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.

tom and liz costley

Tom & Liz Costley


Email Tom

We met at Williams in the 80s and soon discovered a mutual love of education and travel — of shared exploration, shared challenge, and shared purpose.

After graduation, Liz headed abroad to teach in Athens, Greece. The combination of working with students and exploring a beautiful place was an ideal first job. The sense of community she created in her classroom was powerful; the opportunity to learn about Greece and its islands was exciting. She was hooked. A year later, I joined her, and it didn’t take long for me to fall in love with the adventurous traveling that was such an important part of our lives there: hiking the Greek islands, trekking in Nepal, and exploring off the beaten track in Italy.

When we started Overland in 1984, we sought to create experiences for kids that mirrored the adventures we’d found abroad: experiences that were fun, where new friendships could grow, where natural beauty was embraced, where there were real and varied challenges, and where our students would achieve something of importance to them.

When you’re 25 and starting something, you make it up as you go, you try things out, you hope for the best. When you’re in your 60s, and you’ve been at it for almost forty years — as we have with Overland — you make improvements every year, and you hope how much you care comes across in everything you do.

And caring about Overland means a lot of things to us — but most of all, it means staying focused on creating experiences for our students that will help them grow into the kinds of people we — as their parents — hope they’ll become: thoughtful and considerate, kind and eager, enthusiastic and adventurous.

How do we create these experiences? By offering carefully crafted trips with clearly defined goals, led by a pair of caring and capable leaders. At 25 we had an intuitive sense of the importance of these things, in our 60s — and over 40,000 students later — we know this is what makes us Overland.