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.

Francisco Castro Banner

Francisco Castro

Hometown: Houston, Texas
College: Carleton College

I teach high school Spanish and remedial reading intervention on the Northside of Houston where I spend my days learning from incredible high school students, biking around our beautiful nature bayous, and eating delicious Tex Mex.

Originally from the Dominican Republic, I moved to Houston, Texas, at the age of 13. I graduated from Carleton College in 2018 where I studied international relations with a concentration in Latin American studies. During that time, I led mentoring and support programs for local middle school boys and acted in various student-produced plays at Carleton. During the summer of 2015, I taught English and was a research assistant in a rural village in Myanmar where I hiked the mountains of Saigang. I studied abroad during my junior fall in Chile and Argentina, researching grassroots social justice educational projects in Santiago and Argentina—where I fell in love with Patagonia. During my senior spring, I co-led a political science study abroad program in Romania, Croatia, and Serbia. I am an avid photographer and videographer and live to capture experiences through a lens. In my free time, I like to skate, read classic Spanish literature, and grill outdoors for my friends.

In 2017 and 2019, I led Language & Service Costa Rica. Costa Rica has so much to offer — it was a special and unique experience to lead Overland students there. They are filled with wonder, grit, good will, and inspiring stories.