Retreat Planning Service for Remote & Distributed Teams
It shouldn’t be your job to plan company retreats
Let Pilot plan all the time-consuming logistics and crucial details,
so you can stay focused on growing your business.
.png)
Great retreats can take over 100+ hours of planning.
That’s weeks of tedious work. You need a turn-key retreat planning system that designs your custom company retreat, allowing you to reclaim that time for your business.
Consult on decision making, or take everything off your plate.
Hotel Room Blocks
We’ll negotiate on your behalf to secure the best group rate and manage your room block.
Transportation
We handle the research from every angle and ensure your team comes together.
Meals and Activities
We’ll help keep your team engaged with experiences and dining options for teams of all sizes.
Meeting Rooms and Event Spaces
You skip all the back and forth and instead arrive with spaces booked, set up, and ready for you to get down to business.
“Working with Pilot made the event planning decision making process 10x easier than planning an event on our own.”
Mae R.
CHRO, Retreat Client
Trusted by groups to plan over 70,000 trips of every size and style
Especially People leaders, Founders, and Executives building culture that powers today’s fastest-growing companies.
Choose your planning style
Self Serve
Explore places to stay at your own pace in your own way - or have us suggest venues. When you're ready to book, reach out to us, pay a deposit towards your booking, and we’ll negotiate group rates of up to 30% off on your behalf.
Full Service
- Tell us your vision, specifically or generally, for where you’d like to go, and what you’d like to do. Need ideas? We’re here to help with tailored recommendations.
- We’ll research, plan, and build a full itinerary to bring your vision to life, share it for feedback, and make as many changes as you like until it’s perfect.
Book with ease
Once your plan’s quote is ready, billing for all your bookings is simple, easy, and quick
We'll organize everything at your event's destination.
Hotels
Transfers
Tours
Meeting rooms
Conferences
Meals
Tickets to events & theme parks
Porterage at hotels
Room drops
and more!
Just show up!
All your plans will live in the Pilot app - booked, managed, and ready to impress your group.
Have an “in-house” retreat planner - without needing to train them.
Without Pilot
You’re overworked, unclear if your trending over budget, and unaware of the crucial details you might be forgetting.
With Pilot
We use our extensive network, optimize for your budget and desired impact, and deliver a retreat that’s organized, booked, and ready for your arrival.
Q: Is Pilot Retreats worth it?
A: Some things you can’t measure with money.
People. Culture. Alignment. That’s why we bring people together — to build alignment, connect personally, and reinforce your culture.
The alternative is steering a group toward a moving target. Misalignment costs more than the most expensive offsite. What’s the price of everyone drifting 10% off-course? Compounded across dozens of people? Too much.
Invest in people. Business results are the by-product.
Your team aligned, in the same boat ;)
Subscription-free pricing that pays for itself in savings
Save thousands (up to 30%) on bookings.
All rates cover planning and booking services only; actual travel booking costs vary.
This keeps our incentives fully aligned with yours: we’re motivated to find you the best deal, not the most expensive one. Thanks to the savings we unlock, you won’t pay more with us than booking everything on your own.
Pro-Tip: Replace the placeholders below with your details and ask ChatGPT:
"What is the ROI to my [company or group] of [number of people] people for running a retreat?"
An unforgettable offsite. Real team alignment. Zero burnout.
No more forcing smiles or faking fun. Your team’s genuinely energized, because the experience actually delivers. And you? You’re riding the momentum, not recovering from the planning.
Frequently Asked Questions
What are the benefits of using a retreat planning service for company retreats?
A retreat planning service like Pilot simplifies the process by handling logistics like venue selection, schedules, and coordination of activities. It saves time, reduces stress, and ensures the retreat aligns with your goals, whether it’s team building, celebrating milestones, or brainstorming ideas for unforgettable experiences. We use our creativity to work with you as a trusted partner every step of the way for your next corporate retreat or team offsite, incorporating all your preferences to create tailored proposals of memorable experiences for remote teams. We take a strategic approach to securing exclusive discounts from curated venues, letting you focus on creating next level meaningful connections, the big picture, and ultimately, your mission. As a retreat specialist, innovation to us means tailoring our retreat planners to your specific needs.
How does a company retreat planning service save time and money?
A retreat planner streamlines tasks like vendor research, rate comparisons, and bookings. By leveraging partnerships and handling logistics, they save you time and secure group discounts, reducing costs overall.
What’s the typical timeline for planning a corporate retreat?
Smaller retreats can be planned in a few weeks. Larger events typically take a few months to secure the best options. Starting early is ideal, but we can prioritize key elements to meet tighter deadlines.
What does a corporate retreat planning service typically include? Are flights included?
Our service covers the entire process ofvenue sourcing, group rates, transportation, accommodations, itineraries, meals, activities, and special requests like dietary needs or workshops. We organize everything at your event destination itself. All you have to do is get there and enjoy an exceptional experience.
You don’t book flights directly through us, but we can help with flight suggestions. This ensures your group’s travel details are organized and hassle-free from start to finish.
Can you handle large group trip planning for 50+ people?
Yes! While groups of any size can use our service (12 people minimum), we specialize in coordinating accommodations, activities, and logistics for groups of 20-80 (most employee groups we work with are around this size) or more, ensuring a cohesive and inclusive experience for every participant.
How do I get started with your company retreat planning services?
Start with our intake form, where you’ll share your retreat goals. We’ll confirm details and provide venue, activity, and logistics options. Once approved, our team handles coordination and ensures decisions align with your preferences. We simplify payments and adjust plans as needed.