PRIVATE CORPORATE OUTINGS
Private Finger Lakes Corporate Outings
Plan a company outing without managing every route, reservation, and timing detail yourself. Lakeside Trolley handles the transportation, itinerary, timing, and venue coordination so you can enjoy the Finger Lakes with your group.
• Private outings
• One central pickup
• Professionally planned itinerary
• Wineries, craft beverages & scenic experiences
Tell us your date, group size, pickup location, and the kind of experience you have in mind.
We Handle the Details
A Company Outing You Don’t Have to Manage All Day
Choosing where to take the group is only the beginning. Lakeside Trolley brings the transportation, itinerary, venue coordination, and timing together so the person planning the outing can actually enjoy it too.
We Plan the Itinerary
We build a route around your group, timing, pickup location, and the experience you want.
We Coordinate the Venues
We handle the stop coordination and reservation details so you don’t have to manage several venues yourself.
We Handle the Timing
Transportation and scheduling are planned together so your group stays together and the day keeps moving.
You Have One Planning Contact
One Lakeside Trolley contact helps guide the outing from your first inquiry through the final details.
Choose Your Experience
Choose a Starting Experience
You don’t need to build an itinerary from scratch. Choose the experience that feels closest to your group, and Lakeside Trolley will refine the outing around your date, group size, pickup location, and venue availability.
Wineries & Lunch
A classic Finger Lakes outing built around great wine, a planned lunch stop, and time to enjoy the day together.
- 2–3 winery experiences
- Planned lunch stop
- Private transportation
- Itinerary & venue coordination
Wine, Beer & Spirits
A varied Finger Lakes outing for groups that want to mix wineries with breweries, distilleries, or other craft beverage stops.
- Curated beverage mix
- Planned lunch stop
- Private transportation
- Itinerary & venue coordination
Wineries & Waterfalls
Pair Finger Lakes wine country with scenic waterfall stops for a day that combines tastings, lunch, and some of the region’s best views.
- 2 winery experiences
- Planned lunch stop
- 2–3 scenic waterfall stops
- Easy-access sightseeing, not a hiking tour
Choose a starting experience. We’ll help shape the details around your group.
What We Take Care Of
What Lakeside Trolley & Tours Handles
We bring the transportation, planning, and venue coordination together into one private outing. Your Lakeside Trolley package covers the pieces that keep the day organized, while your group keeps control of what it spends at the individual stops.
Included in Your Lakeside Trolley Package
- Private group transportation
- Professional driver
- Professionally planned itinerary
- Venue coordination
- Timing & logistics management
- Driver gratuity
- One central pickup and return location
- One planning contact
Paid Separately as Applicable
- Tastings
- Meals
- Activity fees
A planned lunch stop is part of the itinerary. The cost of the meal is normally separate.
We coordinate the day — your group keeps control of what it spends at the stops.
How It Works
From Idea to Outing in Three Steps
You don’t need to arrive with every detail figured out. Tell us about your group and what you have in mind, and we’ll help turn it into a workable Finger Lakes outing.
Tell Us About Your Group
Share your preferred date, estimated group size, pickup location, and the type of experience that interests you.
We Build the Recommended Plan
Lakeside Trolley reviews your group, timing, route, and available venues and puts together a recommended outing that makes sense for the day.
We Coordinate the Details
Once your outing is confirmed, we handle the venue coordination, itinerary, transportation, and timing so your group knows where to be and when.
Start with the basics. We’ll help with the rest.
The Day at a Glance
What a Typical Corporate Outing Looks Like
Most corporate outings are designed as a five- to six-hour experience with a manageable pace, a planned lunch stop, and enough time to enjoy each destination without making the day feel rushed.
5–6 Hours
Typical outing length
3–4 Total Stops
Planned around your group
Planned Lunch Stop
Built into the itinerary
One Pickup & Return
One central meeting location
Need something shorter? A simplified three- to four-hour outing may work well for conference groups or tighter schedules. Longer outings of up to approximately eight hours may also be possible depending on the itinerary, date, and availability.
