Windstar Cruises Expands Guest Services with New Leadership Appointments

[By: Windstar Cruises]

Windstar Cruises, a leader in small ship luxury cruising, is expanding and rebranding the company’s Guest Services department, including announcing the appointments of Jaymi Fiveash as Senior Director of Vacation Planning and Andrew Ironstone as Director of Outbound Consumer Sales. 

The rebranding from Guest Services to Vacation Planning is meant to better reflect the team’s expertise in organizing Windstar vacations, as well as to mark a fundamental change in the group’s approach. “Rather than just managing the guest booking process, the emphasis will now be on proactive sales as well as specialized expertise to craft personalized vacations for Windstar’s diverse customers and travel partners,” explains Janet Bava, Windstar’s Chief Commercial Officer.    

In the elevated role of Senior Director of Vacation Planning, Fiveash assumes responsibility for overseeing inbound and outbound reservations, the passenger air program, onboard cruise consultants, and pre-cruise guest operations. With more than a decade of experience with Windstar, Fiveash’s journey within the company spans various roles starting as a Vacation Planner in Guest Services. She will now establish dedicated teams specializing in outside sales, inbound reservations, and a groups team to support the trade and sales department. Onboard cruise consultants are also an important part of her Vacation Planning team. All vacation planners are U.S. residents who have sailed with Windstar and are well-versed in the brand. 

“At Windstar, our goal is to provide the best vacation experience for each individual, whether that be a completely all-inclusive vacation with air, hotel, transfers, drinks, excursions, and other onboard amenities, or an a la carte experience created with you by a Vacation Planner,” says Fiveash.  

Andrew Ironstone joins Windstar as the Director of Outbound Consumer Sales, tasked with developing and leading the Outbound Reservations team to drive sales growth initiatives. Ironstone will be responsible for establishing and cultivating relationships with new Windstar guests, as well as providing personalized booking experiences like connecting the company’s most loyal guests with a Vacation Planner to guide them through their entire booking process.  

Ironstone is a seasoned professional in the cruise industry, having previously led the Outbound Sales growth initiatives at Crystal Cruises and Silversea Cruises. Andrew most recently took charge of a team comprising over 100 outbound sales agents at Princess Cruises, where he played a pivotal role in ensuring the achievement of their monthly and yearly sales targets. 

"We are thrilled to refocus our guest services operations as a new Vacation Planning team, combining Jaymi’s wealth of experience cultivated over years of commitment to Windstar Cruises with Andrew’s expertise in building and leading call center teams within the cruise industry,” said Bava. 

Windstar recently announced the addition of two new ships to its Star Class fleet. The first of the two ships, new-build Star Seeker which is currently being constructed in the WestSEA shipyard, is expected to be delivered in December of 2025, followed by Star Explorer in December, 2026.