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.

Raquel Banner Web

Raquel Cuéllar-Parajón

Assistant Director, Leader Hiring

Email Raquel

Many of my favorite memories feature wild backyard adventures with my cousins.

Childhood in Nicaragua is unique in many ways– one of those being how beautiful and diverse our outdoor spaces are. It’s not uncommon to have a jungle behind your house, where you might find pistachio shells to make small turtles, or a crater lake you scheme ways to hike down into, or to spend weekends at the beach climbing large rocks with little purple barnacles on them that hurt your feet.

The common denominator in these memories is how exciting it is to explore the world with others – and how different perspectives shape your experiences.

It is fulfilling to work in a place that strives to make these types of experiences possible for hundreds of students, and that puts so much care into doing so! Working at Overland means that I get to play a part in other kids having their own adventures.