Retreat Planning Service for Remote & Distributed Teams
Planning a retreat or group trip shouldn't cost so much time or money
It doesn’t make sense to hire staff to take it off your plate either. That's why Pilot Retreats handles everything for you and negotiates group rates to save you thousands of dollars.
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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.
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 public rates 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.
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 +100 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 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.
We save you 50+ hours of research and back-and-forth.
Planning fee:
- $49 per person per night + any on-site staff if desired (this is optional, and starts at $150/hour, with an 8hrs per day minimum, and 1 staff minimum per group of 50)
Deposit: 50% of planning fees due at kickoff
All plans have a 25% surcharge for each/either of:
- Retreats planned <45 days out
- Retreats based in non-english speaking countries, both due to the extra work required to coordinate and more follow-ups.
Why this pricing?:
- Our goal is to get you as close to 30% off public rates as possible across hotels and vendors.
- We use APIs and partner networks to check many supplier options across the same inventory and find better value, then negotiate with them with leverage.
- Flat pricing means our incentives are aligned with yours. We win if you feel you got a better retreat and better pricing than doing it alone, so you come back next year.
In the very rare case where additional planning hours beyond the standard number of hours estimated at time of quoting are required, such as if you decide to change the plan drastically, additional planning hours may be billed at $150/hour (plus any taxes).
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?"
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.