Travel Director

Santana Adventures; Claremont (CA); Hybrid; USD 130,000 - 160,000; Full time

Job summary

Santana Adventures in Claremont, CA, is seeking an experienced Tour Director to lead planning, scouting, and on-site operation of our high-end cycling cruise events. This senior role emphasizes international travel, leadership, participant experience, and meticulous execution.

The Tour Director oversees itineraries, coordinates teams, manages on-site communication, and ensures safety and quality across diverse destinations, while representing the company with professionalism and confidence.

Qualifications

• Exceptionally organized and detail-oriented.
• Strong leadership and communication skills.
• Experience in travel operations and event logistics.

Responsibilities

• Assume primary operational responsibility for assigned Santana Adventures events from development through completion.
• Establish itineraries and participant experiences with company leadership; lead Travel Operations team.
• Oversee on-site routes, transportation, vendors, staffing and contingency planning.
• Conduct team briefings and ensure day-to-day plans are executable and safe.
• Make real-time operational decisions during events and coordinate with staff and vendors.

Skills

Public speaking

Leadership

Travel operations

Logistics planning

Communication

Job description

Full-Time | $130,000-$160,000 | Extensive International Travel

Santana Adventures creates and operates high-end cycling cruises and group travel experiences around the world, combining exceptional cycling, carefully planned logistics, cultural discovery, and highly personal participant service.

We are looking for an experienced Tour Director to take primary responsibility for the planning, scouting, and operation of assigned Santana Adventures cycling cruise events.

This senior leadership position combines extensive international travel, complex event operations, team leadership, participant communication, and responsibility for the quality and execution of each assigned event.

During an event, the Tour Director is one of Santana Adventures' most visible representatives - leading daily presentations, communicating with participants, and setting the tone for the group. Behind the scenes, the role requires exceptional preparation, judgment, attention to detail, and rapid problem-solving when circumstances change.

Cycling experience is a significant plus, but this is not a traditional cycling-guide position. We are looking primarily for an exceptional travel and hospitality leader who combines operational ability with confidence, communication skills, judgment, adaptability, and presence.

About the Role

The Tour Director has overall responsibility for assigned events from planning and scouting through final operation.

Working with company leadership, the Tour Director establishes the direction, itinerary, cycling experience, and priorities for each event, then leads a Travel Operations & Experience Manager and Travel Operations Specialist in turning that vision into a detailed operating plan.

The Tour Director remains actively involved in routes, scouting, vendors, logistics, transportation, contingency planning, and participant-experience decisions. They are not expected to complete every planning task personally, but remain accountable for event readiness and Santana Adventures' standards.

Once an event begins, the Tour Director becomes its primary on-site leader, maintaining a confident, approachable participant presence while overseeing the complex operation behind the scenes.

A successful Tour Director must be equally comfortable addressing 300 participants with a microphone and working behind the scenes to solve an unexpected operational problem.

Compensation, Location & Travel

Salary:$130,000-$160,000 annually, depending on experience and qualifications.

Travel:Approximatelyeight months per year, including international cycling cruise events, scouting trips, event preparation, and other company travel. Actual travel may vary based on the event calendar and operational needs.

Work Location:During initial training and the probationary period, when not traveling, the position will generally work in person with company leadership inClaremont, California, Monday through Friday, 8:00 AM-5:00 PM.

After successfully completing training and demonstrating appropriate independence, the employee may work remotely when stateside and not traveling. Periodic in-person work in Claremont will still be required.

Santana Adventures covers approved work-related transportation, lodging, and travel expenses during scouting trips and active events. Additional benefits will be discussed during interviews.

Key Responsibilities

• Assume primary operational responsibility for assigned Santana Adventures events from development through completion.
• Work with company leadership to establish each event’s itinerary, priorities, and participant experience.
• Lead the Travel Operations & Experience Manager, Travel Operations Specialist, and other assigned team members.
• Set priorities, delegate responsibilities, review work, and ensure each event plan is operationally sound.
• Remain involved in routes, destination research, transportation, vendors, reservations, timing, and contingencies.
• Participate extensively in on-site scouting of routes and destinations.
• Evaluate whether routes, experiences, transportation, vendors, and other components will work for a large Santana group.
• Identify and resolve weaknesses, missing information, and potential problems before the event.

