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.

Caroline Bomstein 1

Caroline Bomstein

Hometown: Washington, DC
College: Amherst College

As a history major at Amherst College, I got to dive into my love of reading, writing, and learning about the past; now, as a high school social studies teacher, I get to share that passion with my students at Memphis School of Excellence in Memphis, Tennessee.

I came to Memphis with Teach for America, and I am excited to stay in my placement school for a third school year. Originally from Washington, D.C., I graduated from Amherst College in 2016 with a double major in history and environmental studies. While at Amherst, I played varsity ice hockey and served as an assistant captain my senior year. At Amherst, I was able to pursue my passion for both athletics and academics and was named to the NESCAC All-Academic team for my final four semesters at Amherst. Since graduating, I taught skiing at Park City Mountain Resort in Park City, Utah, and history for two years in Memphis.

In 2015, I led Writing & Hiking New England; in 2016, I led Alps Explorer; in 2017, I led Language & Hiking France; and in 2019, I led Iceland Expedition. Leading trips abroad is a magical experience that has allowed me to watch students immerse themselves in new places, cultures, and languages while having fun in the most beautiful settings.