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Windstar Cruises: Intimate & Casual Luxury – Its History and How it Transformed Itself is “180 Degrees from Ordinary!”

Windstar Cruises is one of my favored cruise lines, offering what I call “casual luxury” on small, even intimate, ships and with two distinct and unique types of “yachts”: Power and Sail.

Two of Windstar Power Yachts

Windstar, in fact has pretty much always been, “different”. It’s tag line is “180 Degrees from Ordinary“, but it is more than that. Windstar has been reborn quite a number of times and, to be sure, the current iteration of the brand is more of a transformation into “What was Old is Really New and Ever-Improving!”

Most people really don’t know much about Windstar and even less about its rather interesting “180 Degrees from Ordinary” history. So let’s take a bit of step back. Trust me: You will really appreciate the “New” after you understand Windstar’s history.  For me, it speaks to the underdog or ugly duckling that ultimately not only succeeding, but impressing.

Windstar Star Breeze in French Polynesia

In the early 1980’s Windstar emerged as a unique one ship motorsailing cruise line with its first 148 passenger four-masted ship, not so ironically named Wind Star, finally being launched in 1986. This was followed by her sister ship, Wind Song, in 1987; later renamed Wind Spirit. During this period Windstar had already started up its plans to build the 342 passenger sailing ship Wind Surf and a sister ship, Wind Saga.

Wind Surf
Wind Surf

For reasons that I (and many others) have never understood Holland America purchased 50% of Windstar in 1987 and eventually the remaining interest. However, the Holland America deal ended the plans for the twin 342 guest ships. And, further complicating Windstar’s history…which has yet to really get complicated, in 1989 Holland America was purchased by Carnival Corp.

But the plans for the ships, with French government assistance, did not stop. Eventually these two 342 guest sailing ships were built for Club Med Cruises and were named Club Med I and Club Med II.  They were known as the largest passenger sailing vessels. Eventually Holland America wanted to purchase these two ships, but only had enough money for one: Club Med I…which was renamed as she was originally intended: Wind Surf.

The operational and marketing conflict between the classic Holland America fleet the quirky, substantially smaller, sailing fleet of Windstar really placed Windstar as sort of the ugly stepchild; not really fitting in – and not receiving – the care and attention it deserved. 

As a result, Holland America sold off Windstar to Ambassador International in 2007 as it was on a bit of buying spree of other cruise assets. Let’s just say Ambassador’s plans did not work out well and it found itself in deep financial trouble almost immediately.  Eventually Ambassador filed for bankruptcy in 2011.

In 2011 Anschutz Corporation bought Windstar Cruises at auction for $39,000,000 and eventually transferred Windstar Cruises into its impressive Xanterra Travel Collection.  Xanterra owns and operates most all of the US National Park hotels, the luxury Broadmoor Hotel, a few tour operators, and more. This is – finally – when Windstar Cruises found a stable home and owners that were committed to it as a cruise line and had the knowledge and experience in the travel industry to make Windstar successful.

Understanding the economies of operating a small cruise line with two 148 passenger and one 342 passenger sailing ships with modest pricing, limited mobility and, thus, limited itineraries, Xanterra understood that expansion was necessary.

Thus, in 2013, as Seabourn was in the middle of fulfilling its plans to upgrade its fleet with the 450 guest Seabourn Odyssey and her sisterships Seabourn Sojourn and Seabourn Quest on the way, and with the potential for two larger 600 guest ships, Seabourn Encore and Seabourn Ovation, Windstar was able to purchase the much beloved Seabourn Triplets: The 212 guest all-suite Seabourn Pride, Seabourn Spirit and Seabourn Legend.

Oh, but now what to do with them? You see Seabourn has been struggling with how to upgrade and transform these circa 1988-1990 aging ships and Windstar’s then management was in a similar situation. But now Windstar had two very different products…and that presented a number of additional challenges.

During the period when Seabourn was still operating the triplets, but after the deal was struck, Windstar invited me onboard the Wind Surf to see what the Windstar product was like and what I felt would need to be modified for the more upscale/luxury focused guests on the triplets after they were acquired. Windstar’s Wind Surf – Caribbean – January 2014

Over the years I had the opportunity to become part of the “Seabourn family” when it was just a small cruise line in Miami…before it, ironically, was pretty much combined with Holland America shortly after HAL offloaded Windstar. One thing – of many – I learned is the triplets are unique, intimate ships that were designed for an international, multi-port, luxury experience…one thing Windstar’s shorter warm weather itinerary sailing ships were not. 

After a bit of a fumble, Windstar then installed new management, hiring a new president: John Delaney, formerly Seabourn’s Senior Vice President. John had been integrally involved with those contemplative discussions over his tenure at Seabourn, so he was a perfect fit. That coupled with quite a number of other former Seabourn executives ranging from hotel to maritime operations having come over from Seabourn (including Windstar’s now president, Chris Prelog) some interesting plans were being developed.

Go Big or Go Home

After the initial modest efforts were made to get the ships up and running with a few modifications, the poor condition of so many systems on the ships and the need to replace them became apparent. So, with a deep breath, Philip Anschutz, made the decision to truly refit the ships rather than merely renovating them.

The “Cutting Edge” Extensive Refit of the Star Power Yachts

Windstar Star Initiative Stretch

It was decided that if the triplets were going to not only attract luxury clients but also have a long economically viable lifespan, drastic measures would have to undertaken: The ships would be cut in two parts, adding a center section to provide the space needed for, among other things, additional venues (two more restaurants, an expanded spa and a larger fitness center as well as additional suites (so as to make the economics of operating the ships more favorable).

