Tour Director

Tour Director

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. Our trips combine exceptional cycling, carefully planned logistics, cultural discovery, and a highly personal style of participant service.

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

This is a senior leadership position combining extensive international travel, complex event operations, team leadership, participant-facing communication, and significant responsibility for the overall quality and execution of each assigned event.

During an event, the Tour Director is one of the most visible representatives of Santana Adventures—leading daily presentations, communicating with participants, and setting the tone for the group. Behind the scenes, the role requires exceptional preparation, attention to detail, sound judgment, and the ability to solve complicated problems quickly when circumstances inevitably 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 Santana Adventures events from planning and scouting through final operation.

Working with company leadership, the Tour Director helps establish the overall direction, itinerary, cycling experience, and priorities for each assigned event. The Tour Director then leads a team that includes a Travel Operations & Experience Manager and Travel Operations Specialist to turn that vision into a detailed operating plan.

The Tour Director remains actively involved in itinerary and route development, scouting, vendor and logistical decisions, transportation, contingency planning, and participant-experience decisions. While the Tour Director is not expected to personally complete every planning task, they are ultimately responsible for ensuring the event is thoroughly prepared and meets Santana Adventures’ standards.

Once an event begins, the Tour Director becomes its primary on-site leader. This requires simultaneously maintaining a commanding and approachable presence with participants while overseeing the complicated operation occurring behind the scenes.

A successful Tour Director must be equally comfortable standing in front of 300 participants with a microphone and working privately with the team to solve an unexpected operational problem.

Compensation, Location & Travel

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

Employment: Full-time, salaried position.

Travel: Approximately eight 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 in Claremont, California, Monday through Friday, 8:00 AM–5:00 PM .

After successfully completing training and demonstrating the ability to perform the position with appropriate independence, the employee may be permitted to 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 other approved travel expenses during scouting trips and active events. Additional benefits will be discussed during the interview process.

Key Responsibilities

Event Planning & Leadership

• Assume primary operational responsibility for assigned Santana Adventures events from development through completion.
• Work with company leadership to establish the overall itinerary, direction, priorities, and participant experience for each event.
• Lead the Travel Operations & Experience Manager, Travel Operations Specialist, and other assigned team members.
• Establish planning priorities, delegate responsibilities, review work, and ensure the final event plan is complete and operationally sound.
• Remain actively involved in itinerary development, cycling routes, destination research, transportation, vendors, reservations, timing, and contingency planning.
• Participate extensively in on-site scouting of routes and destinations.
• Evaluate whether routes, stops, cultural experiences, transportation, vendors, and other components will work successfully for a large Santana group.
• Identify weaknesses, missing information, or potential problems and ensure they are resolved before the event.
• Maintain accountability for the overall quality and readiness of assigned events.

Public Speaking & Participant Leadership

Public speaking is a significant component of this position .

• Deliver daily route talks, event briefings, orientations, announcements, and presentations to groups that may approach 300 participants.
• Clearly explain cycling routes, distances, elevation, stops, transportation, timing, safety considerations, and other daily information.
• Present complicated logistical information in a clear, organized, and engaging manner.
• Communicate schedule or itinerary changes calmly and confidently.
• Develop a strong command of the microphone and the ability to hold the attention of a large room.
• Be personable, approachable, energetic, and professional while maintaining authority and credibility.
• Answer participant questions effectively in both group and individual settings.
• Set a positive tone for the event and help create enthusiasm, confidence, camaraderie, and organization.

Candidates do not need to begin as professional speakers, but they must have the confidence, aptitude, and willingness to develop into 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 execution of cycling routes, transportation, activities, vendors, ship coordination, staffing, and participant logistics.
• Conduct team briefings and ensure staff understand the day’s plan, responsibilities, and potential challenges.
• Make real-time operational decisions when circumstances change.
• Coordinate changes quickly and clearly with staff, participants, vendors, transportation providers, and ship personnel.
• Address significant participant concerns and unusual situations.
• Remain composed, decisive, and solutions-oriented during demanding or rapidly changing event days.
• Ensure the team remains prepared for upcoming days even while resolving current issues.

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

The Tour Director must be particularly effective in these moments. The position requires lateral thinking —the ability to quickly identify alternative solutions, understand the downstream effects of a change, prioritize competing problems, and preserve as much of the intended participant experience as possible.

The goal is not to operate an event where nothing unexpected happens. The goal is to build and lead an operation capable of handling the unexpected without allowing those circumstances 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 accepting significant responsibility and accountability.
• Confident making decisions, including when information is incomplete.
• 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 understand both the big picture and the details required to achieve it.
• Comfortable delegating while retaining visibility into critical details.
• Capable of leading, developing, and motivating a team.
• Service-minded and comfortable working with active, mature, well-traveled participants.
• Able to balance individual participant requests with the needs of a large group.
• Comfortable working closely with senior company leadership.
• Willing to take ownership rather than waiting for someone else to solve a problem.
• Genuinely comfortable with extensive international travel and long periods away from home.

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

Cycling, cycling tourism, 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 the ability to obtain one, and the ability and willingness to drive rental vehicles or vans as needed.

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

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

Although Santana operates cycling cruises, there should be no expectation that this position involves cycling every day . The Tour Director’s responsibility is to the operation and participants, which will frequently require being somewhere other than on a bicycle.

The opportunity to 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. Our participants travel with us for exceptional cycling, thoughtfully planned itineraries, cultural discovery, beautiful destinations, and the camaraderie of an experienced and welcoming group.

We are a small, hands-on team, and the Tour Director plays a central role in bringing the entire experience together —leading the team that builds the event, taking responsibility for its operation, solving the unexpected, and ultimately standing in front of our participants as the person entrusted to lead them through the experience.