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Life on a Windstar Cruise: Billionaire Boating for the Rest of Us

By Sixty and Me November 18, 2017 Travel

There is nothing ordinary about the drive from historic downtown Rome to the port at Civitavecchia. As you leave the capital, you feel the weight of stone and sculpture, culture and commerce lifting from your shoulders. In its place, a gentle breeze lifts your spirits as the Mediterranean pulls you towards your next great adventure.

If there is one word that describes the feeling of approaching Civitavecchia, it is “anticipation.” The warm air makes your skin tingle. The ocean shifts from azure to royal to navy so seamlessly that, at times, the view feels more like a canvas than a coastline.

The Mediterranean is also a playground for the rich and famous. Between the branches of Italy’s Stone Pine trees, you catch glimpses of millionaires and their private yachts. Rather than clash with their surroundings, these moving works of art add a human element – a glitz and glamour – to the natural canvas that they call home.

Bigger is Not Always Better at Civitavecchia

It’s hard to appreciate the scale of some of the ships that dock at Civitavecchia until you see them up close. Some of the vessels that sail from Rome carry thousands of passengers. They are marvels of modern engineering and their crews have mastered the art of providing consistent, acceptable service. They are efficient, practical and just a little intimidating.

Approaching the Windstar Star Pride is a different experience entirely. You are not awed by its size so much as you appreciate its beauty. It looks more like a billionaire’s plaything than an ocean-going people-carrier.

Waiting to board a larger cruise ship makes you feel like a passenger. Waiting to board a small, luxury ship, like the Windstar Star Pride, makes you feel like an owner.


The sense that you are on a private ship extends to many aspects of your journey on the Windstar Star Pride. Here are just a few examples.

The Suites Give You As Much Privacy as You Want

By far the best part of our journey on the Windstar Star Pride was the spaciousness of our suite.

Having a living room, walk-in closet, bathroom and bedroom made our time on the Windstar Star Pride feel like we were sailing on our own ship. We could choose to be social. Or we could sit in our room all day, watching the waves, playing cards and catching up on life.

Every morning, my wife and I stood on our balcony, drinking coffee and watching the sun rise. In those moments, we forgot that we were on a cruise. The moment existed for the two of us alone.


Dinner is a Social Affair – Unless You Want it to Be a Private Experience

Windstar goes out of their way to make luxury dining accessible. Their dress-code is surprisingly casual – just leave your flip-flops, shorts and t-shirts back in your cabin.

The food, while delicious, comes in generous portions. It felt like the chef struck the right balance between culinary art and practical cuisine.

That said, even though dining on the Windstar Star Pride was casual, there were times when you just felt like staying at home. Fortunately, Windstar doesn’t make you compromise when it comes to in-room dining! In fact, all of the dishes that are available in their main restaurant are also available for delivery to your room.

One of our favorite memories from the entire trip was sitting in our room all evening, playing Monopoly on our iPad and munching on course after course of spectacular cuisine.

They Have All the “Toys” You Could Possibly Imagine

No image screams “billionaire boating” louder than a group of travelers jet-skiing, swimming and snorkeling from the lowered back of their own ship.

The Windstar Star Pride embraces this image by offering its guests the opportunity to relax in the water around the ship.

Unfortunately, the waves were a little too “enthusiastic” on this trip. As a result, we weren’t able to break out our swimming trunks – at least not until we reached the beach. But, if we ever travel with Windstar again, we will be the first ones in the water!

Small Ship = Small World

If you want to travel between global capitals, any large cruise ship will do. But, if you want to anchor off the coast of the scenic village of Portofino, you need a smaller vessel.

During our time on the Mediterranean, we only saw the largest cruise ships from a distance. There really was a feeling that we were on a private ship as opposed to a floating hotel.

Once again, this level of privacy and intimacy, contributed to the illusion that we were owners rather than simply guests. It was a refreshing break from the ordinary.


The Private Tours Were Unique and Well Planned

We were pleased to discover that the tours that Windstar offered went beyond the typical “walk around the city.”

Our favorite excursion was the “Ultimate Olive Experience.” For half a day, a group of 6 of us traveled by private car into the hills above Cannes, France.

During the tour, we walked through spectacular olive groves and learned about the art of making luxury olive oil. Then, the proprietor taught us how to taste and describe olive oil. Finally, our day closed with a 7 course meal, featuring lovingly created, olive-oil-based, delicacies.

It was a day that we will never forget!


Of Course, There Was Room for Improvement

Even luxury cruise ships have their flaws and the Windstar Star Pride was no exception. When we arrived, the crew seemed a tad weary from their previous sailing. They warmed up over the next few days, but, there was a noticeable lack of energy at the beginning.

The rooms, while spacious and comfortable, felt like they were ready for a few upgrades. For example, the ship still relies on a DVD library rather than a centralized entertainment system. In addition, the room only had two power outlets. In a world of iPads, computers and phones, it felt like we were doing the “charging dance” to keep all of our devices up and running and I’m sure that many other guests felt the same.

Finally, for a luxury cruise, we were somewhat surprised to discover that no alcohol was included in the standard fee – not even beer or wine. The alcohol packages were as much as $50 per person per day, which felt a little on the steep side.

Experiences Don’t Have to Be Perfect to Be Priceless

Was the Star Pride perfect? Of course not. There is always room for improvement, even on the best run ships.

That said, as we talked to the other passengers on the Star Pride, it became clear that everyone was genuinely having a good time. They appreciated the flexibility that being on a small ship offered. They enjoyed the wonderful food, in the presence of others or from the privacy of their own cabins. They appreciated the warm service that the crew offered. Most importantly, they took advantage of every opportunity to create priceless memories.

If you are looking for a cruise that offers the feeling of being on your own private yacht, Windstar is a great option. We hope you enjoy your next adventure!

If you could go on a cruise anywhere in the world, where would you travel to? Have you ever traveled with Windstar? How would you describe your experience? Please join the conversation!   

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The Author

Sixty and Me is a community of over 500,000 women over 60 founded by Margaret Manning. Our editorial team publishes articles on lifestyle topics including fashion, dating, retirement and money.

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