We Welcome Your Application to Join Us!

We build each of our groups with care, keeping the groups small (no more than twelve students), and paying close attention to age, grade, gender, and the mix of hometowns and schools. Our goal is to put together great groups — groups where nice kids thrive in a supportive, wholesome, and caring environment. Please note: availability as shown is based on students traveling without a friend; if your child is interested in traveling with a friend, please call our office for availability.

Important Information about Availability


This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.


This departure of this trip has limited availability. Apply as soon as possible, and on receipt of your application, if space is still available, we’ll confirm a spot for you. If all of the spots are taken, we’ll call you to discuss options.


This departure of this trip is currently full — please call us to discuss options.

How to Apply

Apply online using a credit card for the $795 deposit (your card will not be charged until we confirm a spot for you). Applications are reviewed in the order in which they are received (we do not hold spots over the phone).

When to Apply

The flow of applications starts in July and peaks in January/February. Some groups fill by the December holidays, and others will have space into the late spring. Our advice? Apply as soon as possible — it only takes a few minutes — and we’ll get to work right away to find a great spot for you.


Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.

Our Current Covid-19 Policy

Updated November 16, 2021

November 16, 2021

Dear Overland Families,

At Overland, summer has always been our most exciting season. This past summer, our excitement was amplified by the promise of a healthier world.

When the summer was over, we looked back on not a single infection on any of our trips!

Grateful? You bet.

We have always approached our Covid-19 policy with thoughtfulness. We consider the health and well-being of: (1) our students, (2) our staff, (3) our leaders, (4) the areas we travel through,  (5) and the families and communities we return home to at trip end.

Looking ahead to summer 2022, we will once again require our staff and leaders to be vaccinated, and we may require all eligible students to be vaccinated (we expect to make this decision in early 2022). For our international trips, we will also need to ensure we’re in compliance with travel requirements for each country we visit.

Everyone here is committed to supporting each of our Overland families—please reach out to us with any questions you might have.

With our very best wishes,

Tom & Liz Costley


Thank you for your support—we appreciate it!


  • Does Overland encourage all eligible students to get vaccinated?

    Yes! While this might change to a requirement, at this time we’re waiting until early 2022 to make this decision.

  • Once my child is fully vaccinated, where do I upload the vaccine card?

    Please log into your family portal, click on Covid-19 Vaccination, and upload the card where indicated.

  • What does Overland expect students to do in the days prior to the trip?

    Please avoid crowded indoor locations. This guideline is necessarily broad—please use common sense, be careful, and stay healthy!

  • What does Overland expect students to do to practice excellent hygiene while traveling to trip start?

    Please wear a mask and maintain social distance from others in airports. While in flight, please wear a mask at all times. Wash your hands frequently.

  • Will a PCR test before the trip be required of fully vaccinated students?

    No (this is no longer recommended by the CDC, and it is no longer required by our licensing).

  • Will a PCR test before the trip be required of unvaccinated students?


  • Where do we upload the results of the PCR test?

    Please log into your family portal, click on Covid-19 Test Results, and upload the results where indicated.

  • Will a pre-trip PCR test be required of a student who has had laboratory-confirmed Covid-19 in the ninety days before the trip?

    No. There is a section on the family portal where parents can indicate that their child has had laboratory-confirmed Covid-19 in the ninety days before the trip. We will be in touch with these families to reconfirm the details of the diagnosis.

  • What happens if a student tests positive during the trip?

    We will make our decisions with a focus on: (1) everyone’s health and well-being, (2) the group’s location, and (3) the trip’s itinerary and activities. A positive case in a group might necessitate the quarantining of any unvaccinated students. We will do everything we can to avoid this outcome—and having as many vaccinated students as possible will help, so please, if you’re eligible, vaccinate!