Director of Port Operations

Windstar Cruises•Miami, FL

About The Position

Join the Windstar Cruises team: 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. Job Summary: We are seeking a talented Director of Port Operations to provide strategic leadership and operational oversight for all port‑related activities across the fleet. This position serves as the primary authority for port operations, drives continuous improvement, and ensures operational excellence across itinerary planning, port logistics, financial management, vendor relations, and systems optimization. The Director leads the full port agency bid process, manages fleetwide budgets and forecasting, negotiates vendor contracts, and oversees accurate port‑related financial tracking. This role is also responsible for leading the implementation and long‑term optimization of the MXP system, ensuring efficiency, compliance, and alignment with corporate and industry standards.

Requirements

5+ years of progressive Port Operations experience within the cruise industry, with proven leadership responsibility.
Strong financial and analytical background, including budgeting, forecasting, and cost management.
In‑depth operational understanding of cruise port logistics and vendor/port agent coordination.
Outstanding written and verbal communication skills with strong professional integrity.
Proven track record of managing complex workflows in a dynamic, fast‑paced environment.
Strong ability to manage multiple priorities, balancing urgent operational needs with long‑term strategic initiatives.
Proficiency in MXP and Microsoft 365 (Word, Excel, Outlook).
Exceptional organizational skills with a high degree of accuracy and attention to detail.
Demonstrated initiative, self‑motivation, and ability to work both independently and collaboratively.

Nice To Haves

Experience with port reservation and invoicing platforms preferred.

Responsibilities

Strategic Leadership & Operational Oversight Serve as the central point of contact and subject‑matter expert for all fleetwide port operations.
Provide strategic direction for itinerary planning, deployment documentation, port setup, and operational readiness.
Collaborate closely with Product Development, Finance, Nautical, and Marine Operations leadership to support commercial and operational decision‑making.
Port Operations Management Manage itinerary and deployment documents, ensuring accurate and timely publication.
Coordinate port budgets, cost analysis, and itinerary‑driven financial modeling.
Oversee port reservations, phantom/double booking processes, and historical port data management.
Maintain and govern key port data sources, including the Port Agent database and Pier Address documentation.
Ensure full adherence to CLIA standards, industry best practices, and internal company policies.
Financial Management & Vendor Relations Lead annual port budgeting, leveraging historical trends, proformas, and strategic cost forecasting.
Continuously monitor financial performance, identifying variances, opportunities for savings, and operational risks.
Oversee accurate coding, processing, and reconciliation of all port and crew movement invoices.
Hold signing authority within approved thresholds, ensuring compliance with financial workflows.
Drive vendor and port agent negotiations to secure favorable terms and optimize long‑term cost structures.
Systems Leadership (MXP) & Process Optimization Lead the end‑to‑end implementation, adoption, and optimization of the MXP system across relevant departments.
Develop process improvements to enhance workflow efficiency, accuracy, and standardization across port operations.
Implement best practices to strengthen documentation, communication, and operational clarity.
Provide analytical and operational support for forecasting, cost trending, and port‑specific performance metrics.
Stakeholder Collaboration & Communications Partner with fleet and shoreside teams to resolve operational discrepancies and ensure smooth day-to-day port activities.
Maintain strong working relationships with Port Agents, vendors, and internal stakeholders to ensure alignment and timely issue resolution.
Support VP Marine Operations with strategic projects, operational assessments, and continuous improvement initiatives.