Made for Company Groups
A Finger Lakes Outing for Your Team, Clients, or Guests
Whether you’re celebrating your team, entertaining clients, or adding an experience to a conference or retreat, Lakeside Trolley can build a private outing around the occasion.
Employee Appreciation
Company Celebrations
Client Entertainment
Conference Activities
Leadership Outings
Retreat Activities
WHY LAKESIDE TROLLEY & TOURS
Local Planning Makes the Difference
A successful Finger Lakes group outing takes more than choosing a few places on a map. Travel time, vehicle access, reservation timing, group size, venue capacity, food needs, and the pace of the day all have to work together.
Lakeside Trolley & Tours already operates tours throughout Finger Lakes wine country. We use that local experience to build private outings that work in the real world — not just on paper.
- Local route knowledge across Finger Lakes wine country
- Experienced venue coordination and itinerary planning
- Experienced drivers and tour staff
- Memorable private transportation that becomes part of the experience
- One Lakeside Trolley planning contact from inquiry through final details
PRIVATE GROUP TRANSPORTATION
Transportation That Becomes
Part of the Outing
Your transportation should feel like part of the Finger Lakes experience — not just a ride between stops.
Lakeside Trolley’s vintage trolley gives private groups a distinctive way to travel together while we handle the route, timing, and logistics throughout the day. A luxury shuttle option may also be available depending on your group and outing.
Our vintage trolley accommodates groups of up to 30 guests. Larger groups may sometimes be accommodated using additional vehicles depending on the date and availability.
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Private to Your Group
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Up to 30 Guests by Trolley
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Additional Vehicle Options May Be Available
What Guests Say
Trusted to Keep the Day Running Smoothly
Lakeside Trolley & Tours already plans and operates group experiences throughout Finger Lakes wine country. Here’s what guests have said about the people behind the experience.
“Both the driver, Rachael and the tour guide were friendly and knowledgeable. We enjoyed them both.”
Jane
Google Review
“Wonderful tour! *Nate and Rachael were great. Very informative and accommodating.”
George Detwiler
Google Review
“Jason our guide & driver did an awesome job. We had a great time. He even took photos for us.”
Diane Goodwin
Google Review
Real guest feedback from Lakeside Trolley & Tours experiences.
Questions About Private
Corporate Outings
COMMON QUESTIONS
Every outing is a little different, but these are some of the most common questions we hear when groups begin planning.
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Your Lakeside package includes private group transportation, a professional driver, itinerary planning, venue coordination, timing and logistics management, driver gratuity, one central pickup and return location, and one Lakeside planning contact.
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Tastings, meals, venue charges, activity fees, and venue-specific deposits are normally separate. We can build a planned lunch stop into your itinerary and coordinate the timing around the rest of your outing.
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Our vintage trolley accommodates private groups of up to approximately 30 guests. A shuttle option may also be available depending on the outing. Larger groups may sometimes be accommodated using additional vehicles depending on the date and availability.
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Yes. Our three outing packages are starting points rather than fixed itineraries. We’ll refine the experience around your group, pickup location, preferences, timing, and venue availability while making sure the route works well for the day.
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Most outings begin and end at one central location, such as a hotel, conference venue, company office, lodging property, or event venue. Pickup availability depends on the location and the itinerary we’re planning.
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Yes. While most corporate outings are approximately five to six hours, a shorter three- to four-hour outing may work well for groups fitting an experience around meetings, conferences, or other scheduled activities.
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Corporate outings are generally best suited for Sunday through Friday. Select Saturday outings may also be possible depending on the date, vehicle availability, and itinerary.
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Outings operate rain or shine. Because most itineraries include indoor experiences as well as transportation between stops, the day can usually continue as planned even when the weather isn’t perfect.
READY TO START PLANNING
Plan Your Company Outing
Tell us a little about your group and what you have in mind. We’ll review your date, group size, pickup location, and preferred experience and help you determine the best next step.
- You don’t need a finished itinerary
- We’ll help refine the experience
- Submitting an inquiry does not commit you to booking
Tell Us About Your Outing
Share the basics below and we’ll help you shape the details.
We’ll use the information above to review your outing and follow up about availability, options, and next steps.