Windstar Cruises Finds Success With Mystery-Destinations Cruise Trend

Forbes

18-05-2025

Windstar's Star Legend yacht sails to its next unknown port..
Jenna Talplin/Windstar Cruises
'Would you book a cruise if you didn't know where you'd be sailing?,' asks Sarah Kuta of TravelPulse.
The idea that you board a cruise ship in one city, but have no idea where you're going next and what other destinations are on the itinerary may seem strange to some. But, this trend has been growing among cruise lines as they look to diversify their offering and appeal to frequent cruisers.
Windstar Cruises is the latest to offer such a mystery cruise with its first official Mediterranean itinerary last month that proved so popular that it many guests locked into the line's next mystery sailing in the Caribbean before this trip even ended.
Star Legend docked in Nice
Windstar Cruises
Travelers book a departure date on a particular cruise ship, but the only details they know are the first and final ports of call on the sailing. From these geographic details, they can get an idea of what clothes to pack, but the rest is a mystery.
What travelers do know, however, is that they will not be visiting the 'traditional' ports (like Freeport, Bahamas or Mykonos, Greece) that are on many other cruise itineraries. Instead, the purpose of these cruises is to bring guests to surprising destinations they may not be familiar with or could not easily reach on another cruise.
An on-deck barbecue at sea aboard a Windstar yacht
Windstar Cruises
'Windstar sets a high bar,' says travel advisor Dana Okamura, No Worries Travel LLC, when explaining why she attributes success to these secret-destination sailings among repeat Windstar customers. 'There is a built trust that can be even more important when so much of the experience is unknown.'
Two Windstar vessels in Monemvasia, Greece, a smaller port not visited by many other cruise lines.
Windstar Cruises
This type of secret cruise is typically in the realm of small-ship cruise lines like Windstar that can get into smaller ports that larger vessels cannot. More than half the ports it visits on these mystery sailings are new to the company. This provides a chance for the cruise line to see how they appeal to travelers, but also experiment with destinations that may have been hidden secrets, says Janet Bava, chief commercial officer for Windstar.
The beach in Reggio Calabria, Italy, which was a new port for Windstar, and now on its future itinerary list.
Jenna Talplin/Windstar Cruises
Two of the destinations on the first official mystery cruise, Taranto and Reggio Calabria in the 'boot' of Italy, were a hit and are now planned for 2026 Italian sailings. Okamura says these new ports inspired some of her clients to book similar cruise itineraries in the future.
Windstar is not the first to offer a mystery cruise. Variety Cruises, Fred Olsen Cruises and Uniworld Boutique River Cruises have all dipped their anchors into this trend. Fred Olsen even goes so far as to identify one particular sailing for beginners (probably a clue of the type of more 'traditional' ports it will visit).
Still, Windstar offers the most upscale product in this category of ocean mystery cruising. The lead-in price for its April cruise on the all-suite Star Legend was $4,399 for two people, with the option to include drinks, gratuities and Wi-Fi for about $800 more on the seven-night trip.
Windstar executives (l to r): Stijn Creupelandt, chief operating officer; Janet Bava, chief commercial officer; Christopher Prelog, president
Jenna Talplin/Windstar Cruises
Windstar President Chris Prelog says the idea came about by accident. He was hosting a sailing to the Tuamotu and Society Islands when a cyclone disrupted the ship's itinerary so much that it was unable to visit the planned ports.
Within hours, he says, the operational team had devised a new itinerary, and one that few cruise lines offer: the Marquesas Islands. It proved to be a big hit with passengers, who understood that sailing into a storm would not be ideal.
Windstar has a high ratio of returning guests, many of whom are already acquaintances from past sailings.
Windstar Cruises
As Prelog tells it, he was dining with a group of loyal Windstar customers (some of whom have sailed dozens of times with the line), and they all shared that the chance to visit a hard-to-get-to place and the serendipity of it all was especially exciting. Prelog posed the idea of a mystery cruise to his table mates, and by the end of the dinner, they had all made their deposits for the April 2025 Mediterranean sailing.
Next year, Windstar will operate a similar sailing in the Caribbean departing March 20 with a starting rate of $2,999 per person, and an 'all-in' rate of $3,692. It will set sail on a roundtrip journey from San Juan on the 224-passenger Star Seeker, the newest yacht for Windstar that will be delivered by December of this year. The sold-out journey now has a waitlist.
Reggio Calabria, Italy
Jenna Talplin/Windstar Cruises
Passengers aboard the initial sailing say it was almost a running joke explaining to friends and even the taxi driver that brought them to the ship that they had no idea where they were going.
Once onboard, passengers received clues throughout the day so they could compete for a prize awarding the passenger that guessed them all correctly.
Okamura, who booked several passengers aboard the mystery cruise, but also sailed herself, says that fellow passengers quickly bonded over guessing where they were going and researching the clues online. But, most people aboard the first President's official mystery cruise were already friends with each other and the crew. Prelog says this cruise had a repeat traveler rate of 80%.
A passenger learns how to fill cannoli in a Sicilian kitchen on a shore excursion.
Jenna Talplin/Windstar Cruises
'Only the captain and senior officers know where the ship is heading, and are sworn to secrecy,' says Cruise Critic Jeannine Williamson, when describing the concept.
Not even Prelog knew where the ship was going.
Each evening, the captain would announce the destination, and guests would gather in the lounge to learn what there would be to do and see once they arrive. In advance of the sailing, the gist of the shore excursions were made available in cheeky riddles hinting at the activity on offer (like hiking to a castle or visiting a vineyard), but it was only once the details were announced that guests needed to finally commit to the tour.
Guests on a shore excursion in Taormina, Sicily
Jenna Talplin/Windstar Cruises
Other ports of call on the Mediterranean trip included Sicily's Naxos Giardini (the port near Taormina, home to 16 Michelin-starred restaurants and filming location of HBO's The White Lotus 2) and Kalamata, Greece.
For passengers who may not be interested in the destination, the on-deck pool, onboard dining venues and sometimes the watersports platform is available.
Windstar Cruises
Windstar's first official mystery cruise was a success, and it has already sold out for 2026.
But, is a mystery cruise for everyone? For those that do not need to over plan a vacation and like a bit of surprise, a mystery cruise is great. But, for those with their heart set on a particular country or type of port, this is an easy recipe for potential disappointment, notes Williamson.
This sentiment is echoed by other industry experts.
'While mystery cruises can be novel and a fun way for cruise lines to entice their most loyal guests, most people do like to know where they are going on their vacation, particularly if they have limited days off or set times when they can travel,' says Chris Gray Faust, executive editor, content innovation, for Cruise Critic.
Star Legend sails along the Thames River.
Windstar Cruises
'It's the type of thing that works much better for a small or a river ship that sails in a relatively contained area of the world rather than a large megaship,' she adds.
The concept for booking a trip to an unknown destination is nothing new. Brands have offered these one-off trips for years. Atlantic Airways of the Faroe Islands has sold mystery flights year after year to warm-weather destinations and they sell out quickly among locals looking to escape the cold (despite not knowing the Mediterranean location until they arrive at the airport).
Outdoor decks on Star Breeze
Windstar Cruises
And the internet is filled with travel advisors and tour agencies that sell these types of hidden adventures. Whodunit Cruises even coordinates 'murder mystery' sailings bringing a bit of the uncertainty on board.
Okamura acknowledges these sailings are unique, but says they are ideal for 'someone with a true sense of adventure who is open to seeing unknown places and those they may have seen before, but in a new way.'
In other words, the ideal mystery cruise customer should have both wanderlust, and even more importantly, flexibility.