Public Speaking & Participant Leadership

Public speaking is a major component of this position.

• Deliver route talks, briefings, orientations, announcements, and presentations to groups approaching 300 participants.
• Clearly explain routes, distances, elevation, stops, transportation, timing, safety, and daily information.
• Present complicated logistical information in a clear, organized, and engaging manner.
• Communicate schedule or itinerary changes calmly and confidently.
• Be personable, energetic, and professional while maintaining authority and credibility.
• Set a positive tone that creates enthusiasm, confidence, camaraderie, and organization.

Candidates need not begin as professional speakers, but must have the confidence, aptitude, and willingness to become effective presenters capable of leading a room of several hundred people.

On-Tour Operations & Problem-Solving

• Serve as the primary on-site leader for assigned events.
• Oversee daily routes, transportation, activities, vendors, ship coordination, staffing, and participant logistics.
• Conduct team briefings so staff understand the day’s plan, responsibilities, and challenges.
• Make real-time operational decisions when circumstances change.
• Coordinate changes clearly with staff, participants, vendors, transportation providers, and ship personnel.
• Remain composed, decisive, and solutions-oriented during demanding or rapidly changing days.
• Keep the team prepared for upcoming days while resolving current issues.

International group travel rarely unfolds exactly as planned. Weather changes, roads close, transportation is delayed, vendors make mistakes, schedules change, and unexpected participant needs arise.

The Tour Director must excel in these moments, using lateral thinking to identify alternatives, understand downstream effects, prioritize competing problems, and preserve the intended participant experience.

The goal is to build and lead an operation capable of handling the unexpected without allowing it to define the participant’s experience.

What We're Looking For

The successful Tour Director combines leadership presence with operational depth:

The ideal candidate is:

• Exceptionally organized and detail-oriented.
• Comfortable with significant responsibility and accountability.
• Confident making decisions with incomplete information.
• An excellent verbal communicator with strong public-speaking potential.
• Personable and engaging while maintaining professional authority.
• Calm, adaptable, and resourceful when plans change.
• Strong at lateral thinking and creative problem-solving.
• Able to balance the big picture with critical details.
• Comfortable delegating while retaining visibility into critical details.
• Service-minded and comfortable with active, mature, well-traveled participants.
• Able to balance individual participant requests with the needs of a large group.
• Takes ownership rather than waiting for others to solve problems.
• Comfortable with extensive international travel and long periods away from home.

Relevant experience may include tour operations, luxury or experiential travel, cruises, hospitality, destination management, large-scale events, international logistics, transportation, high-end guest service, team leadership, or public speaking.

Cycling, route development, mapping, international travel, and foreign-language experience are valuable but not required.

Travel & Physical Requirements

Candidates must have a valid U.S. driver’s license, a valid U.S. passport or ability to obtain one, and be willing to drive rental vehicles or vans as needed.

This is an active working-travel position. Days can be long and include early mornings, evenings, weekends, changing schedules, and variable weather. Candidates must be able to stand and walk for extended periods and occasionally lift or move luggage, supplies, or bicycles up to approximately 50 pounds.

Santana Adventures is a small, hands-on team. A Tour Director responsible for the overall event may still need to move a bicycle, locate luggage, set up signage, assist a participant, or solve a transportation problem.

Although Santana operates cycling cruises, this position does not involve cycling every day. The Tour Director's responsibility is to the operation and participants, frequently requiring them to be somewhere other than on a bicycle.

Travel to remarkable destinations is a significant part of this job, but this is working travel.

About Santana Adventures

Santana Adventures specializes in high-end cycling cruises around the world, combining exceptional cycling, thoughtfully planned itineraries, cultural discovery, beautiful destinations, and an experienced, welcoming group.

We are a small, hands-on team, and the Tour Director brings the experience together - leading the team, owning the operation, solving the unexpected, and serving as the person entrusted to lead our participants through the event.