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!

  • Perched high on a hill in Tuscany is the medieval village of Montepulciano. In the center of town is the piazza grande paved with bricks laid in a herringbone pattern in the 14th century. ⁣
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Standing in the piazza, looking at the bricks, we were filled with a sense of awe at the history these bricks have seen. They've been there for 700 years so have seen times of war and peace, celebration and sorrow. Generation after generation of townsfolk were born, lived and died, and all have walked on these bricks. ⁣
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This is one of the things we love most about traveling. It gives us an authentic feel for history, one we wouldn't have if we just stayed at home.
  • We were so tickled when @thechefandthedish reached out and asked us if we'd like to take a complimentary cooking class with them. They offer private cooking classes with chefs from all over the world that you can take right in your own kitchen. ⁣
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For this class, we Skyped with chef Paola who taught us to make strawberry risotto, traditional bruschetta, and a delicious poached pear dessert that blew our minds. ⁣
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Risotto always seemed like a difficult dish to make, but Chef Paola explained it so well that it wound up being pretty easy. We spent a great afternoon with friends, learned something new, and enjoyed a great meal after. A class with The Chef & The Dish is a great gift idea, as well. Follow the link in our bio, and you can read more about our class on our blog.
  • The world is a big place, and there's so much to discover. Go places, and see things. It doesn't matter if you don't have a detailed itinerary, either. Sometimes, it's more about the journey and what you see and experience along the way, than it is about the destination.
  • During our trip in Tuscany with @italyunfiltered, we stopped at a small family winery. After learning about the organic methods they use to produce high quality Chianti Clasico wines, we had a tasting. ⁣
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Wine tastings in Italy are nothing like those in the US. They are glorious affairs complete with delicious foods paired with the incredible wines. This particular winery brought us samples of homemade, organic jams made from fruits grown in the family's garden. We dabbed these on locally produced pecorino cheese. Yum!⁣
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We're so glad that we had a local driver and guide. Stopping here was a highlight of our Italian adventure, and we never would have found it on our own.
  • The village of Marsaxlokk, Malta, is famous for these brightly painted fishing boats. The design is rather ancient, possibly dating back to Phoenician times, though it's still used today because it is very strong and holds up well in rough weather. One feature of each boat's decorations, are eyes painted on the bow of the boat. These eyes are said to protect the people fishing while they are at sea.
  • The blue cobblestones of Old San Juan, Puerto Rico, are actually part of a recycling project which started 500 years ago. Iron foundries in Spain produced huge piles of waste, called slag. Rather than throw these piles away, the slag was made into blocks which was placed into ships as ballast. The ballast was offloaded in Puerto Rico when they loaded products bound for Spain. The blocks were then used to pave the streets. ⁣
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Pretty good idea, and 500 years later, they are holding up well!
  • The Overseas Highway connects Key West and the Florida Keys to the mainland U.S. While the entire road is a marvel of engineering, the centerpiece is the Seven Mile Bridge, which runs over water for, well, seven miles.⁣
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The next time you're driving, reset your trip odometer and wait until it gets to seven miles. You'll see that's a pretty long distance. And then think about the fact that people built a bridge over water with no land to support them for that distance. Pretty incredible-especially since the first one was built in 1912.
  • We'd never heard of cannonball rocks before we drove past them at North Unit of Theodore Roosevelt National Park and asked each other, "did you see that?" We'd never seen anything quite like these natural "concretions" created when water leaked into pockets of minerals in the ground. Now, as a hill erodes, these formations are exposed.⁣
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Seeing these rocks was such a cool experience because it reminded us of why we travel. We never know when we'll find something new, something that we never knew existed. We got along fine not knowing about cannonball rocks, yet now that we've seen them, our lives are a little richer. ⁣
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The world is a pretty cool place. Check it out.⁣
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@ndlegendary

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