Company Retreats & Planning Service
From team retreats to group getaways, we’ll plan and book your next trip.
We handle the details, so you can spend time on the things that matter, impress your group, and celebrate your success.
Trusted by groups to plan over 50,000+ trips of every size and style
Your in-house retreat
planner — minus the overhead.
With over 2 million direct partners, Pilot Retreats integrates with your team to save you hundreds of hours and up to thousands of dollars with unbeatable exclusive group rates
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
Choose your planning style
Explore things to do and 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.
- 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
We can arrange anything that your group requires, mostly falling within these categories:
- Hotel
- Transfers
- Tours
- Meeting rooms
- Conferences
- Meals (Breakfast, lunch, dinner)
- Tickets to events and theme parks
- Porterage at hotels
- Room drops
Just show up!
Others help you plan — we actually make it happen.
We take retreat planning off your plate, instead of adding more to it. No subscriptions either, and you stay in control. Our on-demand retreat experts work where you do, and cost nothing when you don’t.
We make you look like a rockstar and your group feel amazing.
We’ll create your retreats that build communication, motivate your crew, and create shareable moments that open doors.
As Featured In
Warning: You’ll hate our services if...
You enjoy "jumping on a quick call" with sales
Sorry, we don’t force calls, but we’re happy to hop on if it’s easier for you. We start with an email and then can work wherever you do — Slack, Teams, voice notes, or Looms.
You think spending +60 hours planning a retreat is the best use of your time
Growing teams deserve their time back. Negotiating, researching, and booking every detail of a retreat takes hours you could spend scaling your business. Let us handle the logistics while you focus on what matters.
You prefer paying group premiums over getting group discounts
With over two million partner stays and the power to leverage our booking volume, we get deals travel agents can’t.
Please note: while we can plan and book trips for groups of any size, group discounts only start to kick in at around 8+ attendees.
You’re desperate for commitment
Sadly we don’t do annual contracts or subscriptions — unless you ask for one. You’re only charged when you book your trip or request our planning services.
You love moving slowly, like a turtle
We get things done fast, and can get results back you within 48 business hours on most requests.
You think “Customer Success Managers” are your friends
Honey, those emails are automated.
You hate travel
May we suggest a book instead?
Subscription-free pricing that pays for itself
Save up to 30% on bookings. All rates cover planning and booking services only; booking costs will vary.
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?"
Complimentary Content @PilotPlans
.webp)
FAQs
A retreat planning service like Pilot simplifies the process by handling logistics like venue selection, schedules, and activities. It saves time, reduces stress, and ensures the retreat aligns with your goals, whether it’s team building, celebrating milestones, or brainstorming ideas.
A retreat planner streamlines tasks like venue research, rate comparisons, and bookings. By leveraging partnerships and handling logistics, they save you time and secure group discounts, reducing costs overall.
Smaller retreats can be planned in a few weeks, and we’ve even handled some in under a week. 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.
Our service covers venue sourcing, group rates, transportation, accommodations, itineraries, meals, activities, and special requests like dietary needs or workshops.
You don’t book flights directly through us, but we’ve partnered with a trusted group flight product whose team will handle the bookings. But, we can manage the coordination and logistics on your behalf, making the process as easy as if it were booked directly through us. This ensures your group’s travel details are organized and hassle-free from start to finish.
Yes! While groups of any size can use our service, we specialize in coordinating accommodations, activities, and logistics for groups of 50 or more, ensuring a cohesive and inclusive experience for every participant.
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.
For smaller and more intimate travel, try our free travel planning app.
Simplify how you discover, plan, and book trips your way, for groups or solo. Our free tool to make travel less tedious and costly so you can focus on making the most of every trip.
