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.

Claire Roth Banner

Claire Roth

Hometown: Los Angeles, California
College: University of Wisconsin-Madison

Since the fall of 2016, I’ve worked for the nonprofit Africa Yoga Project based in Nairobi, Kenya, leading service-safari trips for children and adults throughout Kenya.

Originally from Los Angeles, California, I graduated in 2018 from the University of Wisconsin-Madison, where I majored in international studies and political science and gained certificates in African studies and environmental studies. During my junior year, I studied abroad in Nairobi, Kenya, and Paris, France. While in Madison, I worked for Adventure Learning Programs, a student-led organization facilitating leadership and team-building workshops, volunteered for Planned Parenthood, and worked as a city ambassador and advocate for Bicycle Benefits, a national program that supports cycling. Also, I served as the internal chair for Adventure Learning Programs; I held committee meetings, planned events and curated an atmosphere of inclusion within the organization. During the past 16 summers, I’ve participated in and guided many trips throughout the Boundary Waters in northern Minnesota. I feel most alive when biking uphill, navigating rapids in kayaks and canoes, having a passionate and purposeful conversation while building community, and dipping into chilly water after a run with friends.

In 2019, I led Alaska Expedition. I’ve found the harmony of nature and community provides wonderful opportunities to grow as an individual and as a member of a group. It was a pleasure to spend a summer exploring the Last Frontier and guiding students to find that harmony.