Go Behind The Scenes on Windstar’s 56 Day Grand Caribbean Cruise

We took a few moments to sit down with Jess Peterson, Windstar’s  Director of Revenue & Itinerary Planning, to learn more about the philosophy behind the Star Collector: Grand Caribbean Cruise and to get a deeper understanding of how Windstar takes guests closer to unique, small ports for an unforgettable journey.Cruise_Colombia_Cartagena

Can you tell us a little bit about the Grand Caribbean Cruise?

In early 2020, Wind Surf will embark on a  56-night voyage around the entire Caribbean, from St. Maarten to Barbados to Panama to Mexico and back to St Maarten. The long voyage will be segmented into seven different 7-to-11 night cruises. You can join us for the full 56 days or you can join part of the grand cruise. The Star Collector: Grand Caribbean Cruise will be the first time our flagship enters the Panama Canal for a partial transit, and it will be the first time she’ll visit several ports in Panama and Mexico.52_days_Caribbean_cruise

What is your philosophy behind a Grand Caribbean Cruise?

There are two main ideas behind a Grand Caribbean Cruise. First, we know many of our Yacht Club members love Wind Surf and want to sail on her somewhere new. This Caribbean Cruise will visit many places that the Surf has never been or has not visited in more than a decade. Second, we want to give our guests the opportunity to sail for a long period of time on Wind Surf without repeating ports. Guests can choose to join for one week, a few weeks, or the whole 56 days and they’ll continue to visit new places.Wind_Surf_Cruise_Ship

What are you looking for specifically when designing this kind of itinerary?

First, we always visit unique, small ports that make Windstar special. That’s why the Caribbean Cruise visits places like Bocas del Toro in Panama and Cayman Brac in the Cayman Islands. Second, whenever possible we include Windstar Signatures like the Beach Barbecue and the Onboard Barbecue. Perhaps most importantly, we design these cruises to give our guests a comprehensive understanding of a region. To do that, we visit a variety of places including larger cities like Cartagena and smaller islands like Mayreau and Isla San Andres in Colombia.Beach_Barbecue_Windstar_Cruises

What makes a Grand Cruise?

We design long “Grand Cruise” itineraries as in-depth explorations of an entire region. On our Star Collector: Grand Caribbean Cruise we visit every corner of the Caribbean and stop at several places in the countries we cruise to. One thing we’re particularly proud of at Windstar is that our Grand Cruises are so port-intensive. Normally, long cruises are full of sea days. At Windstar, it’s all about the destination and almost every day you’ll visit a new place. Cruise_Barbuda_Caribbean

Why are you proud of the latest Caribbean Cruise itinerary?

I’m particularly proud of the “Grand Caribbean Cruise” because it goes to so many places that Wind Surf has not been to in a long time, and I don’t think there’s another cruise line that does anything like it. Many of our guests love our sailing ships in the Caribbean, and this cruise gives them the opportunity to sail as long as they want while visiting a new place every day.

Great deals happen. Don't miss one.
Sign up for our newsletter!

Notify of
Newest Most Voted
Inline Feedbacks
View all comments
3 years ago


Frank Hanrahan
3 years ago

Sign me up for the full 56 days,, sounds like a fantastic cruise.

Dimitri Lapin
3 years ago

56 days – How much?

Dennis Fitzsimonds
3 years ago

Which boat are you planning to use for the grand cruise?

Dennis Fitzsimonds
Reply to  Dennis Fitzsimonds
3 years ago

I see it’s the Windsurf.

Jerri Ginman
3 years ago

That is fabulous!

j conklin
3 years ago


Would love your thoughts, please comment.x
Scroll to Top