took photos) They loved floating on their backs and enjoying the view of the vines and vegetation above and both said they would do it again.

Meghan and Steve ready to swim in the cenote.

Our daughter, Meghan and Steve ready to swim in the cenote.

Costa Maya is a planned port on a 7-night Western Caribbean sailing on Celebrity’s new Edge, and we are beyond excited to board that ship in early 2019.

Tip: Book your excursion through the ship, especially if you don’t know the language. Their tour operators will get you to and from your destination easily, and you’ll have a wonderful experience.

Don’t forget a few sea days

Of course, our ideal Caribbean Cruise would also include a few sea days. We’ve found plenty to do  when our ship’s at sea and wrote a blog post about it called “21  things to do on a sea day besides eat.” Here’s look at how each of us would spend the ideal sea day:

Let’s face it, the truly ultimate Caribbean cruise would have a stop at every port Celebrity Cruises visits. Most importantly, you would never have to dread the day when your disembarkation luggage tags arrive, because this ultimate Caribbean cruise would go on forever!

  • Strawberry fields forever...⁣
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While traveling, we adore stopping in farmers markets and checking out the fresh produce available for sale. When we saw these strawberries in Tallinn, Estonia, we just had to take a picture.⁣
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The vibrant color of the berries tells us they were ripened naturally on the vine. You just don't get that color trucked in to a supermarket. And that natural ripening means, of course, that these are some of the sweetest strawberries you'll ever taste. Yum! #postcardjar #midlifetravel #emptynesttravel #goplaces #emptynest #emptynesters #midlife #couplestravel #couplestrip #celebritycruises #cruising #seastheday #cruise #sea #beyondborders #humansatsea #cruiseaddict #cruisecritic #tallinn #lifeisbeautiful #cruiseship #cruiselife #estonia #strawberries #farmersmarket #lifeisshort #visitestonia #adventuregirls #tallinngram #berries
  • On our Baltic Sea cruise, we stopped in Stockholm, Sweden. To get there, we had to sail through the Stockholm Archipelago. ⁣
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For days leading up to our arrival in Stockholm, the captain of the ship kept telling us that we should plan to be up early so we could take in the scenery as we passed through the archipelago. After enough repetitions, we resolved to get up early to see what he was so excited about.⁣
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We are so glad we set the alarm. That morning, we sat on our balcony and had breakfast watching some of the most beautiful scenery we'd ever seen pass by our cabins. We had an up-close view of land that we've rarely had from a cruise ship unless it was docked. ⁣
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Sure, we travel to see specific things. Who doesn't? But we really love it when we find something like this that we didn't know existed, but it is so amazing it enriches our lives and makes us want to go back again and again.
  • In the @visitmasoncityiowa airport, is a new restaurant called CAVU American Kitchen & Cocktail Lounge. Offering chef-crafted foods and incredible cocktails, this restaurant has the best airport food we've ever eaten. In fact, we'll call this airport a destination.⁣
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Pictured here is Chef Cassie's fried potato salad. This was her elimination dish from the show, "Master Chef." Apparently, Wolfgang Puck didn't think much of it. After trying it, we don't think much of Wolfgang Puck's taste.⁣
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This dish, which is served warm, is composed of crispy fried potato chunks covered in delicious potato salad dressing. The combination of flavors and textures had us going back for more. #postcardjar #midlifetravel #emptynesttravel #goplaces #emptynest #emptynesters #midlife #couplestravel #couplestrip #midwestliving #midwestlivingmag  #midwestmoment #igersmidwest #midwestisbest #masoncity #clearlake @masoncity
  • In Rochester, Minnesota, in the shadow of the famed Mayo Clinic, is a beautiful pedestrian area called the Peace Plaza. Because of its location, it's often the last area a person walks through as they go to the clinic hoping for help. And, it's the first place people pass as they leave the clinic sometimes with good news, other times to confront their own mortality.⁣
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The designers of the plaza seemed to understand the huge role the space would play in the lives of the people coming through. They designed it as a calming, meditative space filled with tranquility. It's a place you can refocus a little, and take some time to transition from the clinic to the world. And, it's just one more example of the ways that @minnesotas_rochester demonstrates humanity to the hundreds of thousands of visitors who come each year to the clinic.
  • Are these salt and pepper shakers not the cutest?? Pawhuska, Oklahoma, is a magical place at Christmastime. We stopped by the @pwmercantile this morning and snapped a few new pics. Getting excited for the Holiday Lights Parade tonight!
  • We have four holiday gift guides up on the blog for the traveler, home cook, cruise lover, and road tripper on your shopping list! Just click on the link in our bio to check out our blog. ⁣
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One of our all-time favorite items (it made two of our lists) are these @EagleCreek packing items. This starter set goes with us on every single trip. Last year, Steve packed 16 size XXL shirts in on of them. They are super lightweight, safe space in your suitcase, and help you stay organized as your travel. ⁣
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What are your favorite gift ideas for travelers this year? ⁣
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#postcardjar #midlifetravel #emptynesttravel #goplaces #emptynest #emptynesters #midlife #couplestravel #couplestrip #giftideas #giftsfortravelers #traveler #travelgifts #giftguide #roadtrippin #packingtips #packingbags #howtopack #packlight #eaglecreek #celebritycruises #travelblogger #packing #packinghack #giftsph #holidayshopping #giftidea #travelgram #packing101
  • Who's ready for some pumpkin pie??⁣
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The thought of digging in to a piece of pumpkin pie (served with a cup of coffee with pumpkin spice creamer) takes us back to a small town festival we love. ⁣
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A few years ago, our town of Crete, Nebraska, began holding the Great Pumpkin Festival during the first weekend of October.⁣
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From spring to fall, local volunteers tend gardens filled with pumpkin vines so that folks who come to the festival can take home a reasonably priced, locally-grown pumpkin. ⁣
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The festival is full of games, food, performances and fun. It's a wholesome day where the town turns out to celebrate another year together in a relaxed, calm atmosphere.⁣
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Does your town have a festival? Tell us about it in the comments below.
  • ***NEW BLOG POST *** Today is exactly 8 months since we started our weight loss journey using the @noom app. See how we’ve lost 126.3 pounds while traveling. Just click on the link to our blog that’s in our bio to read our answers to your most asked questions about weight loss. And click to the second photo here to see our “before” pic.

Second most popular blog in Pawhuska