If you are planning a school trip for the first time, the thing to look for in a student travel company is not the itinerary — it is how much of the work they take off your desk, and how clearly they tell you what is left on it. Landmark Educational Tours builds every trip privately for one group and runs the logistics, the payments and the on-the-ground management, which leaves a first-time organizer with a much shorter list than most teachers expect.
That is the real test of a student travel company for a first-time trip planner. The honest summary of the list: you decide where and when, you get it approved, you tell families, and you show up. Almost everything else is the company’s job. Most first-timers assume the opposite, and that assumption is what stops trips from happening.
This page sets out exactly who does what on a first class trip, the questions first-timers do not know to ask, and the worries worth naming out loud. You can request a quote at no cost, and planning stays free until you agree to proceed.
Landmark Educational Tours at a Glance
More about the company is on our about page; this section is the short version a first-timer needs before a first call.
| Item | Detail |
|---|---|
| Company | Landmark Educational Tours, Middleton, Massachusetts — 100% employee-owned, 20+ years in student travel |
| Trip type | Private group tours only. Your group is never merged with another school’s. |
| On the trip | A Tour Director assigned to your group alone, handling timing, entries and problems |
| Support | A team member reachable around the clock, before, during and after |
| What it costs to explore | Nothing. Planning, a custom itinerary and a written quote are free until you agree to proceed. |
| Deposit | $50 per traveler for trips traveling by land; $150 per traveler where airfare is included |
| Who collects the money | Landmark, through its own portal. Families pay individually — the teacher does not handle cash or checks. |
| Accreditations | SYTA, American Bus Association, Better Business Bureau and IATA |
| Minimum lead time | 60 days, though six to twelve months is where good first trips get planned |
| Typical cost | $300 to $400+ per traveler per day depending on package inclusions, or about $1,200 to $3,500+ in total for an all-inclusive package. Airfare is an additional variable cost. |
What You Handle, and What the Company Handles
This is the chart worth printing. Almost every first-time organizer overestimates their own column and underestimates ours. Where the itinerary itself is concerned, what customizing actually means sets out how much of it you get to shape.
| Task | Who does it |
|---|---|
| Choosing destination and dates | You, with suggestions from a Travel Consultant if you want them |
| Building the itinerary | Landmark, from what you tell us about your group and curriculum |
| Getting school or board approval | You — we provide the written itinerary and quote you need to do it |
| Booking hotels, coaches, admissions, flights | Landmark |
| Telling families and running the parent meeting | You, with materials from us |
| Collecting payments | Landmark, through the traveler portal |
| Recruiting chaperones | You — your district sets the required ratio, not us |
| Dietary restrictions and allergies | Collected on the portal by Landmark and passed to restaurants ahead |
| Rooming list | You decide who rooms with whom; we arrange it with the hotel |
| Running the days on the trip | Your Tour Director — timing, entries, headcounts and problems |
| Something going wrong at 2am | Landmark, reachable around the clock |
Five rows in your column, and three of those are decisions rather than labor. That is the realistic picture of a first trip, and it is the single biggest thing first-timers get wrong about where their group could actually go.
The Questions First-Timers Do Not Know to Ask
Experienced organizers ask these automatically. If this is your first trip, they are the ones worth writing down before any call — and worth asking of every company you speak to, which is how the comparison actually gets made.
| Question | Why it matters on a first trip |
|---|---|
| Is my group traveling alone or combined with other schools? | It changes who is on your coach and who the Tour Director answers to |
| Is the Tour Director assigned only to us? | On a first trip, having one person who knows your group matters more than anything on the itinerary |
| What exactly is in the per-student price, and what is not? | The line most often missed is gratuities for the Tour Director and step-on guides, which are not included |
| What is the deposit and when is final payment due? | You will be asked at the parent meeting, and “I will find out” is a bad answer |
| What happens if a student has to cancel? | Get the refund schedule in writing before anyone pays anything |
| What trip protection is available and when must it be bought? | Read the plan itself rather than the summary, and ask when the purchase window closes |
| How many students do we need? | Around ten travelers is the usual industry threshold for group rates |
| What are your accreditations? | Names you can check yourself — SYTA, ABA, BBB, IATA |
Our FAQ page answers most of these in Landmark’s own words, and how to choose a reliable student travel agency goes further into due diligence.
The Worries Worth Naming Out Loud
First-time organizers tend to carry these quietly. They are all reasonable and they all have answers.
“What if not enough students sign up?”
The most common fear, and the most preventable. Participation is largely decided by how early you announce, because students have sports seasons, jobs and family calendars of their own. Announce in September for an April trip and most conflicts are still solvable; announce in February and they are not. Around ten travelers is the usual threshold for group rates, and a Travel Consultant will tell you honestly whether your numbers work before you commit to anything.
“Am I responsible if something happens?”
You are a chaperone, not the operator. On a Landmark trip students receive safety bracelets and a safety briefing at their first meeting with the Tour Director, free exploration happens in chaperone groups or on the buddy system depending on the age of the group, and the group does not leave a site until two separate headcounts are done — one by the Tour Director and a final one by the head chaperone. Hotels are student-appropriate with on-site security available. Full detail is on travel safety and support.
“Am I personally liable?”
Liability is the question first-timers are most reluctant to ask and most need answered, so ask it directly — of us and of anyone else you are considering.
