Trip discovery questions

Every Orange Sky field trip begins with a Discovery call with our Launch Team—a quick and friendly conversation that helps us get to know your group and start building the perfect Field Trip Roadmap. During the call, we’ll cover three key areas:

Group Type (Who is traveling?)

We’ll begin by understanding the people at the heart of your trip:

  • Who is traveling together? Is this a single grade level, a performing arts ensemble, a Beta Club, a senior class, or an entire middle school?

  • Who is the group leader? We’ll need to know who’s making trip-level decisions and serving as our main point of contact—before, during, and after the trip.

  • Where is your group based? Knowing your school’s location helps us plan transportation and recommend destinations that make sense for your travel window.

Group Goals (Why is this group traveling?)

Next, we’ll talk about your “why.” Every trip has a purpose—and understanding yours helps us make it meaningful:

  • Is this trip tied to academic standards or curriculum goals?

  • Is it designed to celebrate your students’ hard work or reward positive behavior?

  • Is it part of a school tradition or a once-in-a-lifetime opportunity?

  • Are you hoping to inspire students with new places, people, and experiences?

Group Logistics (What will this trip look like?)

Here’s where we dive into the details that shape your itinerary and budget:

  • How many travelers are expected? What’s the estimated breakdown of students, teachers, and chaperones?

  • What are your preferred travel dates—and any alternate options?

  • How many days and nights do you want to travel?

  • What’s your target budget per traveler? We’ll design a trip that works within your financial goals and offers maximum value.

  • What’s on your wishlist? Share must-see attractions, favorite meals or destinations, and any activities you’d like to avoid.

  • Do you need complimentary (“comp”) packages for educators or chaperones? We’ll factor these into your group pricing.

Other important details:

  • How should hotel rooms be arranged (quad, triple, double, single)?

  • Will your school need substitute teacher reimbursement?

  • Are you planning to use our online payment system? Will the school be paying for any part of the trip?

🚀 Let’s Get Planning

The more we know, the more tailored—and stress-free—your trip will be. When you’re ready, we’ll handle all the logistics, so you can focus on enjoying the journey with your students.


Why Orange Sky Travel?

Comparing travel providers? Asking the right questions of your group travel partner can make the difference between a successful trip and a forgettable experience.

  1. What do Google reviews say about your company?

    • Online reviews show how good travel experiences are. Orange Sky has a 4.8 rating from more than 615 reviews and still growing!

  2. How long have you been in the group travel business? How many employees?

    • Pricing is important, but so are experience and support. Relying on an inexperienced provider for your trip can be risky and frustrating.

  3. How many field trips do you support each year?

    • Student travel is complicated due to changing details. Inquiring about the organization and their expertise can be very helpful.

  4. Do you require a comprehensive background check on all employees and contractors?

    • Travel providers check for problems not just locally but also across multiple states and at the federal level, doing these background checks every year.

  5. What kind of commercial insurance do you carry?

    • Work only with travel providers that have Professional Liability Insurance for Travel Agents and Tour Operators (we have up to $2M coverage).

  6. Do you offer online traveler booking, payment collection, and customer service?

    • These services are essential for easing the burden of student travel from school staff, including administrators, treasurers, and teachers.

  7. Is your company a member of a professional travel organization?

    • Only top travel companies can meet the requirements of organizations like IATA and SYTA.

  8. Do you have vendor references?

    • Good travel partners depend on strong relationships with buses, hotels, restaurants, theme parks, and more. Request references!