Entertainment and Engagement Manager needed for Windstar Cruises!

Entertainment & Engagement Manager

Be at the heart of the guest experience.

As our Entertainment & Engagement Manager, you will lead the onboard entertainment and engagement operation while creating memorable moments and genuine connections with our guests. From hosting signature events and interactive activities to performing your own solo entertainment and developing engaging voyage programming, you will help bring the Windstar experience to life.

This is a highly visible, hands-on leadership role for an experienced entertainer who connects naturally with people, is confident in front of an audience, and understands how to create a warm, personal atmosphere throughout each voyage.

What You’ll Do

• Create meaningful connections with guests and maintain a visible, approachable presence throughout every voyage.
• Host and emcee daytime activities, evening entertainment, and Windstar signature events, including the Captain’s Welcome Reception and Journey Celebration.
• Develop and perform your own solo entertainment offerings.
• Plan and deliver a balanced entertainment and engagement program that reflects the Windstar brand and provides guests with compelling experiences throughout the day and evening.
• Produce and host the onboard Crew Show.
• Lead the onboard entertainment team and work closely with musicians and the AV Manager to deliver high-quality entertainment.
• Set clear expectations, support team development, and foster a collaborative, professional, and guest-focused culture.
• Produce the Daily Program and support additional onboard guest communications.
• Work closely with the Hotel General Manager and other shipboard departments to support the overall guest experience.
• Introduce fresh ideas and continually identify opportunities to strengthen entertainment and guest engagement.

What You’ll Bring

• Proven experience as a live host, entertainer, cruise director, entertainment manager, or similar guest-facing entertainment professional.
• The ability to develop and confidently perform solo entertainment for a live audience.
• Strong communication, presentation, and emcee skills.
• Leadership experience and the ability to motivate and develop a diverse, international team.
• Creativity, enthusiasm, and a genuine passion for creating memorable guest experiences.
• Strong organizational and administrative skills, with the ability to manage programming, communications, and multiple operational priorities.
• Good computer skills, social media knowledge, and a basic understanding of audiovisual equipment.
• Previous cruise ship experience is preferred.
• STCW Basic Safety Training and Security Awareness certification, or the ability to obtain these certifications.

Why Join Windstar?

Windstar’s small ships create opportunities for genuine interaction and a highly personal approach to entertainment. You will have the freedom to connect with guests, develop creative programming, lead an international team, and directly influence the experience of every voyage.

If you are an experienced entertainer and leader who knows how to engage a room, build meaningful guest connections, and bring creative ideas to life, we would love to welcome you aboard.
 

Apply Now