Two things to request in writing before you commit. First, a certificate of insurance showing the operator’s general liability coverage, which most districts require as a matter of procurement anyway. Second, confirmation of whether the company can name your school or district as an additional insured — that is standard district language and the person in your front office who handles contracts will know exactly what it means even if you do not.
Your own district almost certainly has a field trip policy covering chaperone responsibilities and what it expects from a vendor. Read it before the first call rather than after, because it tells you what you are obliged to ask for. None of this is a reason to hesitate; it is a reason to ask early, when the answers are easy to get.
“How much work is this actually going to be?”
Less than the chart above probably suggested before you read it. The heaviest week is the one before departure, and it is mostly communication rather than logistics. The parent meeting is the single biggest piece of work, and it is a meeting rather than a project.
“What if I pick the wrong thing?”
Most of it is reversible until you commit, and planning costs nothing until then. You can hold a written itinerary and a real price without having committed your school to anything, which means a first-timer can take a genuine proposal to an administrator before deciding whether to proceed. If you are at the very beginning, how to start planning a student trip is the step before this one.
A First Trip, in Order
| When | What happens |
|---|---|
| 12 to 9 months out | Pick a destination and a rough window. Request a quote — free, and it gives you a real number to take to your administration. |
| 9 to 6 months out | Get approval with a written itinerary and price in hand. Sign the trip agreement, which sets the terms and the payment schedule. Your group’s portal opens. |
| 6 to 3 months out | Families register and begin paying. Dietary restrictions are collected. Fundraising, if you are doing it, happens here. |
| 3 to 1 months out | Numbers firm up. You submit the rooming list. Chaperones are confirmed. |
| Final weeks | Confirm meeting points and times, brief chaperones, send the packing list to families. |
The two dates that matter most are not on that table: your board’s meeting date, which is usually the real deadline, and the date you announce the trip to students, which largely decides how many of them come. Booking early covers why both matter more than the departure date does.
A First-Timer’s Checklist
If you do nothing else before your first call, have these five things ready. They are what a Travel Consultant needs in order to give you a real number rather than a range.
- A destination and a rough window. Three possible weeks is worth more than one fixed date.
- An approximate passenger breakdown. Students, teachers and chaperones. It does not have to be final.
- Your district’s chaperone ratio. It sets your bed count, which sets your price. This is the single most common reason a first quote comes back higher than expected.
- Your board’s meeting date. Usually the real deadline, rather than the departure date.
- What the trip is actually for. One sentence. It is what lets a route be built around your curriculum rather than from a list.
And one thing not to do: do not wait until you have all five perfect before calling. The conversation is free, and a Consultant can work from partial information — that is most of what the first call is for.
What It Costs, and What Is Free
On average, Landmark’s fully inclusive trips run $300 to $400+ per traveler per day depending on package inclusions, or about $1,200 to $3,500+ in total for an all-inclusive package. Airfare is an additional variable cost.
| Trip length | Typical cost per traveler |
|---|---|
| 3 days | $900 to $1,200+ |
| 4 days | $1,200 to $1,600+ |
| 5 days | $1,500 to $2,000+ |
The number that matters to a first-time organizer is not the base rate — it is the figure that goes on the permission slip, and that depends on trip length, season, group size and how many students share a room. A first quote that looks high is usually a chaperone-ratio or room-occupancy question rather than a pricing one, so ask what would change it before assuming the trip is out of reach.
What costs nothing: the conversation, a custom itinerary, and a written quote. None of it commits your school to anything, which is the single most useful thing for a first-timer to know. Families pay through Landmark’s own portal rather than through you — how payment plans work sets out the deposit, the schedule and the financing option, and what is included in a package covers what the per-student number carries.
Where This Student Travel Company Fits a First-Timer — and Where It Does Not
- A good fit if you want one company handling transport, hotels, admissions and payments, and one person on the ground running the days.
- A good fit if you want the itinerary built around your curriculum rather than chosen from a catalog, and if you would rather be asked what you want than shown a list.
- A good fit if your district requires competing written quotes, because ours costs nothing and is itemized.
- Less of a fit if the lowest possible headline price is the only criterion. A private group carries costs that a combined departure spreads across several schools, and we would rather say so.
- Less of a fit if you want to book a fixed published itinerary off a website today. We build each trip in conversation, which takes longer at the start.
- Less of a fit for a very small group, since around ten travelers is the usual threshold for group rates.
- If you are comparing us against a specific company you have already been quoted by, our pages on shopping against WorldStrides run the same questions.
Who Is Landmark Educational Tours?
Landmark Educational Tours is a 100% employee-owned educational travel company based in Middleton, Massachusetts, with more than twenty years in student travel, sixteen travel experts on staff, and former classroom teachers among them who build the curriculum side of the itineraries.
Every trip is private and built for one group. Landmark is a member of the Student & Youth Travel Association and the American Bus Association, holds Better Business Bureau and IATA accreditation, and is an approved vendor for districts including Broward County Public Schools and the New York City Department of Education — all of which can be verified independently on our accreditations page. More about the company is on our about page, and you can read what groups have said on our testimonials page.
If this is your first trip, say so when you call. It changes how a Travel Consultant works with you, and it is the most useful sentence you can open with. Request a quote or contact us to start.