It was also time to say goodbye to the old, environmentally unfriendly, engines that also were slow and limited the itineraries Windstar could offer to its new luxury, and travel-experienced, guests.  As it was for the old, patched up plumbing (always an issue when they were Seabourn ships) and antiquated and inefficient electrical systems.  

With new systems came all new bathrooms, better lighting, and much more. You can read about all the improvements here: Windstar’s Star Breeze – Major Extension and Modifications Underway!

Major Upgrades to Windstar’s Service, Culinary & Wine Experiences

Fresh Dorade Prepared by the Windstar Chefs

But as is always the case, it is not just about the hardware, but the software (the people and services). Windstar has always been known for friendly, personal, service, but now it was time to elevate service levels and the staff was not only up for it, they were excited about it.

The entire culinary operation was recreated, not only because the two new restaurants (Cuadro 44 and Star Grill) were significant departures from “cruise ship cuisine”, but both Amphora (the main restaurant) and the Veranda (Candles Steakhouse at night) needed to upgrade their culinary experience to compliment these new venues. 

Cuadro 44

In fact, Windstar established an important, and forward-facing, relationship with the James Beard Foundation; now regularly hosting James Beard Foundation sailings and guest chefs.

Recently, with another former Seabourn executive chef coming onboard, Windstar decided not only to continually upgrade its classic offerings, but to install a true vegan menu, more local cuisines, add culinary shore excursions and Shopping with the Chef (complete with a special dinner focused on the day’s purchases). This has put Windstar’s culinary experience at the true luxury level. (The way I explain it is: “Some lines will provide a dish with 12 elements to impress. Windstar will probably provide a dish with 5 elements, but they are all done exceptionally well.” )

Windstar House-Made Pastrami is New York Deli Quality

But what is amazing  Cuisine without amazing wines?  Windstar now has what I consider to be one of the best, most diverse, international wine lists at sea.  As with its ships, it is not the largest, the most expensive, or focused on different vintages, but it is impressive and marries well with the International, Steakhouse, Spanish, Barbeque/Smokehouse, Vegetarian, and Vegan cuisines that are always available on these luxury yachts.

New and Longer Itineraries

Windstar Legend – China Land Extension

With the Star Pride, Star Legend, and Star Breeze now fit out with new engines that can move the ships faster and more efficiently, Windstar took a hard look at its itineraries. With the advantage of being truly small ships (large yachts, if you will) Windstar focused not only on unique small ports, but longer distances between ports. This opened up some truly exotic locations and ports and calling on them in less time that the older version of these ships could offer.

Windstar “prides” itself (sorry, I had to) on its robust international itineraries. I have traveled on Windstar from Hong Kong to Beijing, Turkey, Greece, Israel, Italy, Spain, French Polynesia and more. And, Windstar offers high quality pre- and post- cruise land extensions.

Quite impressive for a small cruise line with small ships! 


One of the biggest issues for those taking longer cruises (and those who are active on social media) is access to dependable internet. The triplets were well-known for having terrible internet. But no longer: Starlink is installed on all of Windstar’s ships, except those located in French Polynesia (as Starlink is not yet available).

While, as of this writing, Starlink is not available everywhere, especially in the more remote and exotic locations, it is another significant improvement by Windstar.

Pricing Structure

With the big changes at Windstar, but with it also having extremely loyal guests who are used to the “old” Windstar, especially on its sailing yachts, Windstar had a pinch point: How to offer an inclusive product for the more luxury client while also having an ala carte product that many of its guests prefer?

The answer is Windstar offers something unique: Two Tier Pricing. Cruise Only and “All In”.  All-In pricing includes an extensive list of premium spirits, wines and beers, unlimited wi-fi, and gratuities.  (There is also an unlimited laundry add-on at a modest cost; something that is automatically included on back-to-back journeys.) 

The Sailing Yachts

Windstar’s sailing yachts remain a unique opportunity to kick back, unfurl the sails, and enjoy a casual experience, but now with elevated levels of service, cuisine, etc. being fairly consistent with the three power yachts. 

The flagship, Wind Surf, underwent an extensive renovation on 2019, adding 16 staterooms and suites with new, neutral, decor, adding a state-of-the-art Wellness Center and refurbishing all of the public areas.

Wind Surf Compass Rose

It also offers Amphora, Veranda, Candles, and Stella Bistro (with French-influenced cuisine) as dining options. Along with it Yacht Club and Compass Rose lounges, Wind Surf aligns well with the triplets.

Windstar’s two smallest sailing yachts, Wind Star and Wind Spirit are even more casual with similar, but downsized, amenities, having also had extensive renovations recently completed. 

The Wind Spirit has been based year-round in Tahiti, but in February 2024 the Star Breeze will be replacing her. 

Star Breeze Whirlpool in French Polynesia

The three sailing yachts, designed for warm weather sailing/cruising will continue to call on the Mediterranean, Caribbean, and Central America. 

Overall Impression

Windstar’s transformation from an unwanted ugly duckling to a financial stable, world-class luxury cruise line, offering what I call “casual luxury” is remarkable.  It has gone from a cruise line that I never would have considered for my upscale and luxury clients to one of my favorites…and theirs too!

Now that is “180 Degrees from Ordinary!”

Interested in a Luxury Journey by Cruise, Expedition, or Land?

Contact Goldring Travel For Truly Expert Advice!

Email: eric@goldringtravel.com 

US: (877) 2GO-LUXURY or (530) 562-9232

UK: 020 8133 3450

AUS: (07) 3102 4685

WhatsApp: +1 732-693-8797

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