Day by Day: Windstar Cruises Caribbean Celebration

Posted onAuthorChris Owen

NOTE: Throughout this post, look for FIND OUT MORE to explore our related social content, posted before and after sailing. Also referenced Windstar Cruises Caribbean itineraries, including ours, a version of Windstar’s Yachtsman’s Caribbean itinerary. There are others.

Looking back at the 2019 Windstar Cruises & Porthole Cruise Magazine Caribbean Celebration, a day by day photo account of what we experienced.

We begin with a pre-cruise overnight hotel stay in St Martin, on the French side where most larger ships do not go. We were sailing aboard Windstar’s flagship, Wind Surf with just over 300 fellow travelers.

These photos capture the day from arrival at the St Martin airport via Jet Blue then into the night at the hotel and in town for dinner.

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Flying in to St Maarten was a entirely different experience than visiting for the day on a ship. First to notice on our flight from Orlando through San Juan then on to St Maarten: devastation.

The hurricane that hit here in 2017 wrecked the island and closed all hotels, including our hotel on the French side of the island, the Meridian Mercure an Accor Hotels Le Club property.

St Maarten Embarkation Day

The next day, we would board Wind Surf in St Maarten on the Dutch side most travelers are accustomed to. Arriving at the port, our ship was positioned right next to Royal Caribbean’s Freedom of the Seas. I did not think much of it at the time. I expected any large ship to dwarf 300 passenger Wind Surf and indeed Freedom did.

Little did I know, coming up shortly on our itinerary was a parallel narrative to this ship I had not thought about. When we get to Barbuda, a scheduled event was “local school to receive funds”. Sounded like a check presentation to me. A nice effort from both Windstar Cruises and Porthole Cruise Magazine in a sailing themed “Caribbean Celebration” which was about giving back “to a part of the world that has given us so much” as Windstar President John Delaney put it.

It was so much more than that. Stick a pin in that thought for now. We come back to that Freedom of the Seas element, what the celebration is all about and more in a couple days.

Sailaway day in St Martin brought settling in on the ship, a safety drill and Champagne sailaway welcome.

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There are travel moments that make is happy in one way or another. A beautiful place we’ve dreamed about, a location from history seen in person or checking off an item on a bucket list commonly come to cruising. Then there are truly profound moments when time stands still while we consider our place in this world. Returning to hurricane-ravaged Barbuda with Windstar Cruises tiny Wind Surf, we visited a school where right in the middle of all the destruction were kids enjoying life as kids do. In serious need of help, Windstar made a generous financial donation in a place that needed it desperately. I have covered the topic of cruise lines giving back for years. This one was so very appropriate, needed and appreciated….and that’s Windstar Cruises. They live, breathe and engage destinations on their tiny little ships like no other cruise line.

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Falmouth, Antigua

In Antigua, we visited a pineapple farm and toured the island from one side to the other.

I have been fortunate enough to visit so many interesting places around the world. Like this place where we met a hearty people recovering from the catastrophic moment we would see commemorated in history at other locations. Think Pompei but in the Caribbean.

Along the way, we passed through time as our guide detailed the social, political and geographic history of the island.

That tour, typical of the customizable Windstar touring experience leveraged what makes Windstar unique: really nice people.

Windstar Small Group Tours Bring Meaningful Travel, Enhance Our Worldview

Barbuda

This particular sailing is the third in a series of Windstar President’s Cruises, hosted by John Delaney, President of Windstar Cruises. 

Regular readers of this space know our mission. The meat of that we should review again today.

” …travel by ship is a great way to experience, understand then change our world in a safe, positive way.”

I can not recall a recent sailing that fulfills what we hope to accomplish here more than this one, on this day.

This day could have been memorable for the destruction viewed first-hand.  I could have told you that all cruise lines stopped coming here because there was basically nothing left.  Still, for the hearty people of Barbuda, a happy life is a priority, regardless of what they have or don’t have.

We talk a lot about the advantages of one cruise line over another and hope to provide a reliable source of information on one of the hardest but most important parts of cruising to describe. In other words: what it feels like. This one felt really good in so many ways.

Unexpected Windstar Port Call Brings Help, Understanding

Road Town, Tortola

The rum cake place. We got off and came back on, too many people. We were spoiled by this time. It is rather easy to become accustomed to being the only ship in port with around 300 people.

Similar to other cruise ships, not everyone gets off the ship at every port here. This image gives you an idea of the size of our ship, next to much larger Norwegian Epic.

Also a difference, the line waiting to go to the beach on a much larger ship than ours.

Jost Van Dyke

In Jost Van Dyke we were there for a day that will stretch into night, visit the legendary Foxy’s bar for an all-passenger party with last tender back to the yacht at 1:00 AM.

Snorkelers, this could be one of the best experiences ever.

Clear Eyes, Full Hearts, Can’t Lose: Windstar Cruises

Virgin Gorda, Fishers Cove

The big event here, the Beach Barbecue where Windstar brings everything they need to do it with them from the ship.

This is no private island experience yet water sports are easy off the Water Sports Platform that extends off the back of Windstar ships

Windstar Cruises: Your Questions Answered

Gustavia, St Barthelemy

Shopping, shopping and more shopping.

Followed by lunch then back to the ship to sail on to St Maartin and the end of our itinerary.

Unique Features Of The Standalone Windstar Cruises Experience

Previous and Upcoming Information Sources For This Cruise

  • Instagram– beautiful scenes not found at home, onboard ambiance and stellar crew members.
  • Facebook– I checked in at every place we visit, with photos.
  • Facebook Photo Albums– details captioned on the photos shown here
  • Google+– ChrisCruises posts in a different place
  • Twitter– Search the tags #WindstarCruises, #PortholeCruise, #WindstarCaribbean and #CaribbeanCelebration
  • Flickr Photo Albums- COMING SOON: one for multiple photos of each onboard event, destination visited, tour experienced and more
  • RSS Feed- everything we post here, delivered as you wish.
  • Exposure Photo Storybooks- COMING SOON- Created after sailing and reflection, these full-size images provide a distinctly different view of destinations and events also depicted elsewhere.
  • Day By Day- check right here for day by day accounts of our journey, posted in reflection.