About Lakeside Trolley & Tours
Lakeside Trolley & Tours provides curated, shared-group wine and craft beverage tours around Seneca Lake and Keuka Lake in the Finger Lakes.
Our Tour Guides are the hosts of the experience. You’ll welcome guests, set the tone for the day, keep the group organized and on schedule, communicate with our drivers and partner establishments, and help create a fun, safe, stress-free day for our guests.
We’re adding one part-time guide to our weekend team for the remainder of the 2026 season.
Position
Seasonal Part-Time Weekend Tour Guide
Watkins Glen, NY
Season runs through late November 2026
This position is primarily for Friday, Saturday, and Sunday tours, with Saturday availability especially important.
Typical shifts are approximately 8–9 hours. Most weeks will offer approximately 1–2 shifts, depending on tour demand, your availability, and our existing staff schedule.
Tour demand is strongest through October and hours decrease significantly after Halloween and into November. Weekly hours are not guaranteed.
There may be an opportunity to return for the 2027 tour season for the right person.
Compensation
- $18–$20/hour, based on experience, availability, and role fit
- Paid training at $16/hour
- Tips can be a significant part of compensation. On a typical busy Saturday, guides currently receive approximately $200–$250 in guest tips.
- Combined with hourly wages, that can bring total compensation on a typical Saturday to approximately $40–$48/hour
- Tip amounts vary by tour, guest count, season, and guest discretion and are not guaranteed
- Tips begin once you are cleared to independently guide tours
Schedule
We are specifically looking for someone who can provide dependable weekend availability.
- Saturdays are our biggest staffing need
- Friday and Sunday shifts may also be available
- Approximately 9–18 hours per week during busier periods
- Hours vary based on tour demand and staffing needs
- Schedule becomes significantly lighter in November, with the opportunity to return in March-May 2027
- This is a seasonal position, not a guaranteed-hours position
This role is especially well suited to someone looking for consistent weekend side work rather than full-time employment.
What You’ll Do
Guest Experience & Hosting
- Welcome guests and explain how the day will work
- Lead groups of up to approximately 30 guests throughout the tour
- Speak comfortably to guests on a microphone
- Keep the atmosphere fun, social, welcoming, and professional
- Share information about the Finger Lakes, the tour, and upcoming stops
- Help guests understand timing and what happens next
- Take occasional guest photos and help groups capture their experience
Tour Operations
- Keep the tour running on schedule
- Organize departures and transitions between stops
- Communicate closely with the driver and Lakeside team
- Coordinate with staff at wineries, breweries, distilleries, and other partner establishments
- Follow established routes, timing, procedures, and contingency plans
- Assist with guest check-in when needed
Safety & Group Management
- Clearly communicate and enforce tour rules
- Maintain a safe and professional environment throughout the day
- Handle late guests, schedule issues, and unexpected situations calmly
- Address alcohol-related behavior respectfully but firmly when necessary
- Know when an issue needs to be escalated to the driver or management
Who We’re Looking For
You do not need to be a wine expert.
We’re much more interested in finding someone who is:
- Reliable and punctual
- Friendly, approachable, and professional
- Confident speaking in front of groups
- Comfortable taking charge when needed
- Calm when plans change or problems arise
- Organized and able to follow a schedule
- Comfortable working with groups where alcohol is being consumed
- Interested in the Finger Lakes and providing a great guest experience
People with backgrounds in hospitality, restaurants, tasting rooms, hotels, events, weddings, tourism, education, customer service, or other public-facing roles may be especially well suited for this position.
Training
New guides complete paid training before independently running tours.
Training includes:
- Guest experience and hosting standards
- Safety procedures and group management
- Tour operations and timing
- Route and partner-establishment knowledge
- Microphone and group communication
- Handling common tour-day situations
- Route-specific training and evaluation
Training typically requires several tour days before a guide is cleared to independently lead a tour.
Requirements
- Reliable transportation to report to Watkins Glen
- Strong punctuality and communication
- Comfortable speaking to groups of up to approximately 30 people
- Comfortable using a microphone
- Able to be on your feet and active throughout a full tour day
- Available for weekend work, with dependable Saturday availability
- Comfortable working around guests who are consuming alcohol
- Able to maintain a professional appearance and demeanor
About the Role
This is not a traditional sightseeing-tour script-reading job, and it is not a party-bus role.
Our tours are structured shared-group experiences. The guide’s job is to make the day feel easy and enjoyable for guests while keeping the group organized, informed, safe, and on schedule.
The best guides are personable and fun, but they’re also dependable, confident, and comfortable taking control of the group when needed.
Pay: $18.00 - $20.00 per hour
Application Question(s):
- Are you comfortable speaking on a microphone and confidently leading groups of up to approximately 30 adults?
- Are you comfortable with a seasonal, variable schedule of approximately 1–2 weekend shifts per week during busier periods, with hours decreasing significantly after October and no guaranteed weekly hours?
- What interests you about working as a Finger Lakes tour guide with Lakeside Trolley & Tours?
Shift availability:
Ability to Commute:
- Watkins Glen, NY (Required)
Work Location: In person
