Pier & Port Experience Manager

Windstar Cruises•Miami, FL

About The Position

Awarded World’s Best Small Ship Cruise line, Windstar Cruises is known for intimate yacht style experience and unique voyages to the world’s best small ports and hidden harbors. Its three sailing yachts and four all-suite yachts carry just 148 to 342 guests and cruise around the world. Our mission is to imagine and deliver personalized and immersive experiences 180 degrees from ordinary. We enrich people’s perspective through inspired travel. Our Mission: Enriching Lives Through Travel Our Values: Guest Obsessed, Open and Inviting, Fun-Loving and Focused, Light-Hearted and Genuine, Casual Yet Polished, Safe and Responsible. Job Summary: Own and elevate the end-to-end guest experience in port — embarkation, debarkation, Destination Discovery Events (DDEs), and special events ashore. This is not a tour development role. It owns everything above the tours: the orchestration, experience design, and operational execution around tours and port-related moments, ensuring they are seamless, on-brand, and operationally sound. It exists to own the port-side experience and operations that surround tour products, and products created by the Land Product Development team.

Requirements

5+ years in cruise, travel, destination management, or large-scale live event operations, with direct turn-port or ground-operations experience.
Proven ability to run complex logistics under time pressure with an unforgiving deadline — the ship sails.
Strong judgement under pressure and a bias toward anticipating problems rather than reacting to them.
Excellent cross-functional communicator; able to direct third-party operators and local staff without direct authority.
Willingness to be on call across time zones during turn days and major events.
Comfort with operational systems and reporting; able to document and standardize what works.

Nice To Haves

Experience with pre- and post-cruise hotel programs, transfers, and cruise tour operations.
Prior experience in a luxury or expedition product where guest experience standards are high and volumes are small.
Systems experience to include MPX, Seaware, Hubspot, or similar
Additional language capability and international port experience.

Responsibilities

Design and oversee the minute-by-minute guest journey for embarkation, debarkation, DDEs, and special events in port.
Understand, assess and prepare for excellence in the full embark/debark flow — where check-in happens, whether the facility is suitable, transportation logistics, and luggage logistics with the Port Operations team. (Check-in itself is executed by Guest Services.)
Own the operational response and preparedness to pier and berth changes: shuttles, directional staffing, and guest movement between locations.
Ensure experiences are consistent, high quality, and aligned with brand standards.
Act as the experience owner for port-side events, focusing on emotional impact, flow, and wow moments.
Work closely and continuously with Product Managers for the assigned regions.
Support Product Managers to remain the tour development artists, while this role owns the operationalization and the experience layer above the tours.
Translate new land concepts and product initiatives into clear port-side operational and experiential plans.
Partner with Product Development on DDE execution — DDE creation remains with the Product Managers; this role ensures seamless and continuous execution of logistics, staffing, timing, and set-up, and leads the recovery when plans change on the day.
Coordinate with relevant internal and external stakeholders — ships, port agents, vendors, Shore Excursions, Hotel Operations, Entertainment — to execute pier and port experiences.
Ensure logistics, staffing, timings, and set-ups for DDEs and special events are aligned and feasible.
Anticipate operational risk at pier and in port, and proactively design solutions that protect the guest experience.
Lead the at-risk port turn review process — identify first calls, new (and unfamiliar) turn ports, and high-complexity turns early, and table-read them with the relevant teams before they happen.
Manage guest-experience shuttle coordination and execution in port. (Contracting and sourcing remain with Product Development; port-required shuttles remain with Port Operations.)
Define the success metrics of pier-side dispatch experiences, and support the execution when required.
Manage the onsite pre- and post-cruise hotel experience, including hospitality staffing levels at the hotel and directional staffing at the pier.
Ensure accurate scheduling and day-of execution of guest transfers at the hotel and pier, including luggage transfers between hotel and pier; develop standards for meet-and-greet and transfer services.
Serve as the day-of operational point of contact for the ship and local tour operators in turn ports — the escalation point when a ship is delayed, a coach is short, or a schedule changes.
Own the operational and logistical response to pier changes, and support Guest Services and Vacation Planning on the related guest communications (arrival letters and pier change notices remain owned by those teams).
Oversee cruise tour arrival and departure execution at the pier, including re-planning onboard and problem resolution when it occurs.
Support the operationalization of special events in port that are not tours or DDEs — anniversaries, naming ceremonies, President's Cruise moments, greetings and receptions — working alongside the Experience Development team, Marketing and other internal stakeholders.
Remain available on an on-call basis for contingencies, emergencies, and unplanned itinerary changes.
Define and maintain SOPs and standards for embark/debark and port events.
Monitor performance and guest feedback across all pier and port experiences, and drive continuous improvement.
Ensure new concepts introduced by Product Development are properly embedded, documented, and repeatable across ships and ports.
Serve as the central point of contact for pier and port experience topics across: Product Development (tour development), Hotel Operations, Shore Excursion teams, Marine Operations and Itinerary Planning, Vacation Planning and Guest Services, Shoreside and shipboard partners, port agents and local operators.
Communicate expectations, event plans, and changes clearly so that local teams can execute reliably and